Review <strong>of</strong> the literatureREVIEW OF THE LITERATURE1. Vitam<strong>in</strong> C – ascorbic acid - ascorbateVitam<strong>in</strong> C is a weak acid and a highly <strong>water</strong>-soluble molecule. Ascorbic acid (C 6H 8O 6) isthe trivial name for <strong>vitam<strong>in</strong></strong> C, while the chemical name, very seldom used <strong>in</strong> the literature,is 2-oxo-L-threo-hexono-1,4-lactone-2,3-enediol or 2-(1,2-dihydroxyethyl)-4,5-dihydroxyfuran-3-one(IUPAC). Biologically it is the L-enantiomer <strong>of</strong> ascorbic acid that is active,while the D-enantiomer shows much lower biological <strong>activity</strong>. 12 Ascorbic acid is the acidicform <strong>of</strong> <strong>vitam<strong>in</strong></strong> C hav<strong>in</strong>g two ionizable –OH groups, with pKa values <strong>of</strong> 4.25 and 11.8. Atphysiological pH, the mono-anion is favoured and therefore ascorbic acid is usuallyreferred to as ascorbate (salt) <strong>in</strong> the literature (Figure 1).HOHOOOHOOpKa 1 = 4.25 HOO pKa 2 = 11.8HOHOOOHO OH_O OH_O_OAscorbic acid Ascorbate Ascorbate dianionFigure 1. Forms <strong>of</strong> <strong>vitam<strong>in</strong></strong> C at various pH1.1. Vitam<strong>in</strong> C deficiency and scurvyThe history <strong>of</strong> <strong>vitam<strong>in</strong></strong> C is largely the history <strong>of</strong> the human disease scurvy, one <strong>of</strong> the firstnutritional deficiency diseases recorded. 13-16 The symptoms <strong>of</strong> scurvy were marked byanaemia, weakness, spongy gums, oedema, <strong>of</strong>ten with open sores <strong>in</strong> the mouth, andloosen<strong>in</strong>g <strong>of</strong> the teeth, bleed<strong>in</strong>g <strong>in</strong> the mucous membranes, and hard bumps <strong>in</strong> the muscles<strong>of</strong> the legs. In 1566, the Dutch physician Ronsseus <strong>in</strong>structed sailors to consume oranges toprevent scurvy. In 1639, John Woodall, a lead<strong>in</strong>g physician <strong>in</strong> England, recommendedlemon juice to treat scurvy. Later a Scottish naval surgeon, James L<strong>in</strong>d, conducted acontrolled trial add<strong>in</strong>g oranges and lemons to the sailors’ diet. The positive observed effect<strong>of</strong> lemons and oranges on scurvy <strong>in</strong> L<strong>in</strong>d’s trial led to the <strong>in</strong>creased usage <strong>of</strong> lemons andoranges <strong>in</strong> the diet <strong>of</strong> sailors on Capta<strong>in</strong> James Cook’s second voyage around the world.However, it was not until 1795 that all sailors <strong>in</strong> England were ordered to <strong>in</strong>gest lemon7
Review <strong>of</strong> the literaturejuice daily. It was later found that <strong>vitam<strong>in</strong></strong> C (ascorbic acid) was the active substance <strong>in</strong> theoranges and lemons that prevented scurvy. With scurvy also came the belief that <strong>vitam<strong>in</strong></strong> Ccould function as an anti<strong>oxidant</strong> protect<strong>in</strong>g aga<strong>in</strong>st oxidation, as the name ascorbate(antiscorbutic) implies. Vitam<strong>in</strong> C was first isolated from cabbages, oranges and adrenalglands by Szent-Györgyi <strong>in</strong> 1928. 15, 17, 181.2. Vitam<strong>in</strong> C - an important enzymatic c<strong>of</strong>actorLater it was found that ascorbic acid is a crucial c<strong>of</strong>actor for many enzymes. Withoutascorbic acid, prol<strong>in</strong>e hydroxylase and lys<strong>in</strong>e hydroxylase cannot hydroxylate collagen. 1, 19, 20This leads to reduced formation <strong>of</strong> collagen fibres, which gives rise to poor wound heal<strong>in</strong>gand fragile blood vessels. The collagen fibres strengthen the connective tissues <strong>in</strong> the bloodvessels, sk<strong>in</strong>, teeth and skeleton. Nowadays, scurvy is a very rare condition, as the quality <strong>of</strong>food <strong>in</strong>take has improved, i.e., more fruits and vegetables are consumed. In addition, manyfood products are nowadays fortified with <strong>vitam<strong>in</strong></strong>s and <strong>vitam<strong>in</strong></strong> C is a common dietarysupplement. 16Vitam<strong>in</strong> C is used as c<strong>of</strong>actor <strong>in</strong> the synthesis <strong>of</strong> noradrenal<strong>in</strong>e and carnit<strong>in</strong>e, tyros<strong>in</strong>emetabolism and amidation <strong>of</strong> peptide hormones. 1 In most <strong>of</strong> these <strong>vitam<strong>in</strong></strong> C-dependentenzymes, <strong>vitam<strong>in</strong></strong> C helps to ma<strong>in</strong>ta<strong>in</strong> the enzyme <strong>in</strong> its active form by keep<strong>in</strong>g the metal(copper and iron) <strong>in</strong> the active centre <strong>in</strong> the reduced form. 201.3. Effects <strong>of</strong> <strong>vitam<strong>in</strong></strong> C supplementationThe body has depots <strong>of</strong> <strong>vitam<strong>in</strong></strong> C but the <strong>vitam<strong>in</strong></strong> will eventually be depleted. The averageadult has a body pool <strong>of</strong> 1.0-2.0 grams <strong>of</strong> <strong>vitam<strong>in</strong></strong> C and the average half-life <strong>of</strong> <strong>vitam<strong>in</strong></strong> C isabout 10-20 days. 21, 22 Scurvy can be prevented with a <strong>vitam<strong>in</strong></strong> C <strong>in</strong>take <strong>of</strong> only 10mg/day. 20A high <strong>in</strong>take <strong>of</strong> <strong>vitam<strong>in</strong></strong> C is generally not believed to be harmful s<strong>in</strong>ce <strong>vitam<strong>in</strong></strong> C is a<strong>water</strong>-soluble compound that is not stored <strong>in</strong> the body and the excess <strong>in</strong>gested <strong>vitam<strong>in</strong></strong> isexcreted <strong>in</strong> the ur<strong>in</strong>e. However, diarrhoea is a directly observable symptom <strong>of</strong> overconsumption<strong>of</strong> <strong>vitam<strong>in</strong></strong> C. 11, 23 The Food and Nutrition Board, Institute <strong>of</strong> Medic<strong>in</strong>e, hasset 2000 mg as a tolerable upper limit for <strong>vitam<strong>in</strong></strong> C <strong>in</strong> healthy adults. 10, 118
- Page 1 and 2: Pro-oxidant activity of vitamin C i
- Page 3 and 4: Supervised byDocent Tommy Nordströ
- Page 5 and 6: ContentsCONTENTSLIST OF ORIGINAL PU
- Page 8 and 9: List of original publicationsLIST O
- Page 10 and 11: AcknowledgementsACKNOWLEDGEMENTSThi
- Page 12 and 13: AbbreviationsABBREVIATIONSAsc …
- Page 16 and 17: Review of the literatureSince vitam
- Page 18 and 19: Review of the literaturestill added
- Page 20 and 21: Review of the literatureantioxidant
- Page 22 and 23: Review of the literatureThe α-toco
- Page 24 and 25: Review of the literatureCopper, wil
- Page 26 and 27: Review of the literatureOH • + H
- Page 28 and 29: Review of the literatureFormation o
- Page 30 and 31: Review of the literature3.2. The ro
- Page 32 and 33: Review of the literaturecopper conc
- Page 34 and 35: Experimental proceduresEXPERIMENTAL
- Page 36 and 37: Experimental procedures2.2. Measure
- Page 38 and 39: Experimental procedurestetrahydrate
- Page 40 and 41: 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
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References127. Park S, Han SS, Park
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References157. Critchley MM, Cromar
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References185. Liao CH, Kang SF, Wu
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References214. Orr CW. Studies on a
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References243. Miller C, Kennington
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Free Radical Research, Volume 38 Nu
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VITAMIN C OXIDATION IN DRINKING WAT
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VITAMIN C OXIDATION IN DRINKING WAT
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Free Radical Research, May 2005; 39
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Iron inhibits Vitamin C/copper-indu
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Iron inhibits Vitamin C/copper-indu
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Free Radical Research, November 200
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Hydrogen peroxide formation in drin
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Hydrogen peroxide formation in drin
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Hydrogen peroxide formation in drin