アセビ薬の成分について(第4報)Pieristoxin F, Pieristoxin Gおよび数種の有毒成分の分離と構造

概要

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The methanolic extract of the leaves of Pieris japonica D.DON was purified and the final extract was submitted to column chromatography from which pieristoxin-F, pieristoxin-G, deacylpieristoxin-B, pieristoxin-C, asebotoxin-I, grayanotoxin-II, and, as the main poisonous principle, grayanotoxin-III (2.7 g, 0.013% yield) were isolated. Hydrolysis of pieristoxin-F affordea 7-hydroxygrayanotoxin-III. Nuclear magnetic resonance (NMR) spectrum of pieristoxin-F indicated the presence of one O-acetyl and one O-propionyl groups, and partial structures of ≡CCH(OR)CH(OH)C≡and-CHOR. Pieristoxin-F is not oxidized by sodium periodate, and its acetate does not agree with tetraacetyl-asebotoxin-IV. Therefore, the structure of pieristoxin-F was presumed to be 6-acetyl-7-hydroxy-14-propionylgrayanotoxin-III. The composition of pieristoxin-G was found to be C_<20>H_<32>O_8・H_2O from its elemental analytical values and highresolution mass spectrometry, while its infrared spectrum did not show absorptions for carbonyl and unsaturated bond(s). Pieristoxin-G is reduced by lithium aluminum hydride and consumes sodium periodate. Its NMR spectrum indicated the presence of a partial structure of≡CCH(OH)-CH(OH)C≡ and an epoxide ring. These facts suggested the structure of pieristoxin-G as 7,9-dihydroxy-2,3-epoxygranotoxin-III.
公益社団法人日本薬学会の論文
1975-07-25