Determination of the importance of in-mouth release of volatile phenol glycoconjugates to the flavor of smoke-tainted wines

Journal of Agricultural and Food Chemistry

Volumn 62, Issue 11, 2014, Pages 2327-2336

  Mayr, Christine M ^a   Parker, Mango ^a   Baldock, Gayle A ^a   Black, Cory A ^a   Pardon, Kevin H ^a   Williamson, Patricia O ^a   Herderich, Markus J ^a   Francis, I Leigh ^a  

^a AUSTRALIAN WINE RESEARCH INSTITUTE   (Australia)

Author keywords

bushfire; flavor reconstitution; glycosides; in mouth release; PLS; sensory descriptive analysis; smoke taint; volatile phenols; wine

Indexed keywords

EXPERIMENTS; GLYCOSIDES; PHENOLS; SUGARS; WINE; CARBOHYDRATES; SENSORY ANALYSIS; SMOKE;

BUSHFIRE; IN-MOUTH RELEASE; PLS; SENSORY DESCRIPTIVE ANALYSIS; SMOKE TAINTS; VOLATILE PHENOLS;

SMOKE; FLAVOR COMPOUNDS;

ALCOHOL; PHENOL;

ADULT; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; FEMALE; HUMAN; MALE; METABOLISM; MIDDLE AGED; MOUTH; PH; SMOKE; TASTE; VITIS; VOLATILIZATION; WINE;

ADULT; ETHANOL; FEMALE; HUMANS; HYDROGEN-ION CONCENTRATION; MALE; MIDDLE AGED; MOLECULAR STRUCTURE; MOUTH; PHENOL; SMOKE; TASTE; VITIS; VOLATILIZATION; WINE;

EID: 84896541239     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf405327s     Document Type: Article

References (17)

1. Høj, P.; Pretorius, I. S.; Blair, R. The Australian Wine Research Institute, Annual Report, 2003, p 37.
2. Prida, A.; Chatonnet, P. Impact of Oak-Derived Compounds on the Olfactory Perception of Barrel-Aged Wines Am. J. Enol. Vitic. 2010, 3, 408-413
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. Parker, M.; Osidacz, P.; Baldock, G.; Hayasaka, Y.; Black, C.; Pardon, K. H.; Jeffery, D. W.; Geue, J. P.; Herderich, M. J.; Francis, I. L. Contribution of Several Volatile Phenols and Their Glycoconjugates to Smoke-Related Sensory Properties of Red Wine J. Agric. Food Chem. 2012, 60, 2629-2637
5. 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
6. 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
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, 10989-10998
8. Hayasaka, Y.; Dungey, K. A.; Baldock, G. A.; Kennison, K. R.; Wilkinson, K. L. Identification of a Beta- d -Glucopyranoside Precursor to Guaiacol in Grape Juice Following Grapevine Exposure to Smoke Anal. Chim. Acta 2010, 660, 143-148
9. 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
10. 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
11. Aihara, K.; Urano, Y.; Higuchi, T.; Hirobe, M. Mechanistic Studies of Selective Catechol Formation from o -Methoxyphenols Using a Copper (II)-Ascorbic Acid-Dioxygen System J. Chem. Soc., Perkin Trans. 2 1993, 2165-2170
12. Hayasaka, Y.; Parker, M.; Baldock, G. A.; Pardon, K. H.; Black, C. A.; Jeffery, D. W.; Herderich, M. J. Assessing the Impact of Smoke Exposure in Grapes: Development and Validation of a HPLC-MS/MS Method for the Quantitative Analysis of Smoke-Derived Phenolic Glycosides in Grapes and Wine J. Agric. Food Chem. 2013, 61, 25-33
13. Zhong, F.-Y.; Zhou, J.-H. 6-Acetoxymethyl-2-(2-Methoxyphenoxy) tetrahydropyran-3,4,5-Triyl Triacetate Acta Crystallogr. 2005, E61, o2701-o2703
14. Dungey, K. A.; Hayasaka, Y.; Wilkinson, K. L. Quantitative Analysis of Glycoconjugate Precursors of Guaiacol in Smoke-Affected Grapes Using Liquid Chromatography-Tandem Mass Spectrometry Based Stable Isotope Dilution Analysis Food Chem. 2011, 126, 801-806
15. Buettner, A. Investigation of Potent Odorants and Afterodor Development in Two Chardonnay Wines Using the Buccal Odor Screening System (BOSS) J. Agric. Food Chem. 2004, 52, 2339-2346
16. Buettner, A.; Otto, S.; Beer, A.; Mestres, M.; Schieberle, P.; Hummel, T. Dynamics of Retronasal Aroma Perception During Consumption: Cross-Linking On-Line Breath Analysis with Medico-Analytical Tools to Elucidate a Complex Process Food Chem. 2008, 108, 1234-1246
17. Hemingway, K. M.; Alston, M. J.; Chappell, C. G.; Taylor, A. J. Carbohydrate-Flavor Conjugates in Wine Carbohydr. Polym. 1999, 38, 283-286