Smoke-derived taint in wine: The release of smoke-derived volatile phenols during fermentation of Merlot juice following grapevine exposure to smoke

Journal of Agricultural and Food Chemistry

Volumn 56, Issue 16, 2008, Pages 7379-7383

  Kennison, Kristen R ^a,b   Gibberd, Mark R ^b   Pollnitz, Alan P ^c   Wilkinson, Kerry L ^b,d  

^a DEPARTMENT OF AGRICULTURE AND FOOD WESTERN AUSTRALIA   (Australia)

^b CURTIN UNIVERSITY   (Australia)

^c AUSTRALIAN WINE RESEARCH INSTITUTE   (Australia)

^d UNIVERSITY OF ADELAIDE   (Australia)

Author keywords

Glucosidase; 4 methylguaiacol; Fermentation; Grapes; Grapevines; Guaiacol; Hydrolysis; Smoke exposure; Smoke taint; Volatile phenols; Wine

Indexed keywords

EUGENOL; GUAIACOL; PHENOL DERIVATIVE;

ARTICLE; CHEMISTRY; FERMENTATION; FRUIT; GRAPE; GROWTH, DEVELOPMENT AND AGING; HYDROLYSIS; ODOR; SMOKE; WINE;

EUGENOL; FERMENTATION; FRUIT; GUAIACOL; HYDROLYSIS; ODORS; PHENOLS; SMOKE; VITIS; WINE;

VITACEAE; VITIS;

EID: 51649084614     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf800927e     Document Type: Article

References (30)

1. Overpeck, J. T.; Rind, D.; Goldberg, R. Climate-induced changes in forest disturbance and vegetation. Nature 1990, 343, 51-53.
2. The Australian Wine Research Institute, Annual Report; Høj, P., Pretorius, I., Blair, R., Eds; The Australian Wine Research Institute: Adelaide, Australia, 2003; Vol. 3, pp 7-38.
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. Chatonnet, P.; Boidron, J. N. Dosages de phénols volatils dans les vins par chromatographie en phase gazeuse. Sci. Aliments 1992, 8, 479-488.
5. Chatonnet, P.; Dubourdieu, D. Comparative study of the characteristics of American white oak (Quercus alba) and European oak (Quercus petraea and Q. robur) for production of barrels used in barrel ageing of wines. Am. J. Enol. Vitic. 1998, 49, 79-85.
6. Boidron, J. N.; Chatonnet, P.; Pons, M. Influence du bois sur certaines substances odorantes des vins. Connaissance Vigne Vin 1988, 22, 275-294.
7. Wittkowski, R.; Ruther, J.; Drinda, H.; Rafiei-Taghanaki, F. Formation of Smoke Flavor Compounds by Thermal Lignin Degradation. In Flavour Precursors; Teranashi, R., Takeoka, G. R., Günert, M., Eds.; ACS Symposium Series 490; American Chemical Society: Washington, DC, 1992; pp 232-243.
8. Chatonnet, P.; Dubourdieu, D.; Boidron, J. N.; Pons, M. The origin of ethylphenols in wine. J. Sci. Food Agric. 1992, 60, 165-178.
9. Fiddler, W.; Doerr, R. C.; Wasserman, A. E. Composition of an ether-soluble fraction of a liquid smoke solution. J. Agric. Food Chem. 1970, 18, 310-312.
10. Kim, K.; Kurata, T.; Fujimaki, M. Identification of flavor constituents in carbonyl, non-carbonyl neutral and basic fractions of aqueous smoke condensates. Agric. Biol. Chem. 1974, 38, 53-63.
11. Baltes, W.; Wittkowski, R.; Söchtig, I.; Block, H.; Toth, L. Ingredients of Smoke and Smoke Flavour Preparations. In The Quality of Food and Beverages; Charalambous, G., Inglett, G., Eds.; Academic Press: New York, 1981; Vol. 2, pp 1-19.
12. Maga, J. A. Smoke in Food Processing; CRC Press: Boca Raton, FL, 1988.
13. Kornreich, M. R.; Issenberg, P. Determination of phenolic wood smoke components as trimethylsilyl ethers. J. Agric. Food Chem. 1972, 20, 1109-1113.
14. Sefton, M. A. Hydrolytically-released volatile secondary metabolites from a juice sample of Vitis vinifera grape cvs Merlot and Cabernet Sauvignon. Aust. J. Grape Wine Res. 1998, 4, 30-38.
15. Skouroumonis, G. K.; Sefton, M. A. Acid-catalysed hydrolysis of alcohols and their β-D-glucopyranosides. J. Agric. Food Chem. 2000, 48, 2033-2039.
16. Wirth, J.; Guo, W.; Baumes, R.; Günata, Z. Volatile compounds released by enzymatic hydrolysis of glycoconjugates of leaves and grape berries from Vitis vinifera Muscat of Alexandria and Shiraz cultivars. J. Agric. Food Chem. 2001, 49, 2917-2923.
17. Wilkinson, K. L.; Elsey, G. M.; Prager, R. H.; Tanaka, T.; Sefton, M. A. Precursors to oak lactone. Part 2: Synthesis, separation and cleavage of several β-D-glucopyranosides of 3-methyl-4-hydroxyoctanoic acid. Tetrahedron 2004, 60, 6091-6100.
18. Dixon, K. W.; Roche, S.; Pate, J. S. The promotive effect of smoke derived from burnt native vegetation on seed germination of Western Australian plants. Oecologia 1995, 101, 185-192.
19. Williams, P. J.; Cynkar, W.; Francis, I. L.; Gray, J. D.; Hand, P. G.; Coombe, B. G. Quantification of glycosides in grapes, juices, and wines through a determination of glycosyl glucose. J. Agric. Food Chem. 1995, 43, 121-128.
20. 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.
21. Pollnitz, A. P.; Pardon, K. H.; Sefton, M. A. Quantitative analysis of 4-ethylphenol and 4-ethylguaiacol in red wine. J. Chromatogr., A. 2000, 874, 101-109.
22. Pollnitz, A. P. The Analysis of Volatile Wine Components Derived from Oak Products during Winemaking and Storage. Ph.D. Thesis, The University of Adelaide, Australia, 2000.
23. Wilkinson, K. L. Oak Derived Flavour Compounds and Their Contribution to Wine and Spirits. Ph.D. Thesis, Flinders University, Australia, 2004.
24. Fujimatu, E.; Ishikawa, T.; Kitajima, J. Aromatic compound glucosides, alkyl glucoside and glucide from the fruit of anise. Phytochem. 2003, 63, 609-616.
25. Ortiz-Serrano, P.; Gil, J. V. Quantitation of free and glycosidically bound volatiles in and effect of glycosidase addition on three volatile tomato varieties (Solanum lycopersicum L.). J. Agric. Food Chem. 2007, 55, 9170-9176.
26. Ollé, D.; Baumes, R. L.; Bayonove, C. L.; Lozano, Y. F.; Sznaper, C.; Brillouet, J.-M. Comparison of free and glycosidically linked volatile components from polyembryonic and monoembryonic mango (Mangifera indica L.) cultivars. J. Agric. Food Chem. 1998, 46, 1094-1100.
27. Osorio, C.; Duque, C.; Suárez, M.; Salamanca, L. E.; Urueńa, F. Free, glycosidically bound, and phosphate bound flavor constituents of badea (Passiflora quadrangularis) fruit pulp. J. Sep. Sci. 2002, 25, 147-154.
28. Shimoda, K.; Sato, N.; Nakajima, N.; Hamada, H.; Ishihara, K.; Hamada, H. Glucosylation of phenols and phenylalkyl alcohols using cultured plant cells. Biotechnol. J. 2007, 2, 1294-1296.
29. Campbell, J. I.; Pollnitz, A. P.; Sefton, M. A.; Herderich, M. J.; Preterius, I. S. Factors affecting the influence of oak chips on wine flavour. Aust. New Zeal. Wine Ind. J. 2006, 21 (4), 38-42.
30. Skouroumounis, G. K. β-Damascenone precursors in grapes and wines. Ph.D. Thesis, The University of Adelaide, Australia, 1991.