Effect of Oxidation on Wine Composition. Andrew L. Waterhouse University of British Columbia, Kelowna Mar 25, 2011

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1 Effect of xidation on Wine Composition Andrew L. Waterhouse University of British Columbia, Kelowna Mar 25, 2011

2 xygen Reduction Cascade +e - +e Superoxide 2 2- Peroxide +e - +e - Hydroxyl radical At wine ph +H + +H + +H + H. 2 H 2 2 Hydroperoxyl Hydrogen peroxide radical 2 Water

3 xidative Changes in Wine Formation of quinones from catechols React with thiols, amino acids Formation of aldehydes Fenton oxidation of alcohols Formation of aldehydes Loss of all other components

4 Polymers Wine Pigments Fe +2 Fe +3 2 H + H + RC= (Hydroperoxyl radical) Anthocyanins + RCH H 2 H (Semiquinone radical) R C H + (Hydroxyl radical) H + RCH 2 Fe +3 Fe +2 + H (Hydrogen peroxide) H 2 Fe +2 recycling by phenolic reduction H Phenolic Coupling (polymerization) Resorcyl (Quinone) Aldehydes RSH AA's, Strecker Degradation S 2 H 2 S R Sulfide Trapping

5 Quinone Reaction with Mercaptans Loss of highly aromatic mercaptans Many negative components Hydrogen sulfide Ethyl mercaptan and others Some positive components 3-mercaptohexanol Rapid reaction with oxidation Trace components

6 Quinone + Gluthathione Formation of GRP Coutaric R R PP, 2 Cafftaric acid Quinone Brown Pigments G-S H R n NH 2 HC-CH 2 -NH-C-CH-NH-C-CH 2 -CH 2 -CH-C CH 2 H C HC CH C C H C H S 2-S-Glutation caftaric acid GRP Quinone

7 Reaction with ther Mercaptans Quinone can react with H 2 S, other mercaptans Reaction to remove reduced aroma H + H 2 S H SH

8 Catechin + 3MH (mercaptohexanol) H + H SH H S

9 Protected Mercaptans Preserved 3MH percursors, i.e. 3MH-S- Cys/Glutathione are not lost to oxidation Roland, A JAFC 58: 4406 (2010)

10 Strecker Degradation AA s react with diketones, release aldehydes

11 Possible Strecker Source of Branched Aldehydes Derived from AA s either directly or via alcohols and yeast conversion NH 2 NH 2 NH 2 CH CH CH

12 Aromatic Aldehydes from Quinones Branched Aldehydes Methylpropanal, 2-methylbutanal, 3- methylbutanal Methional Phenylacetaldehyde Culler at al, JAFC 55:876 (2007)

13 Methional Cooked vegetable, pungent aroma bscures positive aromas Formed by Strecker degradation of amino acids or oxidation of alcohol S S NH 2 CH

14 Phenylacetaldehyde ld wood reduction-descriptor bscures positive aromas Formed by Strecker degradation of phenylalanine NH 2 CH

15 Quinone Alternative Reactions? Phloroglucinol Ascorbate RSH H Phenolic Coupling (polymerization) (Quinone) AA's, Strecker Degradation S R Mercaptan Trapping S 2 Aldehydes?

16 Fenton Products xidation of alcohols (major components) Ethanol rganic Acids Sugars Anything Reduced by S 2 Removes hydrogen peroxide

17 Reactivity of Hydroxyl Radical Extremely reactive xidizes the first molecule it encounters xidation products are determined by concentration Antioxidants cannot protect against this oxidation

18 Wine Minor Components Red Wine Composition, Minor Components Acetaldehyde Volatile Acidity Glycerol Sugar Higher Alcohols Phenols Sorbitol & Mannitol Sulfites Minerals * Esters Amino acids Acid

19 Fenton Products Ethanol yields acetaldehyde Lactic and Malic acids yield pyruvate Glycerol yields glyceraldehyde Color development Aroma if the amounts exceed color reactions, S 2 binding capacityoxidized character

20 Ethanol to Acetaldehyde Ethanol C H 3 C H2 H Hydroxyl radical C H 3 C H 2 C H 3 C H Acetaldehyde C H 3 C H + H

21 Formation of Branched Aldehydes Fenton oxidation of alcohols CH CH CH

22 xidation of Wine Acids (Alcohols) to Carbonyls Pyruvic bserved in wine Reacts with anthocyanins to make wine pigments H CH 3 Lactic Acid (or Malic) H 2 2 Fe +2 CH 3 Pyruvic Acid Glyoxylic bserved in wine Condenses with flavan-3-ols H Tartaric Acid H 2 2 Fe +2 H Hydroxymalonic CH Glyoxylic Acid

23 Loss of isoprenoids by oxidation Ferreira, A., ACA 513: 169 (04) the levels of all nor-isoprenoids decreased after a certain concentration of oxygen was consumed, e.g. 10 mg /L

24 Glycerol xidation H Two novel oxidation products Not previously reported in wine Glycerol Can they affect wine color, etc? They do slightly darken red wine when added + H 2 2 H + Fe +2 Dihydroxyacetone H Glyceraldehyde Laurie and Waterhouse, Journal of Agricultural and Food Chemistry, May 2006

25 Aldehyde Coupling of Phenolics Importance of aldehydes in tannin coupling H + H H + H + H C + -H + model H H H H

26 Glyceraldehyde Bridged Cmpds H H H R H R= H H H H R H + Me Me -Glucose

27 Aldehyde Pigment Reactions D-ring formation by acetaldehyde and pyruvate H + Glu R1 R2 or H H R + Glu R1 R2 R = H,

28 Sotolon xidation product rigin from 2-keto butyric acid? C 2 H + H 2-ketobutyric acid C 2 H Pham JAFC 43: 2616 (95) H sotolon

29 Sotolon Formed from sugars? Ferreira, JAFC 51:4356 (03) Descriptors, 8 ug/l threshold Nutty, Curry, Dried fig, Rancio Important in Vin Jaunes (Jura), port, Vins doux Naturel (fortified) Defect in fresh whites

30 Sotolon from xidation Yeast lees minimize formation Lavigne, JAFC 56: 2688 (08)

31 Fenton Routes Trapping Agent ethanol a b Hydroperoxyl Radical of Ethanol c Hydroxyl radical Ethoxyl radical d e Hydrogen peroxide acetaldehyde Hydroperoxyl radical catechol

32 Fenton Inhibition in Model Wine Inhibition by Phenolics 1.1 Acetaldehyde (Norm)

33 Fenton Inhibition by Cinnamates Acetaldehyde (Norm) R 1 R R 2 1 R 2 (Hydro)Cinnamic Acid: R 1 /R 2 = H (Hydro)Caffeic Acid: R 1 /R 2 = 0.5 NP HCinn HCaff Cinn Caff

34 xidation Product of Cinnamates Two Products Coumaric, Caffeic or Ferulic

35 Ferulic Products H H Me Et H Me H +, Me H Me H +, Et H Me

36 Mechanism of Ethoxyl Trapping C H Me C H H Me Fe(III) Fe(II) C 2, H + C + H Me H Me

37 Cinnamates-Major Free Radical Traps Previously predicted by basic studies Pulse radiolysis generation of radicals First observation in food May be important in many food systems Cinnamates are ubiquitous

38 Acknowledgements American Vineyard Foundation CCGPREV Nomacorc SA Collaborators: University of Copenhagen Nick Gislason, Screaming Eagle

39 UCD Teaching and Research Winery 1,200 m 2 LEED Platinum PV s, rainwater, nat l light, re-use/cycle 600 m 2 fermentation hall 5 x 40 m 2 var temp/hum rooms Bottle storage-2 rooms Classroom, QC lab CIP capability

40 New UC Davis Winery

41 Vineyard View-Water Storage Tanks

42 Fermentation Hall

43 Rodgers-Cypress Fermentors 300L Thermostat Automated pumpovers C 2 capture Wireless Brix monitor Integral press

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