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1987 Fiscal Year Final Research Report Summary

Cleavage Reaction Mechanis of Peroxydative Product in Biogeneration of Leaf Green Odour

Research Project

Project/Area Number 61560147
Research Category

Grant-in-Aid for General Scientific Research (C)

Allocation TypeSingle-year Grants
Research Field 製造化学・食品
Research InstitutionYamaguchi University

Principal Investigator

HATANAKA Akikazu  Faculty of Agriculture, Yamaguchi University, Professor, 農学部, 教授 (90035098)

Project Period (FY) 1986 – 1987
KeywordsLinoleyl alcohol / 12-Hydroxy-(3z)-dodecenal / (3Z)-hexenal / 異性化
Research Abstract

When 13-hydroperoxylinoleic acid is incubated with tea chloroplast, several products including geometrical isomers can be detected.Although the cleavage reaction performed by hydroperoxide lyase was extensively explored in our laboratry, whether this enzyme also progress isomerization or not had notbeen known yet. Investigation of this mechanism was performed with an alcohol derivative of 13-hydroperoxylinoleic acid, 13-hydroperoxylinoleyl alcohol (1). Incubation of synthesized 12-hydroxy-(3z)-dodecenal (2) with tea chloroplast revealed that 12-hydroxy-(2E)-dodecenal (3) was the product of isomerization reaction of 2. This isomerization was found to be caused also by incubation of 2 with heat inactivated chloroplast. Furthermore, this isomerization activity could be extracted with heat ehanol. These results indicate that isomerization is occured by heat-stable factor(s) but not by enzyme(s). This factor(s) was activated in alkaline condition but not affected with salt concentration. When 13-hydroperoxylinoleyl alcohol (1) was incubated with tea chloroplast under conditions which suppresses isomerization, 3 was formed only after cleavage reaction was almostly ceased. And when ^<18>O-(1) was incubated with tea chloroplast under this suppressed condition ^<18>O-(2) was effectively detected. These results indicated that the isomerization reaction was independent from cleavage reaction performed by hydroperoxide lyase. From this finding it is proposed that this enzyme retain cis-configuration of double bond at C-9 position of substrate (1) during cleavage reaction. In fact, when (9E, 11E)-(1) was incubated with this enzyme, there occurred no reaction Double bond at C-9 position of substrate must be recognized by some ligand around active centers of the enzyme but have no contribution on the reaction itself.

  • Research Products

    (13 results)

All Other

All Publications (13 results)

  • [Publications] A,Hatanaka;T,Kajiwara;J,Sekiya: Am,Chem.Soc.(ACS SYMPOSIUM SERIES No.317 Biogenation of Aromas). 167-175 (1986)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] A,Hatanaka;T,Kajiwara;J,Sekiya: THE METABOLISM,STRUCTURE,AND FUNCTION OF PLAT LIPIDS. 391-398 (1987)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] J,Sekiya;H,Koiso;A,Hatanaka & T,Kajiwara: THE METABOLISM,STRUCTURE,AND FUNCTION OF PLANT LIPIDS. 377-380 (1987)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] A,Hatanaka;T,Kajiwara;J,Sekiya: Chemistry and Physics of Lipids. 44. 341-361 (1987)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] A,Hatanaka;T,Kajiwara;K,Matsui: Z.Naturforshing. 43c. (1988)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] A,Hatanaka;T,Kajiwara;K,Matsui;T,Matsunaga: Z.Naturforsching. 43c. (1988)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] 畑中顯和: "みどりの香り-青葉アルコールの秘密" 中央公論社, 225 (1988)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] A. Hatanaka, T. Kajiwara and J. Sekiya: "Fatty Acid Hydroperoxide Lyase in Plant Tissues Volatile Aldehyde Formation from Linoleic and Linolenic Acid" Am. Chem. Soc. (ACS SYMPOSIUM SERIES No.317 Biogenaration of Aromas). 167-175 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] A. Hatanaka, T. Kajiwara and J. Sekiya: "ENZYMIC OXYGENATIVE-CLEAVAGE REACTION OF LINOLENIC ACID IN LEAVES-CHILOROPLASTIC LIPOXYGENASE AND FATTY ACID HYDROPEROXIDE LYASE IN TEA LEAVES" THE METABOLISM, STRUCTURE, AND FUNCTION OF PLANT LIPIDS. 391-398 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] J. Sekiya, H. Koiso, A. Hatanaka and T. Kajiwara: "MOLECULAR SPECIES COMPOSITION OF PHOSPHATIDYLGYCEROL IN LEAVES OF CAMELLIA SPECIES AND CHILLING SENSITIVITY" THE METABOLISM, STRUCTURE, AND FUNCTION OF PLANT LIPIDS. 377-380 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] A. Hatanaka, T. Kajiwara and J. Sekiya: "BIOSYNTHETIC PATHWAY FOR C_6-ALDEHYDES FORMATION FROM LINOLENIC ACID IN GREE LEAVES" Chemistry and physics of Lipids. 44. 341-361 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] A. Hatanaka, T. Kajiwara and K. Matsui: "Concentration of Hydroperoxide Lyase Activities in Root of Cucumber Seedings" Z. Naturforschung. 43c. (1988)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] A. Hatanaka: 「Green Odour」 -from leaf alcohol -. Chyuokoron, 225 (1988)

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 1989-03-30  

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