Flavonoids and their oxidation products protect efficiently albumin-bound linoleic acid in a model of plasma oxidation. 2007

Claire Dufour, and Michèle Loonis
UMR A408 INRA/University of Avignon, Safety and Quality of Plant Products, INRA, Site Agroparc, 84914 Avignon Cedex 9, France. cdufour@avignon.inra.fr

Although LDL esterified polyunsaturated fatty acids (PUFA) contribute largely to the pool of oxidizable lipids in plasma, they coexist with a non-negligible content of free PUFA. In some pathological conditions, the free PUFA/albumin ratio becomes abnormally elevated. Modeling was performed in a system constituted of linoleic acid bound to human serum albumin (HSA) in which oxidation was initiated by hydrophilic AAPH. Inhibition of lipid peroxidation was evaluated for various flavonoids. The accumulations of hydroperoxyoctadecadienoic acids (HPODE), hydroxyoctadecadienoic acids (HODE) and ketooctadecadienoic acids (KODE) were similarly inhibited: isoquercitrin>quercetin>catechin=isorhamnetin>>kaempferol>quercetin-4'-beta-D-glucoside=quercetin-3,4'-di-beta-D-glucoside. Surprisingly, quercetin and isorhamnetin afforded a protection to linoleic acid long after their consumption. Elucidation by mass spectrometry and NMR of the quercetin oxidation products and assessment of their antioxidant capacity pointed out that 3,4-dihydroxybenzoic acid and 2-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxybenzofuran-3(2H)-one are major contributors to the apparent quercetin antioxidant capacity.

UI MeSH Term Description Entries
D008077 Lipoproteins, LDL A class of lipoproteins of small size (18-25 nm) and light (1.019-1.063 g/ml) particles with a core composed mainly of CHOLESTEROL ESTERS and smaller amounts of TRIGLYCERIDES. The surface monolayer consists mostly of PHOSPHOLIPIDS, a single copy of APOLIPOPROTEIN B-100, and free cholesterol molecules. The main LDL function is to transport cholesterol and cholesterol esters to extrahepatic tissues. Low-Density Lipoprotein,Low-Density Lipoproteins,beta-Lipoprotein,beta-Lipoproteins,LDL(1),LDL(2),LDL-1,LDL-2,LDL1,LDL2,Low-Density Lipoprotein 1,Low-Density Lipoprotein 2,LDL Lipoproteins,Lipoprotein, Low-Density,Lipoproteins, Low-Density,Low Density Lipoprotein,Low Density Lipoprotein 1,Low Density Lipoprotein 2,Low Density Lipoproteins,beta Lipoprotein,beta Lipoproteins
D008956 Models, Chemical Theoretical representations that simulate the behavior or activity of chemical processes or phenomena; includes the use of mathematical equations, computers, and other electronic equipment. Chemical Models,Chemical Model,Model, Chemical
D009682 Magnetic Resonance Spectroscopy Spectroscopic method of measuring the magnetic moment of elementary particles such as atomic nuclei, protons or electrons. It is employed in clinical applications such as NMR Tomography (MAGNETIC RESONANCE IMAGING). In Vivo NMR Spectroscopy,MR Spectroscopy,Magnetic Resonance,NMR Spectroscopy,NMR Spectroscopy, In Vivo,Nuclear Magnetic Resonance,Spectroscopy, Magnetic Resonance,Spectroscopy, NMR,Spectroscopy, Nuclear Magnetic Resonance,Magnetic Resonance Spectroscopies,Magnetic Resonance, Nuclear,NMR Spectroscopies,Resonance Spectroscopy, Magnetic,Resonance, Magnetic,Resonance, Nuclear Magnetic,Spectroscopies, NMR,Spectroscopy, MR
D010949 Plasma The residual portion of BLOOD that is left after removal of BLOOD CELLS by CENTRIFUGATION without prior BLOOD COAGULATION. Blood Plasma,Fresh Frozen Plasma,Blood Plasmas,Fresh Frozen Plasmas,Frozen Plasma, Fresh,Frozen Plasmas, Fresh,Plasma, Blood,Plasma, Fresh Frozen,Plasmas,Plasmas, Blood,Plasmas, Fresh Frozen
D011485 Protein Binding The process in which substances, either endogenous or exogenous, bind to proteins, peptides, enzymes, protein precursors, or allied compounds. Specific protein-binding measures are often used as assays in diagnostic assessments. Plasma Protein Binding Capacity,Binding, Protein
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D000975 Antioxidants Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. Anti-Oxidant,Antioxidant,Antioxidant Activity,Endogenous Antioxidant,Endogenous Antioxidants,Anti-Oxidant Effect,Anti-Oxidant Effects,Anti-Oxidants,Antioxidant Effect,Antioxidant Effects,Activity, Antioxidant,Anti Oxidant,Anti Oxidant Effect,Anti Oxidant Effects,Anti Oxidants,Antioxidant, Endogenous,Antioxidants, Endogenous
D012709 Serum Albumin A major protein in the BLOOD. It is important in maintaining the colloidal osmotic pressure and transporting large organic molecules. Plasma Albumin,Albumin, Serum
D015227 Lipid Peroxidation Peroxidase catalyzed oxidation of lipids using hydrogen peroxide as an electron acceptor. Lipid Peroxidations,Peroxidation, Lipid,Peroxidations, Lipid
D044948 Flavonols A group of 3-hydroxy-4-keto-FLAVONOIDS. 2-Phenyl-3-Hydroxy-Benzopyran-4-Ones,3-hydroxy-4-keto-Flavonoids,2 Phenyl 3 Hydroxy Benzopyran 4 Ones,3 hydroxy 4 keto Flavonoids

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