Lignans of Trachelospermum asiaticum var. intermedium. I.Isolation and Structures of Arctiin, Matairesinoside and Tracheloside

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As the components of the stems of Trachelospermum asiaticum NAKAI var. intermedium NAKAI, arctiin (I), matairesinoside(VI) and tracheloside(VIII) were isolated. VI was elucidated as 4,4'-dihydroxy-3,3'-dimethoxy-lignan-olid(9,9')-4'-β-D-glucopyranoside. In addition the formula of VIII established by T.Takano, et al. as C_<36>H_<50>O_<18> was reexamined and revised to C_<27>H_<34>O_<12>・1/2H_2O. VIII gave trachelogenin(X), C_<21>H_<24>O_7,mp 139-141° and D-glucose by acid or emulsin hydrolysis. From chemical and physical data structure of X was proposed as 4', 8'-dihydroxy-3,4,3'-trimethoxy-lignan-olid(9,9')(Xa) or 4,8'-dihydroxy-3,3', 4'-trimethoxylignan-olid(9,9')(Xb). In this paper structure of methyltranchelogenin(XI) with absolute configuration was determined to be 8(S), 8'(S)-8'-dihydroxy-3,4,3', 4'-tetramethoxy-lignan-olid(9,9'). Now we suggest two possible structures for VIII; 8(S), 8'(S)-4', 8'-dihydroxy-3,4,3', -trimethoxy-lignan-olid(9,9')-4'-β-D-glucopyranoside(VIIIa) or 8(S), 8'(S)-4,8'-dihydroxy-3,3', 4'-trimethoxy-lignan-olid(9,9')-4-β-D-glucopyranoside(VIIIb).
社団法人日本薬学会の論文
1972-12-25