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BIOTRANSFORMATION OF MONOTERPENOIDS FOR INSECT BIOLIGICALLY ACTIVE SUBSTANCE BY BIOCATALYST

Research Project

Project/Area Number 07640793
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field 物質変換
Research InstitutionKINKI UNIVERSITY

Principal Investigator

MIYAZAWA Mitsuo  KINKI UNIVERSITY,DEPARTMENT OF APPLIED CHEMISTRY,ASSOCIATE PROFESSOR, 理工学部, 助教授 (40140305)

Co-Investigator(Kenkyū-buntansha) KAMEOKA Hiromu  KINKI UNIVERSITY,DEPARTMENT OF APPLIED CHEMISTRY,PROFESSOR, 理工学部, 教授 (30088330)
Project Period (FY) 1995 – 1996
Project Status Completed (Fiscal Year 1996)
Budget Amount *help
¥1,300,000 (Direct Cost: ¥1,300,000)
Fiscal Year 1996: ¥400,000 (Direct Cost: ¥400,000)
Fiscal Year 1995: ¥900,000 (Direct Cost: ¥900,000)
KeywordsBiotransformation / Terpenoid / Lepidoptera / Hydroxylation / Biocatalyst / マロン酸エステル化 / 不斉還元
Research Abstract

We reported the biotransformation of acyclic terpenoid citronellol by Glomerella cingulata. In this paper, citronellol was transformed into 3,7-dimethyl-1,6,7-octaetriol, which is known synthetic precursor of 3-methyl-6-isopropenyl-9-decen-1-yl acetate (a component of the California red scale phenomone, a major pest os citrus) [Nat.Prod.Lett., 8,303 (1996)]. Resolution of recemic cis and trans-linalool oxide-pyranoid via esterification with malonic acid by G.cingulata was successed, their enantiomerically pure alcohols and malonic esters could be obtained [Tetrahedron asymmetry, 6,1067 (1995)]. In addition, karahanaenone was transformed into (S) -karahanaenol with high enantiometric excess (100%) by G.cingulata, Aspergillus niger, Streptomyces aureofaciens and Bacillus subtilis [Tetrahedron asymmetry, 6,2121-2122 (1995)]. The reduction of (+) -camphorquinone by G.cingulata produced (+) -2-exo-3-exo-2,3-diol with hight stereoselectivility, whereas (-) -camphorquinone yielded (+) -2-endo-3-exo-2,3-diol with hight stereo- and enantioserectivility [Phytochemistry, 44,79 (1997)]. ((]SY+-[)) -Isopinocampheol was transformed into some compounds by G.cingulata, (-) form was obtained a diol by oxydation at 4-position as a major compound, and (+) form was obtained a diol by oxydation at 7-position as a major compound [Phytochemistry, in press (1997)]. Biotransformation of alpha-terpinene in common cutworm larvae (Spodoptera litura Fabricius) obtained mainly 4-isopropyl-1,3-cyclohexadienoic acid and cumic acid, this is first report about biotransformation of terpeniod with lepidoptera [J.Agric.Food Chem., 44,2889 (1996)].

Report

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

    (46 results)

All Other

All Publications (46 results)

  • [Publications] Mitsuo Miyazawa: "Biotransformation of the monoterpenoid,rose oxide,by Aspergillus niger" Phytochemistry. 39. 85-89 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Mitsuo Miyazawa: "Biotransformation of(-)-Nopol by Glomerella cingulata" Phytochemistry. 39. 337-340 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Mitsuo Miyazawa: "Resolution of racemic linalool oxide-pyranoid by microbial esterification" Tetrahedron Asymmetry. 6. 1067-1068 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Mitsuo Miyazawa: "Biotransformation of(+)-and(-)-canphorquinones by Fungi" Phytochemistry. 39. 569-573 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Mitsuo Miyazawa: "Biotransformation of(-)-α-Bisabolol by plant pathogenic Fungus,Glomerella cingulatai" Phytochemistry. 39. 1077-1080 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Mitsuo Miyazawa: "Biotransformation of(+)-Cedrol by Plant pathogenic Fungus" Phytochemistry. 40. 69-72 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Mitsuo Miyazawa: "Biotransformation of acycllc terpenoid(2E,6E)-Farnesol by plant pathogenic fungus Glomerella cingulata" Phytochemistry. 43. 105-109 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Mitsuo Miyazawa: "Biotransformation of(+)-and(-)-camphorquinones to camphanediols by Glomerella cingulata" Phytochemistry. 44. 79-81 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Mitsuo Miyazawa: "Biotransformation of the Sesguiterpenoid,β-Selinene,using the plant pathogenic fungus,Glomerella cingulata" Phytochemistry. 44. 433-436 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Mitsuo Miyazawa: "Biotransformation of(-)-and(+)-Isopinocampheol by Three fungi" Phytochemistry. (in press). (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Mitsuo Miyazawa: "Biotransfromation of(-)-cis-myrtanol and(+)-trans-myrtanol by plant pathogenic fungus,Glomerella Clingulata" Phytochemistry. (in press). (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Mitsuo Miyazawa: "Asymmetric reduction of Karahanaenone with Various Microorganisms" Tetrahedron Asymmetry. 6. 2121-2122 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Mitsuo Miyazawa: "Biotransformation of acyclic terpenoids,(+)-CIS-Nerolidol and Nerylacetone,by plant pathogenic fungus" Phytochemistry. 40. 1133-1137 (1995)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Mitsuo Miyazawa: "Biotransformations of acyclic terpenoidS,【.+-。】-trans-nerolidol and geranylacetone,by Glomerella cingulata" Journal of Agricultural and Food Chemistry. 44. 1543-1547 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Mitsuo Miyazawa: "Biotransformation of α-terpinene in Common cutworm larvae(spodoptera litura Fabricius)" Journal of Agricultural and Food Chemistry. 44. 2889-2893 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Mitsuo Miyazawa: "Microbial oxidation of citronellol by Glomerella cingulata" Natural Product Letters. 8. 303-305 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] Hirokazu Nankai: "Microbial transformation of【.+-。】-citronellal by Glomerella cingulata" Natural Product Letters. 9. 53-55 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] M.Miyazawa, K.Yokote, H.Kameoka: "Biotransformation of the monoterpenoid, rose oxide, by Aspergillus niger" Phytochemistry. 39 (1). 85-89 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] M.Miyazawa, Y.Suzuki, H.Kameoka: "Biotransformation of (-) -Nopol by Glomerella cingulata" Phytochemistry. 39 (2). 337-340 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] M.Miyazawa, K.Yokote, H.Kameoka: "Resolution of racemic linalool oxide-pyranoid by microbial esterification" Tetrahedron Asymmetry. 6 (5). 1067-1068 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] M.Miyazawa, M.Nobata, M.Hyakumachi, H.Kameoka: "Biotransformation of (+) -and (-) -Canphorquinones by Fungi" Phytochemistry. 39 (3). 569-573 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] M.Miyazawa, H.Nankai, H.Kameoka: "Biotransformation of (-) -alpha Bisabolol by Plant Pathogenic Fungus, Glomerella cingulata" Phytochemistry. 39 (5). 1077-1080 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] M.Miyazawa, H.Nankai, H.Kameoka: "Biotransformation of (+) -Cedrol by Plant Pathogenic Fungus, Glomerella cingulata" Phytochemistry. 40 (1). 69-72 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] M.Miyazawa, K.Tsuruno, H.Kameoka: "Asymmetric reduction of Karahanaenone with Various Microorganisms" Tetrahedron Asymmetry. 6 (9). 2121-2122 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] M.Miyazawa, H.Nankai, H.Kameoka: "Biotransformation of acyclic terpenoids, (+) -cis-Nerolidol and Nerylacetone, by plant pathogenic fungus, Glomerella cingurata" Phytochemistry. 40 (4). 1133-1137 (1995)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] M.Miyazawa, H.Nankai, H.Kameoka: "Biotransformation of acyclic terpenoids, ((]SY+-[)) -trans-Nerolidol and Geranylacetone, b Glomerella cingulata" J.Agric.Food Chem.44 (6). 1543-1547 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] M.Miyazawa, T.Wada, H.Kameoka: "Biotransformation of alpha-Terpinene in Common Cutworm Larvae (Spodopotera lituro Fabricius)" J.Agric.Food Chem.44 (9). 2889-2893 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] M.Miyazawa, H.Nankai, H.Kameoka: "Microbial oxidation of Citronellol by Glomerella cingulata" Nat.Prod.Lett.8. 303-305 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] H.Nankai, M.Miyazawa, H.Kameoka: "Microbial Transformation of ((]SY+-[)) -Citronellal by Glomellera cingulata" Nat.Prod.Lett.9. 53-55 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] M.Miyazawa, H.Nankai, H.Kameoka: "Biotransformation of acyclic terpenoid (2E,6E) -Famesol by plant pathogenic fungus Glomerella cingulata" Phytochemistry. 43 (1). 105-109 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] M.Miyazawa, M.Nobata, M.Hyakumachi, H.Kameoka: "Biotransformation of (+) -and (-) Camphorquinones to Camphanediols by Glomerella cingulata" Phytochemistry. 44 (1). 79-81 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] M.Miyazawa, Y.Honjo, H.Kameoka: "Biotransformation of the Sesquiterpenoid, beta-Selinene, using the plant pathogenic fungus, Glomerella cingulata as a biocatalyst" Phytochemistry. 44 (3). 433-436 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1996 Final Research Report Summary
  • [Publications] M.Miyazawa, Y.Suzuki, H.Kameoka: "Biotransformation of (-) -and (+) -Isopinocampheol by Three fungi" Phytochemistry. (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] M.Miyazawa, Y.Suzuki, H.Kameoka: "Biotransformation of (-) -cis-myrtanol and (+) -trnas-myrtanol by plant pathogenic fungus, Glomerella cingulata" Phytochemistry. (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] Mitsuo Miyazawa: "Biotransformations of acyclic terpenoids, (±) -trans-nerolidol and geranylacetone, by Glomerella cingulata" Journal of Agricultural and Food Chemistry. 44. 1543-1547 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Mitsuo Miyazawa: "Biotransformation of α-terpinene in Common cutworm larvae (Spodoptera litura Fabricius)" Journal of Agricultural and Food Chemistry. 44. 2889-2893 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Mitsuo Miyazawa: "Microbial oxidation of citronellol by Glomerella cingulata" Natural Product Letters. 8. 303-305 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Hirokazu Nankai: "Microbial transformation of (±) -citronellal by Glomerella cingulata" Natural Product Letters. 9. 53-55 (1996)

    • Related Report
      1996 Annual Research Report
  • [Publications] Mitsuo Miyazawa: "Biotransformation of (+)-and (-)-camphorquinones to camphanediols by Glomerella cingulata" Phytochemistry. 44. 79-81 (1997)

    • Related Report
      1996 Annual Research Report
  • [Publications] Mitsuo Miyazawa: "Biotransformation of (-)-and (+)-isopinocampheol by three fungi" Phytochemistry. (in press). (1997)

    • Related Report
      1996 Annual Research Report
  • [Publications] Mitsuo Miyazawa: "Resolution of racemic linalool oxide-pyranoid by microbial esterification" TETRAHEDRON ASYMMETRY. 6. 1067-1068 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Mitsuo Miyazawa: "Asymmetric reduction of karahanaenone with various microorganisms" TETRAHEDRON ASYMMETRY. 6. 2121-2122 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Mitsuo Miyazawa: "Biotransformation of (-)-α-bisabolol by plant pathogenic fungus, G. cingulata" Phytochemistry. 39. 1077-1080 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Mitsuo Miyazawa: "Biotransformation of (+)-cedrol by plant pathogenic fungus, G. cingulata" Phytochemistry. 40. 69-72 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Mitsuo Miyazawa: "Biotransformation of sesquiterpenoids,(+)-aromadendrene and (-)-aromadendrene by G. cingulata" Phytochemistry. 40. 793-796 (1995)

    • Related Report
      1995 Annual Research Report
  • [Publications] Mitsuo Miyazawa: "Biotransformation of acyclic terpenoids,(±)-cis-nerolidol and nerylacetone, by plant pathogenic fungus, G. cingulata" Phytochemistry. 40. 1133-1137 (1995)

    • Related Report
      1995 Annual Research Report

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Published: 1995-04-01   Modified: 2016-04-21  

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