Lignan glycosides from the Rhizomes of Smilax trinervula and their Biological activities. (June 2017)

• Record Type: Journal Article
• Authors: Shu, Jicheng; Liang, Fang; Zhu, Genhua; Liu, Xing; Yu, Jiangli; Huang, Huilian
• Is Part Of: Phytochemistry letters. Volume 20(2017:Jun.)
• Page Start: 1
• Page End: 8
• Publication Date: 2017-06
• Subjects: Smilax trinervula -- Smilacaceae -- Lignan glycosides -- Cytotoxic activity; Botanical chemistry -- Periodicals; Chimie végétale -- Périodiques; 572.205
• DOI: 10.1016/j.phytol.2017.03.002
• Languages: English
• ISSNs: 1874-3900

Abstract

Graphical abstract: Highlights: Five new lignan glycosides were isolated from Smilax trinervula. The structures of these new compounds were determined on the basis of 1D and 2D NMR spectroscopy and HR-ESI–MS. Compounds 3 and 5 exhibited cytotoxic activity against Lovo cells, with IC50 value of 10.4 μM and 8.5 μM. Abstract: Phytochemical investigation of the rhizomes of Smilax trinervula led to isolation and structure elucidation of eight lignan glycosides, including five new lignans, namely, (7 S, 8 R, 8′ R )-4, 4′, 9-trihydroxy-3, 3′, 5, 5′-tetramethoxy-7, 9′-epoxylignan-7′-one 4′- O -β-d -glucopyranoside (1 ), (7 S, 8 R, 8′ R )-4, 4′, 9-trihydroxy-3, 3′, 5, 5′-tetramethoxy-7, 9′-epoxylignan-7′-one 4- O -β-d - glucopyranoside (2 ) (7 S, 8 R )-4, 9, 9′-trihydroxy-3, 3′, 5-trimethoxy-4′, 7-epoxy-8, 5′-neolignan 9′- O -β-d -glucopyranoside (3 ), (7 R, 8 R )-4, 9, 9′-trihydroxy-3, 5-dimethoxy-7.O.4′, 8.O.3′- neolignan 9′- O -β-d -glucopyranoside (4 ), and (7 S, 8 R )-4, 9, 9′-trihydroxy-3, 3′, 5-trimethoxy-8, 4′-oxy-neolignan 4- O -β-d -glucopyranoside (5 ), along with three known compounds (6 -8 ). Their structures were established mainly on the basis of 1D and 2D NMR spectral data, ESI–MS and comparison with the literature. Compounds1 -8 were tested in vitro for their cytotoxic activity against four human tumor cell lines (SH-SY5Y, SGC-7901, HCT-116, Lovo). Compounds3 and5 exhibited cytotoxic activity against Lovo cells, with IC50 value of 10.4 μM and 8.5 μM, respectively.