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1994 Fiscal Year Final Research Report Summary

Biotransformation of cannabinoids using plant tissue culture and their activity

Research Project

Project/Area Number 05671828
Research Category

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

Allocation TypeSingle-year Grants
Research Field Biological pharmacy
Research InstitutionKYUSHU UNIVERSITY

Principal Investigator

SHOYAMA Yukihiro  Kyusyu University, 薬学部, 教授 (70037604)

Co-Investigator(Kenkyū-buntansha) MORIMOTO Satoshi  Kyusyu University, 薬学部, 助教授 (60191045)
YAMAMOTO Tuneyuki  Kyusyu University, 薬学部, 助教授 (20091332)
Project Period (FY) 1993 – 1994
KeywordsCannabinoid / Plant tissue culture / Biotransformation / Glycosidation / Cannabinoid receptor / Binding assay
Research Abstract

The breeding of medicinal plants and the production of naturally occurring biologically active compounds have been investigated by plant tissue culture technique in this laboratory. In this project we started to study the biotransformation of cannabinoids using the plant cell and/or tissue as a plant catalyst in ordsr to create some new cannabinoids for resources of new drugs.
Tetrahydrocannabinol (THC), cannabidiol (CBD), cannabidiolic acid (CBDA) and cannabinol (CBN) were incubated individually with the protocorm segment of Pinellia ternata in the medium supplemented with 2,4-D (0.25 mg/l) at 25゚C in the dark condition for 1-3 weeks. The biotransformed products were extracted from the protocorm body and the medium, then purified. These structures were elucidated as THC-monoglycoside, CBD-mono and diglycosides, CBDA-monoglycoside and hydroxy-CBDA-monoglycoside, CBN-mono glycoside and hydroxy-CBN-monoglycoside by ^<13>C and ^1HNMR and FAB-MS,respectively. It became evident that THC-monoglycoside and CBN-monoglycoside (Kd>8 ^<mu>M) and CBD-monoglycoside (Kd>20 ^<mu>M) have the affinity with cannabinoid receptor. From these results, the pharmacological activities of three new cannabinoids will be expected.

  • Research Products

    (6 results)

All Other

All Publications (6 results)

  • [Publications] Hiroyuki Tanaka: "Cannabis 21 Biotransformation of cannabinol to its glycosides by in vitro plant tissue" Journal of Natural products. 56. 2068-2072 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yuri Goto: "Determination of tetrahydro cannabirolic acid-carrier protein conjugate by matrix-assisted Laser desorption/ionization Mass Spectrometry" Organic Mass Spectrometry. 29. 618-671 (1994)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Yukihiro Shoyama: "Winged bean and some other vegetefle and medicinal plants in the tropics and subtropics" 日本特殊農産物協会, 59 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Hiroyuki Tanaka: "Cannabis 21 Biotransformation of cannabinol to its glycosides by in vitro plant tissue" Journal of Natural Products. 56. 2068-2072 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Yuri Goto: "Determination of tetrahydro cannabirolic acid-carrier protein conjuigate by matrix-assisted laser desorption/ionization Mass spectro-metry" Organic Mass Spectrometry. 29. 618-671 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Yukihiro Shoyama: Winged bear and some other vegetable and medicinal plants in the tropics and subtropics. Nihon tokushu nosannbutsu kyokai, 59 (1993)

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

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Published: 1996-04-15  

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