1. Lignans of Trachelospermum asiaticum var. intermedium. I.Isolation and Structures of Arctiin, Matairesinoside and Tracheloside
- Author
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Sueo Hisada, Sansei Nishibe, and Isao Ingaki
- Subjects
chemistry.chemical_compound ,biology ,Chemistry ,Stereochemistry ,Trachelospermum asiaticum ,Tracheloside ,Drug Discovery ,Absolute configuration ,Trachelogenin ,Arctiin ,General Chemistry ,General Medicine ,biology.organism_classification - Abstract
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 C36H50O18 was reexamined and revised to C27H34O12·1/2H2O. VIII gave trachelogenin(X), C21H24O7, 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).
- Published
- 1972