52(P13) チャツムタケ属担子菌のポリイソプレンポリオール類の立体構造(ポスター発表の部)

DOI

書誌事項

タイトル別名
  • 52(P13) STEREOCHEMISTRY OF POLYISOPRENEPOLYOLS ISOLATED FROM FUNGI GENUS GYMNOPILUS

抄録

Gymnopilus spectabilis has been known as a hallucinogenic mushroom from which toxic polyisoprenepolyols such as gymnopilin have been isolated. Since similar mushroom G. aeruginosus has not been known its toxicity, we have investigated its components to isolate two types of polyisoprenepolyols, homologues of gymnopilin and gymnoprenol. The gymnopilin homologue contained an extra isoprene unit compared with known gymnopilin isolated from G. spectabilis. Because of that gymnopilin showed the neuroexitatory activity, G. aeruginosus should be regarded as a poisonous mushroom. For determination of the stereochemistry of newly isolated congeners, we have demonstrated a new procedure for analyzing the configuration at C-3' of hydroxymethylglutaric acid (HMGA) part. The absolute configuration of the ω-tert-hydroxyl was determined as S which implied the configuration of other tert-hydroxyls in 1,5-polyol system in gymnopilin. Namely, we have isolated gymnopilin (3:m=2, n=4) from G. spectabilis and transformed it to γ-Lactone (5). Model lactones having similar asymmetric center at C-5 were synthesized and Cotton effects in CD spectra were compared. γ-Lactone (5) derived from gymnopilin showed positive Cotton effect as shown with S-lactone (25). The above fact proved the S-configuration at ω-position of gymnopilin (3).

収録刊行物

詳細情報 詳細情報について

  • CRID
    1390001206078406784
  • NII論文ID
    110006679780
  • DOI
    10.24496/tennenyuki.38.0_307
  • 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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