Effects of stilbene constituents from rhubarb on nitric oxide production in lipopolysaccharide-activated macrophages.
Two new anthraquinone glucosides [chrysophanol 8-O-beta-D-(6'-galloyl)-glucopyranoside, aloe-emodin 1-O-beta-D-glucopyranoside] together with various known stilbenes and their glucosides, anthraquinone glucosides, and a naphthalene glucoside were isolated from the rhizome of Rheum undulatum L. Three stilbenes (rhapontigenin, piceatannol, resveratrol), a naphthalene glucoside (torachrysone 8-O-beta-D-glucopyranoside), and two stilbene glucoside gallates (rhaponticin 2''-O-gallate, rhaponticin 6''-O-gallate) showed inhibitory activity of NO production in lipopolysaccharide-activated macrophages, (IC50 = 11-69 microM). The oxygen functions (-OH,-OCH3) at the benzene ring were found to be essential to show the activity. Whereas, the glucoside moiety reduced the activity, while the alpha,beta-double bond did not affect the activity. Furthermore, the active stilbenes (rhapontigenin, piceatannol, resveratrol) inhibited iNOS induction.
Matsuda
H
H
Kyoto Pharmaceutical University, Japan.
Kageura
T
T
Morikawa
T
T
Toguchida
I
I
Harima
S
S
Yoshikawa
M
M
D000880:Anthraquinones / Q000737:chemistry; D004642:Emodin / Q000031:analogs & derivatives / Q000737:chemistry; D005707:Gallic Acid / Q000737:chemistry; D005960:Glucosides / Q000737:chemistry; D008070:Lipopolysaccharides / Q000494:pharmacology*; D008262:Macrophage Activation / Q000187:drug effects; D008264:Macrophages / Q000187:drug effects* / Q000201:enzymology*; D009281:Naphthalenes / Q000737:chemistry; D009569:Nitric Oxide / Q000096:biosynthesis*; D019001:Nitric Oxide Synthase / Q000037:antagonists & inhibitors / Q000096:biosynthesis; D052247:Nitric Oxide Synthase Type II; D009573:Nitrites / Q000378:metabolism; D010936:Plant Extracts / Q000032:analysis / Q000737:chemistry* / Q000494:pharmacology*; D010946:Plants, Medicinal; D012250:Rheum / Q000737:chemistry*; D013267:Stilbenes / Q000494:pharmacology*; D013329:Structure-Activity Relationship
D000880:Anthraquinones; D005960:Glucosides; D008070:Lipopolysaccharides; D009281:Naphthalenes; D009573:Nitrites; D010936:Plant Extracts; D013267:Stilbenes; C407723:aloe-emodin 1-O-glucopyranoside; C407722:chrysophanol 8-O-(6'-galloyl)glucopyranoside; D009569:Nitric Oxide; D005707:Gallic Acid; C518327:aloe emodin; D019001:Nitric Oxide Synthase; D052247:Nitric Oxide Synthase Type II; D004642:Emodin