Redox reactions obtained by gamma irradiation of quercetin methanol solution are similar to in vivo metabolism.
The flavonol quercetin is one of the most well-known antioxidant flavonoids. Its antioxidant potential has been studied extensively during the last 10 years, but little is known about the metabolites formed in vivo that lead to the formation of depside and small molecules such as benzoic acids. In this study, gamma irradiation of a quercetin methanol solution was used as a model of certain oxidative reactions that occur in vivo. Qercetin at concentrations ranging from 5 x 10(-5) M to 5 x 10(-3) M, was irradiated with gamma rays at doses of 2-14 kGy. Quercetin degradation was evaluated by HPLC analysis. The major radiolytic metabolite was identified as a depside by NMR and LC-MS. Formation of 3,4-dihydroxybenzoic acid was also observed. The presence of CH3O. formed during methanol radiolysis is invoked to explain depside formation. Transformation of the 8-methoxy substituted depside (Q1) to the 8-hydroxyl substituted depside (Q2) is discussed. The antioxidant properties of quercetin metabolites are evaluated according to their capacity to decrease the EPR DPPH signal and to inhibit superoxide radical formed by the enzymatic reaction (xanthine + xanthine oxidase). For both assays, the IC50 of Q2 is twice as high as that of quercetin.
Marfak
A
A
UPRES EA 1085, "Biomolécules et Cibles Cellulaires Tumorales" Laboratoire de Biophysique, Faculté de Pharmacie, Cedex, France.
Trouillas
P
P
Allais
D P
DP
Calliste
C A
CA
Duroux
J L
JL
D002851:Chromatography, High Pressure Liquid; D005720:Gamma Rays; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D000432:Methanol; D015394:Molecular Structure; D010084:Oxidation-Reduction / Q000528:radiation effects; D011794:Quercetin / Q000737:chemistry* / Q000378:metabolism / Q000528:radiation effects*; D012996:Solutions / Q000737:chemistry* / Q000378:metabolism / Q000528:radiation effects*; D013056:Spectrophotometry, Ultraviolet; D013816:Thermodynamics
D012996:Solutions; D011794:Quercetin; D000432:Methanol