The antioxidant and pro-oxidant activity of vitamin C and trolox in vitro: a comparative study

The antioxidant and pro‐oxidant properties of ascorbic acid (vitamin C) and the water‐soluble analogue of α‐tocopherol (trolox) were compared. Trolox has advantages over α‐tocopherol, the latter being only lipid‐soluble due to the presence of a carboxyl group in lieu of a phytol chain which imparts...

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Published in	Journal of applied toxicology Vol. 28; no. 2; pp. 183 - 188
Main Authors	Poljšak, Borut, Raspor, Peter
Format	Journal Article
Language	English
Published	Chichester, UK John Wiley & Sons, Ltd 01.03.2008 Wiley
Subjects	Antioxidants - chemistry ascorbic acid Ascorbic Acid - chemistry Biological and medical sciences Chromans - chemistry Chromium - chemistry DNA Damage DNA, Superhelical - chemistry Hydrogen Peroxide - chemistry Hydroxyl Radical - chemistry Medical sciences Oxidants - chemistry Oxidation-Reduction oxidative stress Plasmids - chemistry reactive oxygen species Toxicology Trolox Oxidative stress Reactive oxygen species Ascorbic acid DNA damage Vitamin α-Tocopherol Oxidant Antioxidant In vitro Biological activity Free radical Trolox Analog Lesion Damage Comparative study
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Abstract	The antioxidant and pro‐oxidant properties of ascorbic acid (vitamin C) and the water‐soluble analogue of α‐tocopherol (trolox) were compared. Trolox has advantages over α‐tocopherol, the latter being only lipid‐soluble due to the presence of a carboxyl group in lieu of a phytol chain which imparts trolox with water solubility. Trolox is used as a standard antioxidant in biochemical studies against which the antioxidant capacity of compounds is compared. Although ascorbic acid and tocopherols possess strong antioxidant properties, they might also exhibit pro‐oxidant properties in the presence of free transition metals. Thus, reactions detailed in this study were performed in the presence of Cr(VI) in an effort to investigate the potential of ascorbic acid and trolox to generate hydroxyl radicals in a Fenton‐like reaction. Results obtained were derived from reactions containing the same concentration of ascorbic acid and trolox under identical experimental conditions. Hydroxyl radical formation was observed in the reaction of Cr(VI) with ascorbic acid resulting from ascorbic acid auto‐oxidation and H2O2 formation. Hydroxyl radical formation was only detected in the reaction mixture containing Cr(VI) and trolox following the addition of H2O2. Copyright © 2007 John Wiley & Sons, Ltd.
AbstractList	The antioxidant and pro-oxidant properties of ascorbic acid (vitamin C) and the water-soluble analogue of alpha-tocopherol (trolox) were compared. Trolox has advantages over alpha-tocopherol, the latter being only lipid-soluble due to the presence of a carboxyl group in lieu of a phytol chain which imparts trolox with water solubility. Trolox is used as a standard antioxidant in biochemical studies against which the antioxidant capacity of compounds is compared. Although ascorbic acid and tocopherols possess strong antioxidant properties, they might also exhibit pro-oxidant properties in the presence of free transition metals. Thus, reactions detailed in this study were performed in the presence of Cr(VI) in an effort to investigate the potential of ascorbic acid and trolox to generate hydroxyl radicals in a Fenton-like reaction. Results obtained were derived from reactions containing the same concentration of ascorbic acid and trolox under identical experimental conditions. Hydroxyl radical formation was observed in the reaction of Cr(VI) with ascorbic acid resulting from ascorbic acid auto-oxidation and H2O2 formation. Hydroxyl radical formation was only detected in the reaction mixture containing Cr(VI) and trolox following the addition of H2O2.The antioxidant and pro-oxidant properties of ascorbic acid (vitamin C) and the water-soluble analogue of alpha-tocopherol (trolox) were compared. Trolox has advantages over alpha-tocopherol, the latter being only lipid-soluble due to the presence of a carboxyl group in lieu of a phytol chain which imparts trolox with water solubility. Trolox is used as a standard antioxidant in biochemical studies against which the antioxidant capacity of compounds is compared. Although ascorbic acid and tocopherols possess strong antioxidant properties, they might also exhibit pro-oxidant properties in the presence of free transition metals. Thus, reactions detailed in this study were performed in the presence of Cr(VI) in an effort to investigate the potential of ascorbic acid and trolox to generate hydroxyl radicals in a Fenton-like reaction. Results obtained were derived from reactions containing the same concentration of ascorbic acid and trolox under identical experimental conditions. Hydroxyl radical formation was observed in the reaction of Cr(VI) with ascorbic acid resulting from ascorbic acid auto-oxidation and H2O2 formation. Hydroxyl radical formation was only detected in the reaction mixture containing Cr(VI) and trolox following the addition of H2O2. The antioxidant and pro‐oxidant properties of ascorbic acid (vitamin C) and the water‐soluble analogue of α‐tocopherol (trolox) were compared. Trolox has advantages over α‐tocopherol, the latter being only lipid‐soluble due to the presence of a carboxyl group in lieu of a phytol chain which imparts trolox with water solubility. Trolox is used as a standard antioxidant in biochemical studies against which the antioxidant capacity of compounds is compared. Although ascorbic acid and tocopherols possess strong antioxidant properties, they might also exhibit pro‐oxidant properties in the presence of free transition metals. Thus, reactions detailed in this study were performed in the presence of Cr(VI) in an effort to investigate the potential of ascorbic acid and trolox to generate hydroxyl radicals in a Fenton‐like reaction. Results obtained were derived from reactions containing the same concentration of ascorbic acid and trolox under identical experimental conditions. Hydroxyl radical formation was observed in the reaction of Cr(VI) with ascorbic acid resulting from ascorbic acid auto‐oxidation and H2O2 formation. Hydroxyl radical formation was only detected in the reaction mixture containing Cr(VI) and trolox following the addition of H2O2. Copyright © 2007 John Wiley & Sons, Ltd. The antioxidant and pro-oxidant properties of ascorbic acid (vitamin C) and the water-soluble analogue of alpha-tocopherol (trolox) were compared. Trolox has advantages over alpha-tocopherol, the latter being only lipid-soluble due to the presence of a carboxyl group in lieu of a phytol chain which imparts trolox with water solubility. Trolox is used as a standard antioxidant in biochemical studies against which the antioxidant capacity of compounds is compared. Although ascorbic acid and tocopherols possess strong antioxidant properties, they might also exhibit pro-oxidant properties in the presence of free transition metals. Thus, reactions detailed in this study were performed in the presence of Cr(VI) in an effort to investigate the potential of ascorbic acid and trolox to generate hydroxyl radicals in a Fenton-like reaction. Results obtained were derived from reactions containing the same concentration of ascorbic acid and trolox under identical experimental conditions. Hydroxyl radical formation was observed in the reaction of Cr(VI) with ascorbic acid resulting from ascorbic acid auto-oxidation and H2O2 formation. Hydroxyl radical formation was only detected in the reaction mixture containing Cr(VI) and trolox following the addition of H2O2. The antioxidant and pro-oxidant properties of ascorbic acid (vitamin C) and the water-soluble analogue of -tocopherol (trolox) were compared. Trolox has advantages over -tocopherol, the latter being only lipid-soluble due to the presence of a carboxyl group in lieu of a phytol chain which imparts trolox with water solubility. Trolox is used as a standard antioxidant in biochemical studies against which the antioxidant capacity of compounds is compared. Although ascorbic acid and tocopherols possess strong antioxidant properties, they might also exhibit pro-oxidant properties in the presence of free transition metals. Thus, reactions detailed in this study were performed in the presence of Cr(VI) in an effort to investigate the potential of ascorbic acid and trolox to generate hydroxyl radicals in a Fenton-like reaction. Results obtained were derived from reactions containing the same concentration of ascorbic acid and trolox under identical experimental conditions. Hydroxyl radical formation was observed in the reaction of Cr(VI) with ascorbic acid resulting from ascorbic acid auto-oxidation and H2O2 formation. Hydroxyl radical formation was only detected in the reaction mixture containing Cr(VI) and trolox following the addition of H2O2. The antioxidant and pro‐oxidant properties of ascorbic acid (vitamin C) and the water‐soluble analogue of α ‐tocopherol (trolox) were compared. Trolox has advantages over α ‐tocopherol, the latter being only lipid‐soluble due to the presence of a carboxyl group in lieu of a phytol chain which imparts trolox with water solubility. Trolox is used as a standard antioxidant in biochemical studies against which the antioxidant capacity of compounds is compared. Although ascorbic acid and tocopherols possess strong antioxidant properties, they might also exhibit pro‐oxidant properties in the presence of free transition metals. Thus, reactions detailed in this study were performed in the presence of Cr(VI) in an effort to investigate the potential of ascorbic acid and trolox to generate hydroxyl radicals in a Fenton‐like reaction. Results obtained were derived from reactions containing the same concentration of ascorbic acid and trolox under identical experimental conditions. Hydroxyl radical formation was observed in the reaction of Cr(VI) with ascorbic acid resulting from ascorbic acid auto‐oxidation and H 2 O 2 formation. Hydroxyl radical formation was only detected in the reaction mixture containing Cr(VI) and trolox following the addition of H 2 O 2 . Copyright © 2007 John Wiley & Sons, Ltd.
Author	Poljšak, Borut Raspor, Peter
Author_xml	– sequence: 1 givenname: Borut surname: Poljšak fullname: Poljšak, Borut email: borut.poljsak@vsz.uni-lj.si organization: Polytechnic Nova Gorica, School of Environmental Science, Vipavska 13, 5000 Nova Gorica, Slovenia – sequence: 2 givenname: Peter surname: Raspor fullname: Raspor, Peter organization: University of Ljubljana, Biotechnical Faculty, Food Science and Technology Department, Chair of Biotechnology, Jamnikarjeva 101, 1000 Ljubljana, Slovenia
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Cites_doi	10.1016/S1382-6689(02)00003-0 10.1021/bi00003a025 10.1002/jat.1093 10.1111/j.1749-6632.1998.tb09921.x 10.1016/0003-9861(90)90589-Q 10.1016/j.etap.2005.11.004 10.1080/109374099281241 10.1016/0003-9861(90)90417-W 10.1021/tx00038a016 10.1021/ja974240z 10.1006/bbrc.1997.6277 10.2307/3431753 10.2307/3431756 10.1093/oxfordjournals.bmb.a072625 10.1016/0014-5793(95)01481-0 10.1016/j.mrfmmm.2003.09.006
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Keywords	Oxidative stress Reactive oxygen species Ascorbic acid DNA damage Vitamin α-Tocopherol Oxidant Antioxidant In vitro Biological activity Free radical Trolox Analog Lesion Damage Comparative study
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References	Kortenkamp A, O'Brien P. 1994. The generation of DNA single-strand breaks during the reduction of chromate by ascorbic acid and/or glutathione in vitro. Environ. Health Perspect. 102: 237-241. Shi X, Chiu A, Chen CT, Halliwell B, Castranova V, Vallyathan V. 1999. Reduction of Cr(VI) and its relationship to carcinogenesis. J. Toxicol. Environ. Health. 2(B): 87-104. Cheeseman KH, Slater TF. 1993. An introduction to free radical biochemistry. Br. Med. Bull. 49: 481-493. Kagan VE, Tyurina YY. 1999. Recycling and redox cycling of phenolic antioxidants. Ann. N.Y. Acad. Sci. 854: 425-434. Stearns DM, Kennedy LJ, Courtney KD, Giangrande PH, Phieffer LS, Wetterhahn KE. 1995. Reduction of chromium(VI) by ascorbate leads to chromium-DNA binding and DNA strand breaks in vitro. Biochemistry 34: 910-919. Liu KJ, Shi X, Dalal NS. 1997. Synthesis of Cr(VI)-GSH, its identification and its free hydroxyl radical generation: a model compound for Cr(VI) carcinogenicity. Biochem. Biophys. Res. Commun. 235: 54-58. Poljšak B, Gazdag Z, Pesti M, Jenko-Brinovec S, Belagyi J, Plesničar S, Raspor P. 2006. Pro-oxidative versus antioxidative reactions between Trolox and Cr(VI): The role of H2O2. Environ. Toxicol. Pharmacol. 22: 15-19. O'Brien TJ, Ceryak S, Patierno SR. 2003. Complexities of chromium carcinogenesis: role of cellular response, repair and recovery mechanisms. Mutat. Res. 533: 3-36. Halliwell B, Gutteridge J. 1999. Free Radicals in Biology and Medicine, 3nd edn. Clarendon Press: Oxford. Burkitt MJ, Milne L. 1996. Hydroxyl radical formation from Cu(II)-Trolox mixtures: insights into the pro-oxidant properties of α-tocopherol. FEBS Lett. 379: 51-54. Stearns DM, Wetterhahn KE. 1994. Reaction of chromium(VI) with ascorbate produces chromium(V), chromium(IV), and carbon-based radicals. Chem. Res. Toxicol. 7: 219-230. Rietjens I, Boersma M, de Haan L, Spenkelink B, Awad H, Cnubbe N, van Zanden J, van der Woude H, Alink G, Koeman J. 2002. The pro-oxidant chemistry of the natural antioxidants vitamin C, vitamin E, carotenoids and flavonoids. Environ. Toxicol. Pharmacol. 11: 321-333. O'Brien P, Kortenkamp A. 1994. Chemical models important in understanding the ways in which chromate can damage DNA. Environ. Health Perspect. 102: 3-10. Shi X, Dalal NS. 1990a. Evidence for a Fenton-type mechanism for the generation of OH* radicals in the reduction of Cr(VI) in cellular media. Arch. Biochem. Biophys. 281: 90-95. Lay PA, Levina A. 1998. Activation of molecular oxygen during the reactions of chromium (VI/V/IV) with biological reductants: implications for chromium-induced genotoxicities. J. Am. Chem. Soc. 120: 6704-6714. Shi X, Dalal NS. 1990b. On the hydroxyl radical formation in the reaction between hydrogen peroxide and biologically generated chromium(V) species. Arch. Biochem. Biophys. 277: 342-350. Stearns D, Courtney K, Giangrande P, Phieffer L, Wetterhahn K. 1994. Chromium(VI) reduction by ascorbate: role of reactive intermediates in DNA damage in vitro. Environ. Health Perspect. 102: 21-25. Poljsak B, Gazdag Z, Jenko-Brinovec S, Fujs S, Pesti M, Belagyi J, Plesnicar S, Raspor P. 2005. Pro-oxidative vs antioxidative properties of ascorbic acid in chromium(VI)-induced damage: an in vivo and in vitro approach. J. Appl. Toxicol. 25: 535-548. 1994; 102 1997; 235 1993; 49 1990b; 277 1990a; 281 2006; 22 1995; 34 2002; 11 1999; 2(B) 1991 1996; 379 1999; 854 2003; 533 1998; 120 1994; 7 1999 2005; 25 Stocker R (e_1_2_1_20_1) 1991 e_1_2_1_7_1 e_1_2_1_8_1 e_1_2_1_5_1 Halliwell B (e_1_2_1_4_1) 1999 e_1_2_1_3_1 e_1_2_1_12_1 e_1_2_1_13_1 e_1_2_1_10_1 e_1_2_1_2_1 e_1_2_1_11_1 e_1_2_1_16_1 Kortenkamp A (e_1_2_1_6_1) 1994; 102 e_1_2_1_17_1 e_1_2_1_14_1 e_1_2_1_15_1 e_1_2_1_9_1 e_1_2_1_18_1 e_1_2_1_19_1
References_xml	– reference: O'Brien TJ, Ceryak S, Patierno SR. 2003. Complexities of chromium carcinogenesis: role of cellular response, repair and recovery mechanisms. Mutat. Res. 533: 3-36. – reference: Poljsak B, Gazdag Z, Jenko-Brinovec S, Fujs S, Pesti M, Belagyi J, Plesnicar S, Raspor P. 2005. Pro-oxidative vs antioxidative properties of ascorbic acid in chromium(VI)-induced damage: an in vivo and in vitro approach. J. Appl. Toxicol. 25: 535-548. – reference: Halliwell B, Gutteridge J. 1999. Free Radicals in Biology and Medicine, 3nd edn. Clarendon Press: Oxford. – reference: Kagan VE, Tyurina YY. 1999. Recycling and redox cycling of phenolic antioxidants. Ann. N.Y. Acad. Sci. 854: 425-434. – reference: O'Brien P, Kortenkamp A. 1994. Chemical models important in understanding the ways in which chromate can damage DNA. Environ. Health Perspect. 102: 3-10. – reference: Rietjens I, Boersma M, de Haan L, Spenkelink B, Awad H, Cnubbe N, van Zanden J, van der Woude H, Alink G, Koeman J. 2002. The pro-oxidant chemistry of the natural antioxidants vitamin C, vitamin E, carotenoids and flavonoids. Environ. Toxicol. Pharmacol. 11: 321-333. – reference: Shi X, Chiu A, Chen CT, Halliwell B, Castranova V, Vallyathan V. 1999. Reduction of Cr(VI) and its relationship to carcinogenesis. J. Toxicol. Environ. Health. 2(B): 87-104. – reference: Poljšak B, Gazdag Z, Pesti M, Jenko-Brinovec S, Belagyi J, Plesničar S, Raspor P. 2006. Pro-oxidative versus antioxidative reactions between Trolox and Cr(VI): The role of H2O2. Environ. Toxicol. Pharmacol. 22: 15-19. – reference: Cheeseman KH, Slater TF. 1993. An introduction to free radical biochemistry. Br. Med. Bull. 49: 481-493. – reference: Kortenkamp A, O'Brien P. 1994. The generation of DNA single-strand breaks during the reduction of chromate by ascorbic acid and/or glutathione in vitro. Environ. Health Perspect. 102: 237-241. – reference: Shi X, Dalal NS. 1990a. Evidence for a Fenton-type mechanism for the generation of OH* radicals in the reduction of Cr(VI) in cellular media. Arch. Biochem. Biophys. 281: 90-95. – reference: Lay PA, Levina A. 1998. Activation of molecular oxygen during the reactions of chromium (VI/V/IV) with biological reductants: implications for chromium-induced genotoxicities. J. Am. Chem. Soc. 120: 6704-6714. – reference: Stearns D, Courtney K, Giangrande P, Phieffer L, Wetterhahn K. 1994. Chromium(VI) reduction by ascorbate: role of reactive intermediates in DNA damage in vitro. Environ. Health Perspect. 102: 21-25. – reference: Liu KJ, Shi X, Dalal NS. 1997. Synthesis of Cr(VI)-GSH, its identification and its free hydroxyl radical generation: a model compound for Cr(VI) carcinogenicity. Biochem. Biophys. Res. Commun. 235: 54-58. – reference: Shi X, Dalal NS. 1990b. On the hydroxyl radical formation in the reaction between hydrogen peroxide and biologically generated chromium(V) species. Arch. Biochem. Biophys. 277: 342-350. – reference: Burkitt MJ, Milne L. 1996. Hydroxyl radical formation from Cu(II)-Trolox mixtures: insights into the pro-oxidant properties of α-tocopherol. FEBS Lett. 379: 51-54. – reference: Stearns DM, Wetterhahn KE. 1994. Reaction of chromium(VI) with ascorbate produces chromium(V), chromium(IV), and carbon-based radicals. Chem. Res. Toxicol. 7: 219-230. – reference: Stearns DM, Kennedy LJ, Courtney KD, Giangrande PH, Phieffer LS, Wetterhahn KE. 1995. Reduction of chromium(VI) by ascorbate leads to chromium-DNA binding and DNA strand breaks in vitro. 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Snippet	The antioxidant and pro‐oxidant properties of ascorbic acid (vitamin C) and the water‐soluble analogue of α‐tocopherol (trolox) were compared. Trolox has... The antioxidant and pro‐oxidant properties of ascorbic acid (vitamin C) and the water‐soluble analogue of α ‐tocopherol (trolox) were compared. Trolox has... The antioxidant and pro-oxidant properties of ascorbic acid (vitamin C) and the water-soluble analogue of alpha-tocopherol (trolox) were compared. Trolox has... The antioxidant and pro-oxidant properties of ascorbic acid (vitamin C) and the water-soluble analogue of -tocopherol (trolox) were compared. Trolox has...
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SubjectTerms	Antioxidants - chemistry ascorbic acid Ascorbic Acid - chemistry Biological and medical sciences Chromans - chemistry Chromium - chemistry DNA Damage DNA, Superhelical - chemistry Hydrogen Peroxide - chemistry Hydroxyl Radical - chemistry Medical sciences Oxidants - chemistry Oxidation-Reduction oxidative stress Plasmids - chemistry reactive oxygen species Toxicology Trolox
Title	The antioxidant and pro-oxidant activity of vitamin C and trolox in vitro: a comparative study
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