Scavenging effects of tea catechins and their derivatives on 1,1-diphenyl-2-picrylhydrazyl radical

doi:10.1016/0891-5849(96)00237-7

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Scavenging effects of tea catechins and their derivatives on 1,1-diphenyl-2-picrylhydrazyl radical

Journal Article•DOI•

Scavenging effects of tea catechins and their derivatives on 1,1-diphenyl-2-picrylhydrazyl radical

Fumio Nanjo, Keiichi Goto, Ryota Seto, Masayuki Suzuki, Miwa Sakai, Yukihiko Hara - Show less +2 more

01 Jan 1996-Free Radical Biology and Medicine (Free Radic Biol Med)-Vol. 21, Iss: 6, pp 895-902

TL;DR: It is suggested that the galloyl moiety attached to flavan-3-ol at 3 position has a strong scavenging ability on the DPPH radical as well as the ortho-trihydroxyl group in the B ring, which elevates the radical scavenging efficiency above that of the orthosylated group; as has been recognized in other flavonoids such as flavones.

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About: This article is published in Free Radical Biology and Medicine.The article was published on 1996-01-01. It has received 768 citations till now. The article focuses on the topics: DPPH.

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Journal Article•DOI•

Screening of Brazilian plant extracts for antioxidant activity by the use of DPPH free radical method

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Luciana Lopes Mensor¹, Fábio de Sousa Menezes¹, Gilda Guimarães Leitão¹, Alexandre da Silva Reis¹, Tereza Cristina dos Santos¹, Cintia S. Coube¹, Suzana G. Leitão¹ - Show less +3 more•Institutions (1)

Federal University of Rio de Janeiro¹

01 Mar 2001-Phytotherapy Research

TL;DR: As a general rule the ethanol extracts of plants belonging to the Verbenaceae family showed lower EC50 values than the other plant extracts, among the partitions, the more polar ones (ethyl acetate and n‐butanol) are those that generally have higher antioxidant activity (AA).

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Abstract: Brazilian plant extracts belonging to 16 species of 5 different families (71 extracts) were tested against the stable DPPH (2,2-diphenyl-1-picryl-hydrazyl-hydrate) free-radical. The ability to scavenge DPPH radical was measured in these experiments by the discoloration of the solution. Ginkgo biloba and rutin, commonly used as antioxidants for medical purposes, were used as standards. Based on our results, we can say that as a general rule the ethanol extracts of plants belonging to the Verbenaceae family showed lower EC50 values than the other plant extracts. Among the partitions, the more polar ones (ethyl acetate and n-butanol) are those that generally have higher antioxidant activity (AA). Copyright © 2001 John Wiley & Sons, Ltd.

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1,986 citations

Journal Article•DOI•

Tea catechins and polyphenols: health effects, metabolism, and antioxidant functions.

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Jane V. Higdon¹, Balz Frei¹•Institutions (1)

Oregon State University¹

01 Jan 2003-Critical Reviews in Food Science and Nutrition

TL;DR: The effects of tea and green tea catechins on biomarker of oxidative stress, especially oxidative DNA damage, appear very promising in animal models, but data on biomarkers of in vivo oxidative stress in humans are limited.

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Abstract: Increasing interest in the health benefits of tea has led to the inclusion of tea extracts in dietary supplements and functional foods. However, epidemiologic evidence regarding the effects of tea consumption on cancer and cardiovascular disease risk is conflicting. While tea contains a number of bioactive chemicals, it is particularly rich in catechins, of which epigallocatechin gallate (EGCG) is the most abundant. Catechins and their derivatives are thought to contribute to the beneficial effects ascribed to tea. Tea catechins and polyphenols are effective scavengers of reactive oxygen species in vitro and may also function indirectly as antioxidants through their effects on transcription factors and enzyme activities. The fact that catechins are rapidly and extensively metabolized emphasizes the importance of demonstrating their antioxidant activity in vivo. In humans, modest transient increases in plasma antioxidant capacity have been demonstrated following the consumption of tea and green tea catechins. The effects of tea and green tea catechins on biomarkers of oxidative stress, especially oxidative DNA damage, appear very promising in animal models, but data on biomarkers of in vivo oxidative stress in humans are limited. Larger human studies examining the effects of tea and tea catechin intake on biomarkers of oxidative damage to lipids, proteins, and DNA are needed.

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1,688 citations

Journal Article•DOI•

Review: Methods Used to Evaluate the Free Radical Scavenging Activity in Foods and Biological Systems:

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Concepción Sánchez-Moreno

01 Jun 2002-Food Science and Technology International

TL;DR: In this paper, the authors described the methods used for free radical scavenging in both substrates as well as in specific cases of their application, such as superoxide radicals scavenging (O2·-), hydrogen peroxide scavenging(H2O2), hypochlorous acid scavenging, HOCl, and hydroxyl radical scavenges (HO), among them, among them are the methods that use azo-compounds to generate peroxyl radicals.

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Abstract: Free radical generation is directly related with oxidation in foods and biological systems. Therefore, the search for methods to determine free radical scavenging is important. In this work are described the methods used for this purpose in both substrates as well as in specific cases of their application. The main methods comprise superoxide radicals scavenging (O2·-); hydrogen peroxide scavenging (H2O2); hypochlorous acid scavenging (HOCl); hydroxyl radical scavenging (HO.); peroxyl radical scavenging (ROO.), among them are the methods that use azo-compounds to generate peroxyl radicals, such as the ``TRAP'' method (Total Radical-Trapping Antioxidant Parameter) and the ``ORAC'' method (Oxygen-Radical Absorbance Capacity); the scavenging of radical cation 2,2-azinobis-(3-ethylbenzothiazoline-6-sulphonate) or the ABTS or the ``TEAC'' method (Trolox Equivalent Antioxidant Capacity); the scavenging of stable radical 2,2-diphenyl-1-picrylhydrazyl or DPPH . method and the scavenging of radical cation N,N-dime...

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1,085 citations

Cites background from "Scavenging effects of tea catechins..."

...The ability of tea extracts (Yen and Chen, 1995) to scavenge H2O2 is followed by decay in H2O2 concentration....
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...The above assay has been applied to flavonoids and vitamins (Hayashi et al., 1988; Robak and Gryglewski, 1988; Ramanathan et al., 1996), gallic acid and derivatives (Aruoma et al., 1993; Gaujelac et al., 1999; Kubo et al., 2000), processed grain foods (Minamiyama et al., 1995), tea extracts (Yen and Chen, 1995), xylose–lysine maillard reaction products (Yen and Hsieh, 1998), berry extracts (Constantino et al., 1992; Wang and Jiao, 2000) seed extracts from Borago officinalis L. (Wettasinghe and Shahidi, 1999), procyanidins from grape-seed and wine extracts (Saint-Cricq de Gaulejac, 1999a), apple pectic oligosaccharides with small molecular weights (Tazawa et al., 1999), manufactured tomatoes (Lavelli et al., 1999, 2000), pigments from barley bran-fermented broth (Deguchi et al., 2000), polyphenols from apple pomace (Lu and Foo, 2000) and from onion skin (Suh et al., 1999), catechins from tea (Unno et al., 2000), purified garcinol from Garcinia indica (Yamaguchi et al., 2000a,b), honey and related products (Nagai et al., 2001), a high molecular weight hydroxycinnamatederived polymer (Barthomeuf et al., 2001), bamboo (Kweon et al., 2001), and several plants (Calliste et al., 2001)....
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...…Maillard reaction products (Yen and Hsieh, 1995; Chevalier et al., 2001; Morales and Jiménez-Pérez, 2001; Tressi et al., 2001), tea (Yen and Chen, 1995; Nanjo et al., 1996), pigments from barley bran-fermented broth (Deguchi et al., 2000), grape pomace (Larrauri et al., 1998), avellana hulls…...
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...To a minor extent, O 2 is generated using a non-enzymatic reaction of phenazine methosulphate in the presence of NADH and molecular oxygen (Nishikimi et al., 1972; Robak and Gryglewski, 1988; Yen and Chen, 1995; Yen and Hsieh, 1995; Yamaguchi et al., 2000b; Barthomeuf et al., 2001)....
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...The scavenging activity towards O 2 of a wide range of antioxidants is measured in terms of inhibition of generation of O 2 with the hypoxanthine–xanthine oxidase superoxide generating system (HX–XO) (Robak and Gryglewski, 1988; Halliwell, 1990; Mitsuya et al., 1990; Constantino et al., 1992; Minamiyama et al., 1995; Kruedener et al., 1995; Yen and Chen, 1995; Ramanathan et al., 1996; Robak and Sato et al., 1996; Lavelli et al., 1999, 2000; Suh et al., 1999; Saint-Cricq de Gaulejac et al., 1999a,b; Deguchi, 2000; Kubo et al., 2000; Lu and Foo, 2000; Unno et al., 2000; Wang and Jiao, 2000; Yamaguchi et al., 2000a; Calliste et al., 2001; Kweon et al., 2001)....
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Journal Article•DOI•

HPLC method for evaluation of the free radical-scavenging activity of foods by using 1,1-diphenyl-2-picrylhydrazyl

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Tomoko Yamaguchi¹, Hitoshi Takamura¹, Teruyoshi Matoba¹, Junji Terao²•Institutions (2)

Nara Women's University¹, University of Tokushima²

23 Jun 1998-Bioscience, Biotechnology, and Biochemistry

TL;DR: An HPLC method using 1,1-diphenyl-2-picrylhydrazyl (DPPH) determined the free radical-scavenging activity of several antioxidants: ascorbic acid, alpha-tocopherol, Trolox, and cysteine, and the results well agree with those of previous reports.

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Abstract: An HPLC method for evaluation of the free radical-scavenging activity of foods by using 1,1-diphenyl-2-picrylhydrazyl (DPPH) is reported. The activity was evaluated by measuring the decrease of DPPH detected at 517 nm. By using this novel method, we determined the free radical-scavenging activity of several antioxidants: ascorbic acid, α-tocopherol, Trolox, and cysteine. The results gave good correlation between the radical-scavenging activity determined by HPLC and by conventional colorimetry. This methodology was applied to determine the free radical-scavenging activity of 8 beverages. The activity of coffee was the highest, followed by red wine, green tea, oolong tea, black tea, rose wine, white wine, and orange juice. The results well agree with those of previous reports. This method is expected to be useful for a simple and rapid determination of free radical-scavenging activity in colored foods, because coloring substances in foods do not interfere with the measurement.

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1,075 citations

Journal Article•DOI•

Free-radical scavenging capacity and antioxidant activity of selected plant species from the Canadian prairies

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Ryszard Amarowicz¹, Ronald B. Pegg², Parvaneh Rahimi-Moghaddam², Branka Barl², J.A. Weil² - Show less +1 more•Institutions (2)

Polish Academy of Sciences¹, University of Saskatchewan²

01 Mar 2004-Food Chemistry

TL;DR: In this article, a b-carotene-linoleic acid (linoleate) model system was used to evaluate the scavenging effect on the DPPH free radical and capacity to scavenge hydroxyl free radicals.

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1,067 citations

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References

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Journal Article•DOI•

Dietary carcinogens and anticarcinogens Oxygen radicals and degenerative diseases

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Bruce N. Ames¹•Institutions (1)

University of California¹

23 Sep 1983-Science

TL;DR: Dietary intake of natural antioxidants could be an important aspect of the body's defense mechanism against these agents of cancer and other age-related diseases.

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Abstract: The human diet contains a great variety of natural mutagens and carcinogens, as well as many natural antimutagens and anticarcinogens. Many of these mutagens and carcinogens may act through the generation of oxygen radicals. Oxygen radicals may also play a major role as endogenous initiators of degenerative processes, such as DNA damage and mutation (and promotion), that may be related to cancer, heart disease, and aging. Dietary intake of natural antioxidants could be an important aspect of the body’s defense mechanism against these agents. Many antioxidants are being identified as anticarcinogens. Characterizing and optimizing such defense systems may be an important part of a strategy of minimizing cancer and other age-related diseases.

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2,924 citations

Book Chapter•DOI•

Flavonoids as antioxidants: determination of radical-scavenging efficiencies.

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Wolf Bors, Werner Heller, Christa Michel, Manfred Saran

01 Jan 1990-Methods in Enzymology

TL;DR: The radical chemistry of flavonoids not only is of interest from a kinetic or mechanistic point of view but also offers considerable insight into structural relationships of highly evolved plant components.

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Abstract: Publisher Summary This chapter discusses the radical-scavenging efficiencies of flavonoids as antioxidants To test whether a certain substance acts as radical scavenger, the clearest evidence comes from the determination of reaction rate constants with a set of different specifically produced radicals In the tests discussed in the chapter, hydroxyl, azide, superoxide, linoleic acid peroxyl, tert-butoxyl, and sulfite radicals are used The spectral observation of radical reactions with flavonoids is assisted by the strong absorption characteristics of both the parent compounds and their respective aroxyl radicals Owing to the low solubility of flavonoids, conditions for pseudo-first order reactions with radical species can rarely be achieved for flavonoid aglycones Therefore, kinetic modeling calculations are employed The radical chemistry of flavonoids not only is of interest from a kinetic or mechanistic point of view but also offers considerable insight into structural relationships of highly evolved plant components First, the consistently high rate constants for attack by different types of radicals demonstrate the effective radicals scavenging capabilities of most flavonoids Second, owing to extensive electron delocalization as a prerequisite for radical stabilization, multiple mesomeric structures exist for aroxyl radical species of flavonoids

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1,651 citations

Journal Article•DOI•

Flavonoids are scavengers of superoxide anions

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Robak J¹, Ryszard J. Gryglewski¹•Institutions (1)

New York Academy of Medicine¹

01 Mar 1988-Biochemical Pharmacology

TL;DR: It is concluded that antioxidant properties of flavonoids are effected mainly via scavenging of superoxide anions whereas non-flavonoid antioxidants act on further links of free radical chain reactions, most likely by scavenges of hydroxyl radicals.

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1,526 citations

Journal Article•DOI•

Polyphenolic Flavanols as Scavengers of Aqueous Phase Radicals and as Chain-Breaking Antioxidants

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N. Salah¹, Nicholas J. Miller, George Paganga, Lilian B. M. Tijburg, G.P. Bolwell, Catherine Rice-Evans - Show less +2 more•Institutions (1)

University of London¹

01 Oct 1995-Archives of Biochemistry and Biophysics

TL;DR: Against propagating lipid peroxyl radical species, epicatechin and catechin are as effective as ECG and EGCG, the least efficacious being EGC and GA.

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1,291 citations

Journal Article•DOI•

Flavonoids as Antioxidants

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Slobodan V. Jovanovic, Steen Steenken, Mihajlo Tosic, Budimir Marjanović, Michael G. Simic - Show less +1 more

01 Jun 1994-Journal of the American Chemical Society

1,048 citations