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Objective: To characterize the phytochemical constituents of Eupatorium triplinerve using GC – MS and to study the ability of the metabolites to serve as an antagonist to caspase 3 receptors to ascertain its anticancer properties. Methods: Ten grams of the powdered sample was subjected to column chromatography over silica gel (100-200 mesh) and eluted with n-hexane, chloroform, ethanol and methanol respectively. n- Hexane and Chloroform did not elute much of the compounds. The methanol fraction of the Eupatorium triplinerve was taken for GCMS analysis. The analysis was carried out on a GC Clarus 500 GC system with a column packed with Elite – 1 (10% dimethyl poly siloxane, 30 x 0.25 mm ID x 1 EM df), the compounds are separated using with Helium as carrier gas at a constant flow 1ml/min. sample extract (2 μL) injected into the instrument was detected by Turbo gold mass detector (Perkin Elmer) with the aid of the Turbo mass 5.1 software. The important compounds obtained from GC-MS were further studied in silico to study its anticancer activity by docking with caspase 3 receptor of four important metabolites neophytadiene, nitrocyclohexane, octadecane and tetradecanoic acid. Results: The GC MS analysis provided peaks of eleven different phytochemical compounds namely hexadecanoic acid (14.65%), 2,6,10-trimethyl,14-ethylene-14-pentadecne (9.84%), Bicyclo[4.1.0]heptane, 7-butyl- (2.38%), Decanoic acid, 8-methyl-, methyl ester (3.86%), 1-undecanol (7.82%), 1-hexyl-1- nitrocyclohexane (2.09%), 1,14-tetradecanediol (6.78%), Octadecanoic acid, 2-hydroxy-1,3-propanediyl ester (19.18%) and 2- hydroxy-3-[(9E) -9-octadecenoyloxy] propyl(9E)-9-octadecenoate (8.79%). From the docking assay it was found that nitrocyclohexane and neophytadiene compounds exhibited good docking score. Conclusion: The bioactive compounds in the methanolic extract of Eupatorium triplinerve have been screened using this analysis. Isolation of individual components would however, help to find new drugs.