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ORGANIC CHEMISTRY OF THE BIOSYSTEM CONTROL SUBSTANCES

Research Project

Project/Area Number 03303003
Research Category

Grant-in-Aid for Co-operative Research (A)

Allocation TypeSingle-year Grants
Research Field 天然物有機化学
Research InstitutionHOKKAIDO UNIVERSITY,(FACULTY OF SCIENCE)

Principal Investigator

SHIRAHAMA Haruhisa  HOKKAIDO UNIVERSITY, FACULTY OF SCIENCE, PROFESSOR, 理学部, 教授 (00000802)

Co-Investigator(Kenkyū-buntansha) KUSUMOTO Syouichi  OSAKA UNIVERSITY, FACULTY OF SCIENCE, PROFESSOR, 理学部, 教授 (30028253)
ISOBE Minoru  NAGOYA UNIVERSITY, FACULTY OF AGRICULTURE, PROFESSOR, 農学部, 教授 (00023466)
YAMAMURA Syosuke  KEIO UNIVERSITY, FACULTY OF SCIENCE AND TECHNOLOGY, PROFESSOR, 理工学部, 教授 (40076708)
TACHIBANA Kazuo  UNIVERSITY OF TOKYO, FACULTY OF SCIENCE, PROFESSOR, 理学部, 教授 (70142081)
HIRAMA Masahiro  TOHOKU UNIVERSITY, FACULTY OF SCIENCE, PROFESSOR, 理学部, 教授 (30165203)
Project Period (FY) 1991 – 1992
Project Status Completed (Fiscal Year 1992)
Budget Amount *help
¥18,200,000 (Direct Cost: ¥18,200,000)
Fiscal Year 1992: ¥8,500,000 (Direct Cost: ¥8,500,000)
Fiscal Year 1991: ¥9,700,000 (Direct Cost: ¥9,700,000)
KeywordsNeurotoxins / Isolation of neurotoxins / Neurotrophic compounds / Cell grouth control factors / Carcinogenic promotors / Cell decision inhibitors / Antifeedant / Allelopasic substances / 神経毒の合成 / 発癌プロモ-タ- / 発癌性物質
Research Abstract

1.Structural determination,synthesis and transmission mechanism of neurotoxin: Spatial arrangement of action points in glutamate receptor was studied using various substrates(Shirahama). Absolute configuration of cigatoxin was studied using synthesized models(Hirama). Structures of two neurotoxins isolated from wasps were deduced(Okumura). Mechanism of poisoning for palytoxin and okadaic acid was studied(Uemua). An important intermediate for synthesis of tetrodotoxin was synthesized via new method (Isobe). The structures of neurotrophic compounds isolated from plants were determined(Kodama).
2. Control factor for cell growth: (+)-Laurencin and (-)-dactylyne were totally synthesized by newly developed method(Murai). Antiinfection activity of plants is found to be closely related with allylperoxidation of unsaturated fatty acids existing in the cells(T.Kato). The active part of vancomycin was synthesized and the structures of products from hybrid strains were determined(Yamamura). Analogs … More of bracken carcinogen,whose DNA cleaving activities were equivalents to ptaxiloside were synthesized and antitumoric compound was isolated from ptaxiloside, were synthesized and antitumoric compounds was isolated from marine animals (Yamada). Eight antitumoric activity promotors were isolated from Polypolaceae and their structures were determined(Hayashi). The determination of absolute configuration and configurational analysis were performed about various marine bioactive compounds(Kusumi). Cytotoxic ent-udoteatrial diacetate was synthesized (Isoe). Cytotoxic cumarines were isolated from Toddalis species(Mori).
3. Antifeadant,allelopasy and immnoadjuvant activities: The structures of defensive peptides of flatfishes were determined(Tachibana). Immnoadjuvant lipoteichoic acid from gram-negative bacteria was synthesized (Kusumoto). Synthetic studies on clerodane diterpenoids were performed(Tokoroyama). Synthetic studies on jubavion and secopseudopeterocin A were carried out employing nopinone as a starting material(M,Kato). Total synthesis and absolute configuration of dysideapalaunic acid,antienzymatic agent, were achieved(Uda). The compounds showing allelopasy and promotors of iontransport were isolated from ferns(Suga). Antienzymatics were isolated from leaves of perilla(Nakayama). Five diterpenes, which show inhibitory activity on the cell devisoin of fertilized ascidian eggs, were isolated from marine plants and their structures were determined(Ochi). Less

Report

(3 results)
  • 1992 Annual Research Report   Final Research Report Summary
  • 1991 Annual Research Report
  • Research Products

    (169 results)

All Other

All Publications (169 results)

  • [Publications] M. Horikawa: "Efficient Syntheses of Acromelic Acids B and E Which are Potent Neuroexcitatory Amino Acids" Tetrahedron Lett.34. 331-334 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] M.Tanaka: "Chirality of the Acyl Group of Gymnopilin" Phytochemistry. 31. 4355-4356 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] H.Hagiwara: "Total Synthesis and Absolute Stereostructure of (+)-Dysideapalaunic Acid" J.Chem.Soc.,Perkin Trans,1. 1. 1803-1807 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] M.Yamaguchi: "Direct Formation of Reactive Alkyltrichlorotins from 1-Alkynes,SnCl_4,and Bu_3N.A Mild Alkynylation Reagent of Aldehydes,Acetals,and Enones." Chem.Lett.2479-2482 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] M.Yamaguchi: "Desilylation Reactions Poly[(t-butyldimethylsilyloxy)phenylacetylene]s" Chem.lett.2261-2262 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] M.Kato: "Efficient Preparation of a Key Intermediate Suitable for the Asymmetric Synthesis of (+)-Vernolepin and (-)-Vernomenin" J.Chem.Soc.Chem.Commun.697-698 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] M.Kato: "A Stereocontrolled Synthesis of (4aS__-,8aR__-)-(+)-7,7-Ethylenedioxy-4,4,8a-trimethyloctahydro-2(1H__-)-naphtalenone" Bull.Chem.Soc.Jpn.65. 2071-2075 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] I.Ohtani: "An Insight into the Conformation of Ptilomycalin A.The NMR Properties of Trifluoroacetylated Spermidine Analogues" Tetrahebron Lett.33. 2525-2528 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] I.Ohtani: "Structure and Chemical Properties of ptilomycalin A" J.Am.Chem.Soc.114. 8472-8479 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] T.Kato: "Lipoxygenase Activity Increment in Infected Tomato Leaves and Oxidation Product of Linolenic Acid by Its In Vitro Enzyme Reaction." Biosci.Biotech.Biochem.56. 373-375 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] T.Kato: "Selective Terminal Olefin Oxidation of n-3 Polyunsaturated Fatty Acids" Tetrahedron Lett.33. 1475-1478 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] M.Kubota: "Structure of Citerohybridone A" Acta Cryst.C48. 552 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] S.Kosemura: "Citerobenzofurans A,B,and C,First Isolation of Sesquiterpene-type Metabolites of a Hybrid Strain KO 0031 Derived from Penicillium Citero-viride B.IFO 4692 and 6200" Bull.Chem.Soc.Jpn.65. 926 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] M.suganuma: "Biochemical Effects and Tumor Promotion of Okadaic Acid in Glandular Stomach of SD Rats" Carcinogenesis. 13. 1841-1845 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] S.Ikegami: "Effect of Okadaic Acid on Embryonic Development of the Starfish Asterinapectinifera" Biosci.Biotech.Biochem.56. 1007-1011 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] H.Kigoshi: "Synthesis of Analogues of a Bracken Ultimate Carcinogen and Their DNA Cleaving Activities" Tetrahedron Lett.44. 6647-6650 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] C.T.Barrow: "Structure and Activity Studies of Pardaxin and Analogues Using Model Nembranes of PhosphatidyI Choline" Biochem.Biophys.Acta. 112. 235-240 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] A.Takai: "Inhibitory Effect of Okadaic Acid-Derivatives on Protein Phosphatases:A Study on Structure-Affinity Relationship" Biochem.J.284. 539-544 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] T.Tsukiyama: "C-Glycosidation with Silylacetylenes to D-Glucals" Tetrahedron Lett.33. 7911-7914 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Y.Hayashi: "Nagilactones as an Anti-feedant of Podocarpus nagi for Herbivorous Mammals" Biosci.Biotech.Biochem.56. 1302-1303 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] C.S.M.Chairul: "Applanoxidic Acids E,F.G and H,Biologically Active Lanostanoid Triterpenes from Ganoderma applanatum as an Inhibitor against Tumro Promoter" Phytochemistry. (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] S.Katsumura: "Phospholipase A_2 Inhibition by Manoalide:Development of Simple analogues and Necessary Functional Group for Inhibition" Biomed.Chem.Lett.2. 1263-1266 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] S.Katsumura: "Toward Elucidation of The Inhibition of Phospholipase A_2 by Manoalide Analogues" Biomed.Chem.Lett.2. 1267-1268 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] T.Fujita: "Perillpside A.a Monoterpene Glucoside from <Perilla Frutescens>___-" Phytochemistry. 31. 3265-3267 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] H.L.Siddiqui: "Biologically Active Clerodane-type Diterpene Alcohol and Its Glycosides from the Root-stalks of Ferns" J.Chem.Soc.,Perkin Trans 1. 781-785 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] T.Endo: "Demonstration of Geranyl Diphoshate Synthase in Several Higher Plans" Phytochemistry. 31. 2273-2275 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] M.Ochi: "Litophnins I and J.Two New Biologically Active Diterpenoids from the Soft Coral <Litophyton>___- sp." Ohem.Lett.155-158 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] M.Ochi: "Calicogorgins A.B.and C.Three Bioactive Sphinganine Derivatives from the Gorgonian <Calicogorgia>___- sp." Tetrahedron Lett.33. 7531-7534 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Y.Fukuyama: "Prenylated C6-C3 Compounds from <Illicium tashiroi>___-" Phytochemistry. 31. 3975-3979 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Y.Fukuyama: "Illicinolides A and B,Novel Sesquiterpenes form the Wood of <Illicium tashiroi>___-" Tetrahedron. 48. 5847-5854 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] K.Ueda: "Two Sesquiterpene Polyesters from the Ripe Furits of Eunits of Eunymus japonicus Thunb" Bull.Coll.Sci.,Univ.of RyuKyus. 54. 41-46 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] K.Ueda: "A Sesquiterpene Polyester from Euonymus <tanakae>___-" Phytochem.(1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] F.Fukase: "Synthesis of New Serine-linked Oligosaccharides in Blood-Clotting Factor VII and IX and Protain Z" Bull.Chem.Soc,Jpn.65. 436-445 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] F.Fukase: "Iodosobenzene-Triflic Anhydrides as an Efficient Promoter for Glycosidation Reaction Using Thioglycosides as Donons" Tetrahedron Lett.33. 7165-7168 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] K.Tsushima: "Total Synthesis of (+)-Laurencin" Tetrahedron Lett.33. 4345-4348 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] L.Gao: "Total Synthesie of (-)-Dactylyne and (-)-Isodactylyne" Tetrahedron Lett.33. 4349-4352 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] 白濱 晴久: "生物毒の世界" 大日本図書(株), 24 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] H.Shirahama: "Organic Synthesis in Japan:Past,Present,and Future" Tokyo Kagaku Dozin, 12 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] 白濱 晴久: "キノコの化学、生化学" 学会出版センター, 17 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] 平間 正博: "有機合成の最先端一反応の設計と制御" 東京化学同人, 17 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] M.Hirama: "Recent Progress in the Cgemical Synthesis of Antibiotics,Vol.2" Springer-Verlag, (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] 磯部 稔: "海洋資源と医薬I、続一医薬品の開発" 廣川書店, 9 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] 平間 正博: "有機合成の最先端一反応の設計と制御" 東京化学同人, 5 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] 橘 和夫: "化学で探る海洋生物の謎" 化学同人, 8 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] K.Konoki: "Peptide Chemistry 1992" Protein Research Foundation, (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Y.Naya: "Marine Biotechnology,Vol.1:Pharmaceutical and Bioactive Natural Products" Plenum, (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] M. Horikawa: "Efficient Syntheses of Acromelic Acids B and E Which are Potent Neuroexcitatory Amino Acids" Tetrahedron Lett.34. 331-334 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] M. Tanaka: "Chirality of the Acyl Group of Gymnopilin" Phytochemistry. 31. 4355-4356 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] H. Hagiwara: "Total Synthesis and Absolute Stereostructure of (+)-Dysideapalaunic Acid" J. Chem. Soc., Perkin Trans. 1. 1803-1807 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] M. Yamaguchi: "Direct Formation of Reactive Alkyltrichlorotins from 1-Alkines, S_nCl_4 and Bu_3N. A Mild Alkynylation Reagent of Aldehydes, Acetals, and Enones" Chem. Lett.2479-2482 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] M. Yamaguchi: "Desilylation Reactions of Poly [(t-butyldimethylsilyloxy)phenylacetylene]s" Chem. Lett.2261-2262 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] M. Kato: "Efficient Preparation of a Key Intermediate Suitable for the Asymmetric Synthesis of (+)-Vernolepin and (-)-Vernomenin" J. Chem. Soc. Chem. Commun.697-698 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] M. Kato: "A Stereocontrolled Synthesis of (4aS,8aR)-(+)-7,7-Ethylenedioxy-4,4,8a-trimethyloctahydro-2(1H)-naphtalenone" Bull. Chem. Soc. Jpn.65. 2071-2075 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] I. Ohtani: "An Insight into the Conformation of Ptilomycalin A. The NMR Properties of Trifluoroacetylated Spermidine Analogues" Tetrahedron Lett.33. 2525-2528 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] I. Ohtani: "Structure and Chemical Properties of Ptilomycalin A" J. Am. Chem. Soc.114. 8472-8479 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Y. Kato: "Lipoxygenase Activity Increment in Infected Tomato Leaves and Oxidation Product of Linolenic Acid by Its In Vitro Enzyme Reaction" Biosci. Biotech. Biochem.56. 373-375 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] T. Kato: "Selective Terminal Olefin Oxidation of n-3 Polyunsaturated Fatty Acids" Tetrahedron Lett.33. 1475-1478 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] M. Kubota: "Structure of Citreohybridone A" Acta Cryst.C48. 552 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] S. Kosemura: "Citreobenzofurans A, B, and C, First Isolation of Sesquiterpene-type Metabolites of a Hybrid Strain KO 0031 Derived from Penicillium Citreoviride B. IFO 4692 and 6200" Bull. Chem. Soc. Jpn.65. 926 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] M. Suganuma: "Biochemical Effects and Tumor Promotion of Okadaic Acid in Glandular Stomach of SD Rats" Carcinogenesis. 13. 1841-1845 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] S. Ikegami: "Effect of Okadaic Acid on Embryonic Development of the Starfish Asterina pectinifera" Biosci. Biotech. Biochem.56. 1007-1011 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] H. Kigoshi: "Synthesis of Analogues of a Bracken Ultimate Carcinogen and Their DNA Cleaving Activities" Tetrahedron Lett.44. 6647-6650 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] C. T. Barrow: "Structure and Activity Studies of Pardaxin and Analogues Using Model Membranes of Phosphatidyl Choline" Biochem. Biophys. Acta. 112. 285-240 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] A. Takai: "Inhibitory Effect of Okadaic Acid-Derivatives on Protein Phosphatases: A Study on Structure-Affinity Relationship" Biochem. J.284. 539-544 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] T. Tsukiyama: "C-Glycosidation with Silylacetylenes to D-Glucals" Tetrahedron Lett.33. 7911-7914 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Y. Hayashi: "Nagilactones as an Anti-feedant of Podocarpus Mammals" Biosci. Biotech. Biochem.56. 1302-1303 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] C.S.M.Chairul: "Applanoxidic Acids E, F. G and H, Biologically Active Lanostanoid Triterpenes from Ganoderma applanatum as an Inhibitor against Tumor Promoter" Phytochemistry. (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] S. Katsumura: "Phospholipase A_2 Inhibition by Manoalide: Development of Simple analogues and Necessary Functional Group for Inhibition" BioMed. Chem. Lett.2. 1263-1266 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] S. Katsumura: "Toward Elucidation of The Inhibition of Phospholipase A_2 by Manoalide Analogues" BioMed. Chem. Lett.2. 1267-1268 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] T. Fujita: "Perillpside A. a Monoterpene Glucoside from Perilla Frutescens" Phytochemistry. 31. 3265-3267 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] H. L. Siddiqui: "Biologically Active Clerodane-type Diterpene Alcohol and Its Glycosides from the Root-stalks of Ferns" J. Chem. Soc., Perkin Trans. 1. 781-785 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] T. Endo: "Demonstration of Geranyl Diphoshate Synthase in Several Higher Plans" Phytochemistry. 31. 2273-2275 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] M. Ochi: "Litophynins I and J. Two New Biologically Active Diterpenoids from the Soft Coral Litophyton sp." Chem. Lett.155-158. (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] M. Ochi: "Calicogorgins A. B. and C. Three Bioactive Sphinganine Derivatives from the Gorgonian Calicogorgia sp." Tetrahedron Lett.33. 7531-7534 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Y. Fukuyama: "Prenylated C6-C3 Compounds from Illicium tashiroi" Phytochemistry. 31. 3975-3979 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Y. Fukuyama: "Illicinolides A and B, Novel Sesquiterpenes form the Wood of Illicium tashiroi" Tetrahedron. 48. 5847-5854 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] K. Ueda: "Two Sesquiterpene Polyesters from the Ripe Fruits of Euonymus japonicus Thunb" Bull. Coll. Sci., Univ. of Ryukyus. 54. 41-46 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] K. Ueda: "A Sesquiterpene Polyester from Euonymus tanakae" Phytochem.(1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] F. Fukase: "Synthesis of New Serine-linked Oligosaccharides in Blood-Clotting Factor VII and IX and Protain Z" Bull. Chem. Soc., Jpn.65. 436-445 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] F. Fukase: "Iodosobenzene-Triflic Anhydrides as an Efficient Promoter for Glycosidation Reaction Using Thioglycosides as Donons" Tetrahedron Lett.33. 7165-7168 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] K. Tsushima: "Total Synthesis of (+)-Laurencin" Tetrahedron Lett.33. 4345-4348 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] L. Gao: "Total Synthesie of (-)-Dactylyne and (-)-Isodactylyne" Tetrahedron Lett.33. 4349-4352 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] H. Shirahama: "Poisonous Substrances from Fungi" Seibutsudoku no Sekai. 93-116 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] H. Shirahama: "Principle of a Poisonous Mushroom Working as Neurotransmitters. A Dynamic Aspect of Natural Product-Chemistry" Organic Synthesis in Japan. 373-384 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] H. Shirahama: "Naurotoxins and Pungent Principles" Chemistry and Biochemistry of Fungi. 100-110. 161-166 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] M. Hirama: "Structure, Synthesis and Fundation of Complex System of Radical Generation Molecule and Protein" Frontier of Organic Synthesis Planning and Control of Reactions. 129-145 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] M. Hirama: "Synthesis and Chemistry of Neocarzinostatin Analogs" Recent Progress in the Chemical Synthesis of Antibiotics. 2. (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] M. Isobe: "Synthesis of Okadaic Acid" Marine Source and Medicins-I. 10. 303-311 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] K. Tachibana: "Shark-phobous Compounds" Chemistry Will Clarify Mistery of Marine Animals and Plants. 63-70 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] K. Konoki: "Membrane Perturbation of Pardaxins. Defensive Peptides of Flatfish" Peptide Chemistry. (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Y. Naya: "Isolation, Structure and Mode of Action Studies on Bioactive Marine Natural Products" Marine Biotechnology. Pharmaceutical and Bioactive Natural Products. 1.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] M.Horikawa: "Efficient Syntheses of Acromelic Acids B and E Which are Potent Neuroexcitatory Amino Acids" Tetrahedron Lett. 34. 331-334 (1993)

    • Related Report
      1992 Annual Research Report
  • [Publications] M.Tanaka: "Chirality of the Acyl Group of Gymnopilin" Phytochemistry. 31. 4355-4356 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] H.Hagiwara: "Total Synthesis and Absolute Stereostructure of(+)-Dysideapalaunic Acid" J.Chem.Soc,Perkin Trans,1. 1. 1803-1807 (1991)

    • Related Report
      1992 Annual Research Report
  • [Publications] M.Yamaguchi: "Direct Formation of Reactive Alkyltrichlorotins from 1-Alkynes,Sncl^4,and Bu^3N.A Mild Alkynylation Reagent of Aldehydes,Acetals,and Enones." Chem.Lett.2479-2482 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] M.Yamaguchi: "Desilylation Reactions of Poly[(t-butyldimethylsilyloxy)phenylacetylene]s" Chem.Lett.2261-2262 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] M.Kato: "Efficient Preparation of a Key Inteumediate Suitable for the Asymmetric Synthesis of(+)-Vernolepin and(-)-Vernomenin" J.Chem.Soc.Chem.Commun.697-698 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] M.kato: "A Stereocontrollde Synthesis of(4aS,8aR)-(+)-7,7-Ethylenedioxy-4,4,8a-trimethyloctahydro-2(1H)-naphtalenone" Bull.Chen.Soc.Jpn.65. 2071-2075 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] I.Ohtani: "An Insight into the Conformation of Ptilomycalin A.The NMR Properties of Trifluoroacetylated Spermidine Analogues" Tetrahedron Lett.33. 2525-2528 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] I.Ohtani: "Structure and Chemical Properties of Ptilomycalin A" J.Am.Chem.Soc.114. 8472-8479 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] T.Kato: "Lipoxygenase Activity Increment in Infected Tomato Leaves and Oxidation Product of Linolenic Acid by Its In Vitro Enzyme Reaction." Biosci.Biotech.Biochem.56. 373-375 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] T.Kato: "Selective Terminal Olefin Oxidation of n-3 Polyunsaturated Fatty Acids" Tetrahedron Lett.33. 1475-1478 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] M.Kubota: "Structure of Citreohybridone A" Acta Cryst.C48. 552 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] S.kosemura: "Citreobenzofurans A,B,and C,First Isolation of SESquiterpene-type Metaboletes of a Hybrid Strain KO0031Derived from Penicillium Citreo-viride B.IFO4692and6200" Bull.Chem.Soc.Jpn.65. 926 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] M.Suganuma: "Biochemical Effects and Tumor Promotion of Kkadaic Acid in Glandular Stomach of SD Rats" Carcinogenesis. 13. 1841-1845 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] S.Ikegami: "Effect of Okadaic Acid on Embryonic Development of the Starfish Asterina pectinifera" Biosci.Biotech.Biochem.56. 1007-1011 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] H.Kigoshi: "Synthesis of Analogues of a Bracken Ultimate Carcinogen and Their DNA Cleaving Activities" Tetrahedron Lett.44. 6647-6650 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] C.T.Barrow: "Struchure and activity Studies of Pardaxin and Analogues Using Model membranes of Phosphatidyl Choline" Biochem.Biophys.Acta. 112. 235-240 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] A.Takai: "Inhibitory Effect of Okadaic Acid-Derivatives on Protein Phosphatases:A Study on Structure-Affinity Relationship" Biochem.J.284. 539-544 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] T.Tsukiyama: "C-Glycosidation with Silylacetylenes to D-Glucals" Tetrahedron Lett.33. 7911-7914 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Y.Hayashi: "Nagilactones as an Anti-feedant of Podocarpus nagi for Herbivorous Mammals" Biosci.Biotech.Biochem.56. 1302-1303 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] C.S.M.Chairul: "Applanoxidic Acids E,F,G and H,Biologically Active Lanostanoid Triterpenes from Ganoderma applanatum as an Inhibitor against Tumor Promoter" Phytochemistry. (1993)

    • Related Report
      1992 Annual Research Report
  • [Publications] S.Katsumura: "Phospholipase A^2 Inhibition by Manoalide:Development of Simple analogues and Necessary Functional for Inhibition" BioMed.Chem.Lett.2. 1263-1266 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] S.Katsumura: "Toward Elucidation of the Inhibition of Phospholipase A^2 by Manoalide Analogues" BioMed.Chem.Lett.2. 1267-1268 (1993)

    • Related Report
      1992 Annual Research Report
  • [Publications] T.Fujita: "Perillpside A.a Monoterpene Glucoside from Perilla Frutescens" Phytochemistry. 31. 3265-3267 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] H.L.Siddiqui: "Biologically Active Clerodane-type Diterpene Alcohol and Its Glycosides from the Root-stalks of Ferns" J.Chem.Soc.,Oerkin trans1. 781-785 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] T.Endo: "Demonstration of Geranyl Diphoshate Synthase in Several Higher Plans" Phytochemistry. 31. 2273-2275 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] M.Ochi: "Litophynins I and J.Two New Biologically Active Diterpenoids from the Soft Coral Litophyton sp." Chem.Lett.155-158 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] M.Ochi: "Calicogorains A.B.and C.Three Bioactive Sphinganine Derivatives from the Gorgonian Cal icogorgia sp." Tetrahedron Lett.33. 7531-7534 (1993)

    • Related Report
      1992 Annual Research Report
  • [Publications] Y.Fukuyama: "Prenylated C6-C3 compounds from Illicium tashiroi" Phytochimistry. 31. 3975-3979 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] Y.fukuyama: "Illicinolides A and B,Novel Sesquiterpenes form the Wood of Illicium tsahiroi" Tetrahedron. 48. 5847-5854 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] K.Ueda: "Two Sesquiterpene Polyesters from the Ripe Fruits of Eunymus japonicus Thunb" Bull.Coll.Sci.,Univ.of Ryukyus. 54. 41-46 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] K.Ueda: "A Sesquiterpene Oolyester from Euonymus tanakae" Phytochem.(1993)

    • Related Report
      1992 Annual Research Report
  • [Publications] F.Fukase: "Synthesis of New Serine-linked Oligosaccharides in Blood-Clotting Factor vll and ix and Protain Z" Bull.Chem.Soc,Jpn.65. 436-445 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] F.Fukase: "Iodosobenzene-Triflic Anhydrides as an Efficient Promoter for Glysosidation Reaction Using Thisglycosides as Donons" Tetrahedron Lett.33. 7165-7168 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] K.Tsushima: "Total Synthesis of(+)-laurencin" Tetrahedron Lett.33. 4345-4348 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] L.Gao: "Total Synthesie of(-)-Dactylyne and(-)-Isodactylyne" Tetrahidron Lett.33. 4349-4352 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] 白浜 晴久: "生物毒の世界" 大日本図書(株), 24 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] H.Shirahama: "Organic Synthesis in Japan:Past,Present,and Future" Tokyo Kagaku Dozin, 12 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] 白濱 晴久: "キノコの化学、生化学" 学会出版センター, 17 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] 平間 正博: "有機合成の最先端-反応の設計と制御" 東京化学同人, 17 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] M.Hirama: "Recent Progress in the Chemical Synthesis of Antibiotics,Vol.2" Springer-Verlag, (1993)

    • Related Report
      1992 Annual Research Report
  • [Publications] 磯部 稔: "海洋資源と医薬I、続一医薬品の開発" 広川書店, 9 (1991)

    • Related Report
      1992 Annual Research Report
  • [Publications] 平間 正博: "有機合成の最先端-反応の設計と制御" 東京化学同人, 5 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] 橘 和夫: "化学で探る海洋生物の謎" 化学同人, 8 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] K.Konoki: "Peptide Chemistry 1992" Protein Research FounDation, (1993)

    • Related Report
      1992 Annual Research Report
  • [Publications] Y.Naya: "Marin Biotechnology,Vol.1:Pharmaceutical and Bioactive Natural Products" Plenum, (1993)

    • Related Report
      1992 Annual Research Report
  • [Publications] K.Konno: "Synthesis and Neuroexcitatoty Activity of Some Acromelic Acid Analogs" Heterocycles. 33. 303-311 (1992)

    • Related Report
      1991 Annual Research Report
  • [Publications] K.Hashimoto: "Synthesis of New Acromelic Acid Congeners:Novel Neuroexcitatory Amino Acids Acting on Glutamate Receptor" Tetrahedron Lett.32. 2625-2628 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Lian‐xun GAO: "Highly Regioselective Ring Opening of 2,3‐Epoxy Alcohol Methanesulfonates" Chemistry Lett.1787-1790 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Hisahiro Hagiwara: "Total Synthesis and Adsolute Stereostructure of (+)‐Dysideapalaunic Acid" J.Chem.Soc.,Perkin Trans.1. 1803-1807 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] M.Hirama: "Simple Strategy for the Synthesis of the Avermectin‐Melbemycin Family.Total Synthesis of Milbemycin α1." J.Am.Chem.Soc.113. 1830-1832 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] T.Suzuki: "Enantioselective Synthesis of AB Ring Fragment of Gambiertoxin 4B.Implication the for Absolute Configuration of Gambiertoxin 4B and Ciguatoxin." Tetrahedron Lett.32. 4505-4508 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] M.Hirama: "Synthesis and DNA Cleaving Abilities of Functional Neocarzinostatin Chromophore Analogues.Base Discrimination by a Simple Alcohol." J.Am.Chem.Soc.113. 9851-9853 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] M.O.Ishitsuka: "Isolation of a Monomeric Counterpart of the Marine Biscembranoids,a Biogenetic Diels‐Alber Precursor" Tetrahedron Lett.32. 2917-2918 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] K.Iguchi: "Stereostructures of Unique 13‐Membered Carbocyclic Cembranolides from the Soft Coral Lobophytum pauciflorum" Chem.Lett.319-322 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] 生井 恒雄: "Cytotoxixity and Anti‐blast Activity of Hydroperoxide of Linolenic Acid Produced by in Vitro Enzyme Reaction Using Blast‐infected Rice Leaves" Ann.Phytopath.57. 339-344 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Makoto Sasaki: "An Efficient and Stereocontrolled Synthesis of the Nephritogenoside Core Structure" Tetrahedron Letters. 32. 6873-6876 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] S.Kosemura: "The Structures of Citreohybridone A and B,Novel Sesterterperpenoid‐type Metabolites of a Hybrid Strain KO 0031 Derived from Penicillium citreo‐viride B.IFO 6200 and 4692" Tetrahedron Letters. 32. 3543-3546 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] K.Matsunaga: "Isolation and Structure of Citreoindole,a New Metabolite of Hybrid Strain KO 0052 Derived from Prnicillium citreo‐viride B.IFO 6200 and 4692" Tetrahedron Letters. 32. 6883-6884 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] A.Carl: "Reguration of Ca‐Activated K^+ Channels by Protein Kinase A and Phosphatase Inhibitors" Am.J.Physiol.261. C387-C392 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] A.Herunsalee: "Diastereoselective Heteroconjugate Addition of Acetylenec Derivative" Tetrahedron. 47. 3727-3736 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] T.Nishikawa: "Synthetic Studies on the Bicyclo[7.3.1]‐tridecendiyne System in an Antitumor Antibiotic,Dynemicia A" Synlett. 393-394 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] K.Fukase: "Application of 4‐Azidobenzyl Grorp to Protection of Hydroxyl Functions" Tetrahedron Lett.32. 3557-3558 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] C.T.Tokuyama: "Applanoxidic Acids A,B,C and D,Biologically Active Tetracyclic Triterpenes from Ganoderma applanatum" Phytochemistry. 30. 4105-4109 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Yuting Ge: "An Efficient Synthesis of Cerbinal,a 10π Aromatic Iridoid" Chemistry Letters. 139-140 (1992)

    • Related Report
      1991 Annual Research Report
  • [Publications] H.L.Siddiqui: "Biologically Active Novel Clerodane‐type Diterpene Glycosides from the Root‐stalks of Gleichenia japonica" Chem.Lett.701-704 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] K.Munesada: "Biologically Activa Labdane‐type Diterpene Glycosides from the Root‐stalks of Gleichenia japonica" Phytochemistry. 31. (1992)

    • Related Report
      1991 Annual Research Report
  • [Publications] M.Ochi: "Litophynins I and J,Two New Biologically Active Ditepernoids from the Soft Coral Litophyton sp." Chem.Lett.155-158 (1992)

    • Related Report
      1991 Annual Research Report
  • [Publications] Y.Fukuyama: "Prenylaed Xanthones from Garcinia subelliptica" Phytochem.30. 3433-3436 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Y.Fukuyama: "Neurotrophic Sesquiterpene‐neolignans from Magnolia obovata:Structure and Neurotrophic Activity" Tetrahedron. 48. 377-392 (1992)

    • Related Report
      1991 Annual Research Report
  • [Publications] H.Hashimoto: "Trends in Oraganic Chemistry Vo1.2" Research Trends, 32 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] 橋本 貴美子: "キノコの化学・生化学" 学会出版センタ-, 17 (1992)

    • Related Report
      1991 Annual Research Report
  • [Publications] 平間 正博: "ネオカルジノスタチン様人工分子の設計と合成" 有機合成化学協会誌, 11 (1991)

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      1991 Annual Research Report
  • [Publications] 橘 和夫: "化学と生物" 学会出版センタ-, 3 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Yoko Naya: "Marine Biotechnology Vo1.1" Plenum Publishing Corp., (1992)

    • Related Report
      1991 Annual Research Report
  • [Publications] S.Yamamura: "Studies in Natural Products Chemistry" Elsevier Science Publishers, (1992)

    • Related Report
      1991 Annual Research Report
  • [Publications] D.Uemura: "Marine Bioorganic Chemistry Vo1.4" Springer‐Verlag, 31 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] 磯部 稔: "海洋資源と医薬品I 続一医薬品の開発" 廣川書店, 9 (1991)

    • Related Report
      1991 Annual Research Report

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