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Lipoxygenase inhibitory constituents from rhubarb



Phytochemical study on the ethanol extract of rhubarb led to the isolation of fifteen compounds, including five anthraquinones: chrysophanol ( 1 ), physcion ( 2 ), emodin ( 7 ), chrysophanol-8- O-β - d -glucopyranoside ( 9 ) and emodin-8- O-β - d -glucopyranoside ( 15 ), and ten stilbenes: desoxyrhaponticin ( 3 ), rhaponticin ( 4 ), resveratrol ( 5 ), desoxyrhapotigenin ( 6 ), rhapontigenin ( 8 ), piceatannol-3′- O-β - d -glucopyranoside ( 10 ), piceid ( 11 ), ε -viniferin ( 12 ), ampelopsin B ( 13 ) and isorhaponticin ( 14 ). Their structures were identified by comparing the physicochemical data with those of published papers. Among the isolated compounds, stilbene derivatives ( 3–6, 8 and 10–14 ) showed remarkable inhibitory effect on lipoxygenase with IC 50 values ranging from 6.7 to 74.1 μM. The inhibition kinetics analyzed by Lineweaver-Burk plots found that they were competitive inhibitors with the linoleic acid at the active site of lipoxygenase. In addition, stilbenes exhibited significantly free radical scavenging activity against ABTS ·+ with trolox equivalent activity capacity (TEAC) values ranging from 1.16 to 4.64. Whereas, anthraquinone derivatives ( 1–2, 7, 9 and 15 ) neither inhibited lipoxygenase nor scavenged free radical ABTS ·+ . These results indicated that stilbene derivatives were considerate to be mainly lipoxygenase inhibitor and free radical scavenger constituents of rhubarb.



Archives of Pharmacal ResearchSpringer Journals

Published: May 1, 2008

DOI: 10.1007/s12272-001-1199-0

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