Madhucosides A and B, protobassic acid glycosides from Madhuca indica with inhibitory activity on free radical release from phagocytes.
The structures of madhucosides A (1) and B (2), isolated from the bark of Madhuca indica, were established as 3-O-beta-D-apiofuranosyl(1-->2)-beta-D-glucopyranosyl-28-O-[beta-D-xylopyranosyl(1-->2)-[alpha-L-rhamnopyranosyl(1-->4)]-beta-D-glucopyranosyl(1--> 3)-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranosyl]protobassic acid and 3-O-beta-D-apiofuranosyl(1-->2)-beta-D-glucopyranosyl-28-O-[beta-D-xylopyranosyl(1-->2)-[alpha-L-rhamnopyranosyl(1-->4)]-beta-D-glucopyranosyl(1-->3)-alpha-L-rhamnopyranosyl(1-->2)-alpha-L-arabinopyranosyl]protobassic acid, respectively. These two compounds showed significant inhibitory effects on both superoxide release from polymorphonuclear cells in a NBT reduction assay and hypochlorous acid generation from neutrophils assessed in a luminol-enhanced chemiluminescence assay.
Pawar
Rahul S
RS
Department of Natural Products, National Institute of Pharmaceutical Education and Research, Sector 67, SAS Nagar, Punjab 160062, India.
Bhutani
K K
KK
D006027:Glycosides / Q000097:blood / Q000737:chemistry / Q000302:isolation & purification*; D006801:Humans; D007194:India; D020128:Inhibitory Concentration 50; D032128:Madhuca / Q000737:chemistry*; D015394:Molecular Structure; D009504:Neutrophils / Q000187:drug effects; D009580:Nitroblue Tetrazolium; D019906:Nuclear Magnetic Resonance, Biomolecular; D024301:Plant Bark / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D013237:Stereoisomerism; D013481:Superoxides / Q000378:metabolism; D014315:Triterpenes / Q000097:blood / Q000737:chemistry / Q000302:isolation & purification*
D006027:Glycosides; D014315:Triterpenes; C485319:madhucoside A; C485320:madhucoside B; C485321:protobassic acid; D013481:Superoxides; D009580:Nitroblue Tetrazolium