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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
Project Status Completed (Fiscal Year 1994)
Budget Amount *help
¥2,100,000 (Direct Cost: ¥2,100,000)
Fiscal Year 1994: ¥800,000 (Direct Cost: ¥800,000)
Fiscal Year 1993: ¥1,300,000 (Direct Cost: ¥1,300,000)
KeywordsCannabinoid / Plant tissue culture / Biotransformation / Glycosidation / Cannabinoid receptor / Binding assay / カンナビジオール / テトラヒドロカンナビノール / 大麻成分配糖体 / バインデイングアッセイ / カンナビノール / 植物細胞 / カンナビノールグルコシド
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.

Report

(3 results)
  • 1994 Annual Research Report   Final Research Report Summary
  • 1993 Annual Research Report
  • Research Products

    (11 results)

All Other

All Publications (11 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
    • Related Report
      1994 Final Research Report Summary
  • [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
    • Related Report
      1994 Final Research Report Summary
  • [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
    • Related Report
      1994 Final Research Report Summary
  • [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
    • Related Report
      1994 Final Research Report Summary
  • [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
    • Related Report
      1994 Final Research Report Summary
  • [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
    • Related Report
      1994 Final Research Report Summary
  • [Publications] Hiroyuki Tanaka: "Cannabis 21,Biotransformation of Cannabinol to its glycosiles by in vitro plant tissue" Journal of Natural Products. 56. 2068-2072 (1993)

    • Related Report
      1994 Annual Research Report
  • [Publications] Yuri Goto: "Determination of Tetrahydro Cannabiolic acid‐Carrier Protein.Conjugute by Matrix‐assisted Laser Desorption/Lon:3tion Mass Spectronetry" Organic Mass Spectropeter. 29. 668-671 (1994)

    • Related Report
      1994 Annual Research Report
  • [Publications] Yukihiro Shoyama: "Winged been and some other vugetable and medicival plants in the nopics and subtropics" 日本特殊農産物協会, 59 (1993)

    • Related Report
      1994 Annual Research Report
  • [Publications] Hiroyuki Tanaka: "Cannabis 21,Biotransformation of cannabinol to its glycosides by in vitro plant tissue" Jornal of Natural Products. (印刷中). (1994)

    • Related Report
      1993 Annual Research Report
  • [Publications] Yukihiro Shoyama: "Winged been and some other vegetables and medicinal plants in the tropics and subtropics" 日本特殊農産物協会, 59 (1994)

    • Related Report
      1993 Annual Research Report

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Published: 1993-04-01   Modified: 2016-04-21  

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