Molecular properties and myocardial salvage effects of morin hydrate.
Morin hydrate is a bioactive pigment found in yellow Brazil wood. Recently, we reported that morin hydrate prolongs the survival of three types of cells from the human circulatory system against oxyradicals generated in vitro. The protection excels that given by equimolar concentrations of ascorbate, mannitol, and Trolox. Here, we demonstrate that, in vivo, morin hydrate at 5 mumol/kg actually reduced by > 50% the tissue necrosis in post-ischemic and reperfused rabbit hearts. Mechanistically, morin hydrate not only scavenges oxyradicals, but also moderately inhibits xanthine oxidase, a free-radical generating enzyme from the ischemic endothelium. Among other possibilities, morin hydrate appears to chelate some metal ions (e.g. Fe2+) in oxyradical formation, although this needs to be examined further. Nuclear magnetic resonance (at 500 mHz) and electron-impact mass spectrometry also supported a molecular formula of C15H10O7 for morin hydrate. Only by X-ray crystallography was it clearly revealed that there are two water molecules attached by intermolecular hydrogen bonds to a morin molecule. Also, the three rings of morin hydrate approach coplanarity. This conformation favours a delocalization of electrons after oxyradical reduction, making morin an effective antioxidant. Thus, we have documented some of the molecular properties and myocardial salvage effects of morin hydrate.
Wu
T W
TW
Department of Clinical Biochemistry, University of Toronto, Ontario, Canada.
Fung
K P
KP
Zeng
L H
LH
Wu
J
J
Hempel
A
A
Grey
A A
AA
Camerman
N
N
D000818:Animals; D000975:Antioxidants / Q000494:pharmacology*; D003327:Coronary Disease / Q000188:drug therapy* / Q000473:pathology; D018360:Crystallography, X-Ray; D005419:Flavonoids / Q000737:chemistry / Q000494:pharmacology*; D006321:Heart / Q000187:drug effects*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015425:Myocardial Reperfusion; D009206:Myocardium / Q000473:pathology; D009336:Necrosis / Q000517:prevention & control; D011817:Rabbits; D014969:Xanthine Oxidase / Q000037:antagonists & inhibitors; D047309:Flavones
D000975:Antioxidants; D005419:Flavonoids; D014969:Xanthine Oxidase; C008548:morin; D047309:Flavones