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1996 Fiscal Year Final Research Report Summary

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
Keywordsphytotoxin / altemaric acid / abscisterol / AAL-toxin / tautomycin / Diels-Alderase / coronatine / tuber inducing substance
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

  • Research Products

    (86 results)

All Other

All Publications (86 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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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

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Published: 1999-03-09  

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