Cimicifuga属植物の成分研究(第7報) : Cimicifugenolの構造

概要

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Cimicifugenol, C_<30>H_<48>O, occurs as colorless needles, mp 112-113°, [α]^<15>_D+21.4°, and is obtained in a free form and as an ester from the subterranean portion of Cimicifuga acerina, C. simplex, and C. japonica. From its chemical reactions and physicochemical properties, its structure was determined as represented by formula I. I forms an acetate (IV) of mp 118-119°, C_<32>H_<50>O_2. Its hydrogenation in ethanol-ethyl acetate over platinum dioxide or palladium carbon results in the formation of a dihydro compound (V), mp 116.5-117.5°, C_<32>H_<52>O_2. Treatment of V with tert-butyl chromate gives an α, β-unsaturated ketone (VI), mp 185-186°, C_<32>H_<50>O_3,whose treatment with lithium in ammonia gives a ketoacetate (VII), mp 179-180°, C_<32>H_<48>O_3. The Huang-Minlon reduction of VII produces a cycloartanol (III). On the other hand, hydrogenation of I over palladium-carbon in acetic acid-acetic anhydride results in the formation of a tetrahydro compound (X), mp 128-129°, C_<30>H_<52>O, whose treatment with phosphorus pentachloride gives a dehydrated rearrangement product (XII).
社団法人日本薬学会の論文
1970-01-25