ナガバノコウヤボウキから得られるセスキテルペノイドと青葉アルコール配糖体及びコウヤボウキのセスキテルペン配糖体

概要

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From the leaves of Pertya glabrescens SCH. BIP. (Compositae) a new germacranolide, 3-epipertilide (III), C_<15>H_<16>O_4,[α]^<17>_D+52°and a new glycoside (VIII), C_<12>H_<22>O_6,[α]^<24>_D-36.5°were isolated in addition to pertic acid (Ib), 3α-hydroxypertic acid (IIb), benzoic acid, p-coumaric acid and methyl caffeate. On the basis of chemical and physicochemical evidence, III was determined to be stereoisomeric to pertilide (VI) at C-3,namely [1 (10) Z, 4E]-(3S, 7R, 8S)-germacra-1 (10), 4,11 (13)-triene-12,8; 14,3-diolide, and VIII, to be the β-D-glucopyranoside of (Z)-3-hexen-1-ol (leaf alcohol). The conformation of III was assigned from the examination of its derivatives IV, Va and Vb in nuclear Overhouser effect and circular dichroism. A new bitter principle, glucohaageanolide (X), C_<21>H_<30>O_8・H_2O, mp 155-165℃ (dec.), [α]^<20>_D+51.2°was isolated from the leaves of P. scandens (THUNB.) SCH. BIP. On hydrolysis X gave D-glucose and a known sesquiterpene haageanolide (XI). In order to make clear the exact structure of X including its absolute streorchemistry, an X-ray structure analysis of X monohydrate was undertaken, resulting in determination of X to be [1 (10) E, 4E]-(6S, 7S, 9S)-9-β-D-glucopyranosyloxygermacra-1 (10), 4,11 (13)-trien-12,6-olide.
公益社団法人日本薬学会の論文
1984-12-25