title: Triterpene saponins with anti-inflammatory activity from the stems of Entada phaseoloides.
abstract: The phytochemical investigation of the ethanol extract from the stems of Entada phaseoloides (L.) Merr (also called "Guo Gang Long") led to the isolation of eleven triterpene saponins (1-11). Their structures were elucidated by extensive spectroscopic methods including 1D- ((1)H and (13)C) and 2D-NMR ((1)H-(1)H COSY, HSQC, HMBC, HSQC-TOCSY and ROESY) experiments as well as ESIMS analysis and hydrolysis. These saponins comprised entagenic acid as the main aglycon, saccharide moieties at C-3 and C-28, and esterification of C-2 or C-3 hydroxyl group of the terminal β-d-glucopyranose unit with a monoterpenic acid. To further explain the clinical applications of "Guo Gang Long" for its anti-inflammatory effect, the inhibitory activities on the production of NO of the saponins and the related aglycon, entagenic acid (12), were evaluated in vitro. The compounds containing a free hydroxyl at C-3 of aglycon (1 and 4) and entagenic acid showed significant activities against NO production in lipopolysaccharide-stimulated mouse macrophage RAW264.7 cells with IC50 values of 25.08, 20.13 and 23.48 μM, respectively. And the three compounds could also inhibit the release of pro-inflammatory cytokines, such as TNF-α, IL-1β, IL-6 and IL-8.
authors.affiliation: College of Pharmacy, South-Central University for Nationalities, Wuhan 430074, PR China.
authors.forename: Hui
authors.initials: H
authors.lastname: Xiong
authors.affiliation: College of Pharmacy, South-Central University for Nationalities, Wuhan 430074, PR China.
authors.forename: Yanan
authors.initials: Y
authors.lastname: Zheng
authors.affiliation: College of Pharmacy, South-Central University for Nationalities, Wuhan 430074, PR China.
authors.forename: Guangzhong
authors.initials: G
authors.lastname: Yang
authors.affiliation: College of Pharmacy, South-Central University for Nationalities, Wuhan 430074, PR China.
authors.forename: Huixia
authors.initials: H
authors.lastname: Wang
authors.affiliation: College of Pharmacy, South-Central University for Nationalities, Wuhan 430074, PR China. Electronic address: meizhinan@163.com.
authors.forename: Zhinan
authors.initials: Z
authors.lastname: Mei
mesh_terms: D000818:Animals; D000893:Anti-Inflammatory Agents / Q000494:pharmacology*; D016207:Cytokines / Q000378:metabolism; D007887:Fabaceae / Q000737:chemistry*; D008264:Macrophages / Q000187:drug effects; D051379:Mice; D015394:Molecular Structure; D009569:Nitric Oxide / Q000378:metabolism; D018547:Plant Stems / Q000737:chemistry; D012503:Saponins / Q000494:pharmacology*; D014315:Triterpenes / Q000494:pharmacology*
chemical_list: D000893:Anti-Inflammatory Agents; D016207:Cytokines; D012503:Saponins; D014315:Triterpenes; D009569:Nitric Oxide
keywords: Anti-inflammation; Entada phaseoloides; Leguminosae; Triterpene saponins