The herbaceous character of wines
Main Article Content
Keywords
green leaf volatiles, herbaceous, methoxypyrazines, thiols, vegetative, wine aroma
Abstract
The herbaceous (vegetative) character of wine can be pleasant or not depending on different circumstances. It can be specific to a particular grape cultivar (an endogenous varietal character) or produced during the winemaking procedure, from either an endogenous or exogenous cause. Several volatile wine components containing oxygen (aldehydes and alcohols with 6 carbon atoms), nitrogen (alkylmethoxypyrazines), and selected sulfur compounds (thiols, sulfides, disulfides) are reviewed and described. The effects of micro-oxygenation and storage in wood on the herbaceous post-fermentative character are discussed. Thus, the preventive tools and winemaking technologies used to reduce or to control this sensory character are described.
References
Ageron D., Escudier J.L., Abbal P. and Moutounet M. 1995. Pré-traitements des raisins par flash détente sous vide poussé. Revue Française d'Œnologie. 153: 50.
Al Abassi, S., Birkett M. A., Pettersson J., Pickett J. A. and Woodcock C. M. 1998. Ladybird beetle odour identified and found to be responsible for attraction between adults. Cellular and Molecular Life Sciences. 54: 876.
Allen M. S., Lacey M. J. and Boyd S. Methoxypyrazines in red wines: occurrence of 2-methoxy-3-(1-methylethyl) pyrazine. 1995. Journal of Agricultural and Food Chemistry. 43: 769.
Allen M. S., Lacey M. J., Harris R.L.N. and Brown, W.V. 1991. Contribution of methoxypyrazines to Sauvignon Blanc wine aroma. American Journal of Enology and Viticulture 42: 109.
Amerine M. A. and Roessler E. B. 1976. In Wines - Their Sensory Evaluation, W.H. Freeman and Company: San Francisco (USA).
Bayonove C., Cordonnier R. and Dubois P. 1975. Study of an aromatic characteristic fraction of Cabernet Sauvignon grape variety, identification of 2-methoxy-3-isobutyl-pyrazine. Comptes Rendus Hebdomadaires Des Seances De L’Academie Des Sciences Serie D. 281: 75.
Belancic A. and Agosin E. 2007. Methoxypyrazines in grapes and wines of Vitis vinifera cv. Carmenere. American Journal of Enology and Viticulture 58: 462.
Bell S. J. and Henschke P.A. 2005. Implications of nitrogen nutrition for grapes, fermentation and wine. Australian Journal of Grape and Wine Research. 11: 242.
Benkwitz F., Nicolau L., Lund C., Beresford M., Wohlers M. and Kilmartin P.A. 2012. Evaluation of Key Odorants in Sauvignon Blanc Wines Using Three Different Methodologies. Journal of Agricultural and Food Chemistry. 60: 6293.
Blake A., Kotseridis Y., Brindle I. D., Inglis D. and Pickering, G. J. 2010. Effect of light and temperature on 3-alkyl-2-methoxypyrazine concentration and other impact odourants of Riesling and Cabernet Franc wines during bottle ageing. Food Chemistry. 119: 935.
Blake A., Kotseridis Y., Brindle, I. D., Inglis D., Sears M. and Pickering G. J. 2009. Effect of closure and packaging type on 3-alkyl-2-methoxypyrazines and other impact odorants of Riesling and Cabernet Franc wines. Journal of Agricultural and Food Chemistry. 57: 4680.
Borsa D., Asporundi A., Nardi S., Costacurta A., Di Stefano R., and Calò A. 2008. Metaboliti secondari delle cultivar Malvasia. Confronto di due annate. Rivista di Viticultura ed Enologia 2-3-4: 99.
Boselli E., Di Lecce G., Alberti F., and Frega N.G. 2010. Nitrogen Gas Affects The Quality And The Phenolic Profile Of Must Obtained From Vacuum-Pressed White Grapes. LWT-Food Science and Technology. 43, 10:1494.
Boselli E., Giomo A., Minardi M. and Frega N.G. 2008. Characterization of phenolics in Lacrima di Morro d'Alba wine and role on its sensory attributes. European Food Research and Technology. 227(3): 709.
Boselli E., Minardi M., Giomo A. and Frega N.G. 2006. Phenolic composition and quality of white d.o.c. wines from Marche (Italy). Analytica Chimica Acta 563: 93.
Botezatu A. I., Kotseridis Y., Inglis D. and Pickering G. J. 2012. Occurrence and contribution of alkyl methoxypyrazines in wine tainted by Harmonia axyridis and Coccinella septempunctata. Journal of the Science of Food and Agriculture. 93(4): 803.
Buttery R. G., Seifert R. M., Guadagni D. G. and Ling L. C. 1969. Characterization of some volatile constituents of bell peppers. Journal of Agricultural and Food Chemistry. 17(6): 1322.
Cabrita J.M., Freitas C.A.M., Laueano O. and Di Stefano R. 2006. Glycosidic aroma compounds of some Portuguese grape cultivar. Journal of the Science of Food and Agriculture. 86: 922.
Campo E., Ferreira V., Escudero A. and Cacho J. 2005. Prediction of the wine sensory properties related to grape variety from dynamic-headspace gas chromatography-olfactometry data. Journal of Agricultural and Food Chemistry. 53: 5682.
Cejudo-Bastante M.J., Pérez-Coello M.S. and Hermosín-Gutiérrez I. 2011. Effect of wine micro-oxygenation treatment and storage period on colour-related phenolics, volatile composition and sensory characteristics. LWT-Food Science and Technol. 44: 866.
Celotti E. and Zucchetto M. 2003. Esempio di gestione ragionata della microssigenazione applicata ad un vino rosso. Vinidea.net-Rivista internet tecnica del vino. 11: 1.
Chapman D. M., Thorngate J. H., Matthews M. A., Guinard J.-X. and Ebeler S. E. 2004. Yield Effects on 2-Methoxy-3-Isobutylpyrazine Concentration in Cabernet Sauvignon Using a Solid Phase Microextraction Gas Chromatography/Mass Spectrometry Method. Journal of Agricultural and Food Chemistry. 52: 5431.
Crouzet J. 1986. Les enzymes et l'arôme des vins. Revue Française d’Œnologie. 102: 42.
Cudjoe E., Wiederkehr T. B. and Brindle I. D. 2005. Headspace gas chromatography-mass spectrometry: a fast approach to the identification and determination of 2-alkyl-3-methoxypyrazine pheromones in ladybugs. Analyst. 130(2): 152.
D’Auria M., Emanuele L., Mauriello G. and Racioppi R. 2003. On the origin of ‘Gout de Lumiere’ in champagne. Journal of Photochemistry and Photobiology A: Chemistry. 158: 21.
Di Lecce G., Boselli E., D’Ignazi G., and Frega N.G. 2013. Evolution of phenolics and glutathione in Verdicchio wine obtained with maceration under reductive conditions, LWT - Food Science and Technology 53: 54.
Di Stefano R., Bottero S., Pigella R., Borsa D., Bezzo G. and Corino L. 1998. Precursori d'aroma glicosilati presenti nelle uve di alcune cultivar a frutto colorato. L'Enotecnico. 63.
D'Onofrio C. 2011. Caratterizzazione funzionale della biosintesi degli aromi durante lo sviluppo dell'acino e controllo della qualità aromatica delle uve. ItalusHortus. 18(1): 39.
Drawert F., Heimann W., Emberger R. and Tressl R. 1966. Enzymatische Bildung von Hexen-(2)-al-(1), Hexanal und deren Vorstufen. Liebigs Annalen der Chemie. 694: 200.
Du Toit W. J., Lisjak K., Stander M. and Prevoo D. 2007. Using LC–MSMS to assess glutathione levels in South African white grape juices and wines made with different levels of oxygen. Journal of Agricultural and Food Chemistry. 55(8): 2765.
Dunlevy J. D., Dennis E. G., Soole K. L., Perkins M. V., Davies C. and Boss P. K. 2013. A methyltransferase essential for the methoxypyrazine-derived flavour of wine. The Plant Journal 75: 606.
Dunlevy J. D., Soole K. L., Perkins M. V., Dennis E. G., Keyzers R. A., Kalua C. M. and Boss P. K. 2010. Two O-methyltransferases involved in the biosynthesis of methoxypyrazines: grape-derived aroma compounds important to wine flavour. Plant Molecular Biology 74: 77.
Escudier J.L. 2001. Les nouvelles methods pour la vinificationet le traitement des vins rouges, in Guide de la vinification rhodanienne, 5:31. http://www.institut-rhodanien.com/download/646
Escudier J-L., Mikolajczak M. and Moutonnet M. 1998. Pre-traitement des raisins par flash-detente sous vide et caracteristiques des vins. Journal International des Sciences de la Vigne et du Vin. 32: 105.
Etaio I., Elortondo F.J.P., Albisu M., Gaston E., Ojeda M. and Schlich, P. 2011. Effect of winemaking process and addition of white grapes on the sensory and physicochemical characteristics of young red wines. Australian Journal of Grape and Wine Research. 14: 211.
Favarel J.L. Flash-détente technology. Presentation at the 15th Australian Wine Industry Technical Conference (AWITC), Sidney July 16, 2013 (https://www.awri.com.au/wp-content/uploads/2013/08/pera-WS39-AWITC15.pdf) (April 13, 2015).
Ferrandino A., Schubert A. and Carlomagno A. 2012. Varietal and prefermentative volatiles during ripening of Vitis vinifera cv Nebbiolo berries from three growing areas. Food Chemistry. 135(4): 2340.
Galvan T. L., Kells S. and Hutchison W. D. 2008. Determination of 3-alkyl-2-methoxypyrazines in lady beetle-infested wine by solid-phase microextraction headspace sampling. Journal of Agricultural and Food Chemistry. 56(3): 1065.
Gomez-Plaza E. and Cano-Lopez M. 2011. A review on micro-oxygenation of red wines: claims, benefits and the underlying chemistry. Food Chemistry. 125: 1131.
Goniak O. J. and Noble A. C. 1987. Sensory Study of Selected Volatile Sulfur Compounds in White Wine. American Journal of Enology and Viticulture. 38: 223.
Harris S. A., Ryona I. and Sacks G. L. J. 2012. Behavior of 3-Isobutyl-2-hydroxypyrazine (IBHP), a key intermediate in 3-Isobutyl-2-methoxypyrazine (IBMP) metabolism, in ripening wine grapes. Journal of Agricultural and Food Chemistry. 60: 11901.
Harsch M.J., Benkwitz F., Frost A., Colonna-Ceccaldi B., Garner R. C. and Salmon J. M. 2013. New precursor of 3-mercaptohexan-1-ol in grape juice: thiol-forming potential and kinetics during early stages of must fermentation. Journal of Agricultural and Food Chemistry. 61: 3703.
Hashizume K. and Samuta T. 1997. Green odorants of grape cluster stem and their ability to cause a wine stemmy flavor. Journal of Agricultural and Food Chemistry. 45: 1333.
Hashizume K. and Samuta T. 1999. Grape maturity and light exposure affect berry methoxypyrazine concentration. American Journal of Enology and Viticulture. 50(2): 194.
Hashizume K., Tozawa K., Endo M. and Aramaki I. 2001. S-Adenosyl-L-methionine-dependent O-methylation of 2-hydroxy-3-alkylpyrazine in wine grapes: a putative final step of methoxypyrazine biosynthesis. Biosciensce Biotechnology Biochemistry. 65: 795.
He F., Liang N., Mu L., Pan Q., Wang J., Reeves M. J. and Duan, C. 2012. Anthocyanins and their variation in red wines I. monomeric anthocyanins and their expression. Molecules. 17: 1571.
Hein K., Ebeler S.E. and Heymann H. 2009. Perception of fruity and vegetative aromas in red wine. Journal of Sensory Studies 24: 441.
Herbst-Johnstone M., Nicolau L. and Kilmartin P. A. 2011. Stability of varietal thiols in commercial Sauvignon blanc wines. American Journal of Enology and Viticulture. 62: 495.
Hernandez-Orte P., Lapena A. C., Escudero A., Astrain J., Baron, C., Pardo I., Polo L., Ferrer S., Cacho J. and Ferreira V. 2009. Effect of micro-oxygenation on the evolution of aromatic compounds in wines: Malolactic fermentation and ageing in wood. LWT-Food Sc. Technol. 42: 391.
Heymann H., Noble A. C. and Boulton R. B. 1986. Analysis of methoxypyrazines in wines. 1. Development of a quantitative procedure. Journal of Agricultural and Food Chemistry. 34: 268.
Iyer M. M., Sacks G. L. and Padilla-Zakour O.I. 2010. Impact of harvesting and processing conditions on green leaf volatile development and phenolics in concord grape juice. J. Food Sci. 75: C297.
Jones R. and Gnekow B. Flash Détente: implications for luxury winemaking. Presentation at the Napa Valley Wine Technical Group. 23 February 2011 (http://luxury1.org/flash-dtente-implications-for-luxury-winemaking-e1.html) (April 13, 2015)
Kalua C.M. and Boss P.K. 2008. Sample preparation optimization in wine and grapes: dilution and sample/headspace volume equilibrium theory for headspace solid-phase microextraction. Journal of Chromatography A. 1192(1): 25.
Kalua C.M. and Boss P.K. 2010. Comparison of major volatile compounds from Riesling and Cabernet Sauvignon grapes (VitisVinifera L.) from fruit set to harvest. Australian Journal of Grape and Wine Research 16: 337.
Kögel S., Botezatu A., Hoffmann C. and Pickering G. 2014. Methoxypyrazine composition of Coccinellidae-tainted Riesling and Pinot noir wine from Germany. Journal of the Science of Food and Agriculture. 95(3): 509.
Kotseridis Y., Baumes R. L., Bertrand A. and Skouroumounis G. K. 1999. Quantitative determination of 2-methoxy-3-isobutylpyrazine in red wines and grapes of Bordeaux using a stable isotope dilution assay. Journal of Chromatography A. 841: 229.
Kwasniewski M. T., Sacks G. L. and Wilcox W. F. 2014. Persistence of elemental sulfur spray residue on grapes during ripening and vinification. American Journal of Enology and Viticulture. 65: 453.
Lacey M. J., Allen M. S., Harris R. L. N. and Brown W. V. 1991. Methoxypyrazines in Sauvignon blanc Grapes and Wines. American Journal of Enology and Viticulture. 42: 103.
Lanati D., Bonino M. and Mazza G. 2000. Precursori d'aroma e profilo varietale della cultivar ‘Sangiovese’. Atti del Simposio Internazionale, V Sessione: Aspetti enologici. 447-452.
Landaud A., Helinck S. and Bonnarme P. 2008. Formation of volatile sulfur compounds and methabolism of methionine and other sulfur compounds in fermented food. Applied Microbiology and Biotechnology 77: 1191.
Liu S.Q. 2002. Malolactic fermentation in wine – beyond deacidification. Journal of Applied Microbiology 92: 589.
Llaudy M. C., Canals R., Gonzales-Manzano S., Canals J. M., Santos-Buelga C., and Zamora F. 2006. Influence of Micro-Oxygenation Treatment before Oak Aging on Phenolic Compounds Composition, Astringency, and Color of Red Wine. Journal of Agricultural and Food Chemistry. 54: 4246.
Marais J. and Pool H. 1980. Effect of storage time and temperature on the volatile composition and quality of dry white table wines. Vitis. 19: 151.
Mendez?Costabel M. P., Wilkinson K. L., Bastian S. E. P., Jordans C., McCarthy M., Ford C. M., and Dokoozlian N. K. 2014. Effect of increased irrigation and additional nitrogen fertilisation on the concentration of green aroma compounds in Vitis vinifera L. Merlot fruit and wine. Australian Journal of Grape and Wine Research. 20(1): 80.
Mendez?Costabel M. P., Wilkinson K. L., Bastian S. E. P., Jordans C., McCarthy M., Ford C. M. and Dokoozlian, N. 2014. Effect of winter rainfall on yield components and fruit green aromas of Vitisvinifera L. cv. Merlot in California. Australian Journal of Grape and Wine Research. 20, 1: 100.
Mestres M., Busto O. and Guasch J. 2000. Analysis of organic sulfur compounds in wine aroma. Journal of Chromatography A. 881: 569.
Mestres M., Busto O. and Guasch J. 2002. Application of headspace solid-phase microextraction to the determination of sulphur compounds with low volatility in wines. Journal of Chromatography A. 945: 211.
Moreira N., Mendes F., Pereira O., Guedes de Pinho P., Hogg T., and Vasconcelos I. 2002. Volatile sulphur compounds in wines related to yeast metabolism and nitrogen composition of grape musts. Analytica Chimica Acta. 458(1): 157.
Moutounet M. and Escudier J.-L. 2000. Prétraitements des raisins par flash-détente sous vide, influence sur la qualité des vins. Bulletin de l'O.I.V. 73(827-828): 5.
Moutounet M., Mazauric J.-P., Ducournau P. and Lemaire T. 2001. Wine micro-oxygenation. Principles and technological applications. Industria delle Bevande. 30: 253.
Nardin G., Gaudio A., Antonel G. and Simeoni P. 2006. Impiantistica Enologica. Hoepli, Milan (Italy).
Nikolantonaki M., Chichuc I., Teissedre P. L. and Darriet P. 2010. Reactivity of volatile thiols with polyphenols in a wine-model medium: Impact of oxygen, iron, and sulfur dioxide. Analytica Chimica Acta. 660: 102.
Nikolantonaki M. and Waterhouse A. L. 2012. A method to quantify quinine reaction rates with wine relevant nucleophiles: a key to the understanding of oxidative loss of varietal thiols. Journal of Agricultural and Food Chemistry. 60: 8484.
Parish M., Wollan D. and Paul R. 2000. Micro-oxygenation, a review. Australian Grapegrowing Winemaking, 47.
Pickering G. J., Lin J., Reynolds A., Soleas G., Riesen R. and Brindle I. 2005. The in?uence of Harmonia axyridis on wine composition and aging. International Journal of Food Science and Technology 70: 128.
Pickering G. J., Spink M., Kotseridis Y., Brindle I. D., Sears M. and Inglis D. 2008. Morbidity of Harmonia axyridis mediates ladybug taint in red wine. Journal of Food Agriculture Environment. 6: 133.
Pickering G., Lin J., Reynolds A., Soleas G. and Riesen R. 2006. The evaluation of remedial treatments for wine affected by Harmonia axyridis. Journal of Food Science and Technology 41: 77.
Rapp A. 1998. Volatile flavour of wine: correlation between instrumental analysis and sensory perception. Nahrung. 42: 351.
Rapp A. and Mandery H. 1986. Wine aroma. Experientia. 42: 873.
Razungles A. 2010. Extraction technologies and wine quality. In Volume II of Managing Wine Quality, Andy Reynolds, Ed., Woodhead Publishing Limited. 589.
Ribéreau-Gayon P., Glories Y., Maujean A. and Dubourdieu D. 2005. Traité d'oenologie 2. Chemie du vin-Stabilisation et traitements, ed. Dunod, Paris (France).
Robinson A., Boss P.K., Solomon P. S., Trengove R.D., Heymann H. and Ebeler S. E. 2014. Origins of Grape and Wine Aroma. Part 1. Chemical Components and Viticultural Impacts. American Journal of Enology and Viticulture. 65: 1, a.
Robinson A., Boss, P.K., Solomon P. S., Trengove R.D., Heymann H. and Ebeler S. E. 2014. Origins of Grape and Wine Aroma. Part 2. Chemical and Sensory Analysis. American Journal of Enology and Viticulture. 65:25, b.
Roland A., Vialaret J., Razungles A., Rigou P. and Schneider R. 2010. Evolution of S-Cysteinylated and S-glutathionylated thiol precursors during oxidation of Melon B. and Sauvignon blanc musts. Journal of Agricultural and Food Chemistry. 58: 4406.
Roujou de Boubée D., Cumsille A.M., Pons M. and Dubourdieu D. 2002. Location of 2-methoxy-3-isobutylpyrazine in Cabernet Sauvignon grape bunches and its extractability during vinification. American Journal of Enology and Viticulture. 53: 1.
Roujou de Boubee D., Van Leeuwen C. and Dubourdieu D. 2000. Organoleptic impact of 2-methoxy-3-isobutylpyrazine on red Bordeaux and Loire wines effect of environmental conditions on concentrations in grapes during ripening. Journal of Agricultural and Food Chemistry. 48: 4830.
Ryona I., Leclerc S. and Sacks G. L. 2010. Correlation of 3-isobutyl-2-methoxypyrazine to 3-isobutyl-2-hydroxypyrazine during maturation of bell pepper (Capsicum annuum) and wine grapes (Vitisvinifera). Journal of Agricultural and Food Chemistry. 58: 9723.
Ryona I., Pan B. S., Intrigliolo D. S., Lakso A. N. and Sacks G. L. 2008. Effects of cluster light exposure on 3-isobutyl-2-methoxypyrazine accumulation and degradation patterns in red wine grapes (Vitisvinifera L. Cv. Cabernet Franc). Journal of Agricultural and Food Chemistry. 56: 10838.
Ryona I, Reinhardt J. and Sacks G. L. 2012. Treatment of grape juice or must with silicone reduces 3-alkyl-2-methoxypyrazine concentrations in resulting wines without altering fermentation volatiles. Food Research International 47: 70.
Sala C., Busto O., Guasch J. and Zamora F. 2004. Influence of vine training and sunlight exposure on the 3-alkyl-2-methoxypyrazines content in musts and wines from the Vitis vinifera variety Cabernet Sauvignon. Journal of Agricultural and Food Chemistry. 52(11): 3492.
Sala C., Busto O., Guasch J. and Zamora F. 2005. Contents of 3-alkyl-2-methoxypyrazines in musts and wines from Vitis vinifera variety Cabernet Sauvignon: Influence of irrigation and plantation density. Journal of the Science of Food and Agriculture. 85(7): 1131.
Scheiner J. J., Sacks G. L., Pan B., Ennahli S., Tarton L., Wise A., Lerch S. D. and VandenHeuvel J. E. 2010. Impact of severity and timing of basal leaf removal on 3-isobutyl-2-methoxypyrazine concentrations in red wine grapes. American Journal of Enology and Viticulture. 61: 358.
Schmitt P. Conetech could take out wine pyrazines, The Drinks Business, 2014, 18 December. URL (http://www.thedrinksbusiness.com/2014/12/conetech-could-take-out-pyrazines-in-wine/) (April, 13, 2015).
Sefton M.A. 1998. Hydrolytically-released volatile secondary metabolites from a juice sample of Vitis vinifera grape cvs Merlot and Cabernet Sauvignon. Australian Journal of Grape and Wine Research. 4: 30.
Silva M.A., Jourdes M. and Teissedre P.-L. 2011. Impact of closures on wine post-bottling development: a review. European Food Research and Technology 233: 905.
Vidal S. and Aagaard O. 2008. Oxygen management during vinification and storage of Shiraz wine. Wine Industrial Journal. 23(5): 1.
Vinsonneau E., Escaffre P., Crachereau J.C. and Praud S. Evaluation du procédé de vinification par flash déténtedans le bordelaise, ITV France Bordeaux – Blanquefort, 15/05/2006, 1-23, http://www.matevi-france.com/uploads/tx_matevibase/Evaluation_du_procede_de_vinification_par_flash_detente_dans_le_Bordelais.pdf
Waterhouse A. L. and Laurie F. 2006. Oxidation of wine phenolics: a critical evaluation and hypotheses. American Journal of Enology and Viticulture. 57: 306.
Wyngaard E., Brand J., Jacobson D. and Toit W. J. 2014. Sensory interaction between 3-mercaptohexan-1-ol and 2-isobutyl-3methoxypyrazine in dearomatised Sauvignon blanc wine. Australian Journal of Grape and Wine Research. 20: 178.
Yang C.X., Wang Y.J., Liang Z.C., Fan P.G., Wu B.H., Yang L., Wang Y.N. and Li S.H. 2009. Volatiles of grapes berries evaluated at the germplasm level by headspace-SPME with GCMS. Food Chemistry. 114: 1106.
Al Abassi, S., Birkett M. A., Pettersson J., Pickett J. A. and Woodcock C. M. 1998. Ladybird beetle odour identified and found to be responsible for attraction between adults. Cellular and Molecular Life Sciences. 54: 876.
Allen M. S., Lacey M. J. and Boyd S. Methoxypyrazines in red wines: occurrence of 2-methoxy-3-(1-methylethyl) pyrazine. 1995. Journal of Agricultural and Food Chemistry. 43: 769.
Allen M. S., Lacey M. J., Harris R.L.N. and Brown, W.V. 1991. Contribution of methoxypyrazines to Sauvignon Blanc wine aroma. American Journal of Enology and Viticulture 42: 109.
Amerine M. A. and Roessler E. B. 1976. In Wines - Their Sensory Evaluation, W.H. Freeman and Company: San Francisco (USA).
Bayonove C., Cordonnier R. and Dubois P. 1975. Study of an aromatic characteristic fraction of Cabernet Sauvignon grape variety, identification of 2-methoxy-3-isobutyl-pyrazine. Comptes Rendus Hebdomadaires Des Seances De L’Academie Des Sciences Serie D. 281: 75.
Belancic A. and Agosin E. 2007. Methoxypyrazines in grapes and wines of Vitis vinifera cv. Carmenere. American Journal of Enology and Viticulture 58: 462.
Bell S. J. and Henschke P.A. 2005. Implications of nitrogen nutrition for grapes, fermentation and wine. Australian Journal of Grape and Wine Research. 11: 242.
Benkwitz F., Nicolau L., Lund C., Beresford M., Wohlers M. and Kilmartin P.A. 2012. Evaluation of Key Odorants in Sauvignon Blanc Wines Using Three Different Methodologies. Journal of Agricultural and Food Chemistry. 60: 6293.
Blake A., Kotseridis Y., Brindle I. D., Inglis D. and Pickering, G. J. 2010. Effect of light and temperature on 3-alkyl-2-methoxypyrazine concentration and other impact odourants of Riesling and Cabernet Franc wines during bottle ageing. Food Chemistry. 119: 935.
Blake A., Kotseridis Y., Brindle, I. D., Inglis D., Sears M. and Pickering G. J. 2009. Effect of closure and packaging type on 3-alkyl-2-methoxypyrazines and other impact odorants of Riesling and Cabernet Franc wines. Journal of Agricultural and Food Chemistry. 57: 4680.
Borsa D., Asporundi A., Nardi S., Costacurta A., Di Stefano R., and Calò A. 2008. Metaboliti secondari delle cultivar Malvasia. Confronto di due annate. Rivista di Viticultura ed Enologia 2-3-4: 99.
Boselli E., Di Lecce G., Alberti F., and Frega N.G. 2010. Nitrogen Gas Affects The Quality And The Phenolic Profile Of Must Obtained From Vacuum-Pressed White Grapes. LWT-Food Science and Technology. 43, 10:1494.
Boselli E., Giomo A., Minardi M. and Frega N.G. 2008. Characterization of phenolics in Lacrima di Morro d'Alba wine and role on its sensory attributes. European Food Research and Technology. 227(3): 709.
Boselli E., Minardi M., Giomo A. and Frega N.G. 2006. Phenolic composition and quality of white d.o.c. wines from Marche (Italy). Analytica Chimica Acta 563: 93.
Botezatu A. I., Kotseridis Y., Inglis D. and Pickering G. J. 2012. Occurrence and contribution of alkyl methoxypyrazines in wine tainted by Harmonia axyridis and Coccinella septempunctata. Journal of the Science of Food and Agriculture. 93(4): 803.
Buttery R. G., Seifert R. M., Guadagni D. G. and Ling L. C. 1969. Characterization of some volatile constituents of bell peppers. Journal of Agricultural and Food Chemistry. 17(6): 1322.
Cabrita J.M., Freitas C.A.M., Laueano O. and Di Stefano R. 2006. Glycosidic aroma compounds of some Portuguese grape cultivar. Journal of the Science of Food and Agriculture. 86: 922.
Campo E., Ferreira V., Escudero A. and Cacho J. 2005. Prediction of the wine sensory properties related to grape variety from dynamic-headspace gas chromatography-olfactometry data. Journal of Agricultural and Food Chemistry. 53: 5682.
Cejudo-Bastante M.J., Pérez-Coello M.S. and Hermosín-Gutiérrez I. 2011. Effect of wine micro-oxygenation treatment and storage period on colour-related phenolics, volatile composition and sensory characteristics. LWT-Food Science and Technol. 44: 866.
Celotti E. and Zucchetto M. 2003. Esempio di gestione ragionata della microssigenazione applicata ad un vino rosso. Vinidea.net-Rivista internet tecnica del vino. 11: 1.
Chapman D. M., Thorngate J. H., Matthews M. A., Guinard J.-X. and Ebeler S. E. 2004. Yield Effects on 2-Methoxy-3-Isobutylpyrazine Concentration in Cabernet Sauvignon Using a Solid Phase Microextraction Gas Chromatography/Mass Spectrometry Method. Journal of Agricultural and Food Chemistry. 52: 5431.
Crouzet J. 1986. Les enzymes et l'arôme des vins. Revue Française d’Œnologie. 102: 42.
Cudjoe E., Wiederkehr T. B. and Brindle I. D. 2005. Headspace gas chromatography-mass spectrometry: a fast approach to the identification and determination of 2-alkyl-3-methoxypyrazine pheromones in ladybugs. Analyst. 130(2): 152.
D’Auria M., Emanuele L., Mauriello G. and Racioppi R. 2003. On the origin of ‘Gout de Lumiere’ in champagne. Journal of Photochemistry and Photobiology A: Chemistry. 158: 21.
Di Lecce G., Boselli E., D’Ignazi G., and Frega N.G. 2013. Evolution of phenolics and glutathione in Verdicchio wine obtained with maceration under reductive conditions, LWT - Food Science and Technology 53: 54.
Di Stefano R., Bottero S., Pigella R., Borsa D., Bezzo G. and Corino L. 1998. Precursori d'aroma glicosilati presenti nelle uve di alcune cultivar a frutto colorato. L'Enotecnico. 63.
D'Onofrio C. 2011. Caratterizzazione funzionale della biosintesi degli aromi durante lo sviluppo dell'acino e controllo della qualità aromatica delle uve. ItalusHortus. 18(1): 39.
Drawert F., Heimann W., Emberger R. and Tressl R. 1966. Enzymatische Bildung von Hexen-(2)-al-(1), Hexanal und deren Vorstufen. Liebigs Annalen der Chemie. 694: 200.
Du Toit W. J., Lisjak K., Stander M. and Prevoo D. 2007. Using LC–MSMS to assess glutathione levels in South African white grape juices and wines made with different levels of oxygen. Journal of Agricultural and Food Chemistry. 55(8): 2765.
Dunlevy J. D., Dennis E. G., Soole K. L., Perkins M. V., Davies C. and Boss P. K. 2013. A methyltransferase essential for the methoxypyrazine-derived flavour of wine. The Plant Journal 75: 606.
Dunlevy J. D., Soole K. L., Perkins M. V., Dennis E. G., Keyzers R. A., Kalua C. M. and Boss P. K. 2010. Two O-methyltransferases involved in the biosynthesis of methoxypyrazines: grape-derived aroma compounds important to wine flavour. Plant Molecular Biology 74: 77.
Escudier J.L. 2001. Les nouvelles methods pour la vinificationet le traitement des vins rouges, in Guide de la vinification rhodanienne, 5:31. http://www.institut-rhodanien.com/download/646
Escudier J-L., Mikolajczak M. and Moutonnet M. 1998. Pre-traitement des raisins par flash-detente sous vide et caracteristiques des vins. Journal International des Sciences de la Vigne et du Vin. 32: 105.
Etaio I., Elortondo F.J.P., Albisu M., Gaston E., Ojeda M. and Schlich, P. 2011. Effect of winemaking process and addition of white grapes on the sensory and physicochemical characteristics of young red wines. Australian Journal of Grape and Wine Research. 14: 211.
Favarel J.L. Flash-détente technology. Presentation at the 15th Australian Wine Industry Technical Conference (AWITC), Sidney July 16, 2013 (https://www.awri.com.au/wp-content/uploads/2013/08/pera-WS39-AWITC15.pdf) (April 13, 2015).
Ferrandino A., Schubert A. and Carlomagno A. 2012. Varietal and prefermentative volatiles during ripening of Vitis vinifera cv Nebbiolo berries from three growing areas. Food Chemistry. 135(4): 2340.
Galvan T. L., Kells S. and Hutchison W. D. 2008. Determination of 3-alkyl-2-methoxypyrazines in lady beetle-infested wine by solid-phase microextraction headspace sampling. Journal of Agricultural and Food Chemistry. 56(3): 1065.
Gomez-Plaza E. and Cano-Lopez M. 2011. A review on micro-oxygenation of red wines: claims, benefits and the underlying chemistry. Food Chemistry. 125: 1131.
Goniak O. J. and Noble A. C. 1987. Sensory Study of Selected Volatile Sulfur Compounds in White Wine. American Journal of Enology and Viticulture. 38: 223.
Harris S. A., Ryona I. and Sacks G. L. J. 2012. Behavior of 3-Isobutyl-2-hydroxypyrazine (IBHP), a key intermediate in 3-Isobutyl-2-methoxypyrazine (IBMP) metabolism, in ripening wine grapes. Journal of Agricultural and Food Chemistry. 60: 11901.
Harsch M.J., Benkwitz F., Frost A., Colonna-Ceccaldi B., Garner R. C. and Salmon J. M. 2013. New precursor of 3-mercaptohexan-1-ol in grape juice: thiol-forming potential and kinetics during early stages of must fermentation. Journal of Agricultural and Food Chemistry. 61: 3703.
Hashizume K. and Samuta T. 1997. Green odorants of grape cluster stem and their ability to cause a wine stemmy flavor. Journal of Agricultural and Food Chemistry. 45: 1333.
Hashizume K. and Samuta T. 1999. Grape maturity and light exposure affect berry methoxypyrazine concentration. American Journal of Enology and Viticulture. 50(2): 194.
Hashizume K., Tozawa K., Endo M. and Aramaki I. 2001. S-Adenosyl-L-methionine-dependent O-methylation of 2-hydroxy-3-alkylpyrazine in wine grapes: a putative final step of methoxypyrazine biosynthesis. Biosciensce Biotechnology Biochemistry. 65: 795.
He F., Liang N., Mu L., Pan Q., Wang J., Reeves M. J. and Duan, C. 2012. Anthocyanins and their variation in red wines I. monomeric anthocyanins and their expression. Molecules. 17: 1571.
Hein K., Ebeler S.E. and Heymann H. 2009. Perception of fruity and vegetative aromas in red wine. Journal of Sensory Studies 24: 441.
Herbst-Johnstone M., Nicolau L. and Kilmartin P. A. 2011. Stability of varietal thiols in commercial Sauvignon blanc wines. American Journal of Enology and Viticulture. 62: 495.
Hernandez-Orte P., Lapena A. C., Escudero A., Astrain J., Baron, C., Pardo I., Polo L., Ferrer S., Cacho J. and Ferreira V. 2009. Effect of micro-oxygenation on the evolution of aromatic compounds in wines: Malolactic fermentation and ageing in wood. LWT-Food Sc. Technol. 42: 391.
Heymann H., Noble A. C. and Boulton R. B. 1986. Analysis of methoxypyrazines in wines. 1. Development of a quantitative procedure. Journal of Agricultural and Food Chemistry. 34: 268.
Iyer M. M., Sacks G. L. and Padilla-Zakour O.I. 2010. Impact of harvesting and processing conditions on green leaf volatile development and phenolics in concord grape juice. J. Food Sci. 75: C297.
Jones R. and Gnekow B. Flash Détente: implications for luxury winemaking. Presentation at the Napa Valley Wine Technical Group. 23 February 2011 (http://luxury1.org/flash-dtente-implications-for-luxury-winemaking-e1.html) (April 13, 2015)
Kalua C.M. and Boss P.K. 2008. Sample preparation optimization in wine and grapes: dilution and sample/headspace volume equilibrium theory for headspace solid-phase microextraction. Journal of Chromatography A. 1192(1): 25.
Kalua C.M. and Boss P.K. 2010. Comparison of major volatile compounds from Riesling and Cabernet Sauvignon grapes (VitisVinifera L.) from fruit set to harvest. Australian Journal of Grape and Wine Research 16: 337.
Kögel S., Botezatu A., Hoffmann C. and Pickering G. 2014. Methoxypyrazine composition of Coccinellidae-tainted Riesling and Pinot noir wine from Germany. Journal of the Science of Food and Agriculture. 95(3): 509.
Kotseridis Y., Baumes R. L., Bertrand A. and Skouroumounis G. K. 1999. Quantitative determination of 2-methoxy-3-isobutylpyrazine in red wines and grapes of Bordeaux using a stable isotope dilution assay. Journal of Chromatography A. 841: 229.
Kwasniewski M. T., Sacks G. L. and Wilcox W. F. 2014. Persistence of elemental sulfur spray residue on grapes during ripening and vinification. American Journal of Enology and Viticulture. 65: 453.
Lacey M. J., Allen M. S., Harris R. L. N. and Brown W. V. 1991. Methoxypyrazines in Sauvignon blanc Grapes and Wines. American Journal of Enology and Viticulture. 42: 103.
Lanati D., Bonino M. and Mazza G. 2000. Precursori d'aroma e profilo varietale della cultivar ‘Sangiovese’. Atti del Simposio Internazionale, V Sessione: Aspetti enologici. 447-452.
Landaud A., Helinck S. and Bonnarme P. 2008. Formation of volatile sulfur compounds and methabolism of methionine and other sulfur compounds in fermented food. Applied Microbiology and Biotechnology 77: 1191.
Liu S.Q. 2002. Malolactic fermentation in wine – beyond deacidification. Journal of Applied Microbiology 92: 589.
Llaudy M. C., Canals R., Gonzales-Manzano S., Canals J. M., Santos-Buelga C., and Zamora F. 2006. Influence of Micro-Oxygenation Treatment before Oak Aging on Phenolic Compounds Composition, Astringency, and Color of Red Wine. Journal of Agricultural and Food Chemistry. 54: 4246.
Marais J. and Pool H. 1980. Effect of storage time and temperature on the volatile composition and quality of dry white table wines. Vitis. 19: 151.
Mendez?Costabel M. P., Wilkinson K. L., Bastian S. E. P., Jordans C., McCarthy M., Ford C. M., and Dokoozlian N. K. 2014. Effect of increased irrigation and additional nitrogen fertilisation on the concentration of green aroma compounds in Vitis vinifera L. Merlot fruit and wine. Australian Journal of Grape and Wine Research. 20(1): 80.
Mendez?Costabel M. P., Wilkinson K. L., Bastian S. E. P., Jordans C., McCarthy M., Ford C. M. and Dokoozlian, N. 2014. Effect of winter rainfall on yield components and fruit green aromas of Vitisvinifera L. cv. Merlot in California. Australian Journal of Grape and Wine Research. 20, 1: 100.
Mestres M., Busto O. and Guasch J. 2000. Analysis of organic sulfur compounds in wine aroma. Journal of Chromatography A. 881: 569.
Mestres M., Busto O. and Guasch J. 2002. Application of headspace solid-phase microextraction to the determination of sulphur compounds with low volatility in wines. Journal of Chromatography A. 945: 211.
Moreira N., Mendes F., Pereira O., Guedes de Pinho P., Hogg T., and Vasconcelos I. 2002. Volatile sulphur compounds in wines related to yeast metabolism and nitrogen composition of grape musts. Analytica Chimica Acta. 458(1): 157.
Moutounet M. and Escudier J.-L. 2000. Prétraitements des raisins par flash-détente sous vide, influence sur la qualité des vins. Bulletin de l'O.I.V. 73(827-828): 5.
Moutounet M., Mazauric J.-P., Ducournau P. and Lemaire T. 2001. Wine micro-oxygenation. Principles and technological applications. Industria delle Bevande. 30: 253.
Nardin G., Gaudio A., Antonel G. and Simeoni P. 2006. Impiantistica Enologica. Hoepli, Milan (Italy).
Nikolantonaki M., Chichuc I., Teissedre P. L. and Darriet P. 2010. Reactivity of volatile thiols with polyphenols in a wine-model medium: Impact of oxygen, iron, and sulfur dioxide. Analytica Chimica Acta. 660: 102.
Nikolantonaki M. and Waterhouse A. L. 2012. A method to quantify quinine reaction rates with wine relevant nucleophiles: a key to the understanding of oxidative loss of varietal thiols. Journal of Agricultural and Food Chemistry. 60: 8484.
Parish M., Wollan D. and Paul R. 2000. Micro-oxygenation, a review. Australian Grapegrowing Winemaking, 47.
Pickering G. J., Lin J., Reynolds A., Soleas G., Riesen R. and Brindle I. 2005. The in?uence of Harmonia axyridis on wine composition and aging. International Journal of Food Science and Technology 70: 128.
Pickering G. J., Spink M., Kotseridis Y., Brindle I. D., Sears M. and Inglis D. 2008. Morbidity of Harmonia axyridis mediates ladybug taint in red wine. Journal of Food Agriculture Environment. 6: 133.
Pickering G., Lin J., Reynolds A., Soleas G. and Riesen R. 2006. The evaluation of remedial treatments for wine affected by Harmonia axyridis. Journal of Food Science and Technology 41: 77.
Rapp A. 1998. Volatile flavour of wine: correlation between instrumental analysis and sensory perception. Nahrung. 42: 351.
Rapp A. and Mandery H. 1986. Wine aroma. Experientia. 42: 873.
Razungles A. 2010. Extraction technologies and wine quality. In Volume II of Managing Wine Quality, Andy Reynolds, Ed., Woodhead Publishing Limited. 589.
Ribéreau-Gayon P., Glories Y., Maujean A. and Dubourdieu D. 2005. Traité d'oenologie 2. Chemie du vin-Stabilisation et traitements, ed. Dunod, Paris (France).
Robinson A., Boss P.K., Solomon P. S., Trengove R.D., Heymann H. and Ebeler S. E. 2014. Origins of Grape and Wine Aroma. Part 1. Chemical Components and Viticultural Impacts. American Journal of Enology and Viticulture. 65: 1, a.
Robinson A., Boss, P.K., Solomon P. S., Trengove R.D., Heymann H. and Ebeler S. E. 2014. Origins of Grape and Wine Aroma. Part 2. Chemical and Sensory Analysis. American Journal of Enology and Viticulture. 65:25, b.
Roland A., Vialaret J., Razungles A., Rigou P. and Schneider R. 2010. Evolution of S-Cysteinylated and S-glutathionylated thiol precursors during oxidation of Melon B. and Sauvignon blanc musts. Journal of Agricultural and Food Chemistry. 58: 4406.
Roujou de Boubée D., Cumsille A.M., Pons M. and Dubourdieu D. 2002. Location of 2-methoxy-3-isobutylpyrazine in Cabernet Sauvignon grape bunches and its extractability during vinification. American Journal of Enology and Viticulture. 53: 1.
Roujou de Boubee D., Van Leeuwen C. and Dubourdieu D. 2000. Organoleptic impact of 2-methoxy-3-isobutylpyrazine on red Bordeaux and Loire wines effect of environmental conditions on concentrations in grapes during ripening. Journal of Agricultural and Food Chemistry. 48: 4830.
Ryona I., Leclerc S. and Sacks G. L. 2010. Correlation of 3-isobutyl-2-methoxypyrazine to 3-isobutyl-2-hydroxypyrazine during maturation of bell pepper (Capsicum annuum) and wine grapes (Vitisvinifera). Journal of Agricultural and Food Chemistry. 58: 9723.
Ryona I., Pan B. S., Intrigliolo D. S., Lakso A. N. and Sacks G. L. 2008. Effects of cluster light exposure on 3-isobutyl-2-methoxypyrazine accumulation and degradation patterns in red wine grapes (Vitisvinifera L. Cv. Cabernet Franc). Journal of Agricultural and Food Chemistry. 56: 10838.
Ryona I, Reinhardt J. and Sacks G. L. 2012. Treatment of grape juice or must with silicone reduces 3-alkyl-2-methoxypyrazine concentrations in resulting wines without altering fermentation volatiles. Food Research International 47: 70.
Sala C., Busto O., Guasch J. and Zamora F. 2004. Influence of vine training and sunlight exposure on the 3-alkyl-2-methoxypyrazines content in musts and wines from the Vitis vinifera variety Cabernet Sauvignon. Journal of Agricultural and Food Chemistry. 52(11): 3492.
Sala C., Busto O., Guasch J. and Zamora F. 2005. Contents of 3-alkyl-2-methoxypyrazines in musts and wines from Vitis vinifera variety Cabernet Sauvignon: Influence of irrigation and plantation density. Journal of the Science of Food and Agriculture. 85(7): 1131.
Scheiner J. J., Sacks G. L., Pan B., Ennahli S., Tarton L., Wise A., Lerch S. D. and VandenHeuvel J. E. 2010. Impact of severity and timing of basal leaf removal on 3-isobutyl-2-methoxypyrazine concentrations in red wine grapes. American Journal of Enology and Viticulture. 61: 358.
Schmitt P. Conetech could take out wine pyrazines, The Drinks Business, 2014, 18 December. URL (http://www.thedrinksbusiness.com/2014/12/conetech-could-take-out-pyrazines-in-wine/) (April, 13, 2015).
Sefton M.A. 1998. Hydrolytically-released volatile secondary metabolites from a juice sample of Vitis vinifera grape cvs Merlot and Cabernet Sauvignon. Australian Journal of Grape and Wine Research. 4: 30.
Silva M.A., Jourdes M. and Teissedre P.-L. 2011. Impact of closures on wine post-bottling development: a review. European Food Research and Technology 233: 905.
Vidal S. and Aagaard O. 2008. Oxygen management during vinification and storage of Shiraz wine. Wine Industrial Journal. 23(5): 1.
Vinsonneau E., Escaffre P., Crachereau J.C. and Praud S. Evaluation du procédé de vinification par flash déténtedans le bordelaise, ITV France Bordeaux – Blanquefort, 15/05/2006, 1-23, http://www.matevi-france.com/uploads/tx_matevibase/Evaluation_du_procede_de_vinification_par_flash_detente_dans_le_Bordelais.pdf
Waterhouse A. L. and Laurie F. 2006. Oxidation of wine phenolics: a critical evaluation and hypotheses. American Journal of Enology and Viticulture. 57: 306.
Wyngaard E., Brand J., Jacobson D. and Toit W. J. 2014. Sensory interaction between 3-mercaptohexan-1-ol and 2-isobutyl-3methoxypyrazine in dearomatised Sauvignon blanc wine. Australian Journal of Grape and Wine Research. 20: 178.
Yang C.X., Wang Y.J., Liang Z.C., Fan P.G., Wu B.H., Yang L., Wang Y.N. and Li S.H. 2009. Volatiles of grapes berries evaluated at the germplasm level by headspace-SPME with GCMS. Food Chemistry. 114: 1106.
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Jan 21, 2016
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Author Biographies
Massimo Mozzon, Department of Agricultural, Food and Environmental Sciences Marche Polytechnic University Via Brecce Bianche, 10 60131 Ancona (Italy)
Department of Agricultural, Food and Environmental Sciences
Marche Polytechnic University
Ancona (Italy)
Associate Professor
Sara Savini, Department of Agricultural, Food and Environmental Sciences Marche Polytechnic University Via Brecce Bianche, 10 60131 Ancona (Italy)
Department of Agricultural, Food and Environmental Sciences
Marche Polytechnic University
Ancona (Italy)
PhD
Emanuele Boselli, Department of Agricultural, Food and Environmental Sciences Marche Polytechnic University Via Brecce Bianche, 10 60131 Ancona (Italy)
Department of Agricultural, Food and Environmental Sciences
Marche Polytechnic University
Ancona (Italy)
Associate Professor
John H Thorngate, Constellation Brands, Inc., 1178 Galleron Road, Saint Helena, CA 94574, USA
Sensory Department at Constellation Brands
Director