Pro-oxidant activity of vitamin C in drinking water ... - Ãbo Akademi

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VITAMIN C OXIDATION IN DRINKING WATER 859can promote the formation of kidney stones. [23,24]Interestingly, calcium oxalate microcalcification hasalso been observed in benign and malignantbreast biopsy specimens. [25,26] Whether the oxalicacid present in the breast tissue originate fromthe ascorbic acid- or amino acid metabolism iscurrently not known.When ascorbic acid is oxidized in the presenceof divalent copper, monovalent copper is formed.When the reduced copper is re-oxidized in thepresence of oxygen, superoxide is generated. In thepresence of a proton donor, the superoxide is furtherreduced to hydrogen peroxide. Most likely, thehydrogen peroxide formed in the reaction, whenascorbic acid is oxidized by copper, promote thecleavage of dehydroascorbic acid to oxalic acid andthreonic acid. In line with this assumption we foundthat addition of hydrogen peroxide directly toascorbic acid, in the presence of 100 mg/l bicarbonate,resulted in the formation of oxalic acid and threonicacid during the 3 h incubation (Fig. 2B). However,when hydrogen peroxide was added directly todehydroascorbic acid in the presence of 100 mg/lbicarbonate, the same amount of oxalic acid andthreonic acid could be obtained within 10 minincubation (Fig. 2C). Our results indicate that thehydrogen peroxide formed, and not the hydroxylradicals generated during the reaction, is responsiblefor the dehydroascorbic acid decomposition in thewater samples.In conclusion, our results show that significantamounts of either dietary or supplementary ascorbicacid can be rapidly oxidized to dehydroascorbicacid when added to bicarbonate rich (buffered)copper contaminated drinking water. Thus peopleconsuming this type of water will most likely ingest, orgenerate more dehydroascorbic acid in their stomach,than people using bottled water. Dehydroascorbic acidcan enter cells via the GLUT glucose transporter. [27]Intracellular reduction of large amounts of dehydroascorbicacid to ascorbic acid by NADPH- andglutathione-dependent reactions may markedlydecrease the cellular concentrations of NADPH andglutathione in some celltypes. [28–30] In line with thesefindings, dehydroascorbic acid has been shown tocause oxidative stress and apoptosis in pancreaticand neural cells by depleting their intracellularstore of reduced glutathione. [14,31,32] Theimpact of long-term intake of dehydroascorbic acid,the oxidized form of ascorbic acid, on human health,remains to be studied.AcknowledgementsThis work was supported by Magnus Ehrnroothfoundation, Paulon Säätiö, K. Albin JohanssonsStiftelse, Svenska Kulturfonden and The Academyof Finland.References[1] Stahl, W. and Sies, H. (1997) “Antioxidant defense: vitamins Eand C and carotenoids”, Diabetes 46(Suppl. 2), S14–S18.[2] Frei, B. (1999) “On the role of vitamin C and otherantioxidants in atherogenesis and vascular dysfunction”,Proc. Soc. Exp. Biol. Med. 222, 196–204.[3] Padayatty, S.J., Katz, A., Wang, Y., Eck, P., Kwon, O., Lee, J.H.,Chen, S., Corpe, C., Dutta, A., Dutta, S.K. and Levine, M.(2003) “Vitamin C as an antioxidant: evaluation of its role indisease prevention”, J. Am. Coll. Nutr. 22, 18–35.[4] Block, G. (1991) “Vitamin C and cancer prevention: theepidemiologic evidence”, Am. J. Clin. Nutr. 53, 270S–282S.[5] Block, G. (1991) “Epidemiologic evidence regarding vitamin Cand cancer”, Am. J. Clin. Nutr. 54, 1310S–1314S.[6] Martin, A. (2003) “Antioxidant vitamins E and C and risk ofAlzheimer’s disease”, Nutr. Rev. 61, 69–73.[7] Rose, R.C., Richer, S.P. and Bode, A.M. (1998) “Ocularoxidants and antioxidant protection”, Proc. Soc. Exp. Biol. Med.217, 397–407.[8] Buettner, G.R. and Jurkiewicz, B.A. (1996) “Catalytic metals,ascorbate and free radicals: combinations to avoid”, Radiat.Res. 145, 532–541.[9] Halliwell, B. (1996) “Vitamin C antioxidant or pro-oxidantin vivo?”, Free Radic. Res. 25, 439–454.[10] Podmore, I.D., Griffiths, H.R., Herbert, K.E., Mistry, N.,Mistry, P. and Lunec, J. (1998) “Vitamin C exhibits pro-oxidantproperties”, Nature 392, 559.[11] Asplund, K.U., Jansson, P.J., Lindqvist, C. and Nordstrom, T.(2002) “Measurement of ascorbic acid (vitamin C) inducedhydroxyl radical generation in household drinking water”,Free Radic. Res. 36, 1271–1276.[12] Koch, C.J. and Biaglow, J.E. (1978) “Toxicity, radiationsensitivity modification, and metabolic effects of dehydroascorbateand ascorbate in mammalian cells”, J. Cell. Physiol.94, 299–306.[13] Rose, R.C., Choi, J.L. and Bode, A.M. (1992) “Short termeffects of oxidized ascorbic acid on bovine corneal endotheliumand human placenta”, Life Sci. 50, 1543–1549.[14] Song, J.H., Shin, S.H., Wang, W. and Ross, G.M. (2001)“Involvement of oxidative stress in ascorbateinducedproapoptotic death of PC12 cells”, Exp. Neurol. 169,425–437.[15] Jansson, P.J., Asplund, K.U., Makela, J.C., Lindqvist, C. andNordstrom, T. (2003) “Vitamin C (ascorbic acid) inducedhydroxyl radical formation in copper contaminated householddrinking water: role of bicarbonate concentration”,Free Radic. Res. 37, 901–905.[16] Ihara, H., Shino, Y., Aoki, Y., Hashizume, N. and Minegishi, N.(2000) “A simple and rapid method for the routine assay oftotal ascorbic acid in serum and plasma using ascorbate oxidaseand o-phenylenediamine”, J. Nutr. Sci. Vitaminol. (Tokyo) 46,321–324.[17] Lee, W., Roberts, S.M. and Labbe, R.F. (1997) “Ascorbic aciddetermination with an automated enzymatic procedure”,Clin. Chem. 43, 154–157.[18] Bode, A.M., Cunningham, L. and Rose, R.C. (1990)“Spontaneous decay of oxidized ascorbic acid (dehydro-Lascorbicacid) evaluated by high-pressure liquid chromatography”,Clin. Chem. 36, 1807–1809.[19] Koshiishi, I., Mamura, Y. and Imanari, T. (1998) “Bicarbonatepromotes a cleavage of lactone ring of dehydroascorbate”,Biochim. Biophys. Acta 1379, 257–263.[20] Jung, C.H. and Wells, W.W. (1998) “Spontaneous conversionof L-dehydroascorbic acid to L-ascorbic acid and L-erythroascorbicacid”, Arch. Biochem. Biophys. 355, 9–14.[21] Murphy, E.A. (1993) “Effectiveness of flushing on reducinglead and copper levels in school drinking water”, Environ.Health Perspect. 101, 240–241.[22] Pettersson, R. and Rasmussen, F. (1999) “Daily intake ofcopper from drinking water among young children inSweden”, Environ. Health Perspect. 107, 441–446.[23] Hackett, R.L., Shevock, P.N. and Khan, S.R. (1994) “Madin–Darby canine kidney cells are injured by exposure to oxalateand to calcium oxalate crystals”, Urol. Res. 22, 197–203.[24] Miller, C., Kennington, L., Cooney, R., Kohjimoto, Y., Cao, L.C.,Honeyman, T., Pullman, J., Jonassen, J. and Scheid, C. (2000)
860P.J. JANSSON et al.“Oxalate toxicity in renal epithelial cells: characteristics ofapoptosis and necrosis”, Toxicol. Appl. Pharmacol. 162, 132–141.[25] Fandos-Morera, A., Prats-Esteve, M., Tura-Soteras, J.M. andTraveria-Cros, A. (1988) “Breast tumors: composition ofmicrocalcifications”, Radiology 169, 325–327.[26] Haka, A.S., Shafer-Peltier, K.E., Fitzmaurice, M., Crowe, J.,Dasari, R.R. and Feld, M.S. (2002) “Identifying microcalcificationsin benign and malignant breast lesions by probingdifferences in their chemical composition using Ramanspectroscopy”, Cancer Res. 62, 5375–5380.[27] Rumsey, S.C., Kwon, O., Xu, G.W., Burant, C.F., Simpson, I.and Levine, M. (1997) “Glucose transporter isoforms GLUT1and GLUT3 transport dehydroascorbic acid”, J. Biol. Chem.272, 18982–18989.[28] Fiorani, M., De Sanctis, R., Scarlatti, F. and Stocchi, V. (1998)“Substrates of hexokinase, glucose-6-phosphate dehydrogenase,and glyceraldehyde-3-phosphate dehydrogenaseprevent the inhibitory response induced by ascorbicacid/iron and dehydroascorbic acid in rabbit erythrocytes”,Arch. Biochem. Biophys. 356, 159–166.[29] May, J.M., Qu, Z. and Morrow, J.D. (2001) “Mechanisms ofascorbic acid recycling in human erythrocytes”, Biochim.Biophys. Acta 1528, 159–166.[30] Siushansian, R., Tao, L., Dixon, S.J. and Wilson, J.X. (1997)“Cerebral astrocytes transport ascorbic acid and dehydroascorbicacid through distinct mechanisms regulated bycyclic AMP”, J. Neurochem. 68, 2378–2385.[31] Brown, S., Georgatos, M., Reifel, C., Song, J.H., Shin, S.H. andHong, M. (2002) “Recycling processes of cellular ascorbategenerate oxidative stress in pancreatic tissues in in vitrosystem”, Endocrine 18, 91–96.[32] Song, J.H., Shin, S.H. and Ross, G.M. (2001) “Oxidative stressinduced by ascorbate causes neuronal damage in an in vitrosystem”, Brain Res. 895, 66–72.
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Pro-oxidant activity of vitamin C i
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Supervised byDocent Tommy Nordströ
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ContentsCONTENTSLIST OF ORIGINAL PU
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List of original publicationsLIST O
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AcknowledgementsACKNOWLEDGEMENTSThi
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AbbreviationsABBREVIATIONSAsc …
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Review of the literatureREVIEW OF T
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Review of the literatureSince vitam
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Review of the literaturestill added
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Review of the literatureantioxidant
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Review of the literatureThe α-toco
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Review of the literatureCopper, wil
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Review of the literatureOH • + H
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Review of the literatureFormation o
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Review of the literature3.2. The ro
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Review of the literaturecopper conc
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Experimental proceduresEXPERIMENTAL
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Experimental procedures2.2. Measure
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Experimental procedurestetrahydrate
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ResultsRESULTS1. Vitamin C induces
Page 42 and 43: Results3. Oxidative decomposition o
Page 44 and 45: Resultsdifferent water samples vari
Page 46 and 47: DiscussionDISCUSSIONNowadays, ascor
Page 48 and 49: DiscussionCu 2+ + Asc → Cu + + As
Page 50 and 51: Discussion3. Iron inhibits vitamin
Page 52 and 53: Discussionperoxide might have an im
Page 54 and 55: ConclusionsCONCLUSIONSThe main focu
Page 56 and 57: ReferencesREFERENCES1. Arrigoni O,
Page 58 and 59: References34. Padayatty SJ, Katz A,
Page 60 and 61: References66. Sies H, Stahl W, Sund
Page 62 and 63: References95. Halliwell B. Role of
Page 64 and 65: References127. Park S, Han SS, Park
Page 66 and 67: References157. Critchley MM, Cromar
Page 68 and 69: References185. Liao CH, Kang SF, Wu
Page 70 and 71: References214. Orr CW. Studies on a
Page 72: References243. Miller C, Kennington
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