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)
書誌事項
- タイトル別名
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- 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
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- 天然有機化合物討論会講演要旨集
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天然有機化合物討論会講演要旨集 38 (0), 307-312, 1996
天然有機化合物討論会実行委員会
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詳細情報 詳細情報について
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- CRID
- 1390001206078406784
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- NII論文ID
- 110006679780
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- ISSN
- 24331856
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- 本文言語コード
- ja
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- データソース種別
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- JaLC
- CiNii Articles
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- 抄録ライセンスフラグ
- 使用不可