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Structural transformation of saikosaponins by intestinal flora and structure - activity relationship between their derivatives in anti - inflammatory action

Research Project

Project/Area Number 59570901
Research Category

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

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionNagoya City University

Principal Investigator

OGIHARA Yukio  Faculty of Pharmaceutical Sciences, Nagoya City University, 薬学部, 教授 (70080166)

Co-Investigator(Kenkyū-buntansha) AMAGAYA Sakae  Faculty of Pharmaceutical Sciences, Nagoya City University, 薬学部, 助手 (80137124)
Project Period (FY) 1984 – 1986
Project Status Completed (Fiscal Year 1986)
Budget Amount *help
¥1,600,000 (Direct Cost: ¥1,600,000)
Fiscal Year 1986: ¥300,000 (Direct Cost: ¥300,000)
Fiscal Year 1985: ¥300,000 (Direct Cost: ¥300,000)
Fiscal Year 1984: ¥1,000,000 (Direct Cost: ¥1,000,000)
Keywordssaikosaponin a / saikosaponin c / saikosaponin d / intestinal flora / structure-activity relationship / pituitary - adrenocortical axis function / corticosterone / アルカリ反解反応
Research Abstract

Saikosaponin a (sa) and c (sc) were treated with rat or artificial gastric juice to produce saikosaponin <b_1> ( <sb_1> ) and h (sh), possessing heteroannular diene at C-11, 13(18), and saikosaponin g (sg) and i (si), possessing homoannular diene at C-9(11), 12. On the other hand, saikosaponin d (sd) gave only saikosaponin <b_2> ( <sb_2> ), possessing heteroannulardiene, by the same treatment. Then,the incubation of sa, <sb_1> , sg, sd and <sb_2> with mouse intestinal flora gave the partial hydrolysis compounds, prosaikogenin F, A, H, G and D (PSF, PSA, PSH, PSG and PSD) and saikogenin F, A, H, G and D (SF, SA, SH, SG and SD). Although, sc, sh and si gave saikogenin E, C and B (SE, SC and SB), by the treatment with intestinal flora, prosaikogenins were not detected due to their complexity. Therefore, the new cleavage reaction of the glycosidic bond of saponin in alkoholic metal solution containing a trace of water. This reaction never cleaved the ether ring of sc and and gave 9 kinds o … More f prosaikogenins, prosaikogenin <E_1> (PS <E_1> :glc-glc-SE), <E_2> (PS <E_2> :rham-glc-SE) and <E_3> (PS <E_3> :glc-SE), prosaikogenin <C_1> (PS <C_1> :glc-glc-SE), <C_2> (PS <C_2> :rham-glc-SE) and <C_3> (PS <C_3> :glc-SE), and prosaikogenin <B_1> (PS <B_1> :glc-glc-SE), <B_2> (PS <B_2> :rham-glc-SE) and <B_3> (PS <B_3> :glc-SE). The 30 kinds of saikosaponin derivatives those were derived from the oral administration of sa, sc and sd in the alimentary tract were absorbed into the blood stream. Then, the effects of these derivatives on the corticosterone (endogenous glucocorticoid) secretion was investigated. Among sa and sd metabolites, sa and sd showed the strong increasing activity. However, sc was inactive and PS <E_1> and PS <E_2> stimulated the corticosterone secretion among sc derivatives. These results show that the stimulation of pituitary-adrenocortical axis function by saikosaponin metabolites could be due to the differencese of the molar polarity which depends uppon the existence of ether ring and the diffent glycosidic chain. Less

Report

(1 results)
  • 1986 Final Research Report Summary
  • Research Products

    (7 results)

All Other

All Publications (7 results)

  • [Publications] Kenji Fujiwara;Yukio Ogihara: Life Sciences. 39. 297-301 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Yukio Ogihara;Mitsuhiko Nose: J.C.S.Chem.Commun. 1417 (1986)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Koji Shimizu, Sakae Amagaya and Yukio Ogihara: "New derivatives of saikosaponins" Chem. Pharm. Bull.33. 3349-3355 (1985)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Koji Shimizu, Sakae Amagaya and Yukio Ogihara: "Structural transformation of saikosaponins by gastric juice and intestinal flora" J.Pharmacobio-Dyn.8. 718-725 (1985)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Kenji Fujiwara and Yukio Ogihara: "Pharmacological effects of oral saikosaponin a may differ depending on conditions of the gastrointestinal tract" Life Sciences. 39. 297-301 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Yukio Ogihara and Mitsuhiko Nose: "Novel cleavage of the glycosidic bond of saponins in alcoholic metal solution containing a trace of water." J. C. S. Chem. Commun.1417 (1986)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] Mitsuhiko Nose, Sakae Amagaya and Yukio Ogihara: "Effects of saikosaponin metabolites on the serum corticosterone level" J. Med. Pharm. Soc. WAKAN YAKU. in press

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary

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Published: 1987-03-31   Modified: 2016-04-21  

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