Antioxidant flavonol glycosides from Schinus molle.
Chromatographic separation of aqueous MeOH extract of the leaves of Schinus molle L. has yielded two new acylated quercetin glycosides, named isoquercitrin 6''-O-p-hydroxybenzoate (12) and 2''-O-alpha-L-rhamnopyranosyl-hyperin 6''-O-gallate (13), together with 12 known polyphenolic metabolites for the first time from this species, namely gallic acid (1), methyl gallate (2), chlorogenic acid (3), 2''-alpha-L-rhamnopyranosyl-hyperin (4), quercetin 3-O-beta-D-neohesperidoside (5), miquelianin (6), quercetin 3-O-beta-D-galacturonopyranoside (7), isoquercitrin (8), hyperin (9), isoquercitrin 6''-gallate (10), hyperin 6''-O-gallate (11) and (+)-catechin (14). Their structures were established on the basis of chromatographic properties, chemical, spectroscopic (UV, 1H, 13C NMR) and ESI-MS (positive and negative modes) analyses. Compounds 4-9 and 11 exhibited moderate to strong radical scavenging properties on lipid peroxidation, hydroxyl radical and superoxide anion generations with the highest activities shown by 6 and 7 in comparison with that of quercetin as a positive control in vitro.
Marzouk
Mohamed S
MS
Chemistry of Tannins and Leather Technology Department, National Research Center, El-Behoose St. 31, Dokki, Cairo, Egypt. msmarzouk@yahoo.co.uk
Moharram
Fatma A
FA
Haggag
Eman G
EG
Ibrahim
Magda T
MT
Badary
Osama A
OA
D027926:Anacardiaceae / Q000737:chemistry*; D000818:Animals; D000975:Antioxidants / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D044948:Flavonols / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D017665:Hydroxyl Radical / Q000032:analysis; D020128:Inhibitory Concentration 50; D015227:Lipid Peroxidation / Q000187:drug effects*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008297:Male; D008862:Microsomes, Liver / Q000187:drug effects; D010226:Parabens / Q000737:chemistry / Q000302:isolation & purification; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D018515:Plant Leaves / Q000737:chemistry; D010946:Plants, Medicinal; D011794:Quercetin / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification; D051381:Rats; D017208:Rats, Wistar; D012210:Rhamnose / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification; D013481:Superoxides / Q000032:analysis
C510776:2''-O-rhamnopyranosylhyperin 6''-O-gallate; D000975:Antioxidants; D044948:Flavonols; D006027:Glycosides; D010226:Parabens; D010936:Plant Extracts; C510775:isoquercitrin 6''-O-4-hydroxybenzoate; D013481:Superoxides; D017665:Hydroxyl Radical; D011794:Quercetin; D012210:Rhamnose