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Neolignan glycosides from Symplocos caudata.
Phytochemistry. 2008 Feb; 69(3):788-95.P

Abstract

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.

Authors+Show Affiliations

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.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

17905350

Citation

Huo, Changhong, et al. "Neolignan Glycosides From Symplocos Caudata." Phytochemistry, vol. 69, no. 3, 2008, pp. 788-95.
Huo C, Liang H, Zhao Y, et al. Neolignan glycosides from Symplocos caudata. Phytochemistry. 2008;69(3):788-95.
Huo, C., Liang, H., Zhao, Y., Wang, B., & Zhang, Q. (2008). Neolignan glycosides from Symplocos caudata. Phytochemistry, 69(3), 788-95.
Huo C, et al. Neolignan Glycosides From Symplocos Caudata. Phytochemistry. 2008;69(3):788-95. PubMed PMID: 17905350.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Neolignan glycosides from Symplocos caudata. AU - Huo,Changhong, AU - Liang,Hong, AU - Zhao,Yuying, AU - Wang,Bin, AU - Zhang,Qingying, Y1 - 2007/10/01/ PY - 2007/01/05/received PY - 2007/05/10/revised PY - 2007/08/18/accepted PY - 2007/10/2/pubmed PY - 2008/7/19/medline PY - 2007/10/2/entrez SP - 788 EP - 95 JF - Phytochemistry JO - Phytochemistry VL - 69 IS - 3 N2 - 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. SN - 0031-9422 UR - https://www.unboundmedicine.com/medline/citation/17905350/Neolignan_glycosides_from_Symplocos_caudata_ DB - PRIME DP - Unbound Medicine ER -