ABSTRACT
A bio-guided fractionation of Anabasis setifera Moq. (Chenopodiaceae) for anti-inflammatory activity was carried out using carrageenin rat paw edema model in rats. On the basis of percent edema inhibition after 3 h of carrageenin injection, n-butanol fraction showed promising activity through a significant (p < 0.05) decrease in paw volume by 85.6 % from control using indomethacin as reference standard. Moreover, the n-butanol fraction significantly (p < 0.05) decreased PGE2 and TNF-α in the exudates of rat paw edema. Chemical investigation of n-butanol fraction afforded α-amyrin 3-O-glucopyranoside (1), patuletin 7-O-glucopyranoside (2), myricitrin (3) and a new oleanane triterpene saponin derivative (4), sophradiol 3-O-α-L-(1)C4-rhamnopyranosyl-(1'''â4'')-O-ß-D-(4)C1-galactopyranosyl (1''â6')-O-ß-D-(4)C1-glucopyranoside. The structure of the new compound was determined by comprehensive analyses of their 1D and 2D NMR, mass spectral data and comparison with previously known analogs. Only compound 4 revealed a significant (p < 0.05) inhibition of cyclooxygenase 1 and 2 (COX) activities.
Subject(s)
Anti-Inflammatory Agents/pharmacology , Chenopodiaceae/chemistry , Saponins/pharmacology , Triterpenes/pharmacology , Animals , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/isolation & purification , Carrageenan , Cyclooxygenase 1/drug effects , Cyclooxygenase 1/metabolism , Cyclooxygenase 2/drug effects , Cyclooxygenase 2/metabolism , Disease Models, Animal , Edema/drug therapy , Edema/pathology , Inflammation/drug therapy , Inflammation/pathology , Male , Plant Extracts/chemistry , Plant Extracts/pharmacology , Rats , Rats, Sprague-Dawley , Saponins/chemistry , Saponins/isolation & purification , Triterpenes/chemistry , Triterpenes/isolation & purificationABSTRACT
Phytochemical investigations of Calotropis procera leaves have led to the isolation of two new compounds: quercetagetin-6-methyl ether 3-O-beta-D-4C1-galacturonopyranoside (3) and (E)-3-(4-methoxyphenyl-2-O-beta-D-4C1 -glucopyranoside)-methyl propenoate (4), along with eleven known metabolites: nine flavonol and two cinnamic acid derivatives. All metabolites were isolated for the first time from the genus Calotropis, except for 1 isolated previously from Calotropis gigantea. The structures were determined by spectroscopic methods (UV, ESI-MS, 1H, 13C NMR, 1H-1H COSY, HSQC, and HMBC). The radical scavenging activity of the aqueous methanol extract and compounds 8-13 was measured by the 1,1-diphenyl-2-picrylhydrazyl (DPPH) method. Cytotoxic screening of the same compounds was carried out on brine shrimps as well.
