Natural and synthetic 2'-hydroxy-chalcones and aurones: synthesis, characterization and evaluation of the antioxidant and soybean lipoxygenase inhibitory activity.
A series of 2'-hydroxy-chalcones and their oxidative cyclization products, aurones, have been synthesized and tested for their antioxidant and lipoxygenase inhibitory activity. The natural product aureusidin (31) was synthesized in high yield by a new approach. An extensive structure-relationship study was performed and revealed that several chalcones and aurones possess an appealing pharmacological profile combining high antioxidant and lipid peroxidation activity with potent soybean LOX inhibition.
Detsi
Anastasia
A
National Technical University of Athens, School of Chemical Engineering, Department of Chemical Sciences, Laboratory of Organic Chemistry, Zografou Campus, 15773 Athens, Greece. adetsi@chemeng.ntua.gr
Majdalani
Maya
M
Kontogiorgis
Christos A
CA
Hadjipavlou-Litina
Dimitra
D
Kefalas
Panagiotis
P
D000975:Antioxidants / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001713:Biphenyl Compounds / Q000037:antagonists & inhibitors / Q000378:metabolism; D047188:Chalcones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D019787:Linoleic Acid / Q000037:antagonists & inhibitors / Q000378:metabolism; D008084:Lipoxygenase / Q000378:metabolism*; D016859:Lipoxygenase Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010851:Picrates / Q000037:antagonists & inhibitors / Q000378:metabolism
D000975:Antioxidants; D001572:Benzofurans; D001713:Biphenyl Compounds; D047188:Chalcones; D016859:Lipoxygenase Inhibitors; D010851:Picrates; D019787:Linoleic Acid; C004931:1,1-diphenyl-2-picrylhydrazyl; D008084:Lipoxygenase