Dehydro-para-asebotin, a New Chalcone Glucoside in the Flowers of Gnaphalium affine D. DON

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概要

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• Besides luteolin 4'-D-glucoside (I) and luteolin (II), a chalcone glycoside (III), C_<22>H_<24>O_<10>・1 1/2 H_2O, mp 199-200°, [α]^<30>_D-85.2°(methanol), ultraviolet spectrum (UV) λ^<EtOH>_<max> 368 nm, was isolated from the flowers of Gnaphalium affine D. DON. III was acid hydrolyzed to give glucose and a flavanone (V), mp 256°, UV λ^<EtOH>_<max> 228,284 nm, which was identified as 4', 7-dihydroxy-5-methoxyflavanone by chemical and spectral data and by direct comparison of the diethyl ether (VIII) with an authentic sample. The sample, 4', 7-diethoxy-5-methoxyflavanone (VIII) was prepared, according to the result of a preliminary experiment (Table I), by stepwise alkylations of naringenin (IX) with an ether solution of diazoethane in absolute methanol for 3 hr and then with diazomethane in 70% methanol for 24 hr. Further examination of the methanolysis products of III permethylate (XV) and the spectral data of XV evidenced that III is 4'-O-β-D-glucopermethylate of 2', 4,4'-trihydroxy-6'-methoxychalcone (dehydro-para-asebotin), from which V is yielded on acid treatment. This is the first isolation of III and V from natural sources.

• 公益社団法人日本薬学会の論文
• 1974-08-25

著者

• 川崎 敏男

  Faculty of Pharmaceutical Sciences of Kyushu University

• 川崎 敏男

  Faculty Of Pharmaceutical Sciences Kyushu University

• 有富 正和

  Faculty of Education, Kumamoto University

• 有富 正和

  Faculty Of Education Kumamoto University

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