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Chemical Study on Structure and Activity of Cucurbitane type Triterpene Glycosides.

Research Project

Project/Area Number 62570940
Research Category

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

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionHIROSHIMA UNIVERSITY

Principal Investigator

TANAKA Osamu  Hiroshima University School of Medicine, Prof., 医学部, 教授 (30012595)

Project Period (FY) 1987 – 1988
Project Status Completed (Fiscal Year 1988)
Budget Amount *help
¥1,700,000 (Direct Cost: ¥1,700,000)
Fiscal Year 1988: ¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 1987: ¥1,200,000 (Direct Cost: ¥1,200,000)
KeywordsChinese economic plant / Cucurbitaceous plant product / Cucurbitane type triterpene qlycoside / Sweet glycoside / Sweetness-structure relationship / Enzymic trans-glucosylation / Hemsleya species / 羅漢果 / ウリ科植物成分 / 中国民間薬物 / 肉花雪胆 / 藤三七雪胆 / 甘味物質 / 活性構造化学
Research Abstract

Isolation and structure elucidation of cucurbitane glycosides from Chinese cucubitaceous plants, were conducted.
From tubers of Hemsleya carnosiflora. eight new glycoside named carnosifloside I-VI(C-I-CI) were isolated and their structures were established. From tubers of H.panacis-scandens, seven new glycosides named scandenoside R1-7(S-R1-7) were isolated together with C-1-III, V and VI. Structures of S-R1-7 were elucidated.
From fruits of Siraitia siamensis, mogrosides-IV and V sweet principles of Siraitia grosvenorii (=Mordica grosvenori) together with two new glycosides, the structures of which were assigned as 11-keto-mogroside-V and 3-0-B-glucosyl-26-0-[B-glucosyl-(1 2)]-[B-glucosyl-(1 6)]-B-glucosyl-mogro, respectively.
For these natural glycosides as well as compounds derived from the natural glycosides by chemical or enzymic procedures, the relationship between taste and structure was investigated. (1) Compounds with only one or two glucosyl units such as C-i, S-R1-4, are tasteless. (2) 11 -0H glycosides with more than three glucosyl units such as mogroside-V,C-V, -VI and S-R6, are sweet. (3) 11B-0H glycoside a such as S-R7 are tasteless even if they have more than three glucosyl units. (4) 11-keto glycoside a taste bitter. However, the increase of glucosyl unit results in change of taste from bitter to sweet. For example, 11-keto-mogroside V is a glucopentoside, exhibiting sweetss. The bitterness of an 11-keto glucotrioside, C-III is decreased by enzymic glucosylation at the 26-gentiobiosyl moiety with starch and cyclodextrin-glucosyl transferase.

Report

(3 results)
  • 1988 Annual Research Report   Final Research Report Summary
  • 1987 Annual Research Report
  • Research Products

    (10 results)

All Other

All Publications (10 results)

  • [Publications] 田中治: 科学と工業. 61(10). 404-410 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Ryoji Kasai: Phytochemistry. 26(5). 1371-1376 (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Ryoji Kasai: Chemical and Pharmaceutical Bulletin.36(1). 234-243 (1988)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Osamu Tanaka: "Recent Advances in Chemistry of Natural Sweetness." Kagaku-to-Kogyo. 61(10). 401-410 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Ryoji Kasai: "Sweet and Bitter Cucurbitane Glycosides from Hemsleya carnosiflora" Phytochemistry. 26(5). 1371-1376 (1987)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] Ryoji Kasai: "Glycosides from Chinese Medicinal Plants, Hemsleya panacis-scandens, and Structure-Taste Relationship of Cucurbitane Glycosides." Chemical and Pharmaceutical Bulletin.36(1). 234-243 (1988)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1988 Final Research Report Summary
  • [Publications] 笠井良次: Chemical and Pharmaceutical Bulletin. 36. 234-243 (1988)

    • Related Report
      1988 Annual Research Report
  • [Publications] 笠井良次: Phytochemistry. 26(5). 1371-1376 (1987)

    • Related Report
      1987 Annual Research Report
  • [Publications] 笠井良次: Chamical and Pharmaceutical Bulletil. 36(1). (234-243)

    • Related Report
      1987 Annual Research Report
  • [Publications] 田中治: 科学と工業. 61(10). 404-410 (1987)

    • Related Report
      1987 Annual Research Report

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Published: 1987-04-01   Modified: 2016-04-21  

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