Chelating and free radical scavenging mechanisms of inhibitory action of rutin and quercetin in lipid peroxidation

Afanas’ev, Igor B.; Dorozhko, A.I.; Brodskii, A V; Kostyuk, Vladimir; Potapovitch, A I

doi:10.1016/0006-2952(89)90410-3

Cited by 886 publications

(470 citation statements)

References 17 publications

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“…Rutin, which possesses anti-inflammatory, vasoactive, antitumor, antibacterial, antiviral and antiprotozoal properties, has been widely used in treating disease (Calabro et al 2005). In addition, rutin can ameliorate increased capillary fragility associated with some hemorrhagic diseases or hypertension (Yildizogle-Ari et al 1991), has a antioxidant effect (Afanas et al 1989;Lindahl and Tagesson 1997), and is also antispasmodic and anticarcinogenic (Webster et al 1996).…”

Section: Resultsmentioning

confidence: 99%

Changes in phenols contents from buckwheat sprouts during growth stage

Koyama

Nakamura

2011

J Food Sci Technol

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Germinated buckwheat is buckwheat seeds soaked in water just until it begins to bud. Buckwheat sprouts are seedling plants of buckwheat grown up to 10-15 cm. The purpose of this study was to determine the optimal growth period for accumulating the most abundant functional phenol(s) in germinated buckwheat that had been soaked in darkness and buckwheat sprouts cultivated by hydroponic culture. The rutin contained in germinated buckwheat was analyzed by CE (capillary electrophoresis). Phenols, including isoorientin, orientin, isovitexin, vitexin, and rutin were separated from buckwheat sprouts by HPLC and identified by LC-MS. The highest rutin content in germinated buckwheat was found to be 15.8 mg/100 g DW at 20 h after germination. Buckwheat sprouts contained five kinds of major phenols. The highest amounts of isoorientin, orientin, isovitexin, and vitexin were measured at day 3, with the exception of rutin, and then a gradual decrease was observed as the sprouts grew. The quantities of isoorientin, orientin, isovitexin, and vitexin at day 3 were 5.8, 11.7, 26.2, and 28.9 mg/100 g FW, respectively. The rutin content rapidly increased to 109.0 mg/100 g FW until day 6. The highest total phenols in buckwheat sprouts were 162.9 mg/100 g FW at day 6. Germinated buckwheat soaked for 20 h and buckwheat sprouts cultivated for 6 days were rich in dietary phenol(s), which makes these plants a valuable functional food for human consumption.

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Section: Resultsmentioning

confidence: 99%

Changes in phenols contents from buckwheat sprouts during growth stage

Koyama

Nakamura

2011

J Food Sci Technol

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“…Other studies suggest that polyphenols might inhibit free radical formation and the propagation of free radical reactions through the chelation of transition-metal ions, particularly those of iron and copper [11][12][13][14][15][16]. Many studies have demonstrated the antioxidant effects of quercetin in lipid systems in the presence of a range of pro-oxidants [9,17,18].…”

Section: Figure 1 Structural Features Of Flavones and Flavonolsmentioning

confidence: 99%

Structural dependence of flavonoid interactions with Cu2+ ions: implications for their antioxidant properties

Brown

Khodr

Hider

et al. 1998

Biochemical Journal

733

389

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The flavonoids constitute a large group of polyphenolic phytochemicals with antioxidant properties in vitro. The interactions of four structurally related flavonoids (quercetin, kaempferol, rutin and luteolin) with Cu2+ ions were investigated in terms of the extent to which they undergo complex formation through chelation or modification through oxidation, as well as in their structural dependence. The ortho 3ʹ,4ʹ-dihydroxy substitution in the B ring is shown to be important for Cu2+-chelate formation, thereby influencing the antioxidant activity. The presence of a 3-hydroxy group in the flavonoid structure enhances the oxidation of quercetin and kaempferol, whereas luteolin and rutin, each lacking the 3-hydroxy group, do not oxidize as readily in the presence of Cu2+ ions. The results also demonstrate that the reactivities of the flavonoids in protecting low-density lipoprotein (LDL) against Cu2+ ion-induced oxidation are dependent on their structural properties in terms of the response of the particular flavonoid to Cu2+ ions, whether chelation or oxidation, their partitioning abilities between the aqueous compartment and the lipophilic environment within the LDL particle, and their hydrogen-donating antioxidant properties.

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“…Their ability to scavenge free radicals (Robak & Gryglewski, 1988;SanchezMoreno et al, 1998) and chelate metal ions (Afanas'ev et al, 1989) has led to an examination of their activities as antioxidants in in vitro systems of lipid peroxidation. This antioxidant activity is related to chemical structure, partition coef®cients and rate of reaction with the radicals of interest (van Acker et al, 1996;Rice-Evans et al, 1996).…”

Section: Introductionmentioning

confidence: 99%

Bioavailability and efficiency of rutin as an antioxidant: a human supplementation study

Boyle¹,

Dobson²,

Duthie³

et al. 2000

Eur J Clin Nutr

179

107

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Objective: To determine the potential antioxidant effect of rutin (quercetin-3-O-b-rutinoside) supplementation. Design: A 6-week randomized single-blind placebo controlled trial was conducted; 500 mg rutin supplement was compared to an equivalent amount of glucose placebo. In addition, a pharmacokinetic study was carried out. Setting: The Rowett Research Institute, Aberdeen, UK. Subjects: Eighteen healthy non-obese normocholesterolaemic female volunteers in the age range 18 ± 48 y. Main outcome measures: Plasma¯avonoids, ascorbic acid, tocopherols and carotenoids, plasma antioxidant capacity, lymphocyte DNA damage, blood chemistry and haematology, liver function tests, urinary malondialdehyde, 8-hydroxy-2H -deoxyguanosine and 8-iso-prostaglandin F 2a . Results: Eighteen volunteers completed the trial. Rutin supplementation did not induce any adverse changes in blood chemistry or indices of liver function. Plasma¯avonoids were signi®cantly elevated in the rutinsupplemented group. Endogenous oxidation of pyrimidines was signi®cantly decreased in both rutin-and placebo-treated volunteers. There was no signi®cant change in the level of urinary 8-hydroxy-2 H -deoxyguanosine or urinary malondialdehyde in either group. A linear correlation was observed between urinary malondialdehyde and urinary 8-iso-prostaglandin F 2a (R 0.54, P`0.01). Conclusion: Six weeks' rutin supplementation signi®cantly elevated the levels of three plasma¯avonoids (quercetin, kaempferol and isorhamnetin) but there was no signi®cant change in plasma antioxidant status. The decrease in the level of endogenous base oxidation in lymphocyte DNA seen in both the placebo-and rutinsupplemented subjects may re¯ect seasonal changes in other dietary antioxidants.

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Chelating and free radical scavenging mechanisms of inhibitory action of rutin and quercetin in lipid peroxidation

Cited by 886 publications

References 17 publications

Changes in phenols contents from buckwheat sprouts during growth stage

Changes in phenols contents from buckwheat sprouts during growth stage

Structural dependence of flavonoid interactions with Cu2+ ions: implications for their antioxidant properties

Bioavailability and efficiency of rutin as an antioxidant: a human supplementation study

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