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3‐ O ‐Methylquercetin Glucosides from Ophioglossum pedunculosum and Inhibition of Lipopolysaccharide‐Induced Nitric Oxide Production in RAW 264.7 Macrophages
Author(s) -
Wan ChuanXing,
Luo JianGuang,
Guo Chao,
Kong LingYi
Publication year - 2012
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201100500
Subject(s) - chemistry , quercetin , nitric oxide , stereochemistry , biochemistry , organic chemistry , antioxidant
The three new 3‐ O ‐methylquercetin glucosides 1 – 3 , together with three known congeners and 3‐ O ‐methylquercetin, were isolated from the fern Ophioglossum pedunculosum (quercetin=2‐(3,4‐dihydroxyphenyl)‐3,5,7‐trihydroxy‐4 H ‐1‐benzopyran‐4‐one). The new compounds were identified on the basis of spectroscopic analysis as 5′‐isoprenyl‐3‐ O ‐methylquercetin 4′,7‐di‐ β ‐ D ‐glucopyranoside ( 1 ), 3‐ O ‐methylquercetin 4′‐ β ‐ D ‐glucopyranoside 7‐[ O‐β ‐ D ‐glucopyranosyl‐(1→2) ‐β ‐ D ‐glucopyranoside] ( 2 ), and 3‐ O ‐methylquercetin 7‐[ O‐β ‐ D ‐glucopyranosyl‐(1→2) ‐β ‐ D ‐glucopyranoside] ( 3 ). The effect of the isolated compounds on lipopolysaccharide (LPS)‐induced NO production was evaluated. The inhibitory activity of 3‐ O ‐methylquercetin derivatives decreased markedly with the increasing number of glucosyl groups in the structures.