Contribution of several volatile phenols and their glycoconjugates to smoke-related sensory properties of red wine

Journal of Agricultural and Food Chemistry

Volumn 60, Issue 10, 2012, Pages 2629-2637

  Parker, Mango ^a   Osidacz, Patricia ^a   Baldock, Gayle A ^a   Hayasaka, Yoji ^a   Black, Cory A ^a   Pardon, Kevin H ^a   Jeffery, David W ^a,b   Geue, Jason P ^a   Herderich, Markus J ^a   Francis, I Leigh ^a  

^a AUSTRALIAN WINE RESEARCH INSTITUTE   (Australia)

^b UNIVERSITY OF ADELAIDE   (Australia)

Author keywords

bushfire; glycosides; grapes; HPLC MS MS; partial least squares regression; sensory descriptive analysis; smoke taint; Vitis vinifera; wine

Indexed keywords

BUSHFIRE; DESCRIPTIVE ANALYSIS; GRAPES; HPLC-MS/MS; PARTIAL LEAST-SQUARES REGRESSION; VITIS VINIFERA;

ALCOHOLS; DEFORESTATION; FLAVOR COMPOUNDS; FRUITS; GLYCOSIDES; PHENOLS; SUGARS; WINE;

SMOKE;

PHENOL DERIVATIVE; VOLATILE ORGANIC COMPOUND;

ARTICLE; CHEMISTRY; FEMALE; HUMAN; MALE; ODOR; TASTE; VITIS; WINE;

FEMALE; HUMANS; MALE; ODORS; PHENOLS; TASTE; VITIS; VOLATILE ORGANIC COMPOUNDS; WINE;

ALCOHOLS; DEFORESTATION; FLAVOR; FRUITS; GLYCOSIDES; PERCEPTION; PHENOLS; REGRESSION ANALYSIS; SMOKE; SUGARS;

VITACEAE; VITIS VINIFERA;

EID: 84858313657     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf2040548     Document Type: Article

References (36)

1. Hoj, P.; Pretorius, I.; Blair, R. The Australian Wine Research Institute, Annual Report, 2003; p 7.
2. Kennison, K. R.; Gibberd, M. R.; Pollnitz, A. P.; Wilkinson, K. L. Smoke-derived taint in wine: the release of smoke-derived volatile phenols during fermentation of Merlot juice following grapevine exposure to smoke J. Agric. Food Chem. 2008, 56, 7379-7383
3. Kennison, K. R.; Wilkinson, K. L.; Williams, H. G.; Smith, J. H.; Gibberd, M. R. Smoke-derived taint in wine: effect of postharvest smoke exposure of grapes on the chemical composition and sensory characteristics of wine J. Agric. Food Chem. 2007, 55, 10897-10901
4. Prida, A.; Chatonnet, P. Impact of oak-derived compounds on the olfactory perception of barrel-aged wines Am. J. Enol. Vitic. 2010, 61, 408-413
5. Spillman, P. J.; Sefton, M. A.; Gawel, R. The effect of oak wood source, location of seasoning and coopering on the composition of volatile compounds in oak-matured wines Aust. J. Grape Wine Res. 2004, 10, 216-226 (Pubitemid 39651325)
6. Maga, J. A. The flavor chemistry of wood smoke Food Rev. Int. 1987, 3 (1 and 2) 139-183
7. Hayasaka, Y.; Baldock, G. A.; Parker, M.; Pardon, K. H.; Black, C. A.; Herderich, M. J.; Jeffery, D. W. Glycosylation of smoke-derived volatile phenols in grapes as a consequence of grapevine exposure to bushfire smoke J. Agric. Food Chem. 2010, 58, 10989-10998
8. Clifford, M. N. Miscellaneous phenols in foods and beverages - nature, occurrence and dietary burden J. Sci. Food Agric. 2000, 80, 1126-1137 (Pubitemid 30319404)
9. Varlet, V.; Serot, T.; Cardinal, M.; Knockaert, C.; Prost, C. Olfactometric determination of the most potent odor-active compounds in salmon muscle (Salmo salar) smoked by using four smoke generation techniques J. Agric. Food Chem. 2007, 55, 4518-4525 (Pubitemid 46932650)
10. Sérot, T.; Baron, R.; Knockaert, C.; Vallet, J. L. Effect of smoking processes on the contents of 10 major phenolic compounds in smoked fillets of herring (Clupea harengus) Food Chem. 2004, 85, 111-120 (Pubitemid 37414843)
11. Varlet, V.; Knockaert, C.; Prost, C.; Serot, T. Comparison of odor-active volatile compounds of fresh and smoked salmon J. Agric. Food Chem. 2006, 54, 3391-3401 (Pubitemid 43798211)
12. Jounela-Eriksson, P.; Lehtonen, M. Phenols in the aroma of distilled beverages. In The Quality of Foods and Beverages. Vol. 1. Chemistry and Technology; Charalambous, G., Ed.; Academic Press: New York, 1981; pp 167-181.
13. Singh, D. P.; Chong, H. H.; Pitt, K. M.; Cleary, M.; Dokoozlian, N. K.; Downey, M. O. Guaiacol and 4-methylguaiacol accumulate in wines made from smoke-affected fruit because of hydrolysis of their conjugates Aust. J. Grape Wine Res. 2011, 17, S13-S21
14. Hayasaka, Y.; Dungey, K. A.; Baldock, G. A.; Kennison, K. R.; Wilkinson, K. L. Identification of a β- d -glucopyranoside precursor to guaiacol in grape juice following grapevine exposure to smoke Anal. Chim. Acta 2010, 660, 143-148
15. Hemingway, K. M.; Alston, M. J.; Chappell, C. G.; Taylor, A. J. Carbohydrate-flavour conjugates in wine Carbohydr. Polym. 1999, 38, 283-286
16. Walle, T.; Browning, A. M.; Steed, L. L.; Reed, S. G.; Walle, U. K. Flavonoid glucosides are hydrolyzed and thus activated in the oral cavity in humans J. Nutr. 2005, 135, 48-52 (Pubitemid 40094319)
17. Hayasaka, Y.; Baldock, G. A.; Pardon, K. H.; Jeffery, D. W.; Herderich, M. J. Investigation into the formation of guaiacol conjugates in berries and leaves of grapevine Vitis vinifera L. cv. Cabernet Sauvignon using stable isotope tracers combined with HPLC-MS and MS/MS analysis J. Agric. Food Chem. 2010, 58, 2076-2081
18. Pollnitz, A. P.; Pardon, K. H.; Sykes, M.; Sefton, M. A. The effects of sample preparation and gas chromatograph injection techniques on the accuracy of measuring guaiacol, 4-methylguaiacol and other volatile oak compounds in oak extracts by stable isotope dilution analyses J. Agric. Food Chem. 2004, 52, 3244-3252
19. Shao, Y.; Li, Y. L.; Zhou, B. N. Phenolic and triterpenoid glycosides from Aster batangensis Phytochemistry 1996, 41, 1593-1598
20. Sokolov, V. M.; Zakharov, V. I.; Studentsov, E. P. Stereoselectivity of reactions at the glycoside center of carbohydrates: VII. Synthesis of aryl α- and β- d -glucopyranosides by Helferich, catalyzed by boron trifluoride etherate Russ. J. Gen. Chem. 2002, 72, 806-811 (Pubitemid 37116454)
21. Kariyone, T.; Takahashi, M.; Takaishi, K. Syntheses of glucosides. I Yakugaku Zasshi 1952, 72, 13-16
22. Iland, P.; Bruer, N.; Edwards, G.; Weeks, S.; Wilkes, E. Chemical Analysis of Grapes and Wine: Techniques and Concepts; Patrick Iland Wine Promotions: Campbelltown, SA, Australia, 2004; pp 32-58.
23. ASTM E 679-04. Standard practice for determination of odor and taste thresholds by a forced-choice ascending concentration series method of limits., 2004; pp 8.
24. Martens, H.; Martens, M. Modified jack-knife estimation of parameter uncertainty in bilinear modelling by partial least squares regression (PLSR) Food Qual. Pref. 2000, 11, 5-16
25. Ferreira, V.; Lopez, R.; Cacho, J. F. Quantitative determination of the odorants of young red wines from different grape varieties J. Sci. Food Agric. 2000, 80, 1659-1667 (Pubitemid 30661135)
26. Burdock, G. A. Fenaroli's Handbook of Flavor Ingredients, 4 th ed.; CRC Press: Boca Raton, FL, 2002.
27. Czerny, M.; Christlbauer, M.; Christlbauer, M.; Fischer, A.; Granvogl, M.; Hammer, M.; Hartl, C.; Hernandez, N. M.; Schieberle, P. Re-investigation on odour thresholds of key food aroma compounds and development of an aroma language based on odour qualities of defined aqueous odorant solutions Eur. Food Res. Technol. 2008, 228, 265-273
28. Czerny, M.; Brueckner, R.; Kirchhoff, E.; Schmitt, R.; Buettner, A. The influence of molecular structure on odor qualities and odor detection thresholds of volatile alkylated phenols Chem. Senses 2011, 36, 539-553
29. Grosch, W. Evaluation of the key odorants of foods by dilution experiments, aroma models and omission Chem. Senses 2001, 26, 533-545 (Pubitemid 32600182)
30. Ferreira, V.; Juan, F. S.; Escudero, A.; Culleré, L.; Fernández-Zurbano, P.; Saenz-Navajas, M. P.; Cacho, J. Modeling quality of premium Spanish red wines from gas chromatography-olfactometry data J. Agric. Food Chem. 2009, 57, 7490-7498
31. Etiévant, P. X. Wine. In Volatile Compounds in Foods and Beverages; Maarse, H., Ed.; Dekker: New York, 1991; pp 483-546.
32. Genovese, A.; Piombino, P.; Gambuti, A.; Moio, L. Simulation of retronasal aroma of white and red wine in a model mouth system. Investigating the influence of saliva on volatile compound concentrations Food Chem. 2009, 114, 100-107
33. Buettner, A. Influence of human salivary enzymes on odorant concentration changes occurring in vivo. 1. Esters and thiols J. Agric. Food Chem. 2002, 50, 3283-3289 (Pubitemid 34533635)
34. Buettner, A. Influence of human saliva on odorant concentrations. 2. Aldehydes, alcohols, 3-alkyl-2-methoxypyrazines, methoxyphenols, and 3-hydroxy-4,5-dimethyl-2(5 H)-furanone J. Agric. Food Chem. 2002, 50, 7105-7110
35. Pogorzelski, E.; Wilkowska, A. Flavour enhancement through the enzymatic hydrolysis of glycosidic aroma precursors in juices and wine beverages: a review Flavour Fragrance J. 2007, 22, 251-254 (Pubitemid 47073199)
36. Sarry, J.-E.; Günata, Z. Plant and microbial glycoside hydrolases: volatile release from glycosidic aroma precursors Food Chem. 2004, 87, 509-521 (Pubitemid 38757562)