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Chemistry and New Development of Phytotoxin

Research Project

Project/Area Number 06102001
Research Category

Grant-in-Aid for Specially Promoted Research

Allocation TypeSingle-year Grants
Review Section Chemistry
Research InstitutionHOKKAIDO UNIVERSITY

Principal Investigator

ICHIHARA Akitami  Hokkaido Univ., Fac.of Agr., Pro., 農学部, 教授 (20000820)

Co-Investigator(Kenkyū-buntansha) YOSHIZAWA Yuko  Hokkaido Bunkyo Jr.College, Associate Pro., 助教授 (20269202)
SATO Hiroji  Hokkaido Univ., Fac.of Agr., Experiment Farms,, 農学部・付属農場, 助教授 (20002074)
TOSHIMA Hiroaki  Hokkaido Univ., Fac.of Agr., Instructor, 農学部, 助手 (50237088)
OIKAWA Hideaki  Hokkaido Univ., Fac.of Agr., Instructor, 農学部, 助手 (00185175)
YOSHIHARA Teruhiko  Hokkaido Univ., Fac.of Agr., Associate Pro., 農学部, 助教授 (90002071)
Project Period (FY) 1994 – 1996
Project Status Completed (Fiscal Year 1996)
Budget Amount *help
¥193,000,000 (Direct Cost: ¥193,000,000)
Fiscal Year 1996: ¥27,000,000 (Direct Cost: ¥27,000,000)
Fiscal Year 1995: ¥28,000,000 (Direct Cost: ¥28,000,000)
Fiscal Year 1994: ¥138,000,000 (Direct Cost: ¥138,000,000)
Keywordsphytotoxin / altemaric acid / abscisterol / AAL-toxin / tautomycin / Diels-Alderase / coronatine / tuber inducing substance / アポトーシス / ソラナピロン / マクロフォミン酸 / セパシアミドA / ジャスモン酸 / オッシラトキシンD / 生体内ディールス・アルダー反応
Research Abstract

In the project "Chemistry and New Development of Phytotoxin", three main themes were investigated for past three years from 1994 to 1997, and the results are summerized as follows.
1. Synthetic Studies of Bioactive Natural Products
Tautomycin has an antifungal activity against phytopathogenic fungus, Sclerotinia sclerotiorum and a potent inhibitory activity against protein phosphatase. Stereocontrolled total synthesis has been achieved through key aldol coupling of two large subunits, aright-hand ketone (C_1-C_<21>) and a left-hand aldehyde (left from C_<22>). The C_1-C_<10> segment was synthesized through aremote stereochemical control process using a spiroketal template. The first synthesis of oscillatoxin D,which has antileukemic activity, has been completed by intramolecular Michael-type addition as a key step based on a possible biomimetic pathway.
2. Bioorganic Chemistry and Bioactivity of Phytotoxins
Several phytotoxins were isolated from phytopathogenic microorganisms in order to n … More ot only elucidate its role in ecological chemistry but also discover useful plant growth regulators. Practical synthetic method of coronatine has been developed. Similarties of the biological activities of coronatine to those of jasmonic acid in four jasmonate-responsive assay systems, namely in assays for tuber-inducing activity, for cell expansion-inducing activity, for cell division-inhibiting activity and for senescence-promoting activity. In all these assays, coronatine activities exhibited 100 to 10000 times higher than those of jasmonic acid in terms of the threshold concentration for activity. Determination of the stereochemistry and the total synthesis of altemaric acid has been achieved. Three altemaric acid analogs have been isolated and plausible biosynthetic routes have been suggested. The structures and stereochemistries of new bioactive compounds, cepaciamide A,abscisterol A and AAL-toxin, have been elucidated by spectroscopic and synthetic methods.
3. Diels-Alderase in the Biosynthesis of Phytotoxins
The biological Diels-Alder (DA) reaction has been studied with several phytotoxins, betaenone B,chaetoglobosin A,solanapyrone A and macrophomic acid. In the biosynthesis of, partially purified enzyme is able to catalyze intramolecular DA reaction of arising from through oxidation to give optically pure solanapyrone A (99%ee). Further cell free system from Macrophoma commelinae catalyzed intermolecular DA reaction phosphoenolpyruvate derived from (2R)-2-phosphoglycerate and alpha-pyrone to give an intermediate which was converted to macrophomic acid through removal of phosphoric acid and carbon dioxide. These enzymes that catalyze preceding reaction of the cycloaddition also catalyze DA reaction, that is bifunctional enzymes. Less

Report

(4 results)
  • 1996 Annual Research Report   Final Research Report Summary
  • 1995 Annual Research Report
  • 1994 Annual Research Report
  • Research Products

    (119 results)

All Other

All Publications (119 results)

  • [Publications] 市原耿民: "生体内ディールス・アルダー反応の実在性" 学術月報. 47. 615-619 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H. Oikawa: "Absolute Configuration of C(1)-C(5) Fragment of AAL-toxin : Conformationally Rigid Acyclic Aminotriol Moiety" Tetrahedron Lett. 35. 1223-1226 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H. Oikawa: "First Direct Evience in Biological Diels-Alder Reaction of Incorporation of Diene-Dienophile Precursors in the Biosynthesis of Solanapyrones" J. Am. Chem. Soc.116. 3605-3606 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H. Toshima: "Synthetic Study on Oscillatoxin D : Construction of the C1-C26 Spiroether Segment by Intramolecular Alder Condersation and Michael-Type Addition" Tetrahedron Lett.35. 4361-4364 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H. Yada: "The Structure of Abscisterol A :A Novel 21-Nor-Δ^<17(20)>-unsaturated Sterol from Cryptosporiopsis abietina" Tetrahedron Lett.35. 4393-4396 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H. Oikawa: "Total Synthesis of Tautomycin : Efficient Aldol Coupling of Two Large Subunits" Tetrahedron Lett.35. 4809-4812 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H. Tabuchi: "Phytotoxic Metabolites isolated from Scoleco-trichum graminis Fuckel" Biosci. Biotech. Biochem.58. 1933-1935 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H. Tabuchi: "Biosynthetic Study of Alternaric Acid" J. Chem. Soc. Perkin Trans.1. 2833-2839 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H. Tabuchi: "Phytotoxic Metabolites isolated from Scoleco-trichum graminis Fuckel" Biosci. Biotech. Biochem.58. 1933-1935 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H. Oikawa: "Efficient Degradation of Tautomycin to a Useful Synthetic Intermediate" Biosci. Biotech. Biochem.58. 1933-1935 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] A. Noguchi: "Ferric Phosphate-dissolving Compound, Alfafuran, from alfalfa (Medicagosativa L.) in Response to Iron-deficiency Stress," Biosci. Biotech. Biochem.58. 2312-2313 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H. Oikawa: "Absolute Configuration of Main Chain of AAL-toxins" Tetrahedron. 50. 13347-13368 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Y. Jiao: "A New Hydroxytetradecatrienoic Acid and Its Glyceryl Esters from Valsaambiens" Phytochem.38. 419-422 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H. Toshima: "Practical Stereoselective Syntheses of All Four Stereoisomers of Coronamic Acid (2-Ethyl-1-aminocyclopropane-1-carboxylic Acid.)" Biosci. Biotech. Biochem.59.No.3. 497-500 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] F. Greulich: "Coronatine, a Bacterial Phytotoxin, acts as a Stereospecific Analog of Jasmonate Type Signals in Tomato Cells and Potato Tissues" J. Plant Physiol.147. 359-366 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H. Toshima: "Total Synthesis of Oscillatoxin D and 30-Methyl-Oscillatoxin D" Tetrahedron Lett.36. 3373-3374 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Y. Jiao: "Synthesis of (S)-13-Hydroxy (2E, 4E, 8E)-and (2E, 4E, 8Z)-Tetradecatrienoic Acids" Biosci. Biotech. Biochem.59 No.3. 1032-1035 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H. Oikawa: "Enzymatic Activity Catalyzing Exo Selective Diels-Alder Reaction in Solanapyrone Biosynthesis" J. Chem. Soc. Chem. Commun.1321-1322 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] M. Oikawa: "Reductive Opening of a-Methylspiroketals" Tetrahedron. 1321-1322 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] M. Oikawa: "Total Synthesis of Tautomycin" J. Org. Chem.60. 5048-5068 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H. Yada: "Biogenesis of New Abscisterol Family and 21-oic Sterol" Tetrahedron Lett.36. 7471-7474 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] T. Ueno: "Synthetic Study of Tautomycin and Tautomycetin, Stereocontorolled Construction of the Dialkylmaleic Anhydride Segment" Biosci. Biotech. Biochem.59. 2104-2110 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] A. Ichihara: "Bioorganic Chemistry of Alternaric Acid : Stereochemistry, Total Synthesis and Bioactivity" J. Synth. Org. Chem. Japan. 53. 975-985 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] 及川雅人: "トウトマイシンの全合成" 有機合成化学協会誌. 53. 1123-1132 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] 市原耿民: "合成化学を機軸とした生理活性天然物研究と新展開" 日本農芸化学会誌. 70. 759-766 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] 市原耿民: "ディールス・アルダー反応を触媒する酵素が天然にあった!" バイオサイエンスとインダストリー. 54. 572-574 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Y. Koda: "Similarities of the Biological Activities of Coronatine and Coronafacic Acid to Those of Jasmonic Acid" Phytochem.41. 93-96 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] A. Ichihara: "Chaetoglobosin O and Other Phytotoxic Matabolites from Cylindrocladium floridanum, a Causal Fungus of Alfalfa Black Rot Disease" Biosci. Biotech. Biochem.60. 360-361 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Y. Jiao: "Structural Identification of Cepaciamide A, a Novel Fungitoxic Compound from Pseudomonas cepacia D-202" Tetrahedron Lett. 37. 1039-1042 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H. Toshima: "Synthesis of Spiroacetal Enol Ethers via Intramolecular Conjugate Addition of Hemiacetal Alkoxides to Alkynoates" Tetrahedron Lett. 37. 5707-5710 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H. Oikawa: "Synthetic Study of AAL-toxins ; Efficient Construction of Two Vicinal Diol Moieties by Asymmetric Dihydroxylation" Tetrohedron Lett.37. 6169-6172 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] S. Nara: "Intramolecular 1,6-Conjugate Addition Approach for Construction of the Hydrindane Framework ; Total Synthesis of (±)-Coronafacic Acid" Tetrahedron Lett.37. 6745-6748 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] T. Yoshihara: "Metabolism and Transport of [2-14C](±)-Jasmonic Acid in the Potato Plant" Plant Cell Physiol.37. 586-590 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] N. Phay: "NP-101A, Antifungal Antibiotic from Streptomyces aurantiogriseus NPO-101" J. Antibiot.49. 703-705 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] A. Ichihara: "Biosynthesis of Phytotoxins from Alternaria solani" Biosci. Biotech. Biochem.61. 12-18 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] 市原耿民: "ディールス・アルダー反応を触媒する酵素" ファルマシア. 33(印刷中). (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H. Oikawa: "Biosynthesis of Macrophomic Acid ; Plausible Involvement of Intermolecular Diels-Alder Reaction" J. Chem. Soc. Chem. Commun.97-98 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H. Toshima: "Asymmetric Total Syntheses of (+)-Coronafacic Acid and (+)-Coronatine" Biosci. Biotech. Biochem.61(印刷中). (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] K. Yagi: "Enantio-and Stereoselective Synthesis of Monodeuterium Labeled Glycerols" Biosci. Biotech. Biochem.61(印刷中). (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] A. Ichihara: "Studies in Natural Products Chemistry, Vol. 18," Elsevier, NLD, in Ed. Atta-ur-Rahman, 45 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] A. Ichihara: "Dynamic Aspects of Natural Products Chemistry ; Molecular Biological Approaches" Biological Diels-Alder Reaction in Koudansha Scientitic, in Ed. K. Ogura and U. Sankawa, 25 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] 市原耿民: "植物病害の化学,1997,310" 学会出版センター,

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] A. Ichihara: "Current Organic Chemistry," Bentham Science Publishers, B. V., in Ed. Atta-ur-Rahman(印刷中), (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] A.Ichihara: "Actural Exstence of Biological Diels-Alder Reaction" Japanese Scientific Monthly. 47. 615-619 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H.Oikawa, I.Matsuda, A.Ichihara, and K.kohmoto: "Absolute Configuration of C(1)-C(5) Fragment of AAL-toxin : Conformationally Rigid Acyclic Aminotriol Moiety" Tetrahedron Lett.35. 1223-1226 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H.Oikawa, Y.Suzuki, A,Naya, K.Katayama and A.Ichihara: "First Direct Evience in Biological Diels-Alder Reaction of Incorporation of Diene-Dienophile Precursors in the Biosynthesis of Solanapyrones" J.Am.Chem.Soc.116. 3605-3606 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H.Toshima, T.Goto and A.Ichihara: "Synthetic Study on Oscillatoxin D : Construction of the C1-C26 Spiroether Segment by Intramolecular Alder Condersation and Michael-Type Addition" Tetrahedron Lett.35. 4361-4364 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H.Yada, H.Sato and A.Ichihara: "The Structure of Abscisterol A : A Novel 21-Nor-DELTA^<17(20)>-unsaturated Sterol from Cryptosporiopsis abietina" Tetrahedron Lett.35. 4393-4396 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H.Oikawa, M.Oikawa, T.Ueno and A.Ichihara: "Total Synthesis of Tautomycin : Efficient Aldol Coupling of Two Large Subunits" Tetrahedron Lett.35. 4809-4812 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H.Tabuchi, A.Tajimi and A.Ichihara: "Phytotoxic Metabolites isolated from Scoleco-trichum graminis Fuckel" Biosci.Biitech.Biochem.58. 1956-1959 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H.Tabuchi, H.Oikawa and A.Ichihara: "Biosynthetic Study of Alternaric Acid" J.Chem.Soc.Perkin Trans.1. 2833-2839 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H.Tabuchi, A.Tajima and A.Ichihara: "Phytotoxic Metabolites isolated from Scoleco-trichum graminis Fuckel" Biosci, Biotech.Biochem.58. 1993-1935 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H.Oikawa, M.Oikawa, A.Ichihara, M.Ubukata and K.Isono: "Efficient Degradation of Tautomycin to a Useful Synthetic Intermediate" Biosci.Biotech.Biochem.58. 1933-1935 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] A.Noguchi, T.Yoshihara, A.Ichihara, S.Sugihara, M.Koshino, M.Kojima, Y.Masaoka: "Ferric Phosphate-dissolving Compound, Alfafuran, from alfalfa (Medicago sativa L.) in Response to Iron-deficiency Stress" Biosci.Biotech.Biochem.58. 2312-2313 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H.Oikawa, I.Matsuda, T.Kagawa, A.Ichihara and K.Kohmoto: "Absolute Configuration of Main Chain of AAL-toxins" Tetrahedron. 50. 13347-13368 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Y.Jiao, T.Yoshihara, M.Akimoto and A.Ichihara: "A New Hydroxytetradecatrienoic Acid and Its Giyceryl Esters from Valsa ambiens" Phytochem. 38. 419-422 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H.Toshima and A.Ichihara: "Practical Stereoselective Syntheses of All Four Stereoisomers of Coronamic Acid (2-Ethyl-1-aminocyclopropane-1-carboxylic Acid.) (1995)" Biosci.Biotech.Biochem. 59, No.3. 497-500 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] F.Greulich, T.Yoshihara and A.Ichihara: "Coronatine, a Bacterial Phytotoxin, acts as a Stereospecific Analog of Jasmonate Type Signals in Tomato Cells and Potato Tissues" J.Plant Physiol.147. 359-366 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H.Toshima, T.Goto and A.Ichihara: "Total Synthesis of Oscillatoxin D and 30-Methyl-Oscillatoxin D" Tetrahedron Lett. 36. 3373-3374 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Y.Jiao, T.Yoshihara and A.Ichihara: "Synthesis of (S)-13-Hydroxy (2E,4E,8E)-and (2E,4E,8Z)-Tetradecatrienoic Acids" Biosci.Biotech.Biochem. 59, No.5. 1032-1035 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H.Oikawa, K.Katayama, Y.Suzuki and A.Ichihara: "Enzymatic Activity Catalyzing Exo Selective Diels-Alder Reaction in Solanapyrone Biosynthesis" J.Chem.Soc.Chem.Commun.1321-1322 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] M.Oikawa, H.Oikawa and A.Ichihara: "Reductive Opening of a-Methylspiroketals" Tetrahedron. 51. 6237-6254 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] M.Oikawa, T.Ueno, H.Oikawa and A.Ichihara: "Total Synthesis of Tautomycin" J.Org.Chem.60. 5048-5068 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H.Yada, H.Sato and A.Ichihara: "Biogenesis of New Abscisterol Family and 21-oic Sterol" Tetrahedron Lett.36. 7471-7474 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] T.Ueno, M.Oikawa, H.Oikawa and A.Ichihara: "Synthetic Study of Tautomycin and Tautomycetin, Stereocontorolled Construction of the Dialkylmaleic Anhydride Segment" Biosci.Biotech.Biochem.59. 2104-2110 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] A.Ichihara: "Bioorganic Chemistry of Alternaric Acid : Stereochemistry, Total Synthesis and Bioactivity" J.Synth.Org.Chem.Japan. 53. 975-985 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] M.Oikawa, T.Ueno, H.Oikawa and A.Ichihara: "Total Synthesis of Tautomycin" J.Synth.Org.Chem.japan. 53. 1123-1132 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] A.Ichihara: "New Developments of Bioactive Natural products Studies based on Synthetic Chemistry" Nippon Nogeikagakukaishi. 70. 759-766 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] A.Ichihara: "The Enzyme catalyzing Diels-Alder Reaction exists in Nature!" Bioscience and Industry. 54. 572-574 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Y.Koda, K.Takahashi, Y.Kikuta, F.Greulich, H.Toshima and A.Ichihara: "Similarities of the Biological Activities of Coronatine and Coronafacic Acid to Those of Jasmonic Acid" Phytochem. 41. 93-96 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] A.Ichihara, K.Katayama, H.Teshima, T.Oikawa and S.Sakamura: "Chaetoglobosin O and Other Phytotoxic Metabolites from Cylindrocladium floridanum, a Causal Fungus of Alfalta Black Rot Disease" Biosci.Biotech.Biochem.60. 360-361 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Y.Jiao, T.Yoshihara, S.Ishikuri, H.Uchino and A.Ichihara: "Structural Identification of Cepaciamide A,a Novel Fungitoxic Compound from Pseudomonas cepacia D-202" Tetrahedron Lett.37. 1039-1042 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H.Toshima, Y.Furumoto, S.Inamura and A.Ichihara: "Synthesis of Spiroacetal Enol Ethers via Intramolecular Conjugate Addition of Hemiacetal Alkoxides to Alkynoates" Tetrahedron Lett.37. 5707-5710 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H.Oikawa, T.Kagawa, T.Kobayashi and A.Ichihara: "Synthetic Study of AAL-toxins ; Efficient Construction of Two Vicinal Diol Moieties by Asymmetric Dihydroxylation" Tetrohedron Lett.37. 6169-6172 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] S.Nara.H.Toshima and A.Ichihara: "Intramolecular 1,6-Conjugate Addition Approach for Construction of the Hydrindane Framework ; Total Synthesis of ((]SY.+-。[))-" Tetrahedron Lett.37. 6745-6748 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] T.Yoshihara, M.Amanuma, T.Tsutsumi, Y.Okumura and A.Ichihara: "Metabolism and Transport of [2-14C] ((]SY.+-。[)) Jasmonic Acid in the Potato Plant" Plant Cell Physiol.37. 586-590 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] N.Phay, H.Yada, T.Higashiyama, A.Yokota, A.Ichihara and F.Tomita: "NP-101A,Antifungal Antibiotic from Streptomyces aurantiogriseus NPO-101" J.Antibiot. 49. 703-705 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] A.Ichihara and H.Oikawa: "Biosynthesis of Phytotoxins from Alternaria solani" Biosci.Biotech.Biochem.61. 12-18 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] A.Ichihara: "The Enzymes Catalyzing Diels-Alder Reaction" Pharmacia. 33(in press). (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H.Oikawa, K.Yagi, K.Watanabe, M.Hanma and A.Ichihara: "Biosynthesis of Macrophomic Acid ; Plausible Involvement of Intermolecular Diels-Alder Reaction" J.Chem.Soc.Chem.Commun.97-98 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H.Toshima, S.Nara and A.Ichihara: "Asymmetric Total Syntheses of (+)-Coronafacic Acid and (+)-Coronatine" Biosci.Biotech.Biochem.61(in press). (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] K.Yagi, H.Oikawa and A.Ichihara: "Enantio-and Stereoselective Synthesis of Monodeuterium Labeled Glycerols" Biosci.Biotech.Biochem.61(in press). (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] A.Ichihara: Studies in Natural Products Chemistry, Vol.18. Elsevier, NLD,in Ed.Atta-ur-Rahman, 45 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] A.Ichihara: Dynamic Aspects of Natural Products Chemistry ; Molecular Biological Approaches. Biological Diels-Alder Reaction in Koudansha Scientific, in Ed.K.Ogura and U.Sankawa, 25 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] A.Ichihara: Chemistry of Plant Disease. Gakkai Publishing Center, 310 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] A.Ichihara: Current Organic Chemistry. Bentham Science Publishers, B.V., in Ed.Atta-ur-Rahman (in press), (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] 市原 耿民: "合成化学を機軸とした生理活性天然物研究と新展開" 日本農芸化学会誌. 70. 759-766 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] 市原 耿民: "ディースル・アルダー反応を触媒する酵素が天然にあった!" バイオサイエンスとインダストリー. 54. 572-574 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Y. Koda: "Similarities of the Biological Activities of Coronatine and Coronafacic Acid to Those of Jasmonic Acid" Phytochem.,. 41. 93-96 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] A. Ichihara: "Chaetoglobosin O and Other Phytotoxic Metabolites from Cylindrocladiur floridanum, a Causal Fungus of Alfalfa Black Rot Disease" Biosci. Biotech. Biochem.60. 360-361 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Y. Jiao: "Structural ldentification of Cepaciamide A, a Novel Fungitoxic Compound from Pseudomonas cepacia D-202" Tetrahedron Lett,. 37. 1039-1042 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] H. Toshima: "Synthesis of Spiroacetal Enol Ethers via lntramolecular Conjugate Additic of Hemiacetal Alkoxides to Alkynoates" Tetrahedron Lett,. 37. 5707-5710 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] H. Oikawa: "Synthetic Study of AAL-toxins ; Efficient Construction of Two Vicinal Diol Moieties by Asymmetric Dihydroxylation" Tetrohedron Lett.37. 6169-6172 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] S. Nara: "lntramolecular 1, 6-Conjugate Addition Approach for Construction of the Hydrindane Framework ; Total Synthesis of (±)-Coronafacic Acid" Tetrahedron Lett.37. 6745-6748 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] T. Yoshihara: "Metabolism and Transport of [2-14C](±) Jasmonic Acid in the Potato Plant" Plant Cell Physiol.37. 586-590 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] N. Phay: "NP-101A, Antifungal Antibiotic from Streptomyces aurantiogriseus NPO101" J. Antibiot.49. 703-705 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] A. Ichihara: "Biosynthesis of Phytotoxins from Alternaria solani" Biosci. Biotech. Biochem.61. 12-18 (1997)

    • Related Report
      1996 Annual Research Report
  • [Publications] 市原 耿民: "ディールス・アルダー反応を触媒する酵素" ファルマシア. 33(印刷中). (1997)

    • Related Report
      1996 Annual Research Report
  • [Publications] H. Oikawa: "Biosynthesis of Macrophomic Acid ; Plausible lnvolvement of lntermolecular Diels-Alder Reaction" J. Chem. Soc., Chem. Commun.97-98 (1997)

    • Related Report
      1996 Annual Research Report
  • [Publications] H. Toshima: "Asymmetric Total Syntheses of (+) -Coronafacic Acid and (+) -Coronatine" Biosci. Biotech. Biochem.61(印刷中). (1997)

    • Related Report
      1996 Annual Research Report
  • [Publications] K. Yagi: "Enantio-and Stereoselective Synthesis of Monodeuterium Labeled Glycerols" Biosci. Biotech. Biochem.61(印刷中). (1997)

    • Related Report
      1996 Annual Research Report
  • [Publications] A. Ichihara: "Studies in Natural Products Chemistry, Vol. 18," Elsevier, NLD, in Ed. Atta-ur-Rahman, 45 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] A. Ichihara: "Dynamic Aspects of Natural Products Chemistry ; Molecular Biological Approaches" Biological Diels-Alder Reaction in Koudansha Scientific, in Ed. K. Ogura and U. Sankawa, 25 (1997)

    • Related Report
      1996 Annual Research Report
  • [Publications] 市原 耿民: "植物病害の化学" 学会出版センター, 310 (1997)

    • Related Report
      1996 Annual Research Report
  • [Publications] A. Ichihara: "Current Organic Chemistry" Bentham Science Publishers, B. V., in Ed. Atta-ur-Rahman(印刷中), (1997)

    • Related Report
      1996 Annual Research Report
  • [Publications] H.Toshima: "Total Synthesis of Oscillatoxin Dand 30-methyloscillatoxin D" Tetrahedron Lett.36. 3373-3374 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] M.Oikawa: "Total Synthesis of Tautomycin" J.Org.Chem.60. 5048-5068 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] H.Oikawa: "Enzymatic Activity Catalysing Exo-selective Diels-Alder Reaction in Solanapyrone Biosynthesis" J.Chem.Soc.,Chem.Commun.1321-1322 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] H.Yada: "The Biogenesis of New Abscisterols and a 21-oic Acid Type Sterol from Cryptosporiopsis abietina" Tetrahedron Lett.36. 7471-7474 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] T.Ueno: "Synthetic Study of Tautomycin and Tautomycetin Stereocontrolled Construction of the Dialkylmaleic Anhydride Segment" Biosci.Biotech.Biochem.59. 2104-2110 (1959)

    • Related Report
      1995 Annual Research Report
  • [Publications] A.Ichihara: "Bioorganic Chemistry of Alternaric Acid" J.Synth.Org.Chem.Japan. 53. 975-986 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] A.Ichihara: "Studies in Natural Products Chemistry,Vol.12" Elsevier,NLD in Ed,Atta-ur Rahman(印刷中), 45

    • Related Report
      1995 Annual Research Report
  • [Publications] Y.Jiao: "Two Phenolic Compounds from Valsa Ambiens" Biosci.Biotech.Biochem. 58. 221-222 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] H.Oikawa: "First Direct in Biological Diels-Aider Reaction of Diene-Dienophile Precursors in the Biosynthesis of Solanapyrones" J.Am.Chem.Soc.116. 3605-3606 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] H.Toshima: "Synthetic Study on Oscillatoxin D" Tetrahedron Lett.35. 4361-4364 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] H.Yada: "The Structure of Abscisterol A" Tetrahedron Lett.35. 4393-4396 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] H.Tabuchi: "Total Synthesis and Stereochemistry of Alternaric Acid" J.Org.Chem.59. 4797-4759 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] 市原 =民: "生体内ディールス.アルダー反応の実在性" 学術月報. 47. 615-619 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] H.Oikawa: "Host-specific Toxin:Biosynthesis,Receptor and Molecular Biolgy, Eds.K.Kohmoto,O.C.Yodor,Tottori University" Absolute Configurationo and Synthetic Study of AL-Toxin Produced by the Tomato Pathotype of Alternaria alternata, 61-72 (1994)

    • Related Report
      1994 Annual Research Report

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Published: 1994-04-01   Modified: 2018-03-28  

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