Identification of a β-d-glucopyranoside precursor to guaiacol in grape juice following grapevine exposure to smoke

Analytica Chimica Acta

Volumn 660, Issue 1-2, 2010, Pages 143-148

  Hayasaka, Y ^a   Dungey, K A ^b   Baldock, G A ^a   Kennison, K R ^c   Wilkinson, K L ^b  

^a AUSTRALIAN WINE RESEARCH INSTITUTE   (Australia)

^b UNIVERSITY OF ADELAIDE   (Australia)

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

Author keywords

Grapes; Guaiacol; Guaiacol d glucopyranoside; HPLC MS MS; Smoke; Wine

Indexed keywords

ACID TREATMENTS; ENZYME HYDROLYSIS; ENZYME TREATMENT; GLUCOPYRANOSIDE; GLUCOSIDASE; GLUCOSYLATION; GRAPE JUICE; GUAIACOL; HPLC-MS/MS; JUICE EXTRACTS; REFERENCE COMPOUNDS;

ALCOHOLS; ENZYMES; FRUIT JUICES; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SMOKE; SMOKE ABATEMENT; WINE;

FRUITS;

GLUCOPYRANOSIDE; GLUCOSIDE; GUAIACOL;

ARTICLE; CARBOHYDRATE SYNTHESIS; CHEMICAL COMPOSITION; CHEMICAL REACTION KINETICS; CONTROLLED STUDY; FERMENTATION; FOOD ANALYSIS; GLYCOSYLATION; GRAPE JUICE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; LONG TERM EXPOSURE; PRECURSOR; PRIORITY JOURNAL; SMOKE; TANDEM MASS SPECTROMETRY; VINEYARD;

BETA-GLUCOSIDASE; BEVERAGES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; GLUCOSIDES; GUAIACOL; HYDROLYSIS; SMOKE; TANDEM MASS SPECTROMETRY; VITIS;

VITACEAE; VITIS;

EID: 74849113617     PISSN: 00032670     EISSN: 18734324     Source Type: Journal    
DOI: 10.1016/j.aca.2009.10.039     Document Type: Article

References (19)

1. Cordonnier R., and Bayonove C. Demonstration in Alexandria Muscat grape variety of bound monoterpenes using one or more enzymes of the fruit. C. R. Acad. Sci. 278 (1974) 3387-3390
2. Williams P.J., Strauss C.R., Wilson B., and Massy-Westropp R.A. Novel monoterpene disaccharide glycosides of Vitis vinifera grapes and wine. Phytochemistry 21 (1982) 2013-2020
3. Gunata Y.Z., Bayonove C.L., Baumes R.L., and Cordonnier R.E. The aroma of grapes. I. Extraction and determination of free and glycosidically bound fractions of some grape aroma components. J. Chromatogr. 331 (1985) 83-90
4. Wirth J., Guo W., Baumes R., and 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. 49 (2001) 2917-2923
5. Gunata Y.Z., Bayonove C.L., Tapiero C., and Cordonnier R.E. Hydrolysis of grape monoterpenyl β-D-glucosides by various β-glucosidases. J. Agric. Food Chem. 38 (1990) 1232-1236
6. Hernandez-Orte P., Cerosimo M., Loscos N., Cacho J., Garcia-Moruno E., and Ferreira V. The development of varietal aroma from non-floral grapes by yeast of different genera. Food Chem. 107 (2008) 1064-1077
7. 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. 4 (1998) 30-38
8. Skouroumonis G.K., and Sefton M.A. Acid-catalysed hydrolysis of alcohols and their β-D-glucopyranosides. J. Agric. Food Chem. 48 (2000) 2033-2039
9. Williams P.J., Cynkar W., Francis I.L., Gray J.D., Iland P.G., and Coombe B.G. Quantification of glycosides in grapes, juices, and wines through a determination of glycosyl glucose. J. Agric. Food Chem. 43 (1995) 121-128
10. Kennison K.R., Gibberd M.R., Pollnitz A.P., and 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. 56 (2008) 7379-7383
11. Chatonnet P., and Boidron J.N. Dosages de phénols volatils dans les vins par chromatographie en phase gazeuse. Sci. Aliments 8 (1992) 479-488
12. Chatonnet P., Dubourdieu D., Boidron J.N., and Pons M. The origin of ethylphenols in wine. J. Sci. Food Agric. 60 (1992) 165-178
13. Fiddler W., Doerr R.C., and Wasserman A.E. Composition of an ether-soluble fraction of a liquid smoke solution. J. Agric. Food Chem. 18 (1970) 310-312
14. Wittkowski R., Ruther J., Drinda H., and Rafiei-Taghanaki F. Formation of Smoke Flavor Compounds by Thermal Lignin Degradation. In: Teranashi R., Takeoka G.R., and Günert M. (Eds). Flavour Precursors ACS Symposium Series 490. Washington (1992) 232-243
15. Kennison K.R., Wilkinson K.L., Williams H.G., Smith J.H., and 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. 55 (2007) 10897-10901
16. Wilkinson K.L., Elsey G.M., Prager R.H., Tanaka T., and 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 60 (2004) 6091-6100
17. Kunz H., and Harreus A. Glycoside synthesis using 2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide. Liebigs Ann. Chem. 1 (1982) 41-48
18. Pollnitz A.P., Pardon K.H., Sykes M., and 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. 52 (2004) 3244-3252
19. Kennison K.R., Wilkinson K.L., Pollnitz A.P., Williams H.G., and Gibberd M.R. Effect of timing and duration of grapevine exposure to smoke on the composition and sensory properties of wine. Aust. J. Grape Wine Res. 15 (2009) 228-237