P-16 エゾマツ外皮の含有成分 : Epoxyserratane,Picane,及びJezane型新炭素骨格を有するトリテルペノイドの構造と生合成経路の考察(ポスター発表の部)

DOI

書誌事項

タイトル別名
  • P-16 Chemical Constituents of the Cuticle of Picea jezoensis Carr : jezoensis; on the Structures and Biogenesis of Epoxyserratanes, Picane, and Novel Triterpenes having an Unusual Skeletal System named "Jezane"

抄録

Previously, we have reported on the structures and anti-tumor-promoting activity of three triterpeneoids bearing a novel skeltal system of 14(13→12)abeo-12αH-serratane, for which we named "picane", isolated from the stem bark of Picea jezoensis Carr. hondoensis (Pinaceae). The above study prompted us to search for another new consitutents having more potent biological activity from the bark of Picea jezoensis Carr. jezoensis. Recently, we reported the isolation and the structure elucidation of 21α-hydroxy-3β-methoxyserrat-14-en-30-al and three 14β,15β-serratanes from the cuticle of the latter tree. Further examination of the cuticle led to the isolation of six new triterpenoids involving jezanals A (15) and B (16), having a novel skeletal system of 16(15→14)abeo-13βH-serratane which we gave the name of "jezane", and their structures were established as 21α-methoxyserrat-13-en-3,15-dione (11), 13β, 14β-epoxy-21α-methoxyserratan-3-one (12), 13β, 14β-epoxy-3β-methoxyserratan-21β-ol (13), 14β-hydroxypican-3,13,21-trione (14), 21β-hydroxy-3β-methoxyjezan-15β-al(15) and 21β-hydroxy-3α-methoxyjezan-15β-al (16), by chemical, spectral and single crystal X-ray analytical evidence. The most probable biosynthetical routes of 15 and 16 from the known serrat-14-enes via corresponding epoxy-derivatives were also discussed on the basis of success in their one step biomimeitic syntheses using MCPBA and BF_3-etherate.

収録刊行物

詳細情報 詳細情報について

  • CRID
    1390001206077930752
  • NII論文ID
    110006679437
  • DOI
    10.24496/tennenyuki.37.0_361
  • ISSN
    24331856
  • 本文言語コード
    ja
  • データソース種別
    • JaLC
    • CiNii Articles
  • 抄録ライセンスフラグ
    使用不可

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