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      An Essential Difference between the Flavonoids MonoHER and Quercetin in Their Interplay with the Endogenous Antioxidant Network

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          Abstract

          Antioxidants can scavenge highly reactive radicals. As a result the antioxidants are converted into oxidation products that might cause damage to vital cellular components. To prevent this damage, the human body possesses an intricate network of antioxidants that pass over the reactivity from one antioxidant to another in a controlled way. The aim of the present study was to investigate how the semi-synthetic flavonoid 7-mono-O-(β-hydroxyethyl)-rutoside (monoHER), a potential protective agent against doxorubicin-induced cardiotoxicity, fits into this antioxidant network. This position was compared with that of the well-known flavonoid quercetin. The present study shows that the oxidation products of both monoHER and quercetin are reactive towards thiol groups of both GSH and proteins. However, in human blood plasma, oxidized quercetin easily reacts with protein thiols, whereas oxidized monoHER does not react with plasma protein thiols. Our results indicate that this can be explained by the presence of ascorbate in plasma; ascorbate is able to reduce oxidized monoHER to the parent compound monoHER before oxidized monoHER can react with thiols. This is a major difference with oxidized quercetin that preferentially reacts with thiols rather than ascorbate. The difference in selectivity between monoHER and quercetin originates from an intrinsic difference in the chemical nature of their oxidation products, which was corroborated by molecular quantum chemical calculations. These findings point towards an essential difference between structurally closely related flavonoids in their interplay with the endogenous antioxidant network. The advantage of monoHER is that it can safely channel the reactivity of radicals into the antioxidant network where the reactivity is completely neutralized.

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          Most cited references 32

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          Cellular defenses against damage from reactive oxygen species.

           Paul B. Yu (1993)
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            Intake of potentially anticarcinogenic flavonoids and their determinants in adults in The Netherlands.

            Flavonoids are strong antioxidants that occur naturally in foods and can inhibit carcinogenesis in rodents. Accurate data on population-wide intakes of flavonoids are not available. Here, using data of the Dutch National Food Consumption Survey 1987-1988, we report the intake of the potentially anticarcinogenic flavonoids quercetin, kaempferol, myricetin, apigenin, and luteolin among 4,112 adults. The flavonoid content of vegetables, fruits, and beverages was determined by high-performance liquid chromatography. In all subjects, average intake of all flavonoids combined was 23 mg/day. The most important flavonoid was the flavonol quercetin (mean intake 16 mg/day). The most important sources of flavonoids were tea (48% of total intake), onions (29%), and apples (7%). Flavonoid intake did not vary between seasons; it was not correlated with total energy intake (r = 0.001), and it was only weakly correlated with the intake of vitamin A (retinol equivalents, r = 0.14), dietary fiber (r = 0.21), and vitamin C (r = 0.26). Our use of new analytic technology suggests that in the past flavonoid intake has been overestimated fivefold. However, on a milligram-per-day basis, the intake of the antioxidant flavonoids still exceeded that of the antioxidants beta-carotene and vitamin E. Thus flavonoids represent an important source of antioxidants in the human diet.
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              Direct observation of a free radical interaction between vitamin E and vitamin C.

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                Author and article information

                Contributors
                Role: Editor
                Journal
                PLoS One
                plos
                plosone
                PLoS ONE
                Public Library of Science (San Francisco, USA )
                1932-6203
                2010
                8 November 2010
                : 5
                : 11
                Affiliations
                [1 ]Department of Pharmacology and Toxicology, NUTRIM School for Nutrition, Toxicology and Metabolism, Maastricht University Medical Centre (MUMC+), Maastricht, The Netherlands
                [2 ]Faculty of Life Sciences, Hogeschool Zuyd, Heerlen, The Netherlands
                University of Wales Bangor, United Kingdom
                Author notes

                Conceived and designed the experiments: HJ AB WJvdV GRRMH. Performed the experiments: HJ. Analyzed the data: HJ MM AB WJvdV GRRMH. Contributed reagents/materials/analysis tools: HJ MM. Wrote the paper: HJ MM GRRMH.

                Article
                10-PONE-RA-20346R1
                10.1371/journal.pone.0013880
                2975634
                21079733
                04082169-930a-489a-b3f9-2ac4541f140f
                Jacobs et al. This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.
                Page count
                Pages: 9
                Categories
                Research Article
                Chemical Biology
                Nutrition
                Biochemistry/Chemical Biology of the Cell
                Cell Biology/Chemical Biology of the Cell

                Uncategorized

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