Neolignan glycosides from Symplocos caudata.
A phytochemical investigation of the roots of Symplocos caudata Wall (Symplocaceae) resulted in isolation and characterization of four optical isomers of a neolignan glycoside (1-4), a lignan lactone glycoside (5), a phenylpropanoid glycoside (6), as well as two known compounds (7, 8). Their structures were elucidated as (7S,8S)-threo-7,9,9'-trihydroxy-3,3'-dimethoxy-8-O-4'-neolignan-4-O-beta-d-glucopyranoside (1), (7R,8R)-threo-7,9,9'-trihydroxy-3,3'-dimethoxy-8-O-4'-neolignan-4-O-beta-d-glucopyranoside (2), (7R,8S)-erythro-7,9,9'-trihydroxy-3,3'-dimethoxy-8-O-4'-neolignan-4-O-beta-d-glucopyranoside (3), (7S,8R)-erythro-7,9,9'-trihydroxy-3,3'-dimethoxy-8-O-4'-neolignan-4-O-beta-d-glucopyranoside (4), 8R,8'R-matairesinol-4-O-beta-d-xylopyranosyl-(1-->2)-O-beta-d-glucopyranoside (5), 1-O-[beta-d-xylopyranosyl-(1-->6)-O-beta-d-glucopyranosyl]-2,6-dimethoxy-4-propenyl-phenol (6), matairesinoside (7), and (R)-1-O-(beta-d-glucopyranosyl)-2-[2-methoxy-4-(omega-hydroxypropyl)-phenoxyl]-propan-3-ol (8) on the basis of spectroscopic data (1D and 2D NMR, MS and CD) and chemical evidence.
Huo
Changhong
C
Department of Natural Medicines and the State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University Health Science Center, 38 Xueyuan Road, 100083 Beijing, PR China.
Liang
Hong
H
Zhao
Yuying
Y
Wang
Bin
B
Zhang
Qingying
Q
D004365:Drugs, Chinese Herbal / Q000737:chemistry* / Q000302:isolation & purification; D006027:Glycosides / Q000737:chemistry* / Q000302:isolation & purification; D017705:Lignans / Q000737:chemistry* / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy / Q000379:methods / Q000592:standards; D008968:Molecular Conformation; D018517:Plant Roots / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D012015:Reference Standards; D013237:Stereoisomerism
D004365:Drugs, Chinese Herbal; D006027:Glycosides; D017705:Lignans