Oxidation of liposomal membrane suppressed by flavonoids: Quantitative structure–activity relationship

Račková, Lucia; Firáková, S; Kostálová, D; Štefek, Milan; Šturdı́k, Ernest; Májeková, Magdaléna

doi:10.1016/j.bmc.2005.07.047

Cited by 54 publications

(59 citation statements)

References 47 publications

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“…Although structure-activity relationship (SAR) analysis has been reported for various flavonoid antioxidant and antiradical activities (e.g., see [24][25][26][27], only a few QSAR models have been developed [28][29][30][31][32] . Most of these models are limited in scope, however, correlating to only a few molecular parameters and/or limited to structurally-related flavonoids.…”

Section: Introductionmentioning

confidence: 99%

Improved quantitative structure–activity relationship models to predict antioxidant activity of flavonoids in chemical, enzymatic, and cellular systems

Khlebnikov

Schepetkin

Domina

et al. 2007

Bioorganic & Medicinal Chemistry

147

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Quantitative structure-activity relationship (QSAR) models are useful in understanding how chemical structure relates to the biological activity of natural and synthetic chemicals and for design of newer and better therapeutics. In the present study, 46 flavonoids and related polyphenols were evaluated for direct/indirect antioxidant activity in three different assay systems of increasing complexity (chemical, enzymatic, and intact phagocytes). Based on these data, two different QSAR models were developed using i) physicochemical and structural (PC&S) descriptors to generate multiparameter partial least squares (PLS) regression equations derived from optimized molecular structures of the tested compounds and ii) a partial 3D comparison of the 46 compounds with local fingerprints obtained from fragments of the molecules by the frontal polygon (FP) method. We obtained much higher QSAR correlation coefficients (r) for flavonoid end-point antioxidant activity in all 3 assay systems using the FP method (0.966, 0.948, and 0.965 for datasets in evaluated in the biochemical, enzymatic, and whole cells assay systems, respectively). Furthermore, high leave-oneout cross-validation coefficients (q 2 ) of 0.907, 0.821, and 0.897 for these datasets, respectively, indicated enhanced predictive ability and robustness of the model. Using the FP method, structural fragments (submolecules) responsible for the end-point antioxidant activity in the three assay systems were also identified. To our knowledge, this is the first QSAR model derived for description of flavonoid direct/indirect antioxidant effects in a cellular system, and this model could form the basis for further drug development of flavonoid-like antioxidant compounds with therapeutic potential.

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Section: Introductionmentioning

confidence: 99%

Improved quantitative structure–activity relationship models to predict antioxidant activity of flavonoids in chemical, enzymatic, and cellular systems

Khlebnikov

Schepetkin

Domina

et al. 2007

Bioorganic & Medicinal Chemistry

147

View full text Add to dashboard Cite

show abstract

“…The ortho-hydroxylation on the B-ring, the number of free hydroxyl groups, and a C2-C3 double bond in the C-ring are all proposed as conditions of radical scavenging activity (Rackova et al, 2005;Cao et al, 1997;Foti et al, 1996). Also, a free hydroxyl group at the C-3 position in flavonol has been proposed as a structural contributor to the high antioxidative activity against the progress of lipid peroxidation and the increase in 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical (Burda and Oleszek, 2001).…”

Section: Discussionmentioning

confidence: 99%

Effects of Dietary Chrysin Supplementation on Blood Pressure and Oxidative Status of Rats Fed a High-Fat High-Sucrose Diet

Yamamoto¹

2014

FSTR

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Effects of dietary chrysin supplementation on blood pressure and oxidative status of rats were studied in comparison with quercetin. Rats were fed a control diet or a high-fat high-sucrose (HFS) diet with or without 0.25% flavonoids (chrysin or quercetin) for 4 weeks. In rats fed the HFS diet without flavonoids, there was a significant elevation of blood pressure, increase in aortic NADPH oxidase but not xanthine oxidase, an increase in plasma lipid peroxides, and a decrease in liver glutathione, compared to rats fed the control diet. Chrysin suppressed the elevation of blood pressure in rats fed the HFS diets at the same level as quercetin. Chrysin supplementation did not suppress the increase in NADPH oxidase activity and plasma lipid peroxides or the decrease in liver glutathione, whereas these effects were significant with quercetin. Also, the results of an in vitro experiment suggested that chrysin did not exert antioxidative effects on lipid peroxidation in a linoleic acid emulsion. These results suggest that chrysin has an antihypertensive effect similar to quercetin, but unlike quercetin is not antioxidative in normotensive rats fed a HFS diet. Thus, it is probable that a mechanism(s) other than antioxidative activity is responsible for the suppression of hypertension by chrysin.

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“…[2] o-β-d-Glucosides possess higher degree of biological activities such as cell growth regulation, cell differentiation, immunological response, antitumour, antiparasitic, antifungal activities. [3][4][5][6][7][8][9][10][11] Several therapeutically interesting biological activities of certain flavonoids have been reported including anticancer, [12][13][14][15][16][17] anti-HIV, [18][19][20] and antioxidant [21][22][23] properties. Similarly imidazoles show antimalerial, antituberculosis, antifungal, anticonvulsant, antiprotozoal, anticancer, antihypertensive, anorectic, hypoglysacemic activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biological Study of O-β-D-Glucosides of 7-Hydroxy-3-(disubstituted Imidazol-2-yl)-4H-chromen-4-ones

Hatzade¹,

Taile²,

Ingle³

et al. 2013

MHC

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Oxidation of liposomal membrane suppressed by flavonoids: Quantitative structure–activity relationship

Cited by 54 publications

References 47 publications

Improved quantitative structure–activity relationship models to predict antioxidant activity of flavonoids in chemical, enzymatic, and cellular systems

Improved quantitative structure–activity relationship models to predict antioxidant activity of flavonoids in chemical, enzymatic, and cellular systems

Effects of Dietary Chrysin Supplementation on Blood Pressure and Oxidative Status of Rats Fed a High-Fat High-Sucrose Diet

Synthesis and Biological Study of O-β-D-Glucosides of 7-Hydroxy-3-(disubstituted Imidazol-2-yl)-4H-chromen-4-ones

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