ANTIOXIDANT PROPERTIES AND EFFECTS OF APORPHINE ALKALOIDS AND THEIR PHENANTHRENE SECO-ISOMERS ON ACETYLCHOLINESTERASE ACTIVITY

Abstract

For the first time, model’s phenanthrene seco-alkaloids (seco-glaucine and seco-boldine) obtained in the medium of subcritical water SBW) from plant aporphine alkaloids were studied as antioxidants and inhibitors of acetylcholinesterase (AChE). Antioxidant activity (in vitro) of model’s aporphine and phenanthrene alkaloids: boldine, seco-boldine, glaucine and seco-glaucine, (BD, s-BD, GL and s-GL) was studied in the reaction with a stable free radical DPPH (1,1- diphenyl-2-picrylhydrazyl). In vivo, antioxidant activity was determined in a bioluminescent test system using genetically modified E. coli strains. In experiments in vitro (DPPH-test) and in vivo (biotest) phenanthrene alkaloids s-GL and s-BD demonstrate the higher antioxidant activity than their aporphine precursors GL and BD. For the study (in vitro) of the anticholinesterase activity of alkaloids and their phenanthrene seco-isomers used the “Ellman’s method” with minor modifications. The data on the inhibitory activity of the AChE enzyme with aporphine and phenanthrene alkaloids, expressed as IC50 values obtained from dose-response curves, demonstrate that the inhibitory activity for seco-boldine (IC50 = 0.21 mM) and seco-glaucine (IC50 = 0.04 mM ) is higher than for the initial aporphine alkaloids boldine (IC50 = 0.29 mM) and glaucine (IC50 = 0.44 mM), respectively. Thus, it has been shown that phenanthrene alkaloids obtained in SBW exhibit higher antioxidant activity and better inhibiting AChE-activity than their aporphine precursors.