Cimicifuga属植物の成分研究(第2報)オオバショウマの成分その2 : Cimigenolの構造

概要

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A substance, C_<30>H_<48>O_5,of m.p. 216〜217°, [α]^<24>_D +38.20°, obtained as the main component of Cimicifuga acerina, had been named cimicifugol and its structural studies were being carried out. Later, however, this substance was found to be identical with cimigenol, obtained by Corsano and other, ^<2,3)>and expressed by formula (I), by direct comparison. I forms a monoacetate (II) of m.p. 200〜201°, [α]^<24>_D+45.55°, C_<32>H_<50>O_6,a diacetate (III), C_<34>H_<52>O_7,of m.p. 199〜200°, [α]^<24>_D+67.21°, another diacetate (IV), C_<37>H_<52>O_7,of m.p. 222〜223.5°, [α]^<15>_D+37.15°, a monoketo compound (V), C_<30>H_<46>O_5,of m.p. 206°, and a diketo compound (VI), C_<30>H_<44>O_5,of m.p. 212〜213°, Dehydration of III gives a compound (XII), C_<34>H_<50>O_6,of m.p. 220〜221.5°, whose catalytic reduction affords a dihydro compound (XIII), C_<34>H_<52>O_6,of m.p. 191〜192°. α, β-Unsaturated ketone compound (VIII), C_<30>H_<44>O_5,of m.p. 202〜204°, was obtained from V, and an intramolecular rearrangement product (IX), C_<30>H_<46>O_4,of m.p. 206〜207°, from I. From these reactions and other observations, the chemical structure of I would be appropriately formulated as (I).
社団法人日本薬学会の論文
1967-12-25