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.
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
Anastasia
A
Detsi
Maya
M
Majdalani
Christos A
CA
Kontogiorgis
Dimitra
D
Hadjipavlou-Litina
Panagiotis
P
Kefalas
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