IIDA Akira
Department of Applied Biological Chemistry | Professor |
Last Updated :2024/09/14
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■Researcher basic information
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Research Keyword
- 生物有機化学 有機合成化学 天然物化学 Bioorganic chemistry Synthetic Organic Chemistry Natural Product Chemistry
■Career
Career
- 2008/04 - Today Kindai UniversityFaculty of Agriculture教授
- 2006/04 - 2008/03 Takasaki University of Health and WelfareFaculty of Pharmacy教授
- 1997/04 - 2006/03 京都大学大学院薬学研究科准教授
- 1996/04 - 1997/03 Kyoto UniversityFaculty of Pharmaceutical Sciences准教授
- 1988 - 1996 Faculty of Pharmaceutical Sciauces,
- Kyoto University, Research Assistant
Educational Background
■Research activity information
Paper
- Mitsuaki Yamashita; Akari Nakanishi; Chiehming Chang; Kosei Tsurushima; Kiyoshige Nakamoto; Akira IidaChemical & pharmaceutical bulletin 72 (7) 693 - 699 2024This study evaluated the ability of isolated or semisynthesized trichothecene sesquiterpenes to prevent cancer emergence and proliferation and inhibit signal transducer and activator of transcription-3 (STAT3) phosphorylation through in vitro assays. Trichothecinol A (TTC-A), which bears a hydroxy group at C3, exhibited greater cancer prevention, antiproliferation, and STAT3 phosphorylation inhibition effects than trichothecin (TTC), which lacks a hydroxy group at C3. Furthermore, trichothecinol B (TTC-B), which is a reduced derivative of TTC and has similar cytotoxic effect, showed substantially weaker chemoprotection and STAT3 phosphorylation inhibition effects than TTC. These results clearly indicate that the hydroxy group at C3 and carbonyl group at C8 are crucial for inducing both potent chemoprevention and STAT3 phosphorylation inhibition.
- Mitsuaki Yamashita; Yuto Nakamori; Arisa Tsukamoto; Nagisa Furuno; Akira IidaBioorganic & medicinal chemistry 90 117331 - 117331 2023/07Based on previous studies, we synthesized a novel class of ortho- and para-naphthoquinones derivatives bearing a phenolic hydroxy or sulfonamide moiety and evaluated their in vitro antiproliferative and signal transducer and activator of transcription-3 (STAT3) phosphorylation inhibitory activities. The biological evaluations of these naphthoquinones revealed that ortho-naphthoquinones containing a phenolic hydroxyl group exhibited greater antiproliferative activity compared to compounds without a phenolic hydroxyl group. Among the synthesized para-naphthoquinones, 21, which has a condensed sulfonamide structure, showed substantially higher antiproliferative activity than that of the parent compound, and was also found to inhibit the phosphorylation of STAT3(Y705) in a dose-dependent manner. A docking simulation using AutoDock Vina suggested that 21 could directly bind to the hinge region of STAT3.
- Fusako Kawai; Yoshitomo Furushima; Norihiro Mochizuki; Naoki Muraki; Mitsuaki Yamashita; Akira Iida; Rie Mamoto; Takehiko Tosha; Ryo Iizuka; Sakihito KitajimaAMB Express 12 (1) 134 - 134 2022/10The enzymatic recycling of polyethylene terephthalate (PET) can be a promising approach to tackle the problem of plastic waste. The thermostability and activity of PET-hydrolyzing enzymes are still insufficient for practical application. Pretreatment of PET waste is needed for bio-recycling. Here, we analyzed the degradation of PET films, packages, and bottles using the newly engineered cutinase Cut190. Using gel permeation chromatography and high-performance liquid chromatography, the degradation of PET films by the Cut190 variant was shown to proceed via a repeating two-step hydrolysis process; initial endo-type scission of a surface polymer chain, followed by exo-type hydrolysis to produce mono/bis(2-hydroxyethyl) terephthalate and terephthalate from the ends of fragmented polymer molecules. Amorphous PET powders were degraded more than twofold higher than amorphous PET film with the same weight. Moreover, homogenization of post-consumer PET products, such as packages and bottles, increased their degradability, indicating the importance of surface area for the enzymatic hydrolysis of PET. In addition, it was required to maintain an alkaline pH to enable continuous enzymatic hydrolysis, by increasing the buffer concentration (HEPES, pH 9.0) depending on the level of the acidic products formed. The cationic surfactant dodecyltrimethylammonium chloride promoted PET degradation via adsorption on the PET surface and binding to the anionic surface of the Cut190 variant. The Cut190 variant also hydrolyzed polyethylene furanoate. Using the best performing Cut190 variant (L136F/Q138A/S226P/R228S/D250C-E296C/Q123H/N202H/K305del/L306del/N307del) and amorphous PET powders, more than 90 mM degradation products were obtained in 3 days and approximately 80 mM in 1 day.
- Mitsuaki Yamashita; Jun Sawano; Ryuji Umeda; Ayuka Tatsumi; Yuko Kumeda; Akira IidaChemical & pharmaceutical bulletin 69 (7) 661 - 673 2021 [Refereed]
In this study, based on our previous study, derivatives of naphtho[2,3-b]furan-4,9-diones were synthesized and their antimicrobial activities were evaluated. The screening of these naphthoquinones revealed that the fluorine-containing NQ008 compound exhibited potent and broad antimicrobial activities against Gram-positive bacteria including methicillin-resistant Staphylococcus aureus (MRSA), Gram-negative bacteria, and fungi. The results of the ratio of the minimum bactericidal concentration (MBC) to the minimum inhibitory concentrations (MICs) and time-kill assays suggest that the mode of action of NQ008 is bactericidal. Additionally, the results of a drug resistance study revealed that NQ008 exhibited potent antibacterial activity and may delay the development of bacteria resistance. Furthermore, NQ008 exhibited preliminary antiviral activity against the swine influenza virus and Feline calicivirus. - Akane Senga; Nobutaka Numoto; Mitsuaki Yamashita; Akira Iida; Nobutoshi Ito; Fusako Kawai; Masayuki OdaJournal of biochemistry 169 (2) 207 - 213 2020/09 [Refereed]
An enzyme, Cut190, from a thermophilic isolate, Saccharomonospora viridis AHK190 could depolymerize polyethylene terephthalate (PET). The catalytic activity and stability of Cut190 and its S226P/R228S mutant, Cut190*, are regulated by Ca2+ binding. We previously determined the crystal structures of the inactive mutant of Cut190*, Cut190*S176A, in complex with metal ions, Ca2+ and Zn2+, and substrates, monoethyl succinate and monoethyl adipate. In this study, we determined the crystal structures of another mutant of Cut190*, Cut190**, in which the three C-terminal residues of Cut190* are deleted, and the inactive mutant, Cut190**S176A, in complex with metal ions. In addition to the previously observed closed, open, and engaged forms, we determined the ejecting form, which would allow the product to irreversibly dissociate, followed by proceeding to the next cycle of reaction. These multiple forms would be stable or sub-stable states of Cut190, regulated by Ca2+ binding, and would be closely correlated with the enzyme function. Upon the deletion of the C-terminal residues, we found that the thermal stability increased while retaining the activity. The increased stability could be applied for the protein engineering of Cut190 for PET depolymerization as it requires the reaction above the glass transition temperature of PET. - Teruyuki Tahara; Ami Watanabe; Maho Yutani; Yuko Yamano; Mami Sagara; Shizu Nagai; Keita Saito; Mitsuaki Yamashita; Makoto Ihara; Akira IidaBioorganic & medicinal chemistry 28 (6) 115347 - 115347 2020/03 [Refereed]
The extract of Tabebuia avellanedae has been used as a folk medicine, and the various biological activities of T. avellanedae have been extensively studied. However, few studies have reported which natural products play a role in their biological effects. In this study, we evaluated representative naphthoquinones isolated from T. avellanedae and found that furanonaphthoquinones were the key structures required to exhibit STAT3 phosphorylation inhibitory activities. Our SAR analysis indicated that removal of a hydroxyl group enhanced the STAT3 phosphorylation inhibitory activity. In addition, the combined results of a mobility shift assay, SH2 domain binding assay, and docking simulation by Autodock 4.2.6 suggested that (S)-5-hydroxy-2-(1-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione (1) could directly bind to the hinge region of STAT3. - Mitsuaki Yamashita; Syuhei Hata; Jun Sawano; Ryuji Umeda; Akira IidaHETEROCYCLES PERGAMON-ELSEVIER SCIENCE LTD 100 (2) 225 - 240 0385-5414 2020/02 [Refereed]
A concise and efficient synthesis method for the preparation of antiproliferative ortho-naphthoquinones is described. Notably, the synthesis of ortho-furanonaphthoquinone was achieved by utilizing a regioselective oxidative conjugate addition of dimethylamine and the Sonogashira coupling/cyclization reaction as the key steps. Additionally, an improved synthesis of hydroxy-P-lapachone was established and included a regioselective prenylation by directed ortho-lithiation. In vitro antiproliferative effects of the synthesized against a panel of 39 human cancer cell lines were evaluated and the results were directly compared to those previously obtained for 1. - Koichi Yada; Katsuhiko Suzuki; Natsumi Oginome; Sihui Ma; Youichi Fukuda; Akira Iida; Zsolt RadakScientific reports 8 (1) 14625 - 14625 2018/10 [Refereed]
Endurance capacity is important for maintenance of quality of life as well as performance of endurance athletes. In order to improve endurance, intake of nutritional supplements as well as exercise training is also important. Indeed, polyphenolic extracts from plants are known to improve endurance capacity via increase of fatty acid utilization, mitochondrial biogenesis or inhibition of oxidative stress. Taheebo, the extract obtained from inner bark of Tabebuia avellanedae has been reported to have beneficial effects for treatment of inflammation, oxidative stress and obesity. Here, we investigated the effects and mechanisms of polyphenol fraction of taheebo (taheebo polyphenol; TP) on endurance capacity of mice. Single dose administration of TP significantly increased running time until exhaustion. Acute TP administration increased blood glucose and muscle glycogen levels (p < 0.05) through alteration on expression level of genes involved with glycogen metabolism and gluconeogenesis. Furthermore, TP administration decreased exercise-induced increase of protein carbonyls in skeletal muscle. These results suggest that TP administration improve endurance capacity via up-regulation of skeletal muscle glycogen levels and maintenance of blood glucose by acceleration of gluconeogenesis as well as inhibition of exercise-induced oxidative stress. Single administration of TP also increased phosphorylation of AMP-activated protein kinase (AMPK) and gene expression level of sirtuin 1 (SIRT1) but did not change the marker of mitochondrial biogenesis. - Sawabe Akiyoshi; Tagashira Shiho; Yamashita Atsuyuki; Takeda Ryuji; Iida AkiraABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY 256 0065-7727 2018/08 [Refereed]
- Mitsuaki Yamashita; Teruyuki Tahara; Shinya Hayakawa; Hironobu Matsumoto; Shun-Ichi Wada; Kiyoshi Tomioka; Akira IidaBioorganic & medicinal chemistry Elsevier Ltd 26 (8) 1920 - 1928 1464-3391 2018/05 [Refereed]
HDAC inhibitors enable histones to maintain a high degree of acetylation. The resulting looser state of chromatin DNA may increase the accessibility of DNA drug targets and consequently improve the efficiency of anticancer drugs targeting DNA, such as Topo II inhibitors. A novel class of nucleoside-SAHA derivatives has been designed and synthesized based on the synergistic antitumor effects of topoisomerase II and histone deacetylase inhibitors. Their inhibitory activities toward histone deacetylases and Topo II, and their cytotoxicities in cancer cell lines, were evaluated. Among the synthesized hybrid compounds, compound 16b showed the potent HDAC inhibitory activity at a low nanomolar level and exhibited antiproliferative activity toward cancer cell lines including MCF-7 (breast), HCT-116 (colon), and DU-145 (prostate) cancer cells at a low micromolar level. Moreover, compound 16a showed HDAC6-selectivity 20-fold over HDAC1. - SYNTHETIC STUDY OF ANTI-OBESITY IRIDOID ISOLATED FROM TABEBUIA AVELLANEDAEMitsuaki Yamashita; Shinya Hayakawa; Shuhei Hata; Honoka Murakami; Youichi Fukuda; Akira IidaHeterocycles 97 (2) 960 - 967 2018/02 [Refereed]
- Sihui Ma; Koichi Yada; Hyunjin Lee; Youichi Fukuda; Akira Iida; Katsuhiko SuzukiFrontiers in nutrition 5 2 - 2 2018 [Refereed]
[This corrects the article on p. 63 in vol. 4, PMID: 29312947.]. - Hironobu Matsumoto; Mitsuaki Yamashita; Teruyuki Tahara; Shinya Hayakawa; Shun-Ichi Wada; Kiyoshi Tomioka; Akira IidaBioorganic & medicinal chemistry PERGAMON-ELSEVIER SCIENCE LTD 25 (15) 4133 - 4144 0968-0896 2017/08 [Refereed]
We developed novel nucleoside-based topoisomerase II selective inhibitors and showed that small structural units, such as catechols, are essential for DNA topoisomerase II inhibitory activity. Moreover, nucleoside analogues containing TBS and 1,3-dithian moieties had potent and selective DNA topoisomerase II inhibitory activities. In further experiments, compound 25b having a beta configuration of the thymine moiety showed relatively strong growth inhibitory activity against cancer cell lines, and was more potent against all cancer cell lines than compound 26b, which carries a thymine moiety in the alpha configuration. - Sihui Ma; Koichi Yada; Hyunjin Lee; Youichi Fukuda; Akira Iida; Katsuhiko SuzukiFrontiers in nutrition 4 63 - 63 2017 [Refereed]
Aim of study: Taheebo polyphenols (TP) are water extracts of Tabebuia spp. (Bignoniaceae), taken from the inner bark of the Tabebuia avellanedae tree, used extensively as folk medicine in Central and South America. Some anti-inflammatory drugs act by inhibiting both cyclooxygenase-2 (COX-2) and COX-1 enzymes. COX-2 syntheses prostaglandin (PG) E2, which is a species of endogenous pain-producing substance, whereas COX-1 acts as a house-keeping enzyme. Inhibiting both COX-1 and -2 simultaneously can have side effects such as gastrointestinal bleeding and renal dysfunction. Some polyphenols have been reported for its selective inhibiting activity toward COX-2 expression. Our study aimed to demonstrate the potential and mechanisms of TP as an anti-inflammation action without the side effects of COX-1 inhibition. Materials and methods: Free fatty acid-stimulated macrophage cell lines were employed to mimic macrophage behaviors during lifestyle-related diseases such as atherosclerosis and non-alcoholic steatohepatitis. Real-time polymerase chain reaction was used to detect expression of inflammatory cytokine mRNA. Griess assay was used to measure the production of nitric oxide (NO). ELISA was used to measure PG E2 production. Molecular docking was adopted to analyze the interactions between compounds from T. avellanedae and COX-2. Results: TP significantly suppressed the production of NO production, blocked the mRNA expression of iNOS, and COX-2 in both cell lines, blocked the mRNA expression of TNF-α, IL-1β, IL-6, and PGE2 in the murine cell line. However, there was no inhibitory effect on COX-1. Molecular docking result indicated that the inhibitory effects of TP on COX-2 and PGE2 could be attributed to acteoside, which is the main compound of TP that could bind to the catalytic zone of COX-2. After the interaction, catalytic ability of COX-2 is possibly inhibited, followed by which PGE2 production is attenuated. COX inhibitor screening assay showed TP as a selective inhibitor of COX-2 enzyme. Conclusion: The anti-inflammatory effects of TP can possibly regulate macrophages due to the targeted inhibition of COX-2 activity, without affecting COX-1 activity with other anti-inflammatory effects including suppression of iNOS and inflammatory cytokines. As such, TP is potentially useful in prevention and treatment of lifestyle-related disease by attenuating inflammation caused by macrophages infiltration. - Kazuko Iwamoto; Youichi Fukuda; Chisato Tokikura; Mayuko Noda; Ayami Yamamoto; Misato Yamamoto; Mitsuaki Yamashita; Nobuhiro Zaima; Akira Iida; Tatsuya MoriyamaBiochemical and biophysical research communications ACADEMIC PRESS INC ELSEVIER SCIENCE 478 (3) 1136 - 40 0006-291X 2016/09 [Refereed]
Estrogen deficiency-induced obesity has a high risk of visceral fat accumulation and body weight gain. It is also associated with many adverse health conditions. Taheebo extract from Tabebuia avellanedae has been recognized as playing several biological and pharmacological roles. Therefore, we investigated whether the intake of n-BuOH extract of Taheebo shows anti-obesity effect in ovariectomized (OVX) mice. After 16 weeks of feeding, the mice administrated with 0.5% n-BuOH extract of Taheebo showed significantly decreased body weight compared with that of the control mice, and the fat mass also showed a significant decrease. In 3T3-L1 cells, supplementation with n-BuOH extract of Taheebo significantly reduced the triglyceride (TG) levels. Furthermore, bioassay-guided purification of the n-BuOH extract based on the TG levels in 3T3-L1 cells led to the isolation of compound 2 (1-dehydroxy-3,4-dihydroaucubigenin). These results suggested that the anti-obesity effect of Taheebo extract is due to its capability in preventing the accumulation of adipocyte in mice. Taheebo extract might be a promising functional food resources capable of protecting against OVX-induced obesity. - Mitsuaki Yamashita; Yukari Nishizono; Seiya Himekawa; Akira IidaTETRAHEDRON PERGAMON-ELSEVIER SCIENCE LTD 72 (27-28) 4123 - 4131 0040-4020 2016/07 [Refereed]
We developed facile one-pot methods for the transformation of 2-arylindoles to polyhydropyrido[1,2-a]indoles and tetracyclic quinazolinones. The copper-catalyzed oxidation of 2-arylindoles to C-acylimines followed by aza-Diels-Alder reactions or oxidative ring-expansion reactions afforded significant polycyclic heterocycles. (C) 2016 Elsevier Ltd. All rights reserved. - T Takeda; K. Kondo; K. Ueda; A. IidaBiomedical Research on Trace Elements 27 (1) 8 - 14 2016 [Refereed]
- Mitsuaki Yamashita; Akira IidaTETRAHEDRON PERGAMON-ELSEVIER SCIENCE LTD 70 (35) 5746 - 5751 0040-4020 2014/09 [Refereed]
In this study, we describe a one-pot method to obtain a variety of 2-arylbenzoxazinones and N-benzoyl anthranilic acid by using a copper catalyst and molecular oxygen as oxidants. This protocol involves tandem cyclization and oxidative processes of 2-alkynylanilines to afford significant motifs in synthetic and medicinal chemistry with moderate yields. We also demonstrated that combining the Sonogashira coupling and the developed method realized the synthesis of 2-arylbenzoxazinones derivatives from commercially available 2-iodoanilines and terminal acetylenes. (C) 2014 Elsevier Ltd. All rights reserved. - Mitsuaki Yamashita; Akira IidaTETRAHEDRON LETTERS PERGAMON-ELSEVIER SCIENCE LTD 55 (18) 2991 - 2993 0040-4039 2014/04 [Refereed]
We developed an efficient method for the transformation of indoles by utilizing a copper catalyst and molecular oxygen as the oxidant. The transformation involves a tandem oxidative process of 2-arylindoles. Our reaction afforded a variety of N-benzoyl anthranilic acids and benzoxazinones. Our investigation revealed that the choice of solvent and additives is critical in these reactions. (C) 2014 Elsevier Ltd. All rights reserved. - Hsin-Yi Hung; Kyoko Nakagawa-Goto; Harukuni Tokuda; Akira Iida; Nobutaka Suzuki; Ibrahim D Bori; Keduo Qian; Kuo-Hsiung LeeBioorganic & medicinal chemistry letters PERGAMON-ELSEVIER SCIENCE LTD 24 (3) 1005 - 8 0960-894X 2014/02 [Refereed]
Ten new 3,4-seco betulinic acid (BA) derivatives were designed and synthesized. Among them, compounds 7-15 exhibited enhanced chemopreventive ability in an in vitro short-term 12-O-tetradecanoylphorbol-13-acetate (TPA) induced Epstein-Barr virus early antigen (EBV-EA) activation assay in Raji cells. Specifically, analogs with a free C-28 carboxylic acid, including 7, 8, 11, and 13, inhibited EBV-EA activation significantly. The most potent compound 8 displayed 100% inhibition at 1×10(3) mol ratio/TPA and 73.4%, 35.9%, and 8.4% inhibition at 5×10(2), 1×10(2), and 1×10 mol ratio/TPA, respectively, comparable with curcumin at high concentration and better than curcumin at low concentration. The potent chemopreventive activity of novel seco A-ring BAs (8 and 11) was further confirmed in an in vivo mouse skin carcinogenesis assay. - Govind J Kapadia; G Subba Rao; Rajagopalan Sridhar; Eiichiro Ichiishi; Midori Takasaki; Nobutaka Suzuki; Takao Konoshima; Akira Iida; Harukuni TokudaAnti-cancer agents in medicinal chemistry Bentham Science Publishers B.V. 13 (10) 1500 - 7 1875-5992 2013/12 [Refereed]
In continuation of our studies with chemoprevention potential of plant-derived naphthoquinone derivatives, leaf powder of the medicinal plant Lawsonia inermis L, commonly known as 'henna', was evaluated by its inhibition of the Epstein-Barr virus early antigen (EBV-EA) activation induced by the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells. Lawsone (2-hydroxy- 1,4-naphthoquinone), the reddish orange pigment artifact formed during the extraction or preparation of the dye from henna leaves and believed to be the active component, was also assessed in this in vitro assay. Both showed a profound inhibition (>88%) of EBV-EA activation. In the in vivo two-stage mouse skin carcinogenesis study using UV-B radiation for initiation and TPA for tumor promotion, oral feeding of henna (0.0025%) in drinking water ad libitum decreased tumor incidence by 66% and multiplicity by 40% when compared to the positive control at 10 weeks of treatment. Similarly, in the above mouse model, orally fed lawsone (0.0025%) decreased tumor incidence by 72% and multiplicity by 50%. The tumor inhibitory trend continued throughout the 20-week test period. Similar antitumor activities were observed when henna (0.5 mg/ml) was applied topically on the back skin in the UV-B initiated, TPA promoted and peroxynitrite initiated, TPA promoted mouse skin carcinogenesis models. Topically applied lawsone (0.015 mg/ml) also exhibited similar protection against tumor formation in the 7,12-dimtehylbenz(a)anthracene induced and TPA promoted skin cancer in mice. Also, there was a delay of 1 to 2 weeks in tumor appearance in both henna and lawsone treated groups compared to control in all three test models. This study ascertains the skin cancer chemopreventive activity of henna leaf powder and lawsone when administered by either oral (through drinking water) or topical (by application on the back skin) routes. Further, it emphasizes the need for the evaluation of these henna-derived green chemopreventive candidates in combination with currently used sunscreen agents for complementary anticancer potential against UV-induced skin carcinogenesis. - Govind J Kapadia; G Subba Rao; Cheppail Ramachandran; Akira Iida; Nobutaka Suzuki; Harukuni TokudaJournal of complementary & integrative medicine 10 2194-6329 2013/06 [Refereed]
Although a wide variety of cytotoxic plant extracts and phytochemicals are known to act synergistically with anticancer drug doxorubicin (D), their clinical application is hindered by safety concerns of such combination therapy. Our earlier studies showed that red beetroot (Beta vulgaris L.) extract (B), approved by Food and Drug Administration and European Union as red food color E162, reduced multi-organ tumor formations in various animal models when administered in drinking water. This led us to postulate that a long-term daily exposure to low doses of B through diet might be safe and sufficient to produce cancer chemopreventive effect in humans. Further, our recent comparative cytotoxic investigation with B and D in several human cancer cell lines indicated their potential for synergistic activity. Since B is considered safe for human use with no known toxicity, we conducted the present study to evaluate its synergistic antiproliferative activity with D against pancreatic (PaCa), breast (MCF-7) and prostate (PC-3) tumor cells of human origin. Different concentrations of B and D (0.29-290 μg/ml) and in various combinations (B:D ratio = 1:0, 1:1, 5:1, 1:5 and 0:1) were tested for cytotoxic effects against the three cancer cells. The viability of cells was assessed after 72 h incubation with various combinations of B and D using the trypan-blue staining method. The cytotoxic data were analyzed by the combination index method of Chou and Talalay to establish synergy between B and D. The results indicated that an overall positive reduction in drug concentration was achieved by D when combined with B in its cytotoxicity profile in the three human cancer cells tested. The synergistic cytotoxicity was best when the B:D ratio of 1:5 was used in PaCa cells at IC50, IC75 and IC90 dose levels and in MCF-7 cells at IC90 dose level. These results warrant further studies on the potential of red beetroot extract-doxorubicin combination in treating human cancers. - G Subba Rao; Harukuni Tokuda; Eiichiro Ichiishi; Midori Takasaki; Akira Iida; Nobutaka Suzuki; Takao Konoshima; Govind J KapadiaAnticancer research 33 (6) 2535 - 40 0250-7005 2013/06 [Refereed]
BACKGROUND: Sunscreen compounds with added benefit of skin cancer prevention have both public and commercial interests. Our earlier study using the Epstein-Barr virus early antigen in vitro assay reported on skin cancer chemoprevention potential of benzophenone sunscreens. We now report the in vivo antitumor activity of two of the benzophenone sunscreens which tested positively in the in vitro assay, octabenzone (UV-1) and dioxybenzone (UV-2), in the two-stage mouse skin carcinogenesis model using (±)-(E)-4-methyl-2-[-(E)-hydroxyamino]-5-nitro-6-methoxy-3-hexanamide (NOR-1) as inducer and 12-O-tetradecanoyl-phorbol-13-acetate (TPA) as promoter. MATERIALS AND METHODS: Pathogen-free, female hairless mice of HOS:HR-1 strain, 15 animals per control and test groups, were used. Skin tumors were induced by a single dose of NOR-1 (390 nmol in 100 μl of acetone). One week later, TPA (1.7 nmol in 100 μl of acetone) was applied to skin twice weekly for 20 weeks as tumor a promoter. The test compounds UV-I or UV-2 were administered at 0.0025% to mice through drinking water ad libitum, starting one week prior to and stopping one week after tumor initiation. All animals were examined weekly for the development of skin papillomas. RESULTS: In both UV-1- and UV-2-treated mice, a two-week delay in tumor appearance, and significant inhibition (p<0.001) of tumor incidence (50% and 60%, respectively) and tumor burden (papilloma inhibition/mouse, 50% and 70%, respectively) were observed when compared to the positive control group. UV-2 (dihydroxy derivative) was a more potent inhibitor of skin tumor than UV-1 (monohydroxy derivative), which followed their antioxidant activity ranking. CONCLUSION: The results affirm the skin cancer chemoprevention potential of orally-ingested benzophenone sunscreens in mice and warrant studies in humans to validate synergistic protection achievable by complementation of oral and topical sunscreen usage. - Pawel T Szymanski; Safwat A Ahmed; Sherief Khalifa; Harukuni Tokuda; Eiichiro Ichiishi; Akira Iida; Nobutaka Suzuki; Hesham FahmyNatural product communications 8 (2) 153 - 4 1934-578X 2013/02 [Refereed]
The cancer chemopreventive potential of sarcophine-diol in a chemical carcinogen initiation-promotion experimental tumor model in mice was evaluated. Sarcophine-diol, when given orally, afforded significant protection in the mouse skin cancer model initiated by the topical administration of (+/-)-(E)-4-methyl-2-[ (E)-hydroxyamino]-5-nitro-6-methoxy-3-hexanamide (NOR-1) and promoted by 12-O-tetradecanoylphorbol-13-acetate (TPA). These findings, along with our initial reports, suggest that sarcophine-diol is an effective cancer chemopreventive agent, even when administered orally and at a very low dose and thus indicating possible potential human applications in the control of malignancy. - Copper-catalyzed tandem intramolecular cyclization/coupling reaction: solvent effect on reaction pathwayM. Yamashita; T. Noro; A. IidaTetrahedron Letters 54 (50) 6848 - 6851 2013 [Refereed]
- Kazunori Ueda; Mitsuaki Yamashita; Koichi Sakaguchi; Harukuni Tokuda; Akira IidaChemical & pharmaceutical bulletin PHARMACEUTICAL SOC JAPAN 61 (6) 648 - 54 0009-2363 2013 [Refereed]
A concise method for the synthesis of heterocycle-fused naphthoquinones such as naphtho[2,3-b]-furan-4,9-dione, 1H-benz[f]indole-4,9-dione, and naphtho[2,3-b]thiophene-4,9-dione was developed. This method employed Sonogashira coupling and tandem addition-elimination/intramolecular cyclization, and it enabled the preparation of versatile heterocycle-fused naphthoquinones from one substrate. - Hsin-Yi Hung; Kyoko Nakagawa-Goto; Harukuni Tokuda; Akira Iida; Nobutaka Suzuki; Susan L. Morris-Natschke; Kuo-Hsiung LeeABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY AMER CHEMICAL SOC 243 0065-7727 2012/03 [Refereed]
- About the estrogenic activity and the stress reduction and a relaxation effect of odor after stress loading澤邊 昭義; 戸嶋 猛; 中谷 太一; 竹田 竜嗣; 飯田 彰; 高橋 一弘; 山口Aroma Research Fragrance Journal LTD 49 58 - 63 2012/02
- Hsin-Yi Hung; Kyoko Nakagawa-Goto; Harukuni Tokuda; Akira Iida; Nobutaka Suzuki; Susan L Morris-Natschke; Kuo-Hsiung LeePharmaceutical biology INFORMA HEALTHCARE 50 (1) 18 - 24 1388-0209 2012/01 [Refereed]
CONTEXT: Dimethyl dicarboxylate biphenyl (DDB) is a clinically used hepatoprotectant and has also been found to have chemopreventive activity. MATERIALS AND METHODS: Sixteen novel analogs (5-20) were designed, synthesized, and evaluated for their cancer preventive activity. The 2,2'-bismethyl ester (5-18) and ether (19, 20) DDB analogs were synthesized by insertion of various linear alkyl, short fatty acid, polar, and aromatic groups. All synthesized analogs were evaluated in an in vitro short-term 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced Epstein Barr virus early antigen (EBA-EA) activation assay. Three of the most potent compounds were also tested for inhibitory effects on skin tumor promotion in an in vivo two-stage mouse-skin carcinogenesis test using 7,12-dimethylbenz[a]anthracene (DMBA) as an initiator and TPA as a promoter. RESULTS: Compound 19 with bisprenyl ethers had the most significant cancer preventive activity (100% inhibition of activation at 1 × 10(3) mol ratio/TPA, 78.4%, 49.7%, and 10.9% inhibition at 5 × 10(2), 1 × 10(2), 1 × 10 mol ratio/TPA, respectively) in vitro. Compound 19 also exhibited a remarkable inhibitory effect on skin tumor promotion in the in vivo two-stage mouse-skin carcinogenesis test. DISCUSSION AND CONCLUSIONS: Thus, DDB analog 19 could be a valuable candidate as a cancer preventive agent or as a lead for the development of new antitumor promoter drugs. - Yamashita Mitsuaki; Ueda Kazunori; Sakaguchi Koichi; Iida AkiraTETRAHEDRON LETTERS 52 (36) 4665 - 4670 0040-4039 2011/09 [Refereed]
- Govind J Kapadia; Magnus A Azuine; G Subba Rao; Takanari Arai; Akira Iida; Harukuni TokudaAnti-cancer agents in medicinal chemistry BENTHAM SCIENCE PUBL LTD 11 (3) 280 - 4 1871-5206 2011/03 [Refereed]
Previous cancer chemoprevention studies from our laboratories and by other investigators have demonstrated that the extract of red beetroot (Beta vulgaris L.), the FDA approved red food color E162, can be effective in suppressing the development of multi-organ tumors in experimental animals. To further explore this finding, we have compared the cytotoxic effect of the red beetroot extract with anticancer drug, doxorubicin (adriamycin) in the androgen-independent human prostate cancer cells (PC-3) and in the well-established estrogen receptor-positive human breast cancer cells (MCF-7). This red colored anticancer antibiotic was selected for comparative cytotoxic study because its chemical structure with a planar configuration of an aromatic chromophore attached to a sugar molecule is remarkably similar to that of betanin, the beetroot extract constituent primarily responsible for its red color. Both doxorubicin and the beetroot extract exhibited a dose-dependent cytotoxic effect in the two cancer cell lines tested. Although the cytotoxicity of the beetroot extract was significantly lower when compared to doxorubicin, it continued to decrease the growth rate of the PC-3 cells (3.7% in 3 days vs. 12.5% in 7 days) when tested at the concentration of 29 µg/ml. In contrast, doxorubicin, at the same concentration level, completely inhibited the growth of the PC-3 cells in three days. Similarly, comparative studies in the normal human skin FC and liver HC cell lines showed that the beetroot extract had significantly lower cytotoxic effect than doxorubicin (8.6% vs. 100%, respectively, at 29 µg/ml concentration of each, three-day test period). The results suggest that betanin, the major betacyanin constituent, may play an important role in the cytotoxicity exhibited by the red beetroot extract. Further studies are needed to evaluate the chemopreventive potentials of the beetroot extract when used alone or in combination with doxorubicin to mitigate the toxic side-effects of the latter. - Mitsuaki Yamashita; Kazunori Ueda; Koichi Sakaguchi; Harukuni Tokuda; Akira IidaChemical & pharmaceutical bulletin PHARMACEUTICAL SOC JAPAN 59 (10) 1289 - 93 0009-2363 2011 [Refereed]
In this paper, a concise one-pot method for the construction of benzo[f]indole-4,9-dione motifs is described. These transformations proceed via a sequential palladium- and copper-catalyzed coupling reaction of 1,4-naphthoquinones with terminal acetylenes, followed by a copper-catalyzed intramolecular cyclization reaction of the resulting coupling product. - Milind Dangate; Laura Franchini; Fiamma Ronchetti; Takanari Arai; Akira Iida; Harukuni Tokuda; Diego ColomboEUROPEAN JOURNAL OF ORGANIC CHEMISTRY WILEY-V C H VERLAG GMBH 34 (34) 6019 - 6026 1434-193X 2009/12 [Refereed]
A convenient chemoenzymatic synthesis of a new class of non-natural sulfo-glycolipids - 2-O-(beta-D-sulfoquinovosyl)-monoacylglycerols (2-O-beta-D-SQMG) - derived from 2-O-(beta-D-glucopyranosyl)glycerol and carrying acyl chains of various lengths at the 1-position of the sn-glycerol moiety, was performed with the aid of a key step involving regioselective lipase-catalyzed acylation of 2-O-(6-deoxy-6-tosyl-beta-D-glucopyranosyl)-sn-glycerol (4) at its 1-position, reported here for the first time. Elaboration of the sugar moiety - Mitsuaki Yamashita; Masafumi Kaneko; Harukuni Tokuda; Katsumi Nishimura; Yuko Kumeda; Akira IidaBioorganic & medicinal chemistry PERGAMON-ELSEVIER SCIENCE LTD 17 (17) 6286 - 91 0968-0896 2009/09 [Refereed]
A series of naphthoquinones based on the naphtho[2,3-b]furan-4,9-dione skeleton such as (-)-5-hydroxy-2-(1'-hydoxyethyl)naphtho[2,3-b]furan-4,9-dione (1) and its positional isomer, (-)-8-hydroxy-2-(1'-hydoxyethyl)naphtho[2,3-b]furan-4,9-dione (2), which are secondary metabolites found in the inner bark of Tabebuia avellanedae, were stereoselectively synthesized and their biological activities were evaluated in conjunction with those of their corresponding enantiomers. Compound 1 exhibited potent antiproliferative effect against several human tumor cell lines, but its effect against some human normal cell lines was much lower than that of mitomycin. On the other hand, its enantiomer (R)-1 was less active toward the above tumor cell lines than 1. The antiproliferative effect of 2 against all tumor cell lines was significantly reduced. These results indicated the presence of the phenolic hydroxy group at C-5 is of great important for increasing antiproliferative effect. In addition, 1 also showed higher cancer chemopreventive activity than 2, while there were no significant differences between 1 and 2 in antimicrobial activity. Both compounds displayed modest antifungal and antibacterial activity (gram-positive bacteria), whereas they were inactive against gram-negative bacteria. - Milind Dangate; Laura Franchini; Fiamma Ronchetti; Takanari Arai; Akira Iida; Harukuni Tokuda; Diego ColomboBioorganic & medicinal chemistry PERGAMON-ELSEVIER SCIENCE LTD 17 (16) 5968 - 73 0968-0896 2009/08 [Refereed]
New sulfoquinovosyldiacylglycerols derived from 2-O-beta-d-glucopyranosyl-sn-glycerol, carrying acyl chains of various length on the glycerol moiety, were prepared through a convenient synthetic procedure in which a sulfonate is introduced at the C-6 position of glucose by oxidation of a thioacetate in the presence of the unprotected secondary hydroxyl groups, and tested for their anti-tumor-promoting activity using a short-term in vitro assay for Epstein-Barr virus early antigen (EBV-EA) activation. Our study has allowed to ascertain the role of the 6'-sulfonate group and the need of a free hydroxyl group on the glycerol moiety in inhibiting the EBV activation promoted by the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA). - Tokuda Harukuni; Yamashita Mitsuaki; Kaneko Masafumi; Iida AkiraCANCER RESEARCH 69 0008-5472 2009/05 [Refereed]
- Ayyamperumal Sakthivel; Akira Iida; Kenichi Komura; Yoshihiro SugiJournal of nanoscience and nanotechnology 9 (1) 475 - 83 1533-4880 2009/01 [Refereed]
The nano-sizedbeta-zeolites were synthesized first time by dry gel conversion (DGC) method without the use of sodium hydroxide. Resultant beta-zeolites had particle size of 35-80 nm with SiO2/Al2O3 ratios in the range of 25-400. They had BET surface areas in the range of 290-750 m2 x g(-1) and the external surface area of 41-283 m2 x g(-1): cumulative surface areas were in the range of 420-1050 m2 x g(-1). Beta-Zeolites modified with alkaline earth and rare earth metal species, such as Ca, La, and Ce, were synthesized by the introduction of these metal nitrates during the dry-gel preparation. To evaluate catalytic properties of these zeolites, they were applied for the isomerization/cracking of hexane and the phenol octylation. The influence of Ca, La, and Ce oxides on the catalytic properties was also examined. - Yasutomo Yamamoto; Hirokazu Suzuki; Yorinobu Yasuda; Akira Iida; Kiyoshi TomiokaTETRAHEDRON LETTERS PERGAMON-ELSEVIER SCIENCE LTD 49 (31) 4582 - 4584 0040-4039 2008/07A lithium ester enolate was activated by both a chiral etheral ligand and a lithium amide to form a ternary complex reagent that reacted with enoates giving the corresponding Michael addition products in reasonably high enantioselectivity of up to 97% ee. (c) 2008 Elsevier Ltd. All rights reserved.
- Toru Yagura; Tomoko Motomiya; Michiho Ito; Gisho Honda; Akira Iida; Fumiyuki Kiuchi; Harukuni Tokuda; Hoyoku NishinoJournal of natural medicines SPRINGER TOKYO 62 (2) 174 - 8 1340-3443 2008/04 [Refereed]
An ethanol extract of Helichrysum maracandicum showed antiproliferative activity against cultured cells of SENCAR mouse in an in vitro assay, and activity-guided fractionation of the extract resulted in the isolation of isosalipurposide as an active substance. Naringenin chalcone, the aglycone of isosalipurposide, also showed strong antiproliferative activity. An in vivo assay of two-stage carcinogenesis on mouse skin revealed that epidermal application of isosalipurposide resulted in delayed formation of papillomas. Western blot analysis showed that the expression of p38 mitogen-activated protein kinase was suppressed by the administration of naringenin chalcone or isosalipurposide, which might be related to the anticarcinogenic activity. - Mitsuaki Yamashita; Masafumi Kaneko; Akira Iida; Harukuni Tokuda; Katsumi NishimuraBioorganic & medicinal chemistry letters PERGAMON-ELSEVIER SCIENCE LTD 17 (23) 6417 - 20 0960-894X 2007/12 [Refereed]
Stereoselective synthesis of 1, one of biologically active naphthoquinones from a Brazilian traditional medicine Tabebuia avellanedae, was achieved by utilizing Noyori reduction as a key step. Compound 1 displayed potent cytotoxicity against several human tumor cell lines, whereas it showed lower cytotoxicity against some human normal cell lines compared with that of mitomycin. On the other hand, its enantiomer was less active toward the tumor cell lines than 1. - H Tokuda; H Nishino; A IidaCANCER EPIDEMIOLOGY BIOMARKERS & PREVENTION AMER ASSOC CANCER RESEARCH 14 (11) 2690S - 2690S 1055-9965 2005/11
- Akinobu Gotoh; Toshiyuki Sakaeda; Takashi Kimura; Toshiro Shirakawa; Yoshitaka Wada; Atsushi Wada; Tetsutaro Kimachi; Yoshiji Takemoto; Akira Iida; Seigo Iwakawa; Midori Hirai; Hisako Tomita; Noboru Okamura; Tsutomu Nakamura; Katsuhiko OkumuraBiological & pharmaceutical bulletin PHARMACEUTICAL SOC JAPAN 27 (7) 1070 - 4 0918-6158 2004/07 [Refereed]
Rhinacanthus nasutus (L.) Kurz (Acanthaceae) is a shrub widely distributed in South China and India. In this study, the antiproliferative activity of the ethanol extract of root and aqueous extract of leaves of R. nasutus, and the supposed active moiety rhinacanthin C was assessed in vitro using the human cervical carcinoma cell line HeLa, its MDR1-overexpressing subline Hvr100-6, human prostate carcinoma PC-3 cells and human bladder carcinoma T24 cells. Rhinacanthin C was chemically synthesized and its content in the R. nasutus extracts was determined by HPLC with a photodiode array detector. The antiproliferative activity of the R. nasutus extracts was also assessed in vivo using sarcoma 180-bearing mice. It was suggested that 1) the in vitro antiproliferative activity of rhinacanthin C was comparable with or slightly weaker than that of 5-FU, 2) rhinacanthin C showed antiproliferative activity for MDR1-overexpressing Hvr100-6 cells, similarly to parent HeLa cells, 3) the in vitro antiproliferative activity of the ethanol extract of root R. nasutus was due to rhinacanthin C, whereas that of the aqueous extract of leaves of R. nasutus was due to constituents other than rhinacanthin C, and 4) both of the R. nasutus extracts showed in vivo antiproliferative activity after oral administration once daily for 14 d. - J. Chen; Q. Zhou; Y. Liu; M. Jia; A. IidaNatural Medicines 日本生薬学会 58 (4) 167 - 167 1340-3443 2004 [Refereed]
- Kazuhide Konishi; Akira Iida; Masafumi Kaneko; Kiyoshi Tomioka; Harukuni Tokuda; Hoyoku Nishino; Yuko KumedaBioorganic & medicinal chemistry PERGAMON-ELSEVIER SCIENCE LTD 11 (12) 2511 - 8 0968-0896 2003/06 [Refereed]
Bioassay-guided separation of extracts from the culture broth and mycelium of the fungus Trichothecium roseum, aiming at the discovery for cancer preventive agents, resulted in the isolation of three new trichothecene sesquiterpenes, trichothecinols A-C (1-3) together with three known analogues, trichothecin (4), trichodermol (5) and trichothecolone (6). Compounds 1-6 exhibited remarkably potent inhibition against Epstein-Barr virus early antigen (EBV-EA) activation induced by the tumor promoter, 12-O-tetradecanoylphorbol-13-acetate (TPA). Further compound 1 strongly inhibited TPA-induced tumor promotion on mouse skin initiated with 7,12-dimethylbenz[a]anthracene (DMBA) in two-stage carcinogenesis tests. These results suggest that compound 1 might be a valuable lead for further evaluation as a cancer preventive agent. In addition to their cancer preventive activity, compound 2 was found to show modest antifungal activity against Crypotcoccus albidus and Saccharomyces cerevisiae. - A. Iida; F. Kiuchi; M. Ito; G. Honda; Y. Mizushina; H. Yoshida; K. SarsenbaevNatural Medicines 日本生薬学会 57 (4) 146 - 149 1340-3443 2003/04 [Refereed]
In our continuing search to discover bioactive compounds from medicinal plants, a methanolic extract of Verbascum songaricum collected in Kazakhstan was investigated. Activity-guided fractionation of the extract prepared from the plant, using a sensitive assay to monitor DNA polymerase reactions, resulted in the isolation of two known phenylethanoid glycosides, poliumoside (1) and verbascoside (2). Glycoside 1 was shown to inhibit mammalian DNApolymerases α,β,δ and ε with IC_<50> values of 42, 23, 35 and 9 μM, respectively, while those of glycoside 2 were all more than 100 μM. - A Iida; K Konishi; H Matsumoto; M Kaneko; K TomiokaHETEROCYCLES PERGAMON-ELSEVIER SCIENCE LTD 59 (2) 595 - 604 0385-5414 2003/03 [Refereed]
The optically pure trichothecene cis-AB ring moiety (1) was synthesized starting from an optically pure butenolide (7) through the ring closing olefin metathesis for the formation of the A-ring and a Lewis acid mediated cyclization to the cis-fused tetrahedrochromane skeleton that had been converted to natural trichothecene, (+)-calonectrin. - Y. Mizushina; H. Yoshida; H. Matsumoto; A. IidaNatural Medicines 日本生薬学会 57 (1) 36 - 36 1340-3443 2003 [Refereed]
Bioassay-guided fractionation of an extract prepared from Taraxacum officinale, aiming at the search for mammalian DNA polymerase inhibitors, led to the isolation of D-mandelonitrile-β-D-glucoside (prunasin) as the inhibitory principle. - Teruhisa Matsubayashi; Toshiyuki Sakaeda; Tomoko Kita; Tsutomu Nakamura; Mikio Kakumoto; Yoko Funasaka; Masamitsu Ichihashi; Takuya Fujita; Fumio Kamiyama; Akira Yamamoto; James J Nordlund; Masafumi Kaneko; Akira Iida; Katsuhiko OkumuraBiological & pharmaceutical bulletin PHARMACEUTICAL SOC JAPAN 26 (1) 120 - 2 0918-6158 2003/01 [Refereed]
Ointments of the skin depigmentation agent hydroquinone (HQ) have been prepared by extemporaneous nonsterile compounding in our hospital. The HQ ointments were highly effective in the treatment of various types of skin pigmentations; however, various problems have emerged including chromatic aberration of the ointments, a relatively large variability of efficacy, and mild side effects. Chromatic aberration is expected to induce non-compliance, and this may be the reason for the relatively large variability in efficacy. In this paper, the effects of various storage conditions on the chromatic aberration and HQ content of HQ ointments were evaluated, and it was suggested that the chromatic aberration was accelerated by exposure to high temperature, air and light, although these had no effect on the HQ content. In addition, various types of HQ ointments were prepared to find a formulation to minimize chromatic aberration, and it was found that the concentrations of antioxidants, Na(2)SO(3) and L(+)-ascorbic acid (AsA), seemed to be too high, and that the protective effect of AsA on chromatic aberration was mainly due to its acidifying effect. - Shun-ichi Wada; Akira Iida; Reiko TanakaJournal of natural products AMER CHEMICAL SOC 65 (11) 1657 - 9 0163-3864 2002/11 [Refereed]
Three new lanostane-type triterpenoids (1-3) were isolated from the bark of Abies sachalinensis along with a known compound (4). The structures of 1-4 were characterized by spectroscopic methods including NMR and MS. Compound 4 and some derivatives were tested for inhibitory effects on in vitro DNA topoisomerases I and II and found to be selective catalytic inhibitors of topoisomerase II activity with IC(50) values in the range 43-76 microM. - Teruhisa Matsubayashi; Toshiyuki Sakaeda; Tomoko Kita; Michiyo Nara; Yoko Funasaka; Masamitsu Ichihashi; Takuya Fujita; Fumio Kamiyama; Akira Yamamoto; James J Nordlund; Masafumi Kaneko; Akira Iida; Midori Hirai; Katsuhiko OkumuraBiological & pharmaceutical bulletin PHARMACEUTICAL SOC JAPAN 25 (1) 92 - 6 0918-6158 2002/01 [Refereed]
Ointments of the skin depigmentation agent hydroquinone (HQ) have been prepared by extemporaneous nonsterile compounding in Japan by imitating skin lightening creams commercially available in the U.S.A. and European Union. In our hospital, HQ ointments consisting of 5 or 10% HQ, 1.6% L(+)-ascorbic acid (AsA), 0.5% (w/w) Na2SO3, 10% (v/w) glycerin and hydrophilic ointment have been prepared. However, various problems have been observed including chromatic aberration of HQ ointments, relatively large variability of efficacy, and undesirable side effects although they were mild. Herein, the pharmaceutical and clinical properties of the HQ ointments were evaluated. HQ ointments were highly effective for treatment of various types of skin pigmentation. Chromatic aberration occurred during 3 months of storage, but this could be suppressed by storage at 4 degrees C. Chromatic aberration was independent of prescribed HQ content, and was not explained by alterations of HQ or p-benzoquinone (p-BQ) contents. Unexpectedly, removal of both antioxidants resulted in suppression of chromatic aberration, but an increase in p-BQ content. Acidification by removal of Na2SO3 only was further effective for the suppression of chromatic aberration, but with a decrease of p-BQ content except in the initial period. Chromatic aberration was due to water soluble material and insoluble material both formed by co-existence of HQ and p-BQ at a molecular ratio of 5:3 to 1:1. 1H-NMR analysis elucidated that the water soluble material was not HQ or p-BQ, and the insoluble material was a complex of HQ and p-BQ with non-covalent binding. - S Wada; A Iida; R TanakaJOURNAL OF NATURAL PRODUCTS AMER CHEMICAL SOC 64 (12) 1545 - 1547 0163-3864 2001/12 [Refereed]
DNA topoisomerases (Topos) are enzymes that play a crucial role in DNA metabolism events such as replication, transcription, recombination, and chromosome segregation at mitosis. Thus, Topo inhibitors could be expected to have antitumor effects. Naturally occurring lupane- and oleanane-type triterpenoids isolated from the bark of Phyllanthus flexuosus were screened for human Topos I and II inhibitory activities. Olean-12-en-3beta,15alpha-diol (1), olean-12-en-3beta,15alpha,24-triol (3), lupeol (4), and betulin (6) were found to be selective catalytic inhibitors of human Topo 11 activity with IC50 values in the range of 10-39 muM. - Kiyoshi Tomioka; Takaaki Sumiyoshi; Shinobu Narui; Yasuo Nagaoka; Akira Iida; Yoshihisa Miwa; Tooru Taga; Minoru Nakano; Tetsuro HandaJournal of the American Chemical Society American Chemical Society (ACS) 123 (47) 11817 - 11818 0002-7863 2001/11 [Refereed]
- S Wada; A Iida; R TanakaPLANTA MEDICA GEORG THIEME VERLAG KG 67 (7) 659 - 664 0032-0943 2001/10 [Refereed]
Nine lanostane and serratane-type triterpenes including two unknown compounds were isolated from the stem bark of Pinus luchuensis. These new compounds were characterized as 3-oxolanost-9(11)-ene-24S,25-diol (1) and 29-acetoxy-3 beta -methoxyserrat-14-en-21 alpha -ol (2) on the basis of spectroscopic evidence. Some of these triterpenes were tested for the inhibitory effect on DNA topoisomerase 11 activity. Compound 1 showed a slightly less potent inhibitory activity with an IC50 value of 186 muM. - Mizushina Yoshiyuki; Kasai Nobuyuki; Sugawara Fumio; Iida Akira; Yoshida Hiromi; Sakaguchi KengoJ. Biochem. The Japanese Biochemical Society 130 (5) 657 - 664 0021-924X 2001 [Refereed]
The molecular action of lithocholic acid (LCA), a selective inhibitor of mammalian DNA polymerase β (pol β), was investigated. We found that LCA could also strongly inhibit the activity of human DNA topoisomerase II (topo II). No other DNA metabolic enzymes tested were affected by LCA. Therefore, LCA should be classified as an inhibitor of both pol β and topo II. Here, we report the molecular interaction of LCA with pol β and topo II. By three-dimensional structural model analysis and by comparison with the spatial positioning of specific amino acids binding to LCA on pol β(Lys60, Leu77, and Thr79), we obtained supplementary information that allowed us to build a structural model of topo II. Modeling analysis revealed that the LCA-interaction interface in both enzymes has a pocket comprised of three amino acids in common, which binds to the LCA molecule. In topo II, the three amino acid residues were Lys720, Leu760, and Thr791. These results suggested that the LCA binding domains of pol β and topo II are three-dimensionally very similar. - Yoshiyuki Mizushina; Fumio Sugawara; Akira Iida; Kengo SakaguchiJournal of Molecular Biology Elsevier BV 304 (3) 385 - 395 0022-2836 2000/12 [Refereed]
- Y Mizushina; A Iida; K Ohta; F Sugawara; K SakaguchiBIOCHEMICAL JOURNAL PORTLAND PRESS 350 (3) 757 - 763 0264-6021 2000/09 [Refereed]
As described previously, we found that new triterpenoid compounds, designated fomitellic acids A and B, which selectively inhibit the activities of mammalian DNA polymerases alpha and beta [Mizushina, Tanaka, Kitamura, Tamai, Ikeda, Takemura, Sugawara, Arai, Matsukage, Yoshida and Sakaguchi (1998) Biochem. J. 330, 1325-1332; Tanaka, Kitamura, Mizushina, Sugawara and Sakaguchi (1998) J. Nat. Prod. 61, 193-197] and that a known triterpenoid, ursolic acid, is an inhibitor of human DNA topoisomerases I and II (A. Iida, Y. Mizushina and K. Sakaguchi, unpublished work). Here we report that all of these triterpenoids are potent inhibitors of calf DNA polymerase cc, rat DNA polymerase beta and human DNA topoisomerases I and II, and show moderate inhibitory effects on plant DNA polymerase II and human immunodeficiency virus reverse transcriptase. However, these compounds did not influence the activities of prokaryotic DNA polymerases such as Escherichia coli DNA polymerase I or other DNA metabolic enzymes such as human telomerase, T7 RNA polymerase and bovine deoxyribonuclease I. These triterpenoids were not only mammalian DNA polymerase inhibitors but also inhibitors of DNA topoisomerases I and II even though the enzymic characteristics of DNA polymerases and DNA topoisomerases, including their modes of action, amino acid sequences and three-dimensional structures, differed markedly. These triterpenoids did not bind to DNA, suggesting that they act directly on these enzymes. Because the three-dimensional structures of fomitellic acids were shown by computer simulation to be very similar to that of ursolic acid, the DNA-binding sites of both enzymes, which compete for the inhibitors, might be very similar. Fomitellic acid A and ursolic acid prevented the growth of NUGC cancer cells, with LD50 values of 38 and 30 mu M respectively. - A Iida; M Kano; Y Kubota; K Koga; K TomiokaCHEMICAL & PHARMACEUTICAL BULLETIN PHARMACEUTICAL SOC JAPAN 48 (4) 486 - 489 0009-2363 2000/04 [Refereed]
The pendant E-ring moiety of the podophyllotoxin aza-analogue 1 that is a potent inhibitor of microtubule assembly was modified in order to acquire inhibitor? activity of DNA topoisomerase II. The monophenolic analogue 2 did not exhibit human topoisomerase II inhibition, while the ortho-quinone 3 that was obtained by oxidation of 2 inhibited its catalytic activity (decatenation) in a dose-dependent manner and stimulated double strand DNA breaks in supercoiled circular plasmid DNA, resulting in the production of linear DNA. These results showed that the topoisomerase II inhibition of the ortho-quinone 3 is due to stabilization of the topoisomerase II-DNA covalent binary complex. On the other hand, the ortho-quinone 3 did not inhibit the relaxation process of supercoiled DNA by topoisomerase 1 at concentrations up to 100 mu M, nor was intercalation observed in unwinding measurements of 3. Therefore, the ortho-quinone 3 was shown to be a novel nonintercalative topoisomerase II specific inhibitor that stabilizes the cleavable complex. The present results suggest that the 4'-free hydroxyl group on the E-ring and the sugar moiety on the C-ring are not a prerequisite for topoisomerase II inhibition by podophyllotoxin derivatives. - JZ Wu; HL Ruan; NH Yao; QS Zhao; HD Sun; C Morizane; A Iida; T FujitaJOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH HARWOOD ACAD PUBL GMBH 2 (3) 161 - 167 1028-6020 2000 [Refereed]
A new ent-kaurane diterpenoid dimer, fritillebinide C (1) together with one known diterpenoid dimer fritillebinide B (2) were isolated from the bulbs of Fritillaria ebiensis G.D. Yu et G.Q. Ji. Compound 1 has been determined to be eni-3 beta-acetoxy-kauran-16 beta, 17-acetal ent-16 beta-kauran-17(S)-aldehyde (1) by means of spectral analysis and chemical evidence. - JZ Wu; YP Wen; HL Ruan; NH Yao; QS Zhao; HD Sun; C Morizane; A Iida; T FujitaJOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH HARWOOD ACAD PUBL GMBH 2 (3) 213 - 218 1028-6020 2000 [Refereed]
A novel ent-kaurane diterpenoid dimer, fritillebinide B (1) together with one known diterpenoid dimer fritillebinide A (2) were isolated from the bulbs of Fritillaria ebeiensis var. purpurea G.D. Yu ct P. Li. Compound 1 has been established to be ent-3 beta-acetoxy-kauran-16 beta,17-acetal ent-16 beta-kauran-17(R)-aldehyde (1) by means of spectral analysis and chemical evidence. - A Iida; T Mihara; T Fujita; Y TakaishiBIOORGANIC & MEDICINAL CHEMISTRY LETTERS PERGAMON-ELSEVIER SCIENCE LTD 9 (24) 3393 - 3396 0960-894X 1999/12 [Refereed]
Three new 10-residue lipopeptaibols, trichopolyns III-V have been isolated from the fungus Trichoderma polysporum together with the known trichopolyns I and II. Structure determination has been achieved on the basis of spectroscopic and chemical evidence. These peptides have been shown to suppress the proliferation of lymphocytes in mouse allogeneic mixed lymphocyte reaction. (C) 1999 Elsevier Science Ltd. All rights reserved. - Mostafa Ahmed Hussein; Akira Iida; Kiyoshi TomiokaTetrahedron 55 (37) 11219 - 11228 0040-4020 1999/09 [Refereed]
Tridentate chiral amines 7-13 mediated the asymmetric condensation reaction of lithium ester enolate 2 with benzaldehyde p-anisidine imine 3 giving the corresponding β-lactam 4 in up to 75% ee. It became apparent that coexistence of 2 and chiral lithium amides derived from 7-13 is an important factor for the enhancement of the reactivity and enantioselectivity of 2. - Structural elucidation and synthesis of fritillebinide A from bulbs of Fritillaria ebeiensiActa Pharmaceutica Sinica 34,600-604 1999 [Refereed]
- Structure of a new chloro-substituted diterpenoid, fritillaziebinol from Zihua Ebei Beimu bulbs (Fritillaria ebeiensis var. purpurea)Zhongcaoyao 30 804 - 807 1999 [Refereed]
- Takeshi Kambara; Mostafa Ahmed Hussein; Hiroki Fujieda; Akira Iida; Kiyoshi TomiokaTetrahedron Letters Elsevier BV 39 (49) 9055 - 9058 0040-4039 1998/12 [Refereed]
- S Kitagawa; E Tachikawa; T Kashimoto; Y Nagaoka; A Iida; T FujitaBIOCHIMICA ET BIOPHYSICA ACTA-BIOMEMBRANES ELSEVIER SCIENCE BV 1375 (1-2) 93 - 100 0005-2736 1998/10 [Refereed]
We examined membrane fluidity of bovine adrenal chromaffin cells and chromaffin granules using cationic trimethylammonium derivative of diphenylhexatriene (TMA-DPH) as a fluorescence probe. After adding TMA-DPH to the suspension of chromaffin cells and that of granules, it first bound to the outer layer of the plasma membrane of the dells and that of the granule membrane, then gradually penetrated the inner layer of each membrane and distributed to both leaflets of the respective membranes. Accompanying increases in the ratio of incorporated probe on the cytoplasmic side of the chromaffin cell membrane, its fluorescence anisotropy gradually decreased. However, in chromaffin granules,the fluorescence anisotropy gradually increased with increases in the ratio of incorporated probe. These findings suggest that the inner layer of the plasma membrane and outer layer of the granular membrane are more fluid than the corresponding side of each membrane, which is suitable for the fusion between both membranes. We also examined the effect of trichosporin-B VIa, a fungal ion channel forming alpha-aminoisobutyric acid-containing peptide, on the fluidity of chromaffin cells using TMA-DPH. The peptide decreased the fluorescence anisotropy and increased the fluorescence intensity in the concentration range that induced Ca2+ dependent catecholamine secretion, suggesting that a change in lipid dynamics of the lipid bilayer of the plasma membrane was induced by this peptide. (C) 1998 Elsevier Science B.V. All rights reserved. - S Wada; R Tanaka; A Iida; S MatsunagaBIOORGANIC & MEDICINAL CHEMISTRY LETTERS PERGAMON-ELSEVIER SCIENCE LTD 8 (20) 2829 - 2832 0960-894X 1998/10 [Refereed]
Several kinds of naturally occurring fernane-type triterpenoids isolated from a Euphorbia genus were tested on the inhibitory effects of DNA Topoisomerases I (Topo I) and II (Topo II) activities. A-ring cleaved 3,4-seco-8 beta H-ferna-4(23),9(11)-dien-3-oic acid and its 3-hydroxyl derivative were found to be selective inhibitors of Topo II activity without the stabilization of a DNA/Topo II cleavable complex. (C) 1998 Elsevier Science Ltd. All rights reserved. - A Fujiwara; T Mori; A Iida; S Ueda; Y Hano; T Nomura; H Tokuda; H NishinoJOURNAL OF NATURAL PRODUCTS AMER CHEMICAL SOC 61 (5) 629 - 632 0163-3864 1998/05 [Refereed]
Bioassay-directed fractionation of an extract of the stem-bark of Catalpa ovata led to the isolation of three new naphthoquinones: 8-methoxydehydroiso-alpha-lapachone (1), 9-methoxy-4-oxo-alpha-lapachone (2), and (4S,4aR,10R,10aR)-4,10-dihydroxy-2,2-dimethyl-2,3,4,4 alpha,10,10 alpha-hexahydrobenzo[g] chromen-5-one (3), which is a 1,4-reductive form of 6. The known compounds 3-hydroxydehydroiso-alpha-lapachone (4), 4,9-dihydroxy-alpha-lapachone (5), 4-hydroxy-alpha-lapachone (6), and 9-methoxy-alpha-lapachone (7), and catalpalactone (8) were also isolated. Their structures were elucidated by spectral methods. These compounds all exhibited significant inhibitory activity against 1 2-O-tetradecanoylphorbol 13-acetate (TPA)-induced Epstein-Barr virus early antigen (EBV-EA) activation in Raji cells. - K Tomioka; M Satoh; D Taniyama; M Kanai; A IidaHETEROCYCLES PERGAMON-ELSEVIER SCIENCE LTD 47 (1) 77 - 80 0385-5414 1998/01 [Refereed]
The external chiral ligand mediated asymmetric reaction of thiazolyllithium with aldimines was examined. The amino ether (5) gave rise to relatively high selectivity in the reaction of phenylimine, and sparteine (6) provided high selectivity in the reaction of imines bearing an alpha-methylene group. The reaction was applied to the synthesis of (S)-Doe, a component of antileukemic marine natural product, dolastatin 10. - Y Asano; A Iida; K TomiokaCHEMICAL & PHARMACEUTICAL BULLETIN PHARMACEUTICAL SOC JAPAN 46 (1) 184 - 186 0009-2363 1998/01 [Refereed]
The conjugate addition reaction of BHA alkenoates with butyl- and phenyllithiums in toluene at -78 degrees C were catalyzed by a substoichiometric amount of chiral ligands 1 and 2 to give the corresponding 3-substituted alkanoates in good to modest ees. - D Taniyama; M Kanai; A Iida; K TomiokaHETEROCYCLES PERGAMON-ELSEVIER SCIENCE LTD 46 165 - 168 0385-5414 1997/12 [Refereed]
The chiral ligand mediated enantioselective reaction of methyllithium with furylimines was investigated in the presumed 1,4- and 1,2-addition manners. The imines bearing a phosphinoyl or sulfonyl group on the imine nitrogen atom gave rather poor enantioselectivity. On the other hand, the imines bearing a 2-substituted anisidine moiety were found to be the appropriate substrate, giving the corresponding amines with up to 91% ee. - Y Asano; A Iida; K TomiokaTETRAHEDRON LETTERS PERGAMON-ELSEVIER SCIENCE LTD 38 (52) 8973 - 8976 0040-4039 1997/12 [Refereed]
The conjugate addition reactions of BHA alkenoates with organolithiums in toluene or toluene-hexane at -78 degrees C were mediated by the chiral ligands 1 and 2 to give the corresponding 3-substituted alkanoates in high ees and high yields. The two ligands are complementary each other, 1 is effective for phenyl-and vinyllithiums to give the adducts in 64-93% ee, while 2 is effective for butyl-and ethyllithiums to give the adducts in 91-99% ee. (C) 1997 Elsevier Science Ltd. - Asymmetric addition reaction of phenyllithium to 1,2-ethylenediimine with the aid of a chiral ligandD Taniyama; M Kanai; A Iida; K TomiokaCHEMICAL & PHARMACEUTICAL BULLETIN PHARMACEUTICAL SOC JAPAN 45 (10) 1705 - 1707 0009-2363 1997/10 [Refereed]
The reaction of N,N'-bis(4-methoxyphenyl)ethylenediimine with phenyllithium, with the mediation of a chiral ligand, provided the addition products, (1R,2R)-N,N'-bis(4-methoxyphenyl)-1,2-diphenylethanediamine of 67% ee and the meso-product, in a ratio of 41:59, The net reaction involves sequential double additions of phenyllithium. In the first addition a new chiral center is created, but with rather poor selectivity, and in the second addition kinetic discrimination takes place, giving the chiral double addition product. - A Iida; M Kano; Y Kubota; K Koga; K TomiokaBIOORGANIC & MEDICINAL CHEMISTRY LETTERS PERGAMON-ELSEVIER SCIENCE LTD 7 (20) 2565 - 2566 0960-894X 1997/10 [Refereed]
Oxidation of a cytotoxic podophyllotoxin aza-analogue 2 into the quinone 3 succeeded in acquiring DNA topoisomerase II inhibitory activity at a concentration of 25 mu M due to stabilization of the cleavable complex. (C) 1997 Elsevier Science Ltd. - Masashi Mizuno; Motomu Kanai; Akira Iida; Kiyoshi TomiokaTetrahedron Elsevier BV 53 (31) 10699 - 10708 0040-4020 1997/08 [Refereed]
- Shun-Ichi Wada; Akira Iida; Koji Asami; Eiichi Tachikawa; Tetsuro FujitaBiochimica et Biophysica Acta - Biomembranes 1325 (2) 209 - 214 0005-2736 1997/04 [Refereed]
Trichocellins (TC) A-II and B-II, 20-residue peptaibols isolated from conidia of the fungus Trichoderma viride, have the same sequence except for the residue at position 18. Both TCs were found to form voltage-dependent ion-channels in bilayer lipid membranes (BLM) and to induce catecholamine secretion from bovine adrenal chromaffin cells through Ca2+ influx. TC-A-II (Gln18, neutral) was more effective than TC-B-II (Glu18, charged) for macroscopic current induction in BLMs and for catecholamine secretion from chromaffin cells, suggesting that Glu18 is unfavorable for the ion-channel formation in BLMs and chromaffin cell membranes. Nevertheless, single-channel recordings indicated that TC-B-II forms larger pores with longer open lifetimes than those of TC-A-II. This indicates that the negatively charged carboxyl group of Glu at position 18 stabilizes larger pores. The effects of the negative charge of Glu18 on the activities were confirmed by the use of a TC-B-II analog containing the methyl ester of Glu18. - H. Fujieda; M. Kanai; T. Kambara; A. Iida; K. TomiokaJournal of the American Chemical Society 119 (8) 2060 - 2061 0002-7863 1997 [Refereed]
- A Iida; K Konishi; H Kubo; K Tomioka; H Tokuda; H NishinoTETRAHEDRON LETTERS PERGAMON-ELSEVIER SCIENCE LTD 37 (51) 9219 - 9220 0040-4039 1996/12 [Refereed]
Three new trichothecenes, trichothecinols A (1), B (2) and C (3) were isolated from the fungus Trichothecium roseum and unambiguiously characterized on the basis of spectroscopic and chemical evidence. These exhibited potent inhibitory effects on Epstein-Barr virus early antigen (EBV-EA) activation induced by the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA). Copyright (C) 1996 Elsevier Science Ltd - S Wada; A Iida; K Asami; T FujitaBIOORGANIC & MEDICINAL CHEMISTRY LETTERS PERGAMON-ELSEVIER SCIENCE LTD 6 (19) 2275 - 2278 0960-894X 1996/10 [Refereed]
An 11-residue peptaibol, trichorovin-XII, isolated from the fungus Trichoderma viride, was found to form voltage-dependent and cation-selective ion channels in planar lipid bilayer membranes. The channels formed were classified into two types; a short-lived channel whose conductance level was not clearly distinguished and a long-lived channel whose conductance levels were 0.51 and 1.24 nS. Trichorovin-XII is the shortest channel-forming peptide of the peptaibol family so far reported. Copyright (C) 1996 Elsevier Science Ltd - M Mizuno; M Kanai; A Iida; K TomiokaTETRAHEDRON-ASYMMETRY PERGAMON-ELSEVIER SCIENCE LTD 7 (9) 2483 - 2484 0957-4166 1996/09 [Refereed]
Enantioselective opening of oxide ring was achieved by the combination of a chiral ether and phenyllithium in the presence of boron trifluoride to give the corresponding alcohol in 47% ee. Copyright (C) 1996 Published by Elsevier Science Ltd - Y Nagaoka; A Iida; T Kambara; K Asami; E Tachikawa; T FujitaBIOCHIMICA ET BIOPHYSICA ACTA-BIOMEMBRANES ELSEVIER SCIENCE BV 1283 (1) 31 - 36 0005-2736 1996/08 [Refereed]
Trichosporin-B-VIa (TS-B-VIa) has a Pro(14)-kinked helical structure which is considered to be important for the formation of peptaibol-type ion-channels in lipid bilayer membranes. TS-B-VIa and its analog [Aib(14)]TS-B-VIa with Pro --> Aib substitution at position 14, resulting in a straight helical structure, were tested for ion-channel-forming activity in planar lipid bilayer membranes and for ability to induce catecholamine secretion from cultured bovine adrenal chromaffin cells. Voltage-dependent multi-channel conductance, which is characteristic of TS-B-VIa, was also observed for [Aib(14)]TS-B-VIa. In single-channel measurements, current fluctuations induced by [Aib(14)]TS-B-Vla had a shorter life-time and showed fewer substates than those induced by TS-B-VIa. Catecholamine secretion induced by these peptides at low concentrations is completely Ca2+-dependent. At high concentrations, TS-B-VIa-induced secretion was partly independent of external Ca2+, but this was not the case for the analog. The differences of behavior can be explained in terms of the differences of hydrophobicity, amphiphilicity, and magnitude of dipole moment due to the conformational changes around position 14 and the C-terninal domain caused by the Pro --> Aib substitution. - E Tachikawa; K Nogimori; S Takahashi; K Mizuma; K Itoh; T Kashimoto; Y Nagaoka; A Iida; T FujitaBIOCHIMICA ET BIOPHYSICA ACTA-BIOMEMBRANES ELSEVIER SCIENCE BV 1282 (1) 140 - 148 0005-2736 1996/06 [Refereed]
Trichosporin (TS)-B-VIa, a fungal alpha-aminoisobutyric acid (Aib)-containing peptide consisting of 19 amino acid residues and a phenylalaninol, produced both Ca-45(2+) influx into bovine adrenal chromaffin cells and catecholamine secretion from the cells. The secretion induced by TS-B-VIa at lower concentrations (2-5 mu M) was completely dependent on the external Ca2+, while that induced by TS-B-VIa at higher concentrations (10-30 mu M) was partly independent of the Ca2+, The concentration-response curves (2-5 mu M) for the TS-B-VIa-induced Ca2+ influx and secretion correlated well. The TS-B-VIa (at 5 mu M)-induced secretion was not antagonized by diltiazem, a blocker of L-type voltage sensitive Ca2+ channels. The treatment of fura-2-loaded C-6 glioma cells with TS-B-VIa (2-5 mu M) led to an increase in the intracellular free Ca2+ concentration([Ca2+](i)) in a concentration-dependent manner but the stimulatory effects of TS-B-VIa on [Ca2+](i) were only slightly observed in Ca2+-free medium, indicating that TS-B-VIa causes Ca2+ influx from the external medium into the C-6 cells. The TS-B-VIa-induced increase in [Ca2+](i) in the C-6 cells was not antagonized by diltiazem and by SK&F 96365, a novel blocker of receptor-mediated Ca2+ entry. High K+ increased neither [Ca2+](i) in the C-6 cells nor Mn2+ influx into the cells, while TS-B-VIa increased Mn2+ influx. Also in other non-excitable cells, bovine platelets, similar results were obtained. These results strongly suggest that the mechanism of Ca2+ influx by TS-B-VIa at the lower concentrations is distinct from the event of Ca2+ influx through receptor-operated or L-type voltage-sensitive Ca2+ channels in both excitable cells (the chromaffin cells) and non-excitable cells (the C-6 cells and the platelets) and that TS-B-VIa per se may form Ca2+-permeable ion channels in biological membranes. On the other hand, the peptide at the higher concentrations seems to damage cell membranes. - Y Nagaoka; A Iida; T Kambara; K Asami; A FujitaCHEMICAL COMMUNICATIONS ROYAL SOC CHEMISTRY (9) 1079 - 1080 1359-7345 1996/05Replacement of the Gln(7) residue, which is well conserved among ion-channel-forming peptaibols, by an Ala in trichosporin-B-VIa (TS-B-VIa = AcUAUAUUQUIUGLUPVUUQQPheol; U = alpha-aminoisobutyric acid, Pheol = phenylalaninol) alters neither the multilevel nature of the TS-B-VIa channel nor its conductance, but abolished the rectification of the membrane current characteristic of the TS-B-VIa channel.
- M Kanai; A Iida; Y Nagaoka; S Wada; T FujitaJOURNAL OF MASS SPECTROMETRY JOHN WILEY & SONS LTD 31 (2) 177 - 183 1076-5174 1996/02 [Refereed]
The mass spectral characteristics of selected peptaibols were investigated using electrospray ionization in conjunction with low-energy collision-induced dissociation (CID). Protonated and sodiated molecular species were selected as precursor ions and the resulting CID spectra are discussed with respect to fragmentation characteristics related to the structures of peptaibols. The CID spectra of peptaibols with acetylated N-terminus and with the sub-sequences of Aib-Pro were similar. The CID spectra of [M + 2Na](2+) provided structural information more than those of [M + 2H](2+) and [M + H + Na](2+). The CID of [M + 2Na](2+) can be used to deduce complete sequence information for peptaibols. - Y NAGAOKA; A IIDA; T KAMBARA; K ASAMI; E TACHIKAWA; T FUJITAJOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS ROYAL SOC CHEMISTRY (21) 2203 - 2204 0022-4936 1995/11 [Refereed]
Examination of newly synthesized elongated and truncated analogues of the ion-channel-forming peptide, trichosporin-B-Vla (20 residues), for ion-channel-forming activity in lipid bilayer membranes and catecholamine secretion-inducing activity from adrenal chromaffin cells revealed that the natural compound has the optimal molecular length for both activities. - A IIDA; Y TANAKA; T MIHARA; M TABATA; G HONDA; T SHINGU; Y TAKEDA; Y TAKAISHI; E YESILADA; E SEZIK; T FUJITACHEMICAL & PHARMACEUTICAL BULLETIN PHARMACEUTICAL SOC JAPAN 43 (9) 1454 - 1457 0009-2363 1995/09 [Refereed]
Two new labdane diterpenoids, marrubinones A (1) and B (2), were isolated from aerial parts of Marrubium astracanicum collected in Turkey. Compounds 1 and 2 were mostly characterized by two-dimensional NMR. For determination of the absolute configuration, the modified Mosher's method was applied to the 12-hydroxy forms of 1 and 2. Compounds 1 and 2 are pentacyclic diterpenoids, which differ from each other only in the stereochemistry at C-13, and they were identified as 9 alpha,13S:15,16-diepoxy-12-oxo-14-labden-19,6 beta-olide and 9 alpha,13R:15,16-diepoxy-12-oxo-14-labden-19,6 beta-olide, respectively. - JZ WU; C MORIZANE; A IIDA; S UEDA; ZL ZHOU; M XU; M ZHANG; RM LI; T FUJITACHEMICAL & PHARMACEUTICAL BULLETIN PHARMACEUTICAL SOC JAPAN 43 (9) 1448 - 1453 0009-2363 1995/09 [Refereed]
A new diterpenoid, fritillebic acid (1) and four new diterpenoid dimers, fritillebins A (2) and B (3), and fritillebinides A and B, were isolated from a crude drug, bulbs of Fritillaria ebeiensis G. D. YU et G. Q. JI. The structures of compounds 1-3 were determined to be ent-3 beta-acetoxy-16 beta-kauran-17-oic acid (1), ent-16 beta-hydroxykauran-17-yl-ent-3 beta-acetoxg-16 beta-kauran-17-oate (2), and ent-3 beta-acetoxy-16 beta-hydroxykauran-17-yl ent-3 beta-acetoxy-16 beta-kauran-17-oate (3), respectively, on the basis of spectroscopic and chemical evidence. - E TACHIKAWA; S TAKAHASHI; K MIZUMA; T KASHIMOTO; Y NAGAOKA; A IIDA; T FUJITABIOLOGICAL & PHARMACEUTICAL BULLETIN PHARMACEUTICAL SOC JAPAN 18 (8) 1165 - 1167 0918-6158 1995/08 [Refereed]
Trichosporin (TS)-B-VIa, a peptide consisting of 19 amino acid residues and an amino alcohol, causes Ca2+-dependent secretion of catecholamines from bovine adrenal chromaffin cells. The TS-B-VIa-induced secretion was greater under alkaline conditions and at a temperature of 37 degrees C compared with that at 21 degrees or 30 degrees C. It was not observed when the peptide was eliminated from the incubation medium. These results strongly suggest that the stimulatory effect of TS-B-VIa on the secretion is reversible and dependent on the temperature and pH of the incubation medium. - Y NAGAOKA; A IIDA; E TACHIKAWA; T FUJITACHEMICAL & PHARMACEUTICAL BULLETIN PHARMACEUTICAL SOC JAPAN 43 (7) 1119 - 1124 0009-2363 1995/07 [Refereed]
The secondary structures of an ion-channel-forming icosapeptaibol, trichosporin B-VIa, and its Aib(14)-substituted derivative containing no Pro were investigated on the basis of CD and various NMR experiments in methanol, Trichosporin B-VIa has a fully helical structure with a kink stabilized by a 1<--4 hydrogen-bond between the Leu(12) CO and Val(15) NH, The helical structure is composed of 3(10)-helix in the N-terminal first turn and the C-terminal moiety following Leu(12), and a-helix in the middle region, In contrast, the Aib(14) derivative predominantly has a straight a-helical structure except for a 3(10)-helix region in the N-terminal first turn. - S WADA; A IIDA; N AKIMOTO; M KANAI; N TOYAMA; T FUJITACHEMICAL & PHARMACEUTICAL BULLETIN PHARMACEUTICAL SOC JAPAN 43 (6) 910 - 915 0009-2363 1995/06 [Refereed]
Trichorovins (TV)-I-XIV are new antibiotic peptides obtained from conidia of the fungus Trichoderma viride. The peptide mixture of TVs was repeatedly fractionated by preparative HPLC until individual TVs showed a single peak on their analytical HPLC chromatograms. Nevertheless, FAB-MS or NMR indicated that each of TVs-I-XIV was composed of at least two components. We attempted to elucidate their structures within the fractions by electrospray ionization (ESI)-MS, FAB-MS, FAB-MS/MS and NMR. TVs generally have molecular weights of approximately 110-1200 Da, and are characterized by an acetylated N-terminus, the presence of an aminoalcohol, e.g. leucinol, isoleucinol or valinol, at the C-terminus, and eleven residues including three alpha-aminoisobutyric acids in the molecule. Thus, it was determined that TVs belong to the class of peptaibols. - Y NAGAOKA; A IIDA; T KAMBARA; E TACHIKAWA; K ASAMI; T FUJITABIOLOGICAL & PHARMACEUTICAL BULLETIN PHARMACEUTICAL SOC JAPAN 18 (4) 640 - 642 0918-6158 1995/04 [Refereed]
A series of peptaibols, trichosporin (TS) -Bs, induced voltage-activated conductance in lipid bilayer membranes and catecholamine secretion from bovine adrenal chromaffin cells. The order of activities is the same as that of the lipophilicity rank of TS-Bs derived from the reversed-phase HPLC capacity factors. - Akira IIDA; Masaki SANEKATA; Shun-ichi WADA; Tetsuro FUJITA; Hiromi TANAKA; Akio ENOKI; Goro FUSE; Michiko KANAI; Koji ASAMICHEMICAL & PHARMACEUTICAL BULLETIN Pharmaceutical Society of Japan 43 (3) 392 - 397 0009-2363 1995 [Refereed]
- Effects of Ergokonin A;Produced by Trichoderma viride on;the Growth;Morphological Development;of FungiY. Kumeda, T. Asao, A. Iida, S. Wada, S. Futami, T. FujitaJ. Antibact. Antifung. Agents 22 (11) 663 - 670 1994/11 [Refereed]
- PRIMARY STRUCTURES OF ANTIBIOTIC PEPTIDES, TRICHOCELLIN-A AND TRICHOCELLIN-B FROM TRICHODERMA-VIRIDES WADA; T NISHIMURA; A IIDA; N TOYAMA; T FUJITATETRAHEDRON LETTERS PERGAMON-ELSEVIER SCIENCE LTD 35 (19) 3095 - 3098 0040-4039 1994/05 [Refereed]
Trichocellins-A and -B are catecholamine-releasing peptides isolated from the fungus Trichoderma viride. Their amino acid sequences were determined by mars spectrometry and NMR spectroscopy. Trichocellins-A-l similar to VIII and -B-l and -II are each composed of 20 residues, having an N-terminal acetyl group and phenylalaninol as the C-terminal residue. - A IIDA; M SANEKATA; T FUJITA; H TANAKA; A ENOKI; G FUSE; M KANAI; PJ RUDEWICZ; E TACHIKAWACHEMICAL & PHARMACEUTICAL BULLETIN PHARMACEUTICAL SOC JAPAN 42 (5) 1070 - 1075 0009-2363 1994/05 [Refereed]
New peptaibols, trichokindins I-VII, have been isolated from the fungus Trichoderma harzianum. Their structures were characterized by spectrometric methods. Trichokindins, which are 18-residue peptides containing one to three isovaline residues, were found to induce Ca2+-dependent catecholamine secretion from bovine adrenal medullary chromaffin cells. - M OKUDA; A IIDA; S UESATO; Y NAGAOKA; T FUJITA; Y TAKAISHI; H TERADABIOLOGICAL & PHARMACEUTICAL BULLETIN PHARMACEUTICAL SOC JAPAN 17 (4) 482 - 485 0918-6158 1994/04 [Refereed]
The effect of the trichosporin-Bs, peptide antibiotics, on the respiration of mitochondria was investigated. Trichosporin-Bs stimulated the respiratory rate of state 4 rat liver mitochondria in a dose-dependent manner. The maximum respiratory rate obtained by trichosporin-Bs was essentially the same as for 2,4-dinitrophenol and SF6847. Trichosporin-B-VIb released oligomycin-inhibited respiration of mitochondria. This means that trichosporin-Bs are uncouplers of oxidative phosphorylation. The stimulatory effect of trichosporin-B-VIb, a component of trichosporin-Bs, on mitochondrial respiration was increased by inorganic phosphate but not by other permeant anions studied. These results suggest that the stimulation of mitochondrial respiration by trichosporin-B-VIb is mediated by the same mechanism as is operating in the case of hypelcins and alamethicins. Furthermore, the relative potencies of trichosporin-Bs on the mitochondrial respiration and their relative hydrophobicities were examined. A clear relationship was observed between the uncoupling potencies of trichosporin-Bs and their relative hydrophobicities. - T FUJITA; S WADA; A IIDA; T NISHIMURA; M KANAI; N TOYAMACHEMICAL & PHARMACEUTICAL BULLETIN PHARMACEUTICAL SOC JAPAN 42 (3) 489 - 494 0009-2363 1994/03 [Refereed]
Three new groups of peptaibols, trichodecenins, trichorovins and trichocellins, have been isolated from conidia of the fungus, Trichoderma viride. The structures of trichodecenins-I and -II were established by positive-ion fast-atom bombardment, collision-induced dissociation mass spectrometry and two-dimensional NMR spectroscopy. Trichodecenins-I and -II have a (Z)-4-decenoyl group, six amino acid residues and a leucinol moiety in the molecules. Trichodecenin-II was synthesized by the solution-phase method. - Yasuo NAGAOKA; Akira IIDA; Teturo FUJITACHEMICAL & PHARMACEUTICAL BULLETIN Pharmaceutical Society of Japan 42 (6) 1258 - 1263 0009-2363 1994 [Refereed]
- K MATSUURA; A YESILADA; A IIDA; Y NAGAOKA; Y TAKAISHI; T FUJITACHEMICAL & PHARMACEUTICAL BULLETIN PHARMACEUTICAL SOC JAPAN 41 (11) 1955 - 1959 0009-2363 1993/11 [Refereed]
A membrane-modifying peptide antibiotic having uncoupling activity on rat liver mitochondria, hypelcin A-III, has been synthesized by assembling five peptide fragments via the N,N'-dicyclohexylcarbodiimide method. The synthesized hypelcin A-III was identical with the natural product. - K MATSUURA; A YESILADA; A IIDA; Y TAKAISHI; M KANAI; T FUJITAJOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 ROYAL SOC CHEMISTRY 1993 (3) 381 - 387 0300-922X 1993/02 [Refereed]
Hypelcin A is a mixture of antibiotic peptides produced by Hypocrea peltata. Hypelcin A-I, A-II, A-III, A-IV, A-V, A-VI, A-VII, A-VIII and A-IX are components of this mixture purified by reversed-phase high-performance liquid chromatography. The amino acid sequences of these peptides were determined by fast-atom bombardment mass spectrometry and fast-atom bombardment mass spectrometry/mass spectrometry with the help of NMR spectroscopy. The relative molecular masses of these peptides were all approximately 2000 and their structures were very similar. - A IIDA; S UESATO; T SHINGU; Y NAGAOKA; Y KURODA; T FUJITAJOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 ROYAL SOC CHEMISTRY 1993 (3) 375 - 379 0300-922X 1993/02 [Refereed]
The secondary structure of the peptaibol trichosporin B-V in methanol was investigated in detail by 600 MHz nuclear magnetic resonance spectroscopy. Its fundamental secondary structure was characterized as a helix by the circular dichroism spectrum. Inter-residual nuclear Overhauser effect patterns, 3J(NH-CalphaH) amide coupling constants, hydrogen-deuterium (H-D) exchange rates of the amide protons, and inspection of molecular models showed that the secondary structure of this peptide consists of two major alpha-helical structures because of a bent structure around a Pro residue, and that the first three amino acid residues of the N-terminal alpha-helix are arranged predominantly in a 3(10)-helical fashion. - A IIDA; S UESATO; T SHINGU; M OKUDA; Y NAGAOKA; Y KURODA; T FUJITAJOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 ROYAL SOC CHEMISTRY 1993 (3) 367 - 373 0300-922X 1993/02 [Refereed]
Sequence-specific H-1- and C-13-nuclear magnetic resonance assignments of an antibiotic peptide, trichosporin B-V isolated from fungus Trichoderma polysporum, were achieved in methanol by using two-dimensional NMR techniques. The H-1 NMR spectra recorded at various concentrations (1-60 mmol dm-3) suggested that the peptide behaves predominantly as a monomer in methanol and that its conformation is not affected by its concentration. Furthermore, complete or partial H-1-resonance assignments of trichosporin B-Ia, -IIIa, -IVd and -VIb were carried out similarly. Comparison of the H-1 NMR parameters for the amide groups of trichosporin Bs suggested that their backbone conformations are very similar to each other. It is proposed that the significant differences in the biological activity of trichosporin Bs result from the lipophilicity of the individual molecules. - J IIDA; A IIDA; Y TAKAHASHI; Y TAKAISHI; Y NAGAOKA; T FUJITAJOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 ROYAL SOC CHEMISTRY 1993 (3) 357 - 365 0300-922X 1993/02 [Refereed]
From the minor-components mixture of Trichosporin Bs (TS-Bs) produced by Trichoderma polysporum, ten components could be elucidated by means of linked-scan and continuous-flow fast-atom bombardment. The combination of their complementary results made the rapid structure elucidation of the minor components possible without isolation and purification. The identified compounds are antibiotic eicosapeptides and have very similar structures with relative molecular masses of approximately 2000. Four new peptide groups were found. In their structures, the first group has Gly at the amino acid position 3 in contrast to the known TS-Bs, the second one has Vxx (valine or isovaline) at position 12, and the third and the fourth ones have Ala at position 13 or 17, respectively. - Kouji Matsuura; Akgül Yesilada; Akira Iida; Yoshihisa Takaishi; Michiko Kanai; Tetsuro FujitaJournal of the Chemical Society, Perkin Transactions 1 (3) 381 - 387 1472-7781 1993Hypelcin A is a mixture of antibiotic peptides produced by Hypocrea peltata. Hypelcin A-I, A-II, A-III, A-IV, A-V, A-VI, A-VII, A-VIII and A-IX are components of this mixture purified by reversed-phase high-performance liquid chromatography. The amino acid sequences of these peptides were determined by fast-atom bombardment mass spectrometry and fast-atom bombardment mass spectrometry/mass spectrometry with the help of NMR spectroscopy. The relative molecular masses of these peptides were all ∼2000 and their structures were very similar.
- Junko Iida; Akira Iida; Yoshiko Takahashi; Yoshihisa Takaishi; Yasuo Nagaoka; Tetsuro FujitaJournal of the Chemical Society, Perkin Transactions 1 (3) 357 - 365 1472-7781 1993From the minor-components mixture of Trichosporin Bs (TS-Bs) produced by Trichoderma polysporum, ten components could be elucidated by means of linked-scan and continuous-flow fast-atom bombardment. The combination of their complementary results made the rapid structure elucidation of the minor components possible without isolation and purification. The identified compounds are antibiotic eicosapeptides and have very similar structures with relative molecular masses of ∼2000. Four new peptide groups were found. In their structures, the first group has Gly at the amino acid position 3 in contrast to the known TS-Bs, the second one has Vxx (valine or isovaline) at position 12, and the third and the fourth ones have Ala at position 13 or 17, respectively.
- T HAYASHI; K OKAMURA; Y TAMADA; A IIDA; T FUJITA; N MORITAPHYTOCHEMISTRY PERGAMON-ELSEVIER SCIENCE LTD 32 (2) 349 - 352 0031-9422 1993/01 [Refereed]
A new chemotype was found in Scoparia dulcis from Taiwan, China and Thailand based on the diterpene composition. The new chemotype was characterized by the presence of scopadulciol and scopadiol. The structure of a new diterpene was determined to be 6-benzoyl-labda-8(17),13-diene-15,18-diol by spectroscopic methods. - E RESTO; A IIDA; MD VANCLEVE; SM HECHTNUCLEIC ACIDS RESEARCH OXFORD UNIV PRESS UNITED KINGDOM 20 (22) 5979 - 5983 0305-1048 1992/11 [Refereed]
Large quantities of a catalytically active protein have been produced in a cell free system. More than 10(9) copies of protein were produced from each DNA plasmid containing DNA(fol), the bacterial gene encoding dihydrofolate reductase (DHFR). The strategy employed, denoted gene amplification with transcription/translation (GATT), involves sequential coupling of (i) DNA amplification by the polymerase chain reaction (PCR) and (ii) in vitro RNA transcription by T7 RNA polymerase, followed by (iii) translation of the run-off transcripts in a rabbit reticulocyte system. The protein product had the expected size (18 kDa) and catalyzed the NADPH-dependent reduction of 7,8-dihydrofolic acid to 5,6,7,8-tetrahydrofolic acid as efficiently as authentic DHFR. Potential applications of the strategy include large scale production of enzymes containing synthetic amino acids and facilitation of the characterization of the function of genes encountered in genomic mapping studies. - Kunie Ujita; Yoshihisa Takaishi; Akira Iida; Tetsuro FujitaPhytochemistry Elsevier BV 31 (4) 1289 - 1292 0031-9422 1992/04 [Refereed]
- E TACHIKAWA; T KASHIMOTO; A IIDA; Y NAGAOKA; T FUJITA; Y TAKAISHIJOURNAL OF PHARMACOBIO-DYNAMICS PHARMACEUTICAL SOC JAPAN 15 (1) S10 - S10 0386-846X 1992/01 [Refereed]
- E TACHIKAWA; S TAKAHASHI; K FURUMACHI; T KASHIMOTO; A IIDA; Y NAGAOKA; T FUJITA; Y TAKAISHIMOLECULAR PHARMACOLOGY WILLIAMS & WILKINS 40 (5) 790 - 797 0026-895X 1991/11 [Refereed]
We examined the effect of trichosporin-B-III, an alpha-aminoisobutyric acid-containing antibiotic peptide consisting of 19 amino acid residues and a phenylalaninol, on catecholamine secretion from cultured bovine adrenal chromaffin cells. Incubation of the cells with trichosporin-B-III (3-20-mu-M) caused an increase in the secretion of catecholamines. The secretion induced by trichosporin-B-III at low concentrations (3 and 5-mu-M) was completely dependent on external Ca2+, whereas that induced by higher concentrations (10 and 20-mu-M) was partly independent of Ca2+. Trichosporin-B-III at low concentration (5-mu-M) did not increase the release of lactate dehydrogenase, a marker enzyme of cytoplasm, from the cells. In contrast, the peptide at higher concentration (10-mu-M) increased the release of the enzyme. Trichosporin-B-III also caused both Ca-45(2+) influx into the cells and an increase in the intracellular free Ca2+ concentration. The increases in catecholamine secretion and Ca-45(2+) influx behaved similarly in relation to trichosporin-B-III concentration (3-10-mu-M). The time courses of the increases in secretion, Ca-45(2+) influx, and intracellular free Ca2+ concentration induced by trichosporin-B-III were also quite similar. Trichosporin-B-III-induced (at 5-mu-M) secretion was not affected by the elimination of Na+ from the incubation medium or by the addition of tetrodotoxin, a blocker of highly selective voltage-dependent Na+ channels, or hexamethonium, a blocker of nicotinic acetylcholine receptors. On the other hand, both diltiazem (2-200-mu-M) and nicardipine (1-200-mu-M), blockers of voltage-dependent Ca2+ channels, inhibited the secretion induced by trichosporin-B-III (5-mu-M) in a concentration-dependent manner. Trichosporin-B-III-induced (at 5-mu-M) secretion also was suppressed by the addition of Mn2+ (5-mu-M) to the medium. The diltiazem (20-mu-M) inhibition of trichosporin-B-III-induced (at 5-mu-M) secretion was reversed by increasing the external Ca2+ concentration. These results indicate that trichosporin-B-III causes the secretion of catecholamines from bovine adrenal chromaffin cells by two mechanisms, Ca2+ dependent and Ca2+ independent (only at high concentrations of trichosporin-B-III). Furthermore, these results strongly suggest that trichosporin-B-III, in Ca2+-dependent secretion, activates endogenous voltage-dependent Ca2+ channels, or itself forms the channels in the membranes, and induces Ca2+ influx into the cells. - E TACHIKAWA; T KASHIMOTO; A IIDA; Y NAGAOKA; T FUJITA; Y TAKAISHIJOURNAL OF PHARMACOBIO-DYNAMICS PHARMACEUTICAL SOC JAPAN 14 (5) S106 - S106 0386-846X 1991/05 [Refereed]
- A IIDA; M OKUDA; S UESATO; Y TAKAISHI; T SHINGU; M MORITA; T FUJITAJOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 ROYAL SOC CHEMISTRY (12) 3249 - 3255 0300-922X 1990/12 [Refereed]
Trichosporin-B-IIIb, -IIIc, -IVb, -IVc, -IVd, -VIa and -VIb are components of an antibiotic peptide mixture produced by Trichoderma polysporum. Each component was purified by reversed-phase high-performance liquid chromatography (HPLC). The amino acid sequences of these peptides, which have an unstable peptide bond, Aib-Pro, were elucidated by fast-atom bombardment mass spectrometry (FAB MS) and fast-atom bombardment mass spectrometry/mass spectrometry (FAB MS/MS) with the help of NMR spectroscopy. The molecular weights of these peptides were all ca. 2000 and the structures were very similar. - AKira IIDA; Shinya YOSHIMATSU; Masaki SANEKATA; Tetsuro FUJITACHEMICAL & PHARMACEUTICAL BULLETIN Pharmaceutical Society of Japan 38 (11) 2997 - 3003 0009-2363 1990 [Refereed]
- Iida A.; Sanekata M.; Fujita T.; Tanaka H.; Enoki A.; Fuse G.; Rudewicz P. J.; Kanai M.Symposium on the Chemistry of Natural Products, symposium papers Symposium on the chemistry of natural products (31) 372 - 379 1989/09Trichoderma spp. are active as mycoparasites and, therefore, can serve as potential biocontrol agents. We found in dual culture studies on agar medium that Trichoderma harzianum killed most wood decay fungi examined. New antibiotic peptides, trichokindin (TK)-I〜X, which belong to a class of peptaibols like alamethicin and suzukacillin, were isolated from the spores of T. harzianum. The primary structure of TK-X(10) was clearly established by FABMS and FABMS/MS. The N-terminal of (10) is protected by an acetyl group and the C-terminal is linked with an isoleucinol (Iol). The peptide contains a high proportion of abnormal amino acids, α-aminoisobutyric acid (Aib) and isovaline (Iva). The peptides, trichokindin-IV〜IX (4〜9), have all about 1800 of molecular weight and have a similar structure, in which an aminoalcohol is Iol or leicinol (Lol), to TK-X. The other peptides, trichokindin-I〜III (1〜3), whose molecular weights are about 1200, are also protected by an acetyl group. Their total structure are not yet elucidated.
- Fujita T.; Okuda M.; Iida A.; Uesato S.; Takaishi Y.; Shingu T.Symposium on the Chemistry of Natural Products, symposium papers Symposium on the chemistry of natural products (30) 33 - 40 1988/09Trichosporins are a linear peptide mixture produced by Trichoderma polysporum whose structures are closely similar to each other. They inhibits the growth of Lentinus edodes. These peptides belong to peptaibols in which the N-terminal is protected by an acetyl group and the C-terminal by a phenylalaninol. Recently, we have isolated trichosporins[TS]-B-IIIb(1), c(2), IVb(3), c(4), d(5) and VIa(6), b(7) and established their primary structures by positive ion FAB-MS spectrometry, respectively. TS-B-IVb,d and VIb are the first examples of isovaline containing peptides isolated from T. polysporum. The connectivities of amino acid residues are established by means of COSY and NOESY NMR techniques. In addition, uncoupling activities of these peptides on rat liver mitochondria were examined.
- T FUJITA; A IIDA; S UESATO; Y TAKAISHI; T SHINGU; M SAITO; M MORITAJOURNAL OF ANTIBIOTICS JAPAN ANTIBIOT RES ASSN 41 (6) 814 - 818 0021-8820 1988/06 [Refereed]
- Fujita T.; Iida A.; Uesato S.; Takaishi Y.; Shingu T.Symposium on the Chemistry of Natural Products, symposium papers Symposium on the chemistry of natural products (28) 152 - 159 1986/09Trichosporins are a peptide mixture isolated from culture filtrate of Trichoderma polysporum, which is antagonistic to Leutinus edodes. The pure component, trichosporin (TS)-B-V, has been obtained by preparative HPLC from Trichosporin mixture. This novel peptide has been shown to consit of one acetylated N-terminal residue, 19 amino acids and a phenylalaninol, C-terminal amino alcohol. Moreover, since this peptide contains a high proportion of α-aminoisobutyric acid (Aib) and has a moleculor weight near 2000, it belongs to the class of peptaibophols. Sequence determination (Fig. 8) was based on positive ion FAB mass spectrometry. High-field NMR data with two-demensional NMR assignment techniques were very useful in this study. Furthermore, sequences of the congeners, TS-B-I-a, -III-a, and -III-d were elucidated as shown in Fig. 8.
- S UESATO; S KANOMI; A IIDA; H INOUYE; MH ZENKPHYTOCHEMISTRY PERGAMON-ELSEVIER SCIENCE LTD 25 (4) 839 - 842 0031-9422 1986 [Refereed]
- S UESATO; S MATSUDA; A IIDA; H INOUYE; MH ZENKCHEMICAL & PHARMACEUTICAL BULLETIN PHARMACEUTICAL SOC JAPAN 32 (9) 3764 - 3767 0009-2363 1984 [Refereed]
MISC
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- 川村晴希; 竹田竜嗣; 飯田彰; 若林雄平; 濱原典正; 米虫節夫; 沢辺昭義 日本ブドウ・ワイン学会誌 23- (2) 96 -97 2012/11
- 竹中章泰; 上田和典; 山下光明; 徳田春邦; 飯田彰 天然薬物の開発と応用シンポジウム講演要旨集 19th- 149 -151 2012/10
- 上田和典; 山下光明; 阪口晃一; 鵜飼勇介; 徳田春邦; 飯田彰 天然薬物の開発と応用シンポジウム講演要旨集 19th- 39 -41 2012/10
- 上田和典; 山下光明; 阪口晃一; 鵜飼勇介; 徳田春邦; 飯田彰 複素環化学討論会講演要旨集 42nd- 297 -298 2012/09
- H. Tokuda; A. Iida; M. Yamashita; N. Suzuki PLANTA MEDICA 78- (11) 1177 -1177 2012/08
- 沢辺昭義; 向井渉子; 笹井勝章; 澤本拓真; 中島大介; 白石不二雄; 竹田竜嗣; 飯田彰 環境化学討論会要旨集(CD-ROM) 21st- ROMBUNNO.P-205 2012/07
- 澤邊昭義; 戸嶋猛; 中谷太一; 竹田竜嗣; 飯田彰; 高橋一弘; 山口隆司 Aroma Res 13- (1) 58 -63 2012/02
- 福田陽一; 上田和典; 金澤由佳; 徳田春邦; 山下光明; 飯田彰 日本補完代替医療学会学術集会プログラム・抄録集 15th- 45 2012
- 上田和典; 福田陽一; 鈴木郁功; 徳田春邦; 山下光明; 飯田彰 日本補完代替医療学会学術集会プログラム・抄録集 15th- 56 2012
- 飯田彰 日本補完代替医療学会学術集会プログラム・抄録集 15th- 89 -90 2012
- 徳田春邦; 金子雅文; 山下光明; 飯田彰; 鈴木信孝 日本補完代替医療学会学術集会プログラム・抄録集 15th- 58 2012
- 徳田春邦; 金子雅文; 山下光明; 飯田彰; 鈴木信孝 日本分子生物学会年会プログラム・要旨集(Web) 35th- 4P-0371 (WEB ONLY) 2012
- 中谷太一; 竹田竜嗣; 飯田彰; 松浦信康; 若林雄平; 濱原典正; 米虫節夫; 沢辺昭義 日本ブドウ・ワイン学会誌 22- (2) 98 -99 2011/11
- 上田和典; 山嶋千絵; 飯田彰; 徳田春邦; 金子雅文 食品薬学シンポジウム講演要旨集 4th- 167 -169 2011/10
- 笹井勝章; 澤本拓真; 中島大介; 白石不二雄; 飯田彰; 沢辺昭義 環境化学討論会要旨集(CD-ROM) 20th- ROMBUNNO.2C-01 2011/07
- 川村晴希; 竹田竜嗣; 中村貴俊; 藤井善之; 井上俊夫; 飯田彰; 沢辺昭義 日本農芸化学会大会講演要旨集 2011- 227 2011/03
- 沢辺昭義; 中谷太一; 竹田竜嗣; 飯田彰; 東海林大介; 濱田洋 日本農芸化学会大会講演要旨集 2011- 23 2011/03
- 沢辺昭義; 戸島猛; 竹田竜嗣; 湯川千代樹; 田中清文; 飯田彰 日本農芸化学会大会講演要旨集 2011- 235 2011/03
- H. Tokuda; A. Iida; M. Yamashita; M. Kaneko; N. Suzuki ANNALS OF NUTRITION AND METABOLISM 58- 99 -99 2011
- 飯田彰; 徳田春邦 日本補完代替医療学会学術集会プログラム・抄録集 14th- 50 2011
- 徳田春邦; 金子雅文; 山下光明; 飯田彰; 鈴木信孝 日本補完代替医療学会学術集会プログラム・抄録集 14th- 53 2011
- 徳田春邦; 鈴木信孝; 山下光明; 金子雅文; 飯田彰 がん予防大会プログラム・抄録集 2011- 85 2011
- 沢辺昭義; 竹田竜嗣; 山田高也; 頓宮美樹; 川上浩平; 飯田彰; 若林雄平; 濱原典正; 米虫節夫 日本ブドウ・ワイン学会誌 21- (2) 78 -79 2010/11
- 戸嶋猛; 竹田竜嗣; 高橋一弘; 山口隆司; 飯田彰; 沢辺昭義 香料・テルペンおよび精油化学に関する討論会講演要旨集 54th- 220 -222 2010/10
- 沢辺昭義; 竹田竜嗣; 湯川千代樹; 田中清文; 飯田彰 香料・テルペンおよび精油化学に関する討論会講演要旨集 54th- 24 -26 2010/10
- 久保田梨裕; 大黒真也; 飯田彰; 沢辺昭義 香料・テルペンおよび精油化学に関する討論会講演要旨集 54th- 115 -117 2010/10
- 沢辺昭義; 竹田竜嗣; 中村貴俊; 藤井善之; 井上俊夫; 豊田又文; 飯田彰 香料・テルペンおよび精油化学に関する討論会講演要旨集 54th- 118 -120 2010/10
- 笹井勝章; 澤本拓真; 戸嶋猛; 鄭致孝; 竹田竜嗣; 中島大介; 白石不二雄; 飯田彰; 沢辺昭義 日本農芸化学会関西支部講演会講演要旨集 466th- 35 2010/10
- 若林雄平; 仲川一彰; 竹田竜嗣; 飯田彰; 若月利之; 玉木聡史; 岩佐航一郎; 沢辺昭義 日本土壌肥料学会講演要旨集 56- (56) 283 -283 2010/09
- 久保田梨裕; 粟飯原茜; 辻本早智; 竹田竜嗣; 飯田彰; 沢辺昭義 日本きのこ学会大会講演要旨集 14th- 107 2010/09
- 笹井勝章; 戸嶋猛; TYON Tihyo; 竹田竜嗣; 中島大介; 白石不二雄; 飯田彰; 沢辺昭義 環境化学討論会講演要旨集 19th- 70 -71 2010/06
- 富田真人; 竹田竜嗣; 大久保智史; 山本むつみ; 渡邉泉; 飯田彰; 澤邊昭義 環境化学討論会講演要旨集 19th- 832 -833 2010/06
- 笹井勝章; 北澤優也; 竹田竜嗣; 鎌田亮; 影山志保; 中島大介; 白石不二雄; 後藤純雄; 飯田彰; 沢辺昭義 環境化学討論会講演要旨集 19th- 764 -765 2010/06
- 金澤由佳; 田中郁郎; 米山実佐; 廣谷絵理加; 徳田春邦; 飯田彰 日本薬学会年会要旨集 130th- (2) 194 2010/03
- 久保田梨裕; 伊藤まえみ; 大黒真也; 竹田竜嗣; 飯田彰; 沢辺昭義 日本農芸化学会大会講演要旨集 2010- 140 2010/03
- 山下光明; 金子雅文; 徳田春邦; 上田和典; 飯田彰 日本薬学会年会要旨集 130th- (2) 249 2010/03
- 竹中章泰; 清水勇輝; 富田真人; 竹田竜嗣; 沢辺昭義; 金子雅文; 山下光明; 徳田春邦; 飯田彰 日本薬学会年会要旨集 130th- (2) 194 2010/03
- 徳田春邦; 金子雅文; 山下光明; 鈴木信孝; 飯田彰 日本補完代替医療学会学術集会プログラム・抄録集 13th- 71 2010
- 徳田春邦; 金子雅文; 山下光明; 鈴木信孝; 飯田彰 日本補完代替医療学会学術集会プログラム・抄録集 13th- 35 2010
- 沢辺昭義; 竹田竜嗣; 飯田彰; 濱原典正; 米虫節夫 日本ブドウ・ワイン学会誌 20- (3) 104 -105 2009/11
- 粟飯原茜; 久保田梨裕; 飯田彰; 沢辺昭義 香料・テルペンおよび精油化学に関する討論会講演要旨集 53rd- 165 -167 2009/11
- 沢辺昭義; 竹田竜嗣; 湯川千代樹; 田中清文; 飯田彰 香料・テルペンおよび精油化学に関する討論会講演要旨集 53rd- 251 -253 2009/11
- 水野加奈; 中谷太一; 大迫由佳; 中村貴俊; 渡具知豊; 野池利彰; 池内正寿; 竹田竜嗣; 飯田彰; 沢辺昭義 香料・テルペンおよび精油化学に関する討論会講演要旨集 53rd- 171 -173 2009/11
- 久保田梨裕; 伊藤まえみ; 大黒真也; 飯田彰; 沢辺昭義 香料・テルペンおよび精油化学に関する討論会講演要旨集 53rd- 344 -346 2009/11
- 中村貴俊; 藤井善之; 水野加奈; 豊田又文; 笹井勝章; 竹田竜嗣; 飯田彰; 沢辺昭義 香料・テルペンおよび精油化学に関する討論会講演要旨集 53rd- 168 -170 2009/11
- 中村貴俊; 藤井善之; 水野加奈; 中東恵介; 笹井勝章; 竹田竜嗣; 飯田彰; 沢辺昭義 日本農芸化学会関西支部講演会講演要旨集 2009- 167 2009/10
- 粟飯原茜; 久保田梨裕; 竹田竜嗣; 飯田彰; 沢辺昭義 日本農芸化学会関西支部講演会講演要旨集 2009- 168 2009/10
- 水野加奈; 中谷太一; 大迫由佳; 中村貴俊; 渡具知豊; 野池利彰; 池内正寿; 竹田竜嗣; 飯田彰; 沢辺昭義 日本農芸化学会関西支部講演会講演要旨集 2009- 168 2009/10
- 竹田竜嗣; 川上芳緒; 河内幸枝; 飯田彰; 澤邊昭義 食品薬学シンポジウム講演要旨集 3rd- 213 -215 2009/10
- 飯田彰; 金子雅文; 山下光明; 平田章二; 鈴木信孝; 徳田春邦 食品薬学シンポジウム講演要旨集 3rd- 53 -55 2009/10
- 富田真人; 竹田竜嗣; 大久保智史; 南加容; 渡邉泉; 飯田彰; 沢辺昭義 日本土壌肥料学会講演要旨集 55- (55) 297 -297 2009/09
- 粟飯原茜; 久保田梨裕; 中村貴俊; 竹田竜嗣; 飯田彰; 沢辺昭義 日本きのこ学会大会講演要旨集 13th- 81 2009/09
- 仲川一彰; 菊池康太; 竹田竜嗣; 鈴木肖子; 玉木聡史; 岩佐航一郎; 飯田彰; 若月利之; 沢辺昭義 環境化学討論会講演要旨集 18th- 774 -775 2009/06
- 富田真人; 竹田竜嗣; 大久保智史; 南加容; 渡邊泉; 飯田彰; 澤邊昭義 環境化学討論会講演要旨集 18th- 758 -759 2009/06
- 生嶋一貴; 笹井勝章; 竹田竜嗣; 緒方浩史; 鎌田亮; 影山志保; 中島大介; 白石不二雄; 飯田彰; 沢辺昭義 環境化学討論会講演要旨集 18th- 606 -607 2009/06
- 山下光明; 金子雅文; 徳田春邦; 西村克己; 久米田裕子; BACOWSKI Helmut; 飯田彰 日本薬学会年会要旨集 129th- (2) 156 2009/03
- 金子雅文; 山下光明; 徳田春邦; BACOWSKI Helmut; 飯田彰 日本薬学会年会要旨集 129th- (2) 157 2009/03
- 徳田春邦; 金子雅文; 山下光明; バチョフスキー; ヘルムート; 飯田彰 日本補完代替医療学会学術集会プログラム・抄録集 12th- 122 -123 2009
- 徳田春邦; 金子雅文; 山下光明; 鈴木信孝; 飯田彰 日本補完代替医療学会学術集会プログラム・抄録集 12th- 101 2009
- 山下光明; 金子雅文; 徳田春邦; 西村克己; 久米田裕子; BACOWSKI Helmut; 飯田彰 メディシナルケミストリーシンポジウム講演要旨集 27th- 224 -225 2008/11
- 沢辺昭義; 阪谷圭祐; 鈴木史哉; 嶋田奈央子; 千葉友美; 米虫節夫; 飯田彰 天然有機化合物討論会講演要旨集 50th- (50) 291 -296 2008/09
- 金子雅文; 山下光明; 飯田彰; 徳田春邦; BACOWSKI Helmut 日本生薬学会年会講演要旨集 55th- 116 2008/09
- H. Tokuda; M. Kaneko; M. Yamashita; A. Iida PLANTA MEDICA 74- (9) 1007 -1007 2008/07
- 山下光明; 金子雅文; 飯田彰; 西村克己; 徳田春邦; 久米田裕子 日本薬学会年会要旨集 128th- (2) 86 2008/03
- 金子雅文; 山下光明; 飯田彰; 徳田春邦 日本薬学会年会要旨集 128th- (2) 87 2008/03
- 徳田春邦; 山下光明; 金子雅文; 飯田彰 日本補完代替医療学会学術集会プログラム・抄録集 11th- 132 2008
- 金子雅文; 山下光明; 飯田彰; 徳田春邦 日本生薬学会年会講演要旨集 54th- 85 2007/09
- 山下光明; 金子雅文; 飯田彰; 西村克己; 徳田春邦; 西野輔翼 日本薬学会年会要旨集 127th- (4) 126 2007/03
- 金子雅文; 山下光明; 飯田彰; 徳田春邦; 西野輔翼 日本薬学会年会要旨集 127th- (4) 125 2007/03
- Harukuni Tokuda; Akira Iida ANNALS OF NUTRITION AND METABOLISM 51- 244 -244 2007
- 徳田春邦; 飯田彰 薬学雑誌 126- (Suppl.3) 136 -137 2006/10
- 金子雅文; 山下光明; 飯田彰; 徳田春邦; 西野輔翼 日本生薬学会年会講演要旨集 53rd- 76 2006/09
- 徳田春邦; 飯田彰 日本補完代替医療学会学術集会プログラム・抄録集 9th- 63 2006
- 徳田春邦; 飯田彰 日本補完代替医療学会学術集会プログラム・抄録集 9th- 96 -97 2006
- 飯田彰; 松本洋亘; 田原照之; 田中美音; 富岡清; 和田俊一 メディシナルケミストリーシンポジウム講演要旨集 24th- 148 -149 2005/11
- 飯田彰; 西村克己; 徳田春邦; 西野輔翼 日本生薬学会年会講演要旨集 52nd- 104 2005/08
- 飯田彰; 徳田春邦 日本薬学会年会要旨集 125th- (4) 187 2005/03
- 田原照之; 松本洋亘; 飯田彰; 富岡清 日本薬学会年会要旨集 125th- (4) 50 2005/03
- 松本洋亘; 飯田彰; 富岡清; 和田俊一 日本薬学会年会要旨集 125th- (4) 50 2005/03
- 松本洋亘; 飯田彰; 富岡清; 和田俊一 日本薬学会年会要旨集 124th- (2) 51 2004/03
- 田原照之; 飯田彰; 富岡清 日本薬学会年会要旨集 124th- (2) 100 2004/03
- 本宮知子; 伊藤美千穂; 木内文之; 本多義昭; 徳田春邦; 西野輔翼; 飯田彰 日本薬学会年会要旨集 124th- (2) 129 2004/03
- 飯田彰; 松本洋亘; 田原照之; 富岡清; 水品善之 日本薬学会年会要旨集 124th- (2) 90 2004/03
- 飯田彰; 青山宏; 富岡清; 徳田春邦; 西野輔翼; QUI T K 日本生薬学会年会講演要旨集 50th- 66 2003/08
- 松本洋亘; 飯田彰; 富岡清; 和田俊一 日本薬学会年会要旨集 123rd- (2) 47 2003/03
- 和田俊一; 田中麗子; 飯田彰 日本薬学会年会要旨集 123rd- (2) 164 2003/03
- 飯田彰; 金子雅文; 小西一豪; 富岡清; 向仲輝雄; 徳田春邦; 西野輔翼 日本薬学会年会要旨集 123rd- (2) 165 2003/03
- トリコテシウムロゼウムから単離されたトリコテセンの発ガン予防効果生物有機医薬品化学 11- 2511 -2518 2003
- 西洋タンポポから単離された青酸配糖体生薬学雑誌 57- (1、36) 2003
- トリコテセンセスキテルペン(+)-カロネクトリンの光学的に純粋なABリングの立体選択的合成ヘテロサイクルズ 59- (2) 595 -604 2003
- 様々な保存条件と抗酸化成分がヒドロキノン軟膏の色収差に及ぼす効果生物薬学雑誌 26- (1) 120 -122 2003
- 飯田彰; 松本洋亘; 富岡清; 和田俊一 天然有機化合物討論会講演要旨集 44th- (44) 617 -622 2002/09
- 松本洋亘; 飯田彰; 富岡清 日本薬学会年会要旨集 122nd- (2) 43 2002/03
- 飯田彰; 伊藤美千穂; 木内文之; 富岡清; 本多義昭; SARSENBAEV K; 水品善之; 吉田弘美 日本薬学会年会要旨集 122nd- (2) 159 2002/03
- 土肥弘久; 鈴木寛和; 山口陽子; 飯田彰; 山田健一; 富岡清 日本薬学会年会要旨集 122nd- (2) 63 2002/03
- 水品善之; 笠井信幸; 飯田彰; 菅原二三男; 吉田弘美; 坂口謙吾 日本農芸化学会大会講演要旨集 2002- 1 2002/03
- 飯田彰; 金子雅文; 小西一豪; 富岡清; 徳田春邦; 西野輔翼 日本薬学会年会要旨集 122nd- (2) 146 2002/03
- アビエスサッカリネンシスの樹皮から単離されたトリテルペノイド成分65- 2002
- 非滅菌配合によって調製されたヒドロキノン軟膏の薬理学的臨床的評価25- (1) 92 -96 2002
- 飯田彰 日本生薬学会年会講演要旨集 48th- 43 2001/08
- 金子雅文; 飯田彰; 富岡清 日本薬学会年会要旨集 121st- (2) 120 2001/03
- 飯田彰; 金子雅文; 富岡清; 徳田春邦; 向仲輝雄; 西野輔翼 日本薬学会年会要旨集 121st- (2) 150 2001/03
- 和田俊一; 田中麗子; 飯田彰 日本薬学会年会要旨集 121st- (2) 155 2001/03
- 飯田 彰 環境保全 16- (16) 30 -37 2001
- シロイヌナズナの開花を調節する因子37- (2) 149 -150 2001
- フィランタスフレクソサスから単離されたトリテルペノイドのDNAトポイソメラーゼ阻害活性スクリーニング64- (12) 1545 -1547 2001
- パイナスルクエンシスの樹皮から単離されたトリテルペン成分とそれらのトポイソメラーゼII阻害効果67- (7) 659 -664 2001
- DNAポリメラーゼβとDNAトポイソメラーゼII両方の阻害剤、リトコリック酸のD結合部位の三次元構造モデル分析130- (5) 657 -664 2001
- 水品善之; 飯田彰; 菅原二三男; 坂口謙吾 日本分子生物学会年会プログラム・講演要旨集 23rd- 516 2000/11
- 水品善之; 飯田彰; 菅原二三男; 坂口謙吾 日本分子生物学会年会プログラム・講演要旨集 23rd- 515 2000/11
- 飯田彰; 小西一豪; 富岡清; 徳田春邦; 西野輔翼 天然有機化合物討論会講演要旨集 42nd- (42) 757 -762 2000/10
- 水品善之; 菅原二三男; 坂口謙吾; 飯田彰; 大久保忠恭 天然有機化合物討論会講演要旨集 42nd- (42) 505 -510 2000/10
- 飯田彰; 藤多哲朗 バイオサイエンスとインダストリー 58- (5) 345 -346 2000/05
- 鈴木寛和; 小西一豪; 飯田彰; 富岡清 日本薬学会年会要旨集 120th- (2) 110 2000/03
- 飯田彰; 小西一豪; 富岡清; 徳田春邦; 一石英一郎; 西野輔翼 日本薬学会年会要旨集 120th- (2) 126 2000/03
- トリコデルマ属菌から発見された新しい免疫抑制ペプチドバイオサイエンスとインダストリー 58- (5) 2000
- MIZUSHINA Y; SUGAWARA F; IIDA A; SAKAGUCHI K Journal of Molecular Biology 304- (3) 385 -395 2000
- 新規なトリテルペノイドがDNAポリメラーゼとDNAトポイソメラーゼの両方を阻害する350- 753 -763 2000
- ポドフィロトキシンアザ誘導体、新規なトポイソメラーゼII阻害剤48- (4) 486 -489 2000
- フリチラリアエベイエンシスの根茎からから得られた二つのジテルペン二量体の構造161 -167 2000
- フリチラリアエベイエンシスの根茎からから得られた二つのエントカウラン二量体の構造決定213 -218 2000
- Mostafa Ahmed Hussein; Akira Iida; Kiyoshi Tomioka Tetrahedron 55- (37) 11219 -11228 1999/09
- トリコデルマポリスポーラムから単離されたペプチド性免疫抑制活性ペプチド9- 3393 -3396 1999
- フリチラリアエベイエンシスの根茎からから得られた新規クロロ置換ジテルペンの構造30- 804 -807 1999
- フリチラリアエベイエンシスの根茎からから得られたフレチレビナイドAの構造決定と合成34- 600 -604 1999
- Takeshi Kambara; Mostafa Ahmed Hussein; Hiroki Fujieda; Akira Iida; Kiyoshi Tomioka Tetrahedron Letters 39- (49) 9055 -9058 1998/12
- 飯田彰; 加古尊温; 加納正裕; 富岡清 天然有機化合物討論会講演要旨集 40th- 139 -144 1998/08
- 飯田彰; 富岡清 日本薬学会年会要旨集 118th- (2) 176 1998/03
- 藤原秀豪; 飯田彰; 富岡清 日本薬学会年会要旨集 118th- (2) 15 1998/03
- 富岡清; 飯田彰 天然超分子の化学 平成6-8年度成果報告書 No.06240106 55 -58 1998
- カタルパオバータから得られた抗発ガン促進活性ナフトキノン61- (5) 629 -632 1998
- ユーフォルビア属から単離されたフェルナン型トリテルペンによるDNAトポイソメラーゼIIの阻害効果8- 2829 -2832 1998
- 牛副腎髄質クロマフィン細胞と顆粒の非対称膜流動性とトリコスポリン類の効果1375- 93 -100 1998
- キラル配位子により触媒される有機リチウムのBHAエノエイトへのエナンチオ選択的共役付加46- (1) 184 -186 1998
- キラル配位子補助によるチアゾイルリチウムのアルジミンへのエナンチオ選択的付加 海洋天然物ドラスタチン10のコンポーネント合成47- (1) 77 -80 1998
- Masashi Mizuno; Motomu Kanai; Akira Iida; Kiyoshi Tomioka Tetrahedron 53- (31) 10699 -10708 1997/08
- 飯田彰; 小西一豪; 富岡清; 徳田春邦; 西野輔翼 天然有機化合物討論会講演要旨集 39th- 157 -162 1997/07
- 加納正裕; 飯田彰; 稲家千明; 上田伸一; 富岡清 日本薬学会年会要旨集 117th- (2) 187 1997/03
- 水野雅; 飯田彰; 富岡清 日本薬学会年会要旨集 117th- (2) 52 1997/03
- 長岡康夫; 畑中成樹; 飯田彰; 富岡清; 浅見耕司; 藤多哲朗 日本薬学会年会要旨集 117th- (2) 37 1997/03
- 飯田彰; 小西一豪; 富岡清; 徳田春邦; 西野輔翼 日本薬学会年会要旨集 117th- (2) 187 1997/03
- 赤路真佐子; 実方正樹; 長岡康夫; 飯田彰; 藤多哲朗 日本薬学会年会要旨集 117th- (2) 37 1997/03
- 和田俊一; 田中麗子; 松永春洋; 飯田彰 日本薬学会年会要旨集 117th- (2) 167 1997/03
- 小西一豪; 飯田彰; 富岡清; 徳田春邦; 西野輔翼 日本薬学会年会要旨集 117th- (2) 187 1997/03
- 飯田彰 生体機能制御活性を有する微生物由来医薬品素材の開発 平成8年度 No.06303014 27 -33 1997
- ポドフィロトキシンアザ誘導体を用いてトポイソメラーゼIIを標的にする7- (20) 2565 -2566 1997
- キラル配位子仲介による有機リチウムのBHAエノエイトへのエナンチオ選択的共役付加38- (52) 8973 -8976 1997
- キラル配位子補助によるフェニルリチウムの1,2-エチレンジアミンへの不斉付加反応45- (10) 1705 -1707 1997
- キラル配位子補助によるメチルリチウムの2-フラルデヒドイミンへのエナンチオ選択的付加46- 165 -168 1997
- ジスルフィド結合によって2量化されたペプタイボール、トリコスポリン-B-VIaのチャンネル特性189 1997
- リチウムエステルエノラートのイミンとの不斉反応のための3成分錯体試薬アメリカ化学界誌 119- (8) 2060 1997
- NAGAOKA Yasuo; IIDA Akira; HATANAKA Shigeki; TOMIOKA Kiyoshi; ASAMI Koji; FUJITA Tetsuro Peptide chemistry : proceedings of the ... Symposium on Peptide Chemistry 1996- 189 -192 1996/10
- 藤原亜妃; 森俊之; 飯田彰; 上田伸一; 羽野芳生; 野村太郎; 徳田春邦; 西野輔翼 日本生薬学会年会講演要旨集 43rd- 235 1996/08
- 小西一豪; 久保弘樹; 飯田彰 日本薬学会年会要旨集 116th- (Pt 2) 203 1996/03
- 畑中成樹; 長岡康夫; NEOH I P; 飯田彰; 浅見耕司; 藤多哲朗 日本薬学会年会要旨集 116th- (Pt 4) 181 1996/03
- 長岡康夫; 畑中成樹; 飯田彰; 浅見耕司; 藤多哲朗 日本薬学会年会要旨集 116th- (Pt 4) 181 1996/03
- 菌類代謝産物第21報 エレクトロスプレイイオン化質量分析を利用したペプタイボールの低エネルギー衝突誘導解裂の特性31- 177 -183 1996
- ペプタイボール・トリコスポリンB-VIaのチャンネル形成特性におけるグルタミン残基の役割英国化学界誌 1996- (9) 1078 -1080 1996
- トリコセリンA-II/B-IIのGln/Glu残基の脂質膜におけるイオンチャンネル形成とクロマフィンセルからのカテコールアミン分泌における役割1325- 209 1996
- トリコテシノールIVA,BとC、トリコテシウムロゼウムから単離された強力な抗発がん捉進活性セスキテルベノイド37- (51) 9219 1996
- トリコデルマビリデから単離された11残基ペプタイボール、トリコロビン-XIIの脂質2分子膜におけるイオンチャンネル形成特性6- (19) 2275 1996
- キラル配位子制御によるオキシランとオキセタンのエナンチオ選択的開環7- (9) 2483 1996
- ペプタイボール・トリコスポリンB-VIaのチャンネル形成とカテコールアミン放出活性におけるプロリン残基の役割1283- 31 1996
- トリコデルマポリスポーラムから単離されたα-アミノ酪酸含有ペプチド,トリコスポリンB-VIaによる細胞内へのカルシウムイオン流入経路1282- 140 1996
- 浅見耕司; 小出典宏; 松原晃; 長岡康夫; 飯田彰; 和田俊一; 藤多哲朗; 赤木有; 西野憲和 膜シンポジウム (7) 57 -60 1995/11
- 長岡康夫; 飯田彰; 畑中成樹; 浅見耕司; 立川英一; 藤多哲朗 生体膜と薬物の相互作用シンポジウム講演要旨集 17th- 111 -112 1995/10
- 飯田彰; 田中善仁; 本多義昭; 田端守; 藤多哲朗; 高石喜久; 武田美雄; エシラダ エルデム; セジック エクレム 日本生薬学会年会講演要旨集 42nd- 67 1995/08
- 和田俊一; 飯田彰; 藤多哲朗; 浅見耕司 日本薬学会年会要旨集 115th- (Pt 4) 194 1995/03
- 長岡康夫; 飯田彰; 神原武志; 藤多哲朗; 浅見耕司; 立川英一 日本薬学会年会要旨集 115th- (Pt 4) 194 1995/03
- 呉継洲; 森実千香子; 飯田彰; 藤多哲朗 日本薬学会年会要旨集 115th- (Pt 2) 248 1995/03
- イオンチャンネル形成ペプチド、トリコスポリン混合物のLC/ES-MSMSによる講造決定277 1995
- 抗生ペプチド、トリコスポリン-B-VIaとその誘導体の脂質2分子膜におけるチャンネル形成特性97 1995
- トリコスポリンの長鎖および短鎖誘導体のイオンチャンネル形成活性とカテコールアミン放出活性英国化学界誌 1995- (21) 2203 -2204 1995
- トリコスポリンによって誘導されれる牛副腎髄質細胞からのカテコールアミン分泌の特性日本薬学会誌 18- (8) 1165 -1167 1995
- マルルビウムアストラカニクムから単離された新規ラブダン型ジテルペン、マルルビノン類日本薬学会誌 43- (9) 1454 -1457 1995
- フリチラリアエベイエンシスの根茎から得られた3種の新規ジテルペンの構造日本薬学会誌 43- (9) 1448 -1453 1995
- イオンチャンネル形成とカテコールアミン放出活性に対するトリコスポリン類の脂溶性の効果日本薬学会誌 18- (4) 640 -642 1995
- 菌類代謝産物第20報 イオンチャンネル形成ペプチド、トリコスポリンの構造に関するプロリン残基の効果日本薬学会誌 43- (7) 1119 -1124 1995
- 菌類代謝産物第19報 トリコデルマビリデから単離されたチャンネル形成ペプチド、トリコロビン類の構造決定日本薬学会誌 43- (6) 910 -915 1995
- 菌類代謝産物第18報 真菌トリコデルマハルツィアナムから単離された新規膜修飾ペプチド、トリコロジンI-IV日本薬学会誌 43- (3) 392 -397 1995
- LP NEOH; Y NAGAOKA; A IIDA; T FUJITA PEPTIDE CHEMISTRY 1994 277 -280 1995
- Y NAGAOKA; T KAMBARA; A IIDA; K ASAMI; T FUJITA PEPTIDE CHEMISTRY 1994 97 -100 1995
- 久米田裕子; 浅尾努; 飯田彰; 和田俊一; 二見真一郎; 藤多哲朗 防菌防ばい 22- (11) 663 -670 1994/11
- 藤多哲朗; 飯田彰; 田中善仁; 三原知浩; 田端守; 新宮徹朗; 武田美雄; YESILADA E; SEZIK E 香料・テルペンおよび精油化学に関する討論会講演要旨集 38th- 305 -307 1994/09
- 呉継洲; 森実千香子; 飯田彰; 藤多哲朗 日本生薬学会年会講演要旨集 41st- 189 1994/09
- 三原知浩; 飯田彰; 秋元直茂; 藤多哲朗; 高石喜久; 井上謙一郎; 久志本理 天然有機化合物討論会講演要旨集 36th- 713 -720 1994/09
- 浅見耕司; 神原武志; 和田俊一; 長岡康夫; 飯田彰; 藤多哲郎 日本膜学会年会講演要旨集 16th- 108 1994/05
- 長岡康夫; 神原武志; 飯田彰; 藤多哲朗; 浅見耕司 日本薬学会年会要旨集 114th- (Pt 4) 196 1994/03
- 和田俊一; 西村徹也; 飯田彰; 藤多哲朗; 浅見耕司 日本薬学会年会要旨集 114th- (Pt 4) 209 1994/03
- 城内正寿; 飯田彰; 藤多哲朗; 佐々木重夫; 米田雅彦; 広瀬良治; 井上謙一郎 日本薬学会年会要旨集 114th- (Pt 2) 212 1994/03
- トリコデルマビリデが産生するエルゴニンAの真菌の発育と形態に及ぼす作用防菌防黴誌 22- (11) 663 -670 1994
- イオンチャンネル形成ペプチド、トリコスポリンB-VIaとAib14-トリコスポリンB-VIaの脂質2分子膜と生体膜における構造と機能361 -364 1994
- トリコデルマビリデから単離された抗生ペプチド、トリコセリンA類とB類の1次構造35- (19) 3095 -3098 1994
- Yasuo Nagaoka; Akira Iida; Tetsuro Fujita Chemical and Pharmaceutical Bulletin 42- (6) 1258 -1263 1994
- 菌類代謝産物第16報 菌類トリコデルマハルツィアナムから単離された新規ペプタイボール、トリコキンジン1-VIIの構造日本薬学会誌 42- (5) 1070 -1075 1994
- 菌類代謝産物第13報 新規ペプタイボール、トリコデセニンIとIIのトリコデルマビリデからの単離と構造解析日本薬学会誌 42- (3) 489 -494 1994
- 菌類代謝産物第10報 ペプチド性抗生物質トリコスポリンB類のミトコンドリアの呼吸活性に関する効果日本薬学会誌 42- (4) 482 -485 1994
- Y NAGAOKA; A IIDA; T KANBARA; NL PIN; T FUJITA; K ASAMI; K ASAKA; E TACHIKAWA; T KASHIMOTO PEPTIDE CHEMISTRY 1993 361 -364 1994
- 呉継洲; 森実千香子; 飯田彰; 藤多哲朗 香料・テルペンおよび精油化学に関する討論会講演要旨集 37th- 409 -411 1993/10
- 西村徹也; 和田俊一; 飯田彰; 藤多哲朗; 外山信男 天然有機化合物討論会講演要旨集 35th- 242 -249 1993/09
- 安積欣志; 浅見耕司; 長岡康夫; 神原武志; 飯田彰; 藤多哲朗 日本膜学会年会講演要旨集 15th- 67 1993/05
- 長岡康夫; 飯田彰; 藤多哲朗; 立川英一; 樫本威志 日本薬学会年会要旨集 113th- (Pt 2) 224 1993/03
- 松浦耕司; 長岡康夫; 飯田彰; 藤多哲朗; 高石喜久 日本薬学会年会要旨集 113th- (Pt 2) 224 1993/03
- 和田俊一; 飯田彰; 藤多哲朗 日本薬学会年会要旨集 113th- (Pt 2) 205 1993/03
- 林利光; 玉田陽子; 森田直賢; 三輪嘉尚; 多賀徹; 飯田彰; 藤多哲朗 日本薬学会年会要旨集 113th- (Pt 2) 236 1993/03
- 西村徹也; 和田俊一; 飯田彰; 藤多哲朗; 外山信男 日本薬学会年会要旨集 113th- (Pt 2) 224 1993/03
- 菌類代謝産物第9報,膜修飾ペプチド,ヒペルシンの合成日本薬学会誌 41- (11) 1955 -1959 1993
- 菌類代謝産物第8報,抗生ペプチド,ヒペルシンの一次構造英国化学会誌 1993- (2) 381 -387 1993
- 菌類代謝産物第7報,抗生ペプチド,トリコスポリンの溶液中での構造英国化学会誌 1993- (2) 375 -379 1993
- 菌類代謝産物第6報,抗生ペプチド,トリコスポリン類のNMR研究英国化学会誌 1993- (2) 367 -373 1993
- 菌類代謝産物第5報,抗生ペプチド,トリコスポリン微量成分の迅速構造決定法英国化学会誌 1993- (2) 357 -365 1993
- 南米産植物スコポリアヅルシスの新化学物質植物化学 32- (2) 349 -352 1993
- 和田俊一; 飯田彰; 藤多哲朗; 金井みち子; 外山信男 日本薬学会年会要旨集 112th- (Pt 2) 210 1992/03
- 長岡康夫; 飯田彰; 藤多哲朗; 立川英一; 樫本威志 日本薬学会年会要旨集 112th- (Pt 2) 173 1992/03
- 松浦耕司; 飯田彰; 藤多哲朗; 高石喜久; 金井みち子 日本薬学会年会要旨集 112th- (Pt 2) 173 1992/03
- セルフリー系におけるタンパク発現の増幅核酸研究 20- (22) 5979 -5983 1992
- ユーオニジンA-1〜A-5,マユミ含有セスキテルペンエステル植物化学 31- (4) 1289 -1292 1992
- カルシウムイオン依存性カテコールアミン放出活性を有する抗生ペプチドの構造活性相関薬物動態 15,S10- 1992
- 和田俊一; 飯田彰; 実方正樹; 藤多哲朗; 田中裕美; 布施五郎; 金井みち子; RUDEWICZ P J; 外山信男 天然有機化合物討論会講演要旨集 33rd- 675 -682 1991/09
- 飯田順子; 村田武; IRELAND P; 高石善久; 飯田彰; 藤田哲朗 日本医用マススペクトル学会講演集 16- 199 -202 1991/09
- 実方正樹; 飯田彰; 藤多哲朗; 田中浩美; 榎章郎; 布施五郎; 金井みち子; RUDEWICZ P J 日本薬学会年会要旨集 111th- (Pt 2) 170 1991/03
- 長岡康夫; 飯田彰; 藤多哲朗 日本薬学会年会要旨集 111th- (Pt 2) 169 1991/03
- カルシウムイオン依存性に副賢髄質細胞からカテコールアミンを放出させる抗生ペプチドトリコスポリン類の単離と構造活性相関薬物動態 14,S106- 1991
- トリコスポリンB-3の副腎髄質細胞に対するカテコ-ルアミン放出活性分子薬理学 40- 1991
- 菌類代謝産物第4報.抗生ペプチドトリコスポリン-B-Vの合成日本薬学誌 38- (11) 2997 -3003 1990
- 菌代謝産物第3報 トリコスポリンB3bc,4b,c,d,6a,b,の構造英国化学会誌 8- (2) 1990
- トリコデルマポリスポーラムの産生する抗生ペプチドトリコスポリン類の構造決定抗生物質学会誌 41- (6) 814 -818 1988
- ロニセラタタリカ,ニチニチソウならびにインドジャボクのセコロガニンとインドールカルカロイドの生合成におけるイリダン骨格形成機構植物化学 25- (4) 839 -842 1986
- インドジャボクアルカロイド,アジマリンとボメリニンの生合成中間体日本薬学会誌 32- (9) 3764 -3767 1984
Books and other publications
- Proceedings of First AFSSA Conference on Food Safety and Food Security, GEO-REX RAPID ANALYSIS ASSESSMENT OF HEAVY METALS IN RICE, PADDY-RICE, AND SOILS.澤邊 昭義; 仲川 一彰; 竹田 竜嗣; 飯田 彰; 米虫 節夫; 玉木 聡史; 岩佐; 航一 (Joint work)Asian Food Safety and Security Association 2013/01
- Proceedings of the 4th European Conference on Chemistry for Life Science, Food additives or Cosmetic ingredients in Plygonum cuspidatum澤邊 昭義; 中村 貴俊; 藤井 善之; 竹田 竜嗣; 飯田 彰 (Joint work)Medimond s.r.l. 2011/12
- シロイヌナズナの開花を調節する因子飯田 彰 (Contributor)ファルマシア 2001/02
- 身近なカビから見つかった新しい発がんプロモーター飯田 彰 (Contributor)環境保全(京都大学) 2001
- トリコデルマ属菌から発見された新しい免疫抑制ペプチド飯田彰; 藤多哲朗 (Contributor)バイオサイエンスとインダストリー 2000/05
- Ion Channnel Properties of Disulfide-Linked Dimer Derivatives of Peptaibol, Trichosporin-B-VIaY. Nagaoka; A. Iida; S. Hatanaka; K. Tomioka; K. Asami; T. Fujita Peptide Chemistry 1996 1997
- Structure Determination of Ion Channel Forming Peptides, Trichosporins, in a Complex Mixture by LC/ES-MSMSL.-P. Neoh; Y. Nagaoka; A. Iida; T. Fujita Peptide Chemistry 1994 1995
- Ion Channel Forming Properties of Antibiotic Peptides, Trichosporin-B-VIa and Its Derivatives, in Planar Lipid BilayersY. Nagaoka; T. Kambara; A. Iida; K. Asami; T. Fujita Peptide Chemistry 1994 1995
- Structure and Function of Channel Forming Peptide, Trichosporin-B-VIa and Aib14-Trichosporin-B-VIa in Lipid Bilayers and BiomembranesY. Nagaoka; A. Iida; T. Kambara; Neoh Lian Pim; T. Fujita; K. Asami; K Asaka; E. Tachikawa; T. Kashimoto Peptide Chemistry 1993 1994
Lectures, oral presentations, etc.
- Isolation and evaluation of anti-inflammatory components in Tabebuia avellanedaeHikari Imazu; Mitsuaki Yamashita; Yoichi Fukuda; Akira IidaAIMECS 2023 2023/06
- STAT3 inhibitory activity of fluorine-containing naphthoquinone derivativesArisa Tsukamoto; Mitsuaki Yamashita; Akira IidaAIMECS 2023 2023/06
- Synthesis and antimicrobial activities of biosynthetic intermediates of furanonaphthoquinones derived from Tabebuia avellanedae [Not invited]Minami Koya; Mitsuaki Yamashita; Akira IidaAIMECS 2023 2023/06
- Synthetic Study of Anti-Obesity Iridoidhuhei Hata; Mitsuaki Yamashita; Shinya Hayakawa; Honoka Murakami; Youichi Fukuda; Akira Iida18th ACC 2019/12
- Design and synthesis of antibacterial and agrochemical naphthoquinonesRyuji Umeda, Mituaki Yamashita, Jun Sawano, Ayuka Tatsumi, Akira Iida18th ACC 2019/12
- Design and Synthesis of Class II-Selective Histone Deacetylase InhibitorsMurakami, H; Yamashita, M; Shimizu, Y; Tahara, T; Hayakawa, S; Iida, A18th ACC 2019/12
- Synthesis and evaluation of antimicrobial heterocycle-fused naphthoquinone derivativesJun Sawano; Mitsuaki Yamashita; Ryuji Umeda; Yuko Kumeda; Youichi Fukuda; Akira Iida18th ACC 2019/12
- Synthesis and structure activity relationship study of anti-obesity lignans [Not invited]Sena Okamura; Mitsuaki Yamashita; Youichi Fukuda; Akane Iwamoto; Ayana Ieda; Kazuko Iwamoto; Nobuhiro Zaima; Tatsuya Moriyama; Akira Iida22nd IUPAC International Conference of Organic Synthesis 2018/09
- Identification of novel lignan-based JAK/STAT pathway inhibitors by HEK-blue IL-6 reporter gene assay [Not invited]Ami Watanabe; Teruyuki Tahara; Yuko Yamano; Sena Okamura; Mitsuaki Yamashita; Youichi Fukuda; Akane Iwamoto; Akira Iida22nd IUPAC International Conference of Organic Synthesis 2018/09
- Total Synthesis of anti-obesity iridoid isolated from Tabebuia avellanedae [Not invited]Mitsuaki Yamashita; Shuhei Hata; Shinya Hayakawa; Honoka Murakami; Youichi Fukuda; Ayana Ieda; Kazuko Iwamoto; Nobuhiro Zaima; Tatsuya Moriyama; Akira Iida22nd IUPAC International Conference of Organic Synthesis 2018/09
- Synthesis and evaluation of antimicrobial heterocycle-fused naphthoquinone derivatives [Not invited]Jun Sawano; Mituaki Yamashita; Tomoyuki Kishida; Kakeru Shimanouchi; Yuko Kumeda; Youichi Fukuda; Akira Iida22nd IUPAC International Conference of Organic Synthesis 2018/09
- Copper-mediated Oxidative Tandem Reactions: One-pot synthesis of Polyhydropyrido[1,2-a]indoles and Tetracyclic Quinazolinones from 2-Arylindoles [Not invited]M. Yamashita; Y. Nishizono; S. Himekawa; A. Iida18th TETRAHEDRON SYMPOSIUM Asia Edition 2017/07
- Anti-obesity Effect of Taheebo Extract in Ovariectomized Mice [Not invited]Y. Fukuda; K. Iwamoto; C. Tokikura; A. Yamamoto; N. Zaima; M. Yamamoto; M. Noda; A. Ieda; W. Morita; M. Yamashita; A. IidaAIMECS 2017 2017/07
- Synthesis of Dual Inhibitor of Topoisomerase II and Histone Deacetylase [Not invited]S. Hayakawa; M. Yamashita; T. Tahara; A. Isse; Y. Sato; A. IidaAIMECS 2017 2017/07
- Chemopreventive activity of trichothecenes from Trichothecium roseum and their derivatives [Not invited]M. Fujiwara; K. Shimoura; Y. Fukuda; M. Yamashita; A. IidaInternational Chemical Congress of Pacific Basin Societies (PACIFICHEM 2015) 2015/12
- Production of bioactive furanonaphthoquinones by callus cultures of the Brazilian medicinal plant, Tabebuia avellanedae [Not invited]S. Kusakabe; Y. Fukuda; M. Yamashita; A. IidaInternational Chemical Congress of Pacific Basin Societies (PACIFICHEM 2015) 2015/12
- The effect of the Brazilian medicinal plant Myrcia sphaerocarpa on hyperglycemia and its active constituents [Not invited]M. Yoneda; D. Kida; T. Ohkawa; K. Ueda; Y. Fukuda; M. Yamashita; A. IidaInternational Chemical Congress of Pacific Basin Societies (PACIFICHEM 2015) 2015/12
- Production of chemopreventive naphthoquinones by callus cultures of Catalpa bungei [Not invited]M. Ohmiya; M. Mizukami; Y. Fukuda; S. Kasai; M. Yamashita; A. IidaInternational Chemical Congress of Pacific Basin Societies (PACIFICHEM 2015) 2015/12
- Anti-oxidative constituents of the Brazilian traditional medicine, Tabebuia avellanedae [Not invited]R. Hidaka; Y. Fukuda; S. Kasai; M. Yamashita; A. IidaInternational Chemical Congress of Pacific Basin Societies (PACIFICHEM 2015) 2015/12
- Production of bioactive furanonaphthoquinones by callus cultures of the Brazilian medicinal plant, Tabebuia avellanedae [Not invited]A. Takenaka; K. Ueda; M. Yamashita; M. Mizukami; T. Okawa; Y. Fukuda; H. Tokuda; A. IidaThe 15th Tetrahedron Symposium 2014/10
- Synthesis and evaluation of bioactive naphthoquinones from the Brazilian medicinal plant, Tabebuia avellanedae [Not invited]K. Ueda; M. Yamashita; M. Noda; K. Sakaguchi; Y. Fukuda; H. Tokuda; A. IidaThe 15th Tetrahedron Symposium 2014/10
- Synthesis of 2-Arylbenzoxazinone Derivatives from Indoles using Copper-mediated Oxidative Tandem Reactions with Molecular Oxygen [Not invited]Mitsuaki Yamashita; Seiya Himekawa; Akira IidaThe 15th Tetrahedron Symposium 2014/10
- Copper-mediated Tandem Intramolecular Cyclization/Coupling Reaction: Solvent Effect on Reaction Pathway [Not invited]Mitsuaki Yamashita; Akira IidaThe 15th Tetrahedron Symposium 2014/10
- Conjugates of Antitumor Naphthoquinones with NSAIDs: Synthesis and Evaluation of New Class of Cancer-preventing Agents [Not invited]hinichi Yamamoto; Takahiro Nishitani; Kazunori Ueda; Mitsuaki Yamashita; Harukuni Tokuda; Akira lidaAIMECS 2013 2013/10
- Production of Antitumor Furanonaphthoquinones by Callus Cultures of The Brazilian Medicinal plant, Tabebuia avellanedae [Not invited]Akiyasu Takenaka; Kazunori Ueda; Takahiro Okawa; Mitsuaki Yamashita; Harukuni Tokuda; Akira IidaAIMECS 2013 2013/10
- Conjugates of Naphthoquinones Isolated from Tabebuia avellanedae with NSAIDs: Synthesis and Evaluation of New Class of Cancer-preventing Agents [Not invited]M. Yamashita; T. Nishitani; T. Yamashita; K. Ueda; H. Tokuda; A. IidaThe 13th Tetrahedron Symposium 2012/11
- One-pot Synthesis of Indolequinones from 1,4-Naphthoquinones and Terminal Acetylenes [Not invited]M. Yamashita; K. Ueda; K. Sakaguchi; H. Tokuda; A. IidaThe 13th Tetrahedron Symposium 2012/11
- Concise Synthesis of Heterocycle-fused Naphthoquinones Utilizing A Tandem Addition-elimination/intramolecular Cyclization Reaction [Not invited]K. Ueda; D. Kurimoto; M. Yamashita; K. Sakaguchi; Y. Ugai; H. Tokuda; A. IidaThe 13th Tetrahedron Symposium 2012/11
- Synthesis of Indolequinones by Cascade Reaction of Sonogashira Coupling and Intramolecular Cyclization [Not invited]Mitsuaki Yamashita; Kazunori Ueda; Koichi Sakaguchi; Akira IidaAIMECS 2011 2011/11
- Efficient Synthesis of Antitumor Furanonaphthoquinone Utilizing Sonogashira Coupling and Hyolysis-cyclization Reaction [Not invited]Kazunori Ueda; Akira Iida; Mitsuaki YamashitaAIMECS 2011 2011/11
- CHEMOPREVENTIVE EFFECTS OF TRADITIONAL HERB TEA, TABEBUIA AVELLANEDAE ON IN VITRO AND IN VIVO CARCINOGENESIS SYSTEM [Not invited]Tokuda H; Iida A; Yamashita M; Kaneko M; Suzuki N11th European Nutrition Conference 2011/10
- Chemopreventive effects of Brazilian traditional medicine, Tabebuia avellanedae on in vitro and in vivo carcinogetic systems [Not invited]Tokuda H; Iida H; Suzuki NSecond AACR Conference on Frontiers in Basic Cancer Research 2011/09
- Synergistic cytotoxic effects of red beetroot (Beta vulgaris) food colorant E162 with anticancer drug doxorubicin (Adriamycin) against human prostate, Breast and Pancreatic tumor cells [Not invited]Kapadia G.J; Rao G.S; Iida A; Suzuki N; Tokuda H52th Annual Meeting of American Society of Pharmacognosy 2011/07
- The tea type Brazilian herb prevent lung cancer induced by 4-nitoroquinoline 1-oxie and glycerol [Not invited]Tokuda H; Yamashita M; Kaneko M; Suzuki N; Iida AAn AACR Special Conference “Stem cells, Development, and Cancer” 2011/03
- Physiological activities of health tea in Shimane [Not invited]M. Tongu; T. Yamada; K. Kawakami; R. Takeda; H. Kawamura; N. Hamahara; S. Komemushi; A. Iida; A. SawabeInternational Chemical Congress of Pacific Basin Societies 2010/12
- Skin-whitening agents in Smilax glabra [Not invited]R. Kubota; M. Itou; S. Ooguro; A. Iida; A. SawabeInternational Chemical Congress of Pacific Basin Societies 2010/12
- Atherosclerosis inhibitors in wine compression residue [Not invited]T. Yamada; M. Tongu; K. Kawakami; R. Takeda; H. Kawamura; N. Hamahara; S. Komemushi; A. Iida; A. SawabeInternational Chemical Congress of Pacific Basin Societies 2010/12
- Environmental analysis and water quality exposure monitoring of Yamato river water system using an in vitro bioassay system in Japan [Not invited]A. Sawabe; K. Ikushima; K. Sasai; R. Takeda; R. Kamata; S. Kageyama; D. Nakajima; F. Shiraishi; A. IidaInternational Chemical Congress of Pacific Basin Societies 2010/12
- Production of bioactive furanonaphthoquinones by callus cultures of the Brazilian medicinal plant, Tabebuia avellanedae [Not invited]A. Takenaka; R. Takeda; Y. Shimizu; M. Tomita; A. Sawabe; M. Yamashita; M. Kaneko; H. Tokuda; A. IidaInternational Chemical Congress of Pacific Basin Societies 2010/12
- Stereoselective synthesis and biological evaluation of bioactive constituents from the Brazilian plant Tabebuia avellanedae [Not invited]K. Ueda; M. Kotera; T. Nishitani; M. Yamashita; M. Kaneko; K. Nishimura; H. Tokuda; A. IidaInternational Chemical Congress of Pacific Basin Societies 2010/12
- Search for anti-inflammatory compounds using the SENCAR mouse-induced SST cells [Not invited]Kanazawa; I. Tanaka; M. Yoneyama; E. Hirotani; H. Tokuda; A. IidaInternational Chemical Congress of Pacific Basin Societies 2010/12
- Chemopreventive activity of Brazilian herbal tea, Tabebuia avellanedae; [Not invited]Tokuda H; Mitsuaki Y; Kaneko M; Suzuki T; Iida AThe 4th International Conference O-CHA (Tea) Culture and Science 2010/10
- Environmental Analysis and Water Quality Exposure Monitoring of Environmental Waters using an In Vitro Bioassay System in Nara. II [Not invited]A. Sawabe; K. Ikushima; K. Sasai; R. Takeda; R. Kamata; S. Kageyama; D. Nakajima; F. Shiraishi; A. IidaThe 26th Annual Conference on Soils, Sediments, Water and Energy 2010/10
- Heavy metal accumulation of Phytolacca americana hairy root [Not invited]R. Takeda; K. Minami; M. Tomita; A. Iida; T. Wakatsuki; A. Sawabehe 26th Annual Conference on Soils, Sediments, Water and Energy 2010/10
- Antiallergic active agents in Plygonum cuspidatum [Not invited]A. Sawabe; T. Nakamura; Y. Fujii; R. Takeda; A. Iida25th International Conference on Polyphenols 2010/08
- Environmental analysis and water quality exposure monitoring of Yamato river water system using an in vitro bioassay system in Nara [Not invited]A. SAWABE; K. IKUSHIMA; K. SASAI; R. TAKEDA; H. OGATA; R. KAMATA; S. KAGEYAMA; D. NAKAJIMA; F. SHIRAISHI; A. IIDAThe 58th Annual Conference on Mass Spectrometry and The 1st Asian & Oceanic Mass Spectrometry Conference 2010/06
- Prevention of MAPK pathway by Brazilian medicinal plant, Tabebuia avellanedae on peroxynitrite induced carcinogenesis [Not invited]Tokuda H; Kaneko M; Yamashita M; Suzuki N; Iida A101th Annual Meeting of American Association for Cancer Research 2010/04
- CHEMOPREVENTATIVE COMPONENTS FROM BRAZILIAN MEDICINAL PLANT, TABEBUIA AVELLANEDAE [Not invited]Harukuni Tokuda; Masafumi Kaneko; Mitsuaki Yamashita; Helmut Bacowsky; Akira IidaThe 50th Anniversary Meeting of the American Society of Pharmacognosy 2009/07
- ANTI-PROLIFERATIVE ACTIVITY OF THE TABEBUIA AVELLANEDAE EXTRACT AND ITS COMPONENTS [Not invited]Akira Iida; Masafumi Kaneko; Mitsuaki Yamashita; Harukuni TokudaThe 50th Anniversary Meeting of the American Society of Pharmacognosy 2009/06
- Regulation of the cell cycle on progression in A549 human lung cells and MCF-7 human breast cells treatment by Brazilian medicinal plant [Not invited]H. Tokuda; M. Kaneko; M. Yamashita; A. Iida8th Annual meeting of American Society for Cell Biology 2008/12
- Anti-cancer properties of extracts and constituents from Brazilian medicinal plant, Tabebuia avellanedae [Not invited]Harukuni Tokuda; Masamufi Kaneko; Helmut Bacowsky; Akira Iida5th International Conference of Society for Integrative Oncology 2008/11
- Chemopreventive effects of Brazilian herb oral feeding on UVB induced photocarcinogensis [Not invited]Harukuni Tokuda; Masafumi Kaneko; Mitsuaki Yamashita; Akira IidaSeventh Annual AACR International Conference Frontiers in Cancer Prevention Research 2008/11
- CONVENTIONAL SCREENING METHOD OF SHORT TERM IN VITRO ASSAY FOR CHEMOPREVENTIVE AGENTS [Not invited]Harukuni Tokuda; Mitsuaki Yamashita; Masafumi Kaneko; Akira Iida9th International Conference for Cell Biology 2008/10
- Tabebuia avellanedae and its constituents as antagonists of human derived tumor cells [Not invited]Harukuni Tokuda; Masafumi Kaneko; Mituaki Yamashita; Akira Iida7th Joint Meeting of AFERP, ASP, GA, PSE & SIF 2008/08
- Anti-cancer properties of extracts and constitutes from Brazilian medicinal plant [Not invited]Iida A; Kaneko M; Yamashita M; Bacowsky H; Tokuda HSecond JCA-AACR Special Joint Conference “The Latest Advances in Breast Cancer Research from Basic Science to Therapeutic” 2008/07
- Tabebuia avellanedae extract and its constituents as natural anti-tumor and anti-tumor promoting substance [Not invited]Tokuda H; Kaneko M; Hatanaka S; Suekata S; Iida ASociety for Integrative Oncology Shanghai International Symposium 2008/04
- Growth inhibitory effects of naphthoquinones type compound in human original cancer cell line [Not invited]Tokuda H; Kaneko M; Iida A99th Annual Meeting of American Associaiton for Cancer Research 2008/04
- Evaluation for anti-tumor and anti-tumor promoting activity from herbal medicine, Tabebuia avellanedae and its constituents [Not invited]H. Tokuda; A. Iida4th International Conference of SIO 2007/11
- Cancer chemopreventive activity of a traditional plant against advanced glycation endproduct-induced carcinogenesis [Not invited]Tokuda H; Konoshima T; Takasaki M; Iida A48th Annual Meeting of American Society of Pharmacognosy 2007/07
- Efficacy evaluation of Brazilian herbal material against tumor promoting stage [Not invited]Tokuda H; Iida A10th European Nutrition Conference 2007/07
- Ultraviolet B light initiating activity of two-stage mouse skin carcinogenesis and its regulation of cGMP [Not invited]Tokuda H; Takayasu J; Iida A3rd International Conference on cGMP 2007/06
- Chemopreventive Activity of Natural Source Compounds against Advanced Glycation Endproduct Induced Carcinogenesis [Not invited]Tokuda H; Iida A; Kapadia G; Nishino H98th Annual Meeting of American Associaiton for Cancer Research 2007/04
- ANTI-TUMOR ANDANTI-TUMOR PROMOTING ACTIVITY FROM BRAZILIAN TRADITIONAL MEDICINE,TABEBUIA AVELLANEDAE [Not invited]Tokuda H; Iida A; Nishino HAmerican Association for Cancer Research and American Chemical Society joint Conference 2007/02
- Chemopreventive Constituents of Brazilian Traditional Medicine, Tabebuia avellanedae (Taheebo) [Not invited]A. Iida; H. Tokuda; H. Nishino; S. UedaThe 9th International Congress on Ethnopharmacology 2006/08
- Chemopreventive Effect of Brazilian Traditional Medicine, Tabebuia avellanedae [Not invited]Chemopreventive Effect of Brazilian; Traditional Medicine; Tabebuia avellanedaeThe 47th Annual Meeting of the American Society of Pharmacy 2006/08
- Chemopreventive Effect of Brazilian Traditional Medicine, Tabebuia avellanedae [Not invited]H. Tokuda; A. Iida; S. Ueda4th International Conference on Aromatic and Medicinal Plants From French Overseas Regions 2006/07
- Chemopreventive activity of natural compoinds on nitric acid donors induced mouse skin carcinogegenesis [Not invited]H. Tokuda; F. Enjo; T. Konoshima; M. Takasaki; J. Takayasu; A. Iida; H. HoyokuFourth International Conference Biology, Chemistry and Therapeutic Applications of Nitric Oxide 2006/06
- Potential natural compounds for chemopreventive activity on UVB-induced carcinogenesis [Not invited]H. Tokuda; A. Iida; M. Okada; J. Takayasu; G. J. Kapadia; N. HoyokuAmerican Association for Cancer Research 97th Annual Meeting 2006 2006/04
- Design and synthesis nucleoside-based on novel topoisomerase II inhibitors [Not invited]H. Matsumoto; A. Iida; K. Tomioka; S. WadaPACIFICHEM 2005 2005/12
- Chemopreventive activity of nitric oxide donors induced by natural resource compounds [Not invited]H. Tokuda; A. IidaPACIFICHEM 2005 2005/12
- Chemopreventive Effect of Brazilian Traditional Medicine, Tabebuia avellanedae [Not invited]A. Iida; H. Tokuda; H. Nishino; S. UedaPACIFICHEM 2005 2005/12
- Chemopreventive Activity of Naturally Occurring Compounds against Advanced Glycation Endproducts Induced Carcinogenesis [Not invited]H. Tokuda; M. Ogata; F. Enjo; J. Takayasu; A. Iida; H. NishinoInternational Congress and 53rd Annual Meeting of the Society for Medicinal Plant Research 2005/08
- Chemopreventive Activity of Natural Compounds on Nitric Oxide Donors Induced Mouse Skin Carcinogenesis [Not invited]H. Tokuda; F. Enjo; T. Konoshima; M. Takasaki; A. Iida; H. NishinoInternational Congress and 53rd Annual Meeting of the Society for Medicinal Plant Research 2005/08
- Chemopreventive Effect of Brazilian Traditional Medicine, Tabebuia avellanedae [Not invited]A. Iida; H. Tokuda; H. Nishino; S. Uedanternational Congress and 53rd Annual Meeting of the Society for Medicinal Plant Research 2005/08
- Brazilian Traditional Medicine, Tabebuia avellanedaeext.: A New Useful Tea as Chemopreventor [Not invited]A. Iida; H. Tokuda; H. Nishino; S. UedaISCap Symposium in Kyoto 2005/05
- DESIGN AND SYNTHESIS OF NUCLEOSIDE-BASED NOVEL TOPOISOMERASE II INHIBITORS [Not invited]Akira Iida; Kiyoshi Tomioka; Shun-ichi Wada6th Australia/Japan Synposium on Drug Design & Development 2004/07
- Design and Synthesis of Nucleoside-based DNA Topoisomerase II Inhibitors [Not invited]Akira Iida; Hironobu Matsumoto; Kiyoshi Tomioka; Shun-ichi WadaKorea-Japan Young Scientists Joint Symposium 2003/07
- A Novel Tumor Promoting Sesquiterpene from Trichothecium roseum [Not invited]Akira Iida; Masafumi Kaneko; Kazuhide Konishi; Kiyoshi Tomioka; Harukuni Tokuda; Hoyoku Nishino3rd IUPAC 2002 International Symposium on the Chemistry of Natural Products 2002/07
- TRICHOTHECINOL A, B and C, POTENT ANTITUMOR PROMOTOING SESQUITERPENOIDS FROM TRICHOTHECIUM ROSEUM [Not invited]Akira Iida; Harukuni Tokuda; Kazuhide Konishi; Kiyoshi Tomioka; Teruo Mukainaka; Junko Takayasu; Masato Okuda; Hoyoku Nishino43rd Annual Meeting of the American Chemical Society of Pharmacognosy and 3rd Monroe Wall Symposium 2002/07
- Formal total synthesis of (+)-calonectrin [Not invited]Akira Iida; Konishi Kazuhide; Kiyoshi TomiokaInternational Chemical Congress of Pacific Basin Societies 2000/12
- External Chiral Ligand Controlled Asymmetric Michael Addition of Lithium Ester Enolates to alpha, beta-Unsaturated Esters [Not invited]Akira Iida; Hirokazu Suzuki; Konishi Kazuhide; Kiyoshi TomiokaThe 8th International Conference on New Aspects of Organic Chemistry 2000/07
- Enantioselective conjugate addition reaction of organolithiums with BHA enoates mediated by an external chiral ligand [Not invited]Y. Asano; A. Iida; K. TomiokaThe 7th International Kyoto Conference on New Aspects of Organic Chemistry 1997/11
- 3-DEOXYURSOLIC ACID, A NOVEL HUMAN DNA TOPOISOMERASE II INHIBITOR [Not invited]kira Iida; Masahiro Kano; Kiyoshi TomiokaInternational Symposium on Natural Medicines 1997/10
- ION CHANNEL PROPERTIES AND ACTIVITY OF CATECHOLAMINE SECRETING ACTIVITY OF PEPTAIBOLSTRICHOSPORIN-B-VIA, AND ITS DERIVATIVES [Not invited]Yasuo NAGAOKA; Akira IIDA; Takeshi KAMBARA; Koji ASAMI; Eiichi TACHIKAWA; Tetsuro FUJITAThe Fourth International Conferenceon Biotechnology of Microbial Products: Novel Pharmacological and Agrobiological Activities 1995/04
- TRICHOCELLINS, CHANNEL-FORMINHG PEPTIDES FROM TRICHODERMA VIRIDE [Not invited]Akira IIDA; Shun-ichi WADA; Tetsuya NISHIMURA; Koji ASAMI; Tetsuro FUJITAThe Fourth International Conferenceon Biotechnology of Microbial Products 1995/04
- New Peptaibols from Trichoderma viride [Not invited]Syun-ichi Wada; Akira Iida; Tetsuro Fujita; Michiko Kanai; Nobuo ToyamaInternational Conference on Biological Mass Spectrometry 1992/09
- Structural Elucidation of New Antibiotic Peptides from Hypocrea peltata [Not invited]Koji Matsuura; Akgul Yesilada; Akira Iida; Tetsuro Fujita; Yoshihisa Takaishi; Michiko KanaiInternational Conference on Biological Mass Spectrometry 1992/09
- Synthesis of Trichosporin-B-VIa and VIb, Which cause Catecholamine Secretion from Adrenal Chromaffin Cells [Not invited]Yasuo Nagaoka; Akira Iida; Tetsuro Fujita; Eiichi Tachikawa; Takeshi Kashimoto18th IUPAC Symposium on the Chemistry of Natural Products 1992/08
- Identification of New Antibiotics from Trichoderma polysporu [Not invited]J. Iida; A. Iida; T. Fujita; Y. Takaishi; P. A. IrelandThe 39th ASMS Conference on Mass Spectrometry and Allied Topics 1991/04
- Stractural Determination of of New Antibiotic Peptides from Trichoderma Harzianum [Not invited]Akira Iida; Tetsuro Fujita; Masahiro Okuda; Shinichi UesatoThe 17th IUPAC International Symposium on the Chemistry of Natural Products 1989/10
- Structure of Trichosporin-B-IIIb, c, IVb, c, d and VIa, b from Trichoderma polysporum [Not invited]Akira Iida; Tetsuro Fujita; Masahiro Okuda; Shinichi UesatoThe Meeting on Peptides Forming Voltage Dependent Channels 1988/10
- Isolation of Antibiotic Peptides, Hypelecin-B-I, II, III, IV, and V from Hypocrea peltata [Not invited]Tetsuro Fujita; Akira IidaThe Meeting on Peptides Forming Voltage Dependent Channels 1988/10
- Conformational Analysis of Trichosporin-B-V by CD and NMR Spectroscopy [Not invited]Tetsuro Fujita; Akira Iida; Shinichi Uesato; Yoshihiro Kuroda; Tetsuro Shingu1988 The 16th IUPAC International Symposium on the Chemistry of Natural Products 1988/05
- Trichosporin-B-III causes Catecholamine Secretion from Adrenal Chromaffin Cells: A Possible Voltage-Dependent Ca2+ Channel Forming Ionophore [Not invited]Eiichi Tachikawa; Saburo Takahashi; Katsuro Furumachi; Takeshi Kashimoto; Akira Iida; Yasuo Nagaoka; Tetsuro Fujita; Yoshihisa Takaishi1st IUBMB Coference Biochemistry of Diseases
Affiliated academic society
Research Themes
- Japan Society for the Promotion of Science:Grants-in-Aid for Scientific ResearchDate (from‐to) : 2009 -2011Author : IIDA Akira; KANEKO MasafumiSufficient quantities of sesquiterpene TTC-A, which is a metabolite of Trichothecium roseum showing anti-tumor promoting and tumor promoting effects simultaneously, were obtained by selecting various strains and modifying cultural conditions. TTC-A is known to be an inducer of multinucleated Raji cells. This was deduced to result from modulation of cell cycles regulated by signal transductions associated with ras gene and cell differentiation.
- Japan Society for the Promotion of Science:Grants-in-Aid for Scientific ResearchDate (from‐to) : 2003 -2005Author : HONDA Gisho; TAKEDA Yoshio; KIUCHI Fumiyuki; IIDA Akira; ITO Michiho; HAYASHI HiroakiAs the third project of comparative study on traditional medicines of Turkic people, we performed ; Field surveys in the area of the Northwest (Aral Sea) region of Uzbekistan (2003), Alborze mountain region along the Caspian Sea in Iran (2004), and Shinjan provinces in China (2005), and Phytochemical analysis of plant materials collected in the field survey, and published 13 scientific reports during these 3 years. In Uzbekistan, the environmental destruction around Aral Sea has been progressed because of the irrigation of desert nearby Amu Dar Ya basin. Samples of wild licorice (Glycyrrhiza glabra), one of the most popular and the most valuable medicinal plants in this region, and some other medicinal plants were collected for the purpose of evaluation. Although folk healers called "Tabib" inherit the traditional knowledge of folk medicines in Uzbekistan, their knowledge is the mixture of domestic in Uzbekistan and of introduced from Europe during the period of Soviet Union. In 2004, we went into the Alborze mountains where the Turkmen people isolated from Iranian people keep their tradition till today and got some interesting information on folk medicines having similar names and uses to those of Turkey and Uzbekistan. We made field research in the West of China where Uygur, one of a Turkic people, are dominant in 2005, and confirmed that Hotan still keep the tradition of Arabic medicines introduced in the Middle Ages.
- Japan Society for the Promotion of Science:Grants-in-Aid for Scientific ResearchDate (from‐to) : 2003 -2005Author : TOMIOKA Kiyoshi; IIDA Akira; YAMADA Ken-ichi1)A precursor of Taxol side chain was stereoselectively synthesized in high yield by the oxidation of the dianion resulting from the asymmetric addition of a chiral lithium enolate, derived from a chiral acetate, to N-PMP imine in the presence of a lithum amide. 2)A formal total synthesis of (-)-1-deoxylycorine was achieved using tandem conjugate addition-cyclization reaction of aryllithium and alkenoate controled by a chiral ligand. 3)5-Arylcyclohexenones and trans-3,6-disubstituted cyclohexanons were synthesized with high stereoselectivity in good yields using an amidophosphane-rhodium catalyzed asymmetric addition of arylborane reagents to substituted cyclohexenones. 4)Chiral amino alcohol controlled asymmetric addition of alkynylzincs to nitroalkenes and aldehydes was developed. 5)Chiral oxazoline ligand controlled catalytic asymmetric intramolecular hydroamination was developed. 6)Chiral amidophosphane ligand controlled asymmetric addition of dialkylzincs to nitroalkene was developed. 7)A formal synthesis of (+)-halichlorine was achieved using tandem Michael addition-alkylation protocol controlled by a chiral diether ligand.
- 日本学術振興会:科学研究費助成事業Date (from‐to) : 2003 -2004Author : 富岡 清; 飯田 彰; 山田 健一当研究室ではこれまでにジメチル亜鉛と酸素をラジカル開始剤とする、エーテルα位水素引き抜きによる直接的新規エーテルラジカル発生法を見出している。発生したエーテルラジカルはイミンと反応し高収率で付加体を与える。本研究は我々の見いだしたエーテルラジカルの直接的発生法を機軸とする反応を開発するとともに、新たな反応設計の基盤となる活性種の化学的性質に関する新知見を得ることを目的とする。本年度は以下に示す成果を上げた。 1)ジメチル亜鉛を開始剤とするヨウ化アルキルからの一級アルキルラジカルの発生とイミンに対する付加反応を検討した。その結果、三フッ化ホウ素エチルエーテル錯体と触媒量の二価銅トリフラート存在下反応が劇的に加速することを見出し、一級アルキル付加体を高収率で得ることに成功した。本手法は二級アルキルラジカルの発生および付加反応にも適用可能である。 2)ジメチル亜鉛を開始剤とするα,β-不飽和カルボニル化合物に対するエーテル類の付加反応を検討した。α,β-不飽和N-トシルイミンをTHFおよびジメチル亜鉛の溶液に六時間かけてゆっくり滴下するとTHFの1,4-付加体が高収率で得られた。また、三フッ化ホウ素エチルエーテル錯体存在下、アルキリデンマロネートに対する付加体が高収率で得られた。 3)ジメチル亜鉛を開始剤としてキラルN-スルフィニルイミンに対する一炭素、二炭素単位エーテルの付加反応を検討した。その結果3:2〜9:1の立体選択性、および良好な収率で付加体を得ることに成功した。
- Japan Society for the Promotion of Science:Grants-in-Aid for Scientific ResearchDate (from‐to) : 2000 -2002Author : HONDA Gisho; KIUCHI Fumiyuki; TAKAISHI Yoshihisa; TAKEDA Yoshio; ITO Michiho; IIDA AkiraThis research was the secondary project of the field survey on traditional medicines of Turkic people in Central Asia. We performed; (1) Field survey on traditional and/or folk medicines and on medicinal plants of Uzbekistan in the area of Tardkurgan and Namangan which are along Tienshan-North road of the Silk Road, (2) Phytochemical analysis of plant materials collected in the field survey. Finally, specimens of folk medicines and medicinal plants collected for the project (1) were counted up to 400, and results of (2) were published in 26 of scientific papers during these 3 years. As for specimens collected for (1), most of the origins of them were identified. Not a few herb samples were turned out to be affected by European and Russian medicines. And licorice samples, aerial and underground parts and also seeds, were collected in the area from Almaty (Kazakhstan) to Tashkent (Uzbekistan). Vegetation area of licorice plants, Glycyrrhiza uralensis and G. glabra, was wide, and it turned out to be interesting that there were many licorice plants which was supposed to be a crosshybridized species between G. uralensis and G. glabra. This presumptive hybrids might be good samples for the phylogenetic relationship between these two species. As for the phytochemical studies of (2), 13 species of Gentiana olivieri, Inula macrophylla, Ferula foetida, F. kuhistanica, F. pallida, F. penninervis, F. sumble, Rheum maximowiczii, Scutellaria hematochlora, Prangos tschimganica, P. pabularia, Phlomis spinidens, Dracocephalum komarovi, were analyzed for their characteristic components as well as their biological activities, and finally, more than 100 secondary metabolites including many new compounds, such as terpenoids (sesquiterpenes, diterpenes), coumarines, flavonoids, and sulphate-containing compounds, had been isolated and were determined their structures.
- Japan Society for the Promotion of Science:Grants-in-Aid for Scientific ResearchDate (from‐to) : 2000 -2002Author : IIDA AkiraDNA topoisomerases are nuclear enzymes responsible for biological processes of DNA metabolism such as replication, transcription, recombination and chromosome segregation at mitosis. Therefore, compounds that inhibit these enzymes as the primary cellular target are of special interest since those are promising candidates for anticancer drugs. Our previous studies demonstrated that the ortho-quinone or catechol moiety in aza-deoxypodophyllotoxin analogues plays a critical role in showing topoisomerase II (topo II) enzyme inhibition, in which proton transport during cutting and resealing of DNA is presumed to be blocked by a small structural unit like ortho-quinone. In this research project, we have aimed at the synthesis and biological evaluation of nucleoside analogues as novel topo II inhibitors that are hybrids with aza-podophyllotoxin analogues. Our synthesis contains a Michael addition reaction of 1, 3-dithianes to chiral butenolide, an equivalent to the deoxyribose moiety of a nucleoside, and a Silyl-Hilbert-Johnson reaction as key reactions. As predicted, ortho-quinone and catechol showed topo II inhibition, while dimethoxy derivative was inactive. In addition to the active nucleosides, it was found that several lactone derivatives lacking a thymine base also inhibited topo II, indicating that a thymine base is not requisite to topo II inhibition. Structure-activity relationship of these lactone derivatives showed that the presence of the TBS group or dithiane moiety in the molecule is essential for topo II inhibition in the case of non-nucleoside derivatives.
- 日本学術振興会:科学研究費助成事業Date (from‐to) : 1999 -2001Author : 富岡 清; 山田 健一; 飯田 彰; 長岡 康夫α,β-不飽和カルボニル化合物に対する有機金属化合物及びヘテロ原子求核剤の共役付加反応は有機化合物の骨格形成の根幹をなす炭素-炭素結合や炭素-ヘテロ原子結合の形成法として極めて重要であり汎用されてきた。一方、アルケニルホスホナートは不飽和カルボニル化合物と同様に共役付加反応における捕捉剤の一つであるが、その反応特性の理解、その特性を生かした合成化学的利用が未だ不充分である。本研究の目的はアルケニルホスホナートに対する炭素求核剤及び窒素求核剤の反応特性の理解の深化とその特性を利用した新規合成反応の開発である。本研究により昨年までにアルケニルホスホナートのHorner-Wadswors-Emmons型反応を用いる新規アレン合成法及び分子内に二つのアルケニルホスホナート部位を有する基質を用いる分子内環化反応について報告した。 本年度は昨年度報告した環化反応を用いて酒石酸から誘導したキラル環状ビスホスフィンオキシドを中間体としてキラル環状ビスホスフィン、及びキラル環状ホスフィノカルボン酸を合成した。キラル環状ビスホスフィンオキシドをロジウム触媒による不斉水素化反応の不斉配位子として用いると、プロキラルなエナミドから高収率、高エナンチオ選択的に光学活性アミノ酸誘導体が得られた。またキラル環状ホスフィノカルボン酸をパラジウム触媒による不斉アリル化反応の不斉配位子として用いると、マロン酸エステルが良好な化学収率、高いエナンチオ選択性でアリル化されることを見いだした。
- Japan Society for the Promotion of Science:Grants-in-Aid for Scientific ResearchDate (from‐to) : 1998 -2001Author : TOMIOKA Kiyoshi; YAMADA Ken-ichi; IIDA AkiraWe have developed three types of new activation technology ; the activation of lithium ester enolates by a chiral lithium amide having ether moiety (1), of less reactive organometallic reagents, such as organozinc and organoboran by a complex of a chiral amidophosphine and a transition metal (2), and of lithium thiolate by a chiral amino ether (3). 1. In the presence of a chiral lithium amide having ether moiety, thereaction of lithium ester enolates with imines gave β-lactains in up to 96% yield and 74% ee. This technology was also applicable to the addition of lithium ester enolates to α,β-unsaturated esters to give the adducts in up to 67% yield and 92% ee. 2. In the presence of a catalytic amount of a chiral amidophosphine and copper(II) triflate ; the reaction of 4,4-dimethyl-2-cyclohexenone and diethylzinc gave the ethyl adduct with 64% ee. The application of this amidophosphine-copper-diethylzinc system to the reaction with imine was successful, giving ethyl adducts in up to 97% yield and 94% ee. Furthermore, the chiral amidophosphine ligand was applicable to the rhodium-arylboronic acid system. In the presence of a catalytic amount of the chiral amidophosphine and rhodium(I), aryl boronic acidsreacted with 2-alkenones to provide 3-arylalkanones in up to 99% yield and 96% ee. We are accumulating the experimental evidence that the chiral amidophosphine ligand is a so-called hemilabile ligand in this rhodium complex. 3. In the presence of a chiral amino ether, lithium thiolates added to α,β-unsaturated esters and the resulting lithium ester enolate was enantioselectively protonated. Thus, using α,β-unsaturated esters having no β-substitoent, the addncts with up to 92% ee were obtained. When a chiral α,β-unsaturated ester having formyl group was used as an acceptor, the intermediate lithium enolate reacted withthe formyl group in the intramolecular fashion to give cyclized products in good diastereoselectivity. This cyclization was nicely applied to the synthesis of (-)-neplanocin A.
- 日本学術振興会:科学研究費助成事業Date (from‐to) : 2000 -2000Author : 石橋 正己; 小鹿 一; 大島 吉輝; 太田 富久; 飯田 彰; 貫名 学; 浪越 通夫本企画調査研究は、将来、「特定領域研究」への申請を視野に入れて、これまであまり科学者が手がけて来なかった未利用菌類を対象として、新規有用物質の探索ならびに持続的資源化システムの開発をめざすものであり、本年度の活動実績は以下の通りである。 1.研究打合わせ会議の開催:本企画調査研究の活動の一環として、研究打合わせ会議を平成12年9月8日学術総合センターで開催した(研究組織メンバー6名参加)。活発な意見交換の結果、将来の「特定領域研究」への申請のためには、(1)メンバー個々のさらなる研究実績の積み重ね、および(2)シンポジウムならびに総説特集の出版等による本研究分野の啓蒙活動を行うことが必須であるという結論に至った。従って本研究課題のもと企画調査研究を平成13年度も継続させることが重要であり、平成13年秋に特定領域研究(B)を申請するという計画を立てた。 2.シンポジウム開催と総説出版:上記会議の結果に基づき、(1)シンポジウム開催、(2)総説出版に関して、具体的活動を行った。(1)平成13年度日本生薬学会年会における公募シンポジウムに「未利用菌類の資源化」というタイトルで申込み、採択された。従って、平成13年9月8日(土)金沢において開催することが決定した。第2回目の同シンポジウムの開催も平成14年春に計画している。(2)中編あるいは短編の総説を各メンバーが執筆することで合意し、日本農芸化学会から出版されている「化学と生物」誌への投稿を同誌編集委員へ申込んだ。編集委員会で議論後、既に一部のメンバーへの執筆依頼が来ている。 3.セミナー活動:関東地区では、微生物(菌類)を対象とした天然物化学研究者・学生が集うセミナーとして、「菌化学セミナー」が毎年開催されており、平成12年度も10月28日に明治薬科大学で第12回目が開催され、研究代表者およびその研究室メンバーが参加・発表した。
- Japan Society for the Promotion of Science:Grants-in-Aid for Scientific ResearchDate (from‐to) : 1998 -1999Author : IIDA AkiraNovel trichothecenes, trichothecinol A, B and C isolated from Trichothecium roseum, acts as strong tumor promoters. Their mode of action in tumor promotion is different from those of other known tumor promoters, suggesting the presence of unknown mechanisms on carcinogenesis. In this project, an efficient synthetic route of trichithecenes has been developed in order to investigate biological properties of trichothecinols. There are two important steps in the present synthetic strategy for trichothecenes. One is a stereoselective introduction of a methyl group into the chiral butenolide derived from D-mannitol in the early stage of the synthesis. The other is a construction of the cis A/B ring via the steric inversion at the γ-position of the lactone. According to the synthetic scheme, the first key intermediate was stereoselectively prepared from the chiral butenolide, followed by the steric inversion and ring closing olefin metathesis to afford the desired spirolactone in high chemical yield. Reductive opening of the lactone moiety, protection, oxidation and methylation gave the tertiary alcohol that is a intermediate before ring closing to the cis A/B ring. One flask reaction by acidic treatment of the alcohol yielded the ring closing product that has desired ring juncture for the cis A/B ring in good yield. Several steps led to an authentic compound reported by the Kraus group. In conclusion, a formal total synthesis of trichothecene was enantioselectively done in high yield using D-mannitol as the starting material. Ring closing olefin metathesiswas a very useful method for the construction of the spirolactone, one of the most important key intermediate in the synthetic route.
- Japan Society for the Promotion of Science:Grants-in-Aid for Scientific ResearchDate (from‐to) : 1995 -1997Author : TOMIOKA Kiyoshi; INOUE Isao; NAGAOKA Yasuo; IIDA AkiraAs our continuing studies toward enantioselective reactions of organolithiums based on an external chiral ligand, we have developed the catalytic asymmetric addition of thiophenol to enoates using lithium thiophenolate as a catalytic nucleophile which has higher reactivity than thiophenol activated by amine. The 2-substituent of thiophenol exerts profound effects on reactivity and enantioselectivity in the asymmetric addition reaction with enoates catalyzed by lithium thiophenolate and a chiral ligand. The bulky substituent gave the higher reactivity and enantioselectivity. The asymmetric reaction of 2-trimethylsilylthiophenol with methyl enoates was catalyzed by the combination of 0.08 eq of lithium 2-trimethylsilylthiophenolate and 0.1 eq of the chiral ligand, (1R,2R)-1-dimethylamino-2-(2-methoxyphenoxy)-1,2-diphenylethane, in toluene-hexane (1 : 1) to afford the corresponding methyl 3-(2-trimethylsilylphenylthio) carboxylates in excellently high ees. The chiral ligand was recovered quantitatively for reuse without racemization. The 2-trimethylsilyl group was protodesilylated by treatment with triflic acid to give the corresponding 3-phenylthiocarboxylates in excellently high yield without racemization. The kinetic control is operative in the asymmetric addition reaction.
- Japan Society for the Promotion of Science:Grants-in-Aid for Scientific ResearchDate (from‐to) : 1995 -1997Author : TOMIOKA Kiyoshi; NAGAOKA Yasuo; IIDA AkiraWe have reported the successful chiral ligand-mediated asymmetric 1,2- and 1,4-addition reactions of organolithiums to various imines of aryl and alpha, beta-unsaturated aldehydes Thus, organo-lithiums add to the cyclohexylimines 1,2 (R=c-C6Hll) in 1,4-fashion to give, after hydrolysis, the corresponding aldehydes in up to 99% ee and in high to good yields. On the other hand, the reactions with arylimines exclusively afford 1,2-adducts in up to 90% ee and in nearly quantitative yields, giving us a good method for the preparation of chiral amines. It is also interesting in that the reactions with both cyclohexyl- and arylimines of 1-fluoronaphthalene-2-carbaldehyde exclusively proceed in 1,4-fashion to provide nucleophilic aromatic substitution products in high yields. Since deep understanding of the factors governing regioselectivity is a long-standing problem and essential for further development of the much more effective catalytic asymmetric reactions of the ene-imines. we carried out molecular orbital calculations and revealed that the experimentally observed regioselectivity is rationalized by the relative magnitude of the LUMO coefficients.
- 日本学術振興会:科学研究費助成事業Date (from‐to) : 1996 -1996Author : 富岡 清; 飯田 彰本年度から京大薬学部に研究拠点を移したのに伴って、トポイソメラーゼ阻害活性天然物の探索研究者を共同研究者に加えることが可能となったので、一層の今後の進展が期待できる。 非天然型リグナン系化合物の構造をほんの一部修飾すると、微小管の凝集阻害に加えてDNAトポイソメラ-セ阻害活性をも示すこと、或いは、微小管凝集作用を全く失うがトポイソメラーゼ阻害活性は維持すること、など興味深い事実が明らかになってきた。 本研究では、天然物を手本とした微小管凝集阻害とトポイソメラ-セ阻害活性発現の分子構造論的基礎の確立を合成化学的に展開すると共に、より有効な抗腫瘍活性の発現を可能とする分子構造の創製を目論んだ。合成非天然型リグナン系化合物、特にポドフィロトキシン及びステガナシン系化合物のトポイソメラーゼII阻害活性発現分子の構造の特徴を、既に合成したもの及び新規合成化合物をもとに明らかにした。 1 基本構造の各部分に特徴ある化学修飾を加えた化合物を合成した。 2 また、微小管の凝集阻害活性及び細胞成長阻害活性と分子構造との相関を明らかにした。 3 次いで、凝集阻害活性とトポイソメラーゼ阻害活性を併せ持つ有効な新規化合物を化学合成的に明らかにする検討を行った。そのために、配座の固定可能な6原子直鎖状分子の設計、合成、さらに配座の検討を行った。 さらに、天然物を手本としたトポイソメラーゼ阻害活性を発現する分子構造についても例示的ではあるが、新たな展開を得た。
- Japan Society for the Promotion of Science:Grants-in-Aid for Scientific ResearchDate (from‐to) : 1995 -1996Author : IIDA Akira; NAGAOKA Yasuo20-residue peptaibols, trichosporins-B produced by the fungus Trichoderma polysporum, forms voltage-dependent ion channels in planar lipid bilayr membranes. To clarify primary factors for channel stabilization and to develop new functional materials such as artificial ion channels, trichosporin derivatives including a template-assembled dimer and tetramer and two disulfide-linked dimers were synthesized and their channel-forming properties were investigated. The results obtained in this study were summarized as followes ; 1.The chennels induced by truncated and elongated derivertives were unstable, suggesting that peptide length fitting the membrane thickness is quite important. 2.The Pro-kinked structure is not essential for voltage-dependent channel formation and very important for forming stable channels with large pore size. 3.Peptide lipophilicity promotes peptide aggregation and this is not in accordance with channel stability. 4.Stability of channels is influenced by the states of supermolecules consisting of pepides, lipids and water. 5.All chemically assembled peptides (helix bundle) form very long-lasting channels, supporting that peptaibol channels can be explained through the barrel stave model. 6.Success in formation of the stable channels may lead to developing novel functional materials.
- Japan Society for the Promotion of Science:Grants-in-Aid for Scientific ResearchDate (from‐to) : 1993 -1995Author : FUJII Nobutaka; FUJIMOTO Masafumi; HAYASHI Kyozo; IIDA Akira; TAMAMURA HirokazuThe following investigations were caried out for development of diagnostic immunoassay method for senile dementia. The report which deny the significant correlation between the plasma levels of neurotrophins and Alzheimer's disease forced us to change the initial plan, however, basic study conducted here should contribute to the future research on daignostic and/or therapeutic use of neurotrophins for senile dementia. 1. A new chemoselective purication method of synthetic peptides based on the bifunctional SH-introducing reagent was developed. In addition, specific affinity purification method using a reversible biotinylating reagent was developed for the final purification of synthetic peptides by solid phase technique. 2. Synthetic study on neuroprophins was carried out in combination with newly-developed chemoseletcive purification method of synthetic peptides and fragment condensation method on solid support. However, low purification yields of Cys-containing peptide fragments and lowering yields in solid phase fragment condensations along with chain elongation compelled us to abandon the total synthesis of neurotrophins. 3. In order to facilitate the final disulfide bond formation of neurotrophins containing three disulfide bonds, new sulfoxide-mediated disulfide bond- forming reactions were developed and successfully applied for unambiguous regioselectie sidulfide-bond formation of several biologically active peptides including anti-HIV peptides and memory enhancing peptides which stimulate NGF synthesis. 4. In order to investigate the intracellular signal transductin pathway of neurotrophin Trk-receptors and the abnormal phosphorylations of Tau-protein associated with Alzheimer's Disease, an efficient synthetic method of phosphopeptides by solid phase technique was developed. Furthermore, stereoselective synthetic methods of phosphatase-resisted phosphoaminoacids mimetics and (E) -alkene-dipeptide isoseres as nonhydrolyzable dipeptide mimetics were investigated. These nonhydrolyzable phosphopeptide mimetics will serve as useful tools for biochemical study on protein phosphorylation associated with Alzheimer's disease.
- 日本学術振興会:科学研究費助成事業Date (from‐to) : 1994 -1994Author : 飯田 彰; 長岡 康夫カテコールアミンは、神経終末から分泌される神経伝達物質である。Trichoderma virideの生産する20残基の抗菌性ペプチドtrichocellin類は、神経細胞類似の副腎髄質細胞からカテコールアミンを放出させた。最初に、trichocellin類の2次構造を詳細に検討し、その構造が両親媒性を生み出す事を明らかにした。このことから、カテコールアミンの放出は、trichocellinのペプチドモノマーが細胞膜中で自己凝集することにより形成された人工的なイオンチャンネル(barrel-stave model)を経由してイオンが細胞外から細胞内に流入することにより引き起こされるという機構が推察された。電気生理学的な手法によりマクロレベルならびにシングルチャンネルレベルでのtrichocellin類により引き起こされる2分子膜のコンダクタンス値の変化を詳細に検討したところ、予想どおりペプチド分子がパラレルに4から9個凝集したイオンチャンネル(barrel-stave)を形成していることが分った。さらに、2次構造を変化させた誘導体ならびにペプチド鎖の長さの異なる誘導体を種々合成し、そのイオンチャンネル形成能を比較した。その結果、安定なイオンチャンネル形成には、20残基から構成されたプロリンによる折れ曲がりを有するヘリックス構造が重要な因子であることを明らかにした。また、イオンチャンネル形成能とカテコールアミン放出活性が一致したことから、本研究に用いた電気生理学的な手法が、カテコールアミン放出活性を有するペプチドを探索するためのプローブとなる可能性を示した。
- Japan Society for the Promotion of Science:Grants-in-Aid for Scientific ResearchDate (from‐to) : 1993 -1994Author : UEDA Shinichi; NAGAOKA Yasuo; IIDA AkiraBiological activity of neutral, acidic, and basic compounds bearing dibenzo-p-dioxin (D) skeleton as well as phenoxathiin (OSD) , and thianthrene (SSD) was examined in vivo. [1] On Tumor-promotion experiments indexed by the expression of Epstein-Barr virus early antigen caused by a tumor promotor TPA,most of neutral D derivatives indicated abti-tumor-promoting activity. Especially, 2,7-dichloro-D has a remarkable activity. At 500 times concentration relative to TPA,it inhabited tumor promotion by 80% without giving injuries on Raji cells even at 32 nano moles. [2] Acidic D derivatives such as D-1,6- and 2,7-dicarboxylic acid, their methyl esters, 2,7-disulfonic acid, 2,7-dimethyl-3,8-disulfonic cid, 1,6-dimethoxy-3,8-dicarboxylic acid, and its methyl ester indicated remarkable anti-tumor-promoting activity. Although D itself has no significant activity, neutral 1,6- and 2,7-dimethyl-D,1,6-dimethoxy-3,8-dimethyl-D,1,6-dimethoxy-D-3,8-dialde-hyde, 2,7-dimethoxy1-3,8-dinitro-D,as well as basic 2,7-dimethyl-3,8-diamino-D and 1,6-dimethoxy-3,8-diethylamino-D have anti-tumor-promoting activity. Among these compounds, the most active methyl D-2,7-dicarboxylate inhibits tumor promotion by 80% at 100 times concentration relative to TPA. [3] At 100 times concentration relative to TPA,trilobine and isotrilobine, bisbenzyl-isoquinoline alkaloids of Cocculus trilobus comprising a dibenzo-p-dioxin skeleton in the molecule, inhibit the tumor promotion by 60 and 50%, respectively. The viability of the Raji cells were 40 and 50%, respectively. [4] At 1000 times concentration relative to TPA,SSD and OSD completely inhibit tumor promotion. At this concentration, both compounds did not show toxicity to Raji cells.
- Japan Society for the Promotion of Science:Grants-in-Aid for Scientific ResearchDate (from‐to) : 1992 -1994Author : UEDA Shinichi; TOKUDA Harukuni; NAGAOKA Yasuo; IIDA AkiraIridoid type monoterpene glucosides, prenylchalcones, and furanonaphthoquinones indicating promissing anti-tumor-promoting activities were obtained from the cell cultures of the plants of the families Rubiaceae, Moraceae, and Bignoniaceae, respectively. The biosynthetic mechanism as well as in vitro and in vivo anti-tumor-promoting activity of these secondary metabolites were examined. [1] Genipin, the aglucone of geniposide, a main iridoid glucoside of Gardenia and Genipa fruits as well as Gardenia jasminoides cell cultures remarkably inhibits tumor-promotion caused by TPA on Raji cells. It also inhibits mouse pulmonary tumorigenesis promoted by glycerol and papilloma formation promoted by TPA.[2] Mulberry cell prenylchalcones, chalcomoracin and kuwanon J completely inhibit tumor-promotion on Raji cells at 1000 times concentration relative to TPA.The viability of Raji cells was 30%. Equimolar mixture of both compounds inhibitory activity. The prenyl moieties of both compounds were found to be biosynthesized as follows : starter acetate unit for mevalonate synthesis is of glycolytic origin, while the second and third acetate units originate from the pentose phosphate cycle. [3] Administration of [^<13>C] labeled phenylalanine and tyrosine to Morus alba cell cultures revealed that both amino acids participate in parallel in the biosynthesis of the phenylpropanoid moieties of chalcomoracin and kuwanon J.[4] 5-Hydroxy-2- (1-hydroxyethyl) -naphtho [2,3-b] furan-4,9-dione and related naphthoquinones produced by a South American bignoniaceous plant Tabebuia avellanedae were found to have promissing anti-tumor-promoting activity.
- 日本学術振興会:科学研究費助成事業Date (from‐to) : 1991 -1992Author : 藤多 哲朗; 飯田 彰; 井上 謙一郎; 上田 伸一菌類の生産する免疫抑制物質の探索を冬虫夏草菌類について行い、活性物質数種を単離しその作用機作を検討すると共に合成を計画した。 1)ISP-I並びにその類縁体の単離:ISP-Iは免疫抑制活性物質としてI.sinclairiiから、初めて単離された。いわゆる冬虫夏草菌Cordyceps sinensisの培養液について免疫抑制活性を指標として成分を検索したところISP-Iを単離同定することができた。ISP-IはMycelia sterilia菌によりI.sinclairii菌よりも効率よく生産される。その培養液から既知のISP-II、-IIIb、-Vの他に、新規活性物質として、ISP-IIIa、-Vを得た。また新たにそれらのdihidro体に相当する物質もえられた。 2)ISP-I並びに誘導体の免疫抑制活性:ISP-I及び14-deoxo-ISP-Iの動物を用いた移植実験では毒性が強く、使用にさいし安全域の狭いことが判明した。また新規天然物についてマウス同種リンパ球混合培養反応(MLR)、細胞毒性、皮膚移植について試験した。その結果はISP-Iのそれらと大きな差異は認められなかった。 3)ISP-Iの免疫抑制機作:ISP-Iはin vitroにおいて同種抗原刺激による同種細胞障害T細胞(alloCTL)の誘導をサイクロスポリン(CsA)よりも強力に抑制した。そこでin vivoにおけるISP-IのalloCTL誘導抑制について検討した。その結果ISP-IはCsAと異なりインターロイキン(IL)-2依存性のT細胞の増殖を特異的に抑制することが強く示唆された。 4)ISP-Iの合成:ISP-Iの合成の設計方針としてFragmentA〜Cに三分割した。AはD-セリン部、Bはグリコール部、Cはケトアルキル部よりなる。A部はD-バリンからSchollkopfらのcyclo(D-Val-2-amino-malonyl)bis-lactam dimethyl etherを合成した。B部はスズエノレートを活用する不斉アルドール反応により、またC部は1、8-octanediolから合成した。AとB部の結合は不斉アルキル化、A-B部とC部の結合はWittig反応により結合させISP-Iの合成を完成させることができる。
- 日本学術振興会:科学研究費助成事業Date (from‐to) : 1990 -1990Author : 藤多 哲朗; 飯田 彰; 井上 謙一郎; 上田 伸一イリドイド系化合物は薬用植物成分としてに広く分布している。なかでも、抗腫瘍活性を始め種々の生理活性を有するインド-ルアルカロイドの非トリプタミン部分がイリドイド配糖体より生合成されることはよく知られている。従って、イリドイド配糖体の基本骨格であるイリダン骨格の形成機構を酵素レベルで解明することは、イリドイド関連物質の生合成研究にとって非常に重要なことである。そこで、本研究ではインド蛇木の培養細胞を酵素源として以下の研究を行い、ほぼ初期の目的を達した。 1.鎖状モノテルペン脱水素酵素。イリダン骨格を形成する閉環反応の鎖状生合成前駆物質である10ーhydroxygeraniolから10ーoxogeranialの形成にあずかる脱水素酵素を活生収率10%、87倍で、かつ単一なタンパク質として単離した。本酵素は分子量44,000のモノマ-タンパク質で、等電点pH5.4、亜鉛原子を含み、NADP(H)依存性である。Ca^<2+>,Mg^<2+>の添加は酵素反応を活性化し、チオ-ル試薬に阻害効果が認められた。本酵素反応の立体化学的過程を(4R)ー[4ー ^2H]NADPHを用いて調べた結果、proーR特異的であることが分かった。本酵素のN末端アミノ酸配列19個は、植物から単離されている他のアルコ-ル脱水素酵素との間に相同性は認められなかった。 2.イリダン骨格閉環機構。鎖状前駆体10ーoxogeranialから環状前駆体イリドジア-ルへNADPH存在下閉環反応を触媒する酵素を440倍に精製した。本酵素は分子量118,000の4量体であることが明かとなり、NADPHはNADHより2倍高い活性を示した。本酵素が還元的機構により閉環反応を触媒することは、環状モノテルペンの生合成における、geranyl pyrophosphateが関与する従来の閉環機構とは異なり新しいタイプのものである。この酵素を単離し、反応機構を解明したことは非常に意義あることである。
- Japan Society for the Promotion of Science:Grants-in-Aid for Scientific ResearchDate (from‐to) : 1989 -1990Author : FUJITA Tetsuro; OKUMOTO Takeki; IKUMOTO Takeshi; IIDA Akira; INOUE Kenichiro; UEDA ShinichiWe have found the immunosuppressive activity in the culture broth of Isaria sinclairii and then isolated an immunosuppressant, ISP-I, which was characterized as (2S, 3S, 4R)- (E) -2-amino-3, 4-dihydroxy-2-hydroxymethy1-14-oxoeicos-6-enoic acid. Immunosuppressive activities of ISP-I and the derivatives are as follows : 1) The suppressive activity on mouse allogeneic mixed lymphocyte reaction was equal to or higher than that of cyclosporin A (CsA). 2) Examination of its 13 derivatives resulted in the expression and increment of the activity attributable to the amino group at C-2, the double bond at C-6 and the carbon chain from C-8 to C-20.14-Deoxo-ISP-I was 10 times more active than ISP-I. 3) In the suppression on the mouse anti-sheep red blood cell antibody production and on the induction of allo-reactive cytotoxic T cells, 14-deoxo-ISP-I was 10 times more effective than ISP-I which was 100 times more active than CsA. 4) In the suppression on the mouse allo-reactive specific antibody production by the oral administration, ISP-I was 100 times more effective than CsA. 5) Among the 13 derivatives, ISP-I and its 14-deoxo derivative were most toxic to various human tumor cells and less than CsA. 6) CsA inhibits the production of the cytokines such as interleukin 2 (IL-2), while ISP-I suppresses the proliferation of T cells by IL-2, indicating the different mechanisms in the expression of immunosuppression. Moreover, three ISP-I congeners were isolated from the mycelia of the highly ISP-I producing species of Mycelia sterilia and their structures were determined. Therefore, ISP-I and the derivatives are new immunosuppressants having different mechanism from that of CsA. Their usefulness remains to be proved in practical grafting experiments.
- 抗腫瘍活性分子の設計と合成
- 生物活性分子の生物有機化学的研究
- 薬用植物成分の化学的研究
- 菌類の代謝産物に関する研究
- Design and synthesis of antitumor molecules
- Bioorganic study on Biologically active compounds.
- Chemical Study on Medicinal Plants
- Study on Fungal Metabolites
Industrial Property Rights
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