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Confomational analysis and antiallergic activity of triterpenes

Research Project

Project/Area Number 05671870
Research Category

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

Allocation TypeSingle-year Grants
Research Field 医薬分子機能学
Research InstitutionKYOTO UNIVERSITY

Principal Investigator

TANAKA Shigeo  Kyoto Univ., Fac.Pharm.Sci., As.Prof., 薬学部, 助教授 (30115878)

Co-Investigator(Kenkyū-buntansha) KAMISAKO Wasuke  Mukogawa Women's Univ., Fac.Pharm.Sci., Prof., 薬学部, 教授 (60085280)
Project Period (FY) 1993 – 1994
Project Status Completed (Fiscal Year 1994)
Budget Amount *help
¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 1994: ¥400,000 (Direct Cost: ¥400,000)
Fiscal Year 1993: ¥1,600,000 (Direct Cost: ¥1,600,000)
KeywordsCucurbitaceae / Luffa cylindrica / Plant cell culture / Triterpene / Bryonolic acid / Confomational analysis / Anti-allergic activity / Structure-activity relationship / ウリ科植物 / 植物培養細胞 / バイオテクノロジー / 物質生産 / アレルギー
Research Abstract

Cell suspension cultures of Luffa cylindrica accumulate large quantities of bryonolic acid (BA,D : C-friedoolean-8-en-3beta-ol-29-oic acid) , an acidic, pentacyclic tritepene found exclusively in the roots of the intact plant. Pharmacological tests using mice demonstrated that BA or its derivative is active against at least three types of allergies and that its activity could be increased significantly by preparing synthetic derivatives, in particular a potassium salt of its succinate ester (BS) . To study the relationship between conformation and antiallergic activity of triterpenes, synthetic BS derivatives that differ in the conformation of D/E rings (Fold type, Stretch type, and Equilibrium type) were subjected to an antiallergic test (passive cutaneous anaphylaxis) . The results of experiments suggested that not only Fold type conformation but also a functional group containing oxygen at C-29 is needed for the potentiation of antiallergic activity. A succinate ester (K salt) of D : C-friedoolean-7,9 (11) -dien-3beta-ol-29-oic acid was less effective than BS,suggesting that the conformation between B and C rings is also of importance in modulating the biological activity.

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] M.Tabata: "Production of anti‐allergic triterpene,bryonolic acid,by plant cel cultures" J.Nat.Prod.56. 165-174 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] H.J.Cho: "Biosynthesis of bryonolic acid in cultured cells of watermelon" Phytochemistry. 33. 1407-1413 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] J.Shimakura: "Intracellular distribution of the hydrophobic triterpene,bryonolic acid,in cultured cells of Luffa cylindrica L." Plant Cell Rep.12. 264-267 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] M.Tabata, S.Tanaka, H.J.Cho, C.Uno, J.Shimakura, M.Ito, W.Kamisako and C.Honda: "Production of anti-allergic triterpene, bryonolic acid, by plant cell cultures" J.Nat.Prod.56. 165-174 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] H.J.Cho, M.Ito, S.Tanaka, W.Kamisako and M.Tabata: "Biosynthesis of bryonolic acid in cultured cells of watermelon" Phytochemistry. 33. 1407-1413 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] J.Shimakura, H.J.Cho, S.Tanaka, H.Fukui and M.Tabata: "Intracellular distribution of the hydrophobic triterpene, bryonolic acid, in cultured cells of Luffa cylindrica L." Plant Cell Rep.12. 264-267 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1994 Final Research Report Summary
  • [Publications] M.Tabata: "Production of anti-allergic triterpene,bryonolic acid,by plant cell cultures" J.Nat.Prod.56. 165-174 (1993)

    • Related Report
      1994 Annual Research Report
  • [Publications] H.J.Cho: "Biosynthesis of bryonolic acid in cultured cells of watermelon" Phytochemistry. 33. 1407-1413 (1993)

    • Related Report
      1994 Annual Research Report
  • [Publications] J.Shimakura: "Intracellular distribution of the hydrophobic triterpene,bryonolic acid,in cultured cells of Luffa cylindrica L." Plant Cell Rep.12. 264-267 (1993)

    • Related Report
      1994 Annual Research Report
  • [Publications] M.Tabata: "Production of an anti-allergic triterpene,bryonolic acid,by plant cell cultures" J.Nat.Prod.56. 165-174 (1993)

    • Related Report
      1993 Annual Research Report
  • [Publications] Hi Jae Cho: "Biosynthesis of bryonolic acid in cultured cells of watermelon" Phytochemistry. 33. 1407-1413 (1993)

    • Related Report
      1993 Annual Research Report

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

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