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1992 Fiscal Year Final Research Report Summary

Regulatory Mechanisms of Terpene Biosynthesis in Plant Cultured Cells

Research Project

Project/Area Number 03660123
Research Category

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

Allocation TypeSingle-year Grants
Research Field 製造化学・食品
Research InstitutionObihiro University of Agriculture and Veterinary Medicine

Principal Investigator

NABETA Kensuke  Obihiro University of Agriculture and Veterinary Medicine Bioresource Chemistry Associate Professor, 畜産学部, 助教授 (70093911)

Co-Investigator(Kenkyū-buntansha) TAZAKI Hiroyuki  Obihiro University of Agriculture and Veterinary Medicine Bioresource Chemistry, 畜産学部, 助手 (80231405)
Project Period (FY) 1991 – 1992
KeywordsJapanese Larch (Larix leptolepis) / Liverwort (Heteroscyphus planus) / Perilla sp. (Akachirimenshiso) / Cultured Cells / Sesquiterpenes / Deuterated Mevalonates / Farnesyl Pyrophosphate / Cyclization
Research Abstract

1. A Cyclization of farnesyl pyrophophate (FPP) to bisabolane class sesquiterpenes including alpha-cedrene by cell-free extract from Larix leptolepis callus was investigated. The cell-free extracts specifically converted the 2Z-isomers of FPP to form alpha- cedrene. The cell-free extract was fractionated by centrifugation. The activity to form alpha-cedrene was present in 2000 g supernatant, but absent in 46,200 g supernatant. The activity was solubilized by detergents, but not EDTA. The results suggested that the enzyme is amphipathic or hydrophobic membrane protein. The absolute configuration of alpha-cedrene which is accumulated in Larix leptolepis callus was determined as (+)-alpha- isomer by GC and GC/MS using a chiral capillary column. The occurrence of (+)-alpha-cedrene was confirmed for the first time in nature. These properties of enzymes and a stereochemical course to form (+)-alpha-cedrene were markedly different from those reported for the enzymes from intact plants.
2. Lower terpenes produced by liverwort (Heteroscyphus planus) suspension cells were isolated. Structures of (-)-(1S)-7-Methoxy- 1,2-dihydrocadalene, (+)-(1S, 4R)-7-methoxycalamenene (a nobel compound), (+)-(1S,4R)-hydroxycalamenene (a nobel compound), and 7-methoxycadalene were determined by their spectral data and the chemical correlation. Feeding experiments of the specifically deuterated mevalonates indicated several hydride shifts during biosynthesis of cadalene derivatives. A cell-free extract from the suspension cells specifically converted the 6E-isomers of FPP to form sesquiterpenes of cadinane-type.
3. The hydride shifts during the formation of bisabolane class compound in Perilla (Akachirimenshiso) callus were confirmed by the feeding experiment using the specifically deuterated mevalonates.

  • Research Products

    (12 results)

All Other

All Publications (12 results)

  • [Publications] NABETA,K. et. al.: "Lignan Biosynthesis in Larix leotoleois callus" Phytoohemistry. 30. 3591-3593 (1991)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] NABETA,K. et. al.: "Sesquiterpenes of cadinane-type from cultured cells of the liverwort,Heterosoyohus planus" Phytoohemistry. 30. 117-122 (1991)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] NABETA,K. et. al.: "Occurrence of (+)-α-cedrene in Larix leotoleois callus" Biosoi. Bioteoh. Bioohem.

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] NABETA,K. et. al.: "Biosynthesis of sesquiterpenes from deuterated Mevalonates in Perilla callus" Biosoi. Bioteoh. Bioohem.

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] NABETA,K.et.al.: "Sesquiterpene synthesis by cell-free extracts of Larix leotoleois callus"

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Nabeta,K.,: "Biotechnology in Agriculture and Forestry,Vol VII Medicinal and Aromatic Plants 印刷中" Springer-Verlag,

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Nabeta,K.: "Lignan biosynthesis in Larix leptolepis callus" Phytochemistry. 30. 3591-3593 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Nabeta,K.: "Sesquiterpenes of cadinane-Type from culrured cells of the liverwort, Heteroscyphus planus" Phytochemistry. 32. 117-122 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Nabeta,K.: "Occurrence of (+)-alpha-cedrene in Larix leptolepis callus" Biosci.Biotech. Biochem. 57. (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Nabeta,K.: "Biosynthesis of sesquiterpenes from deuterated mevalonates in Perilla sp." Biosci.Biotech. Biochem. 57. (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Nabeta,K.: "Sesquiterpene synthesis by cell free extracts of Larix leptolepis callus"

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Nabeta,K.: Springer-Verlag. Biotechnology in Agriculture and Forestry Vo1. Vll Medicinal and Aromatic Plants,

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

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Published: 1994-03-24  

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