Direct hydrolysis and analysis of glycosidically bound aroma compounds in grapes and wines: Comparison of hydrolysis conditions and sample preparation methods

Australian Journal of Grape and Wine Research

Volumn 20, Issue 3, 2014, Pages 361-377

  Hampel, D ^a   Robinson, A L ^a,b   Johnson, A J ^a   Ebeler, Susan E ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b Department of Nutrition University of California ^*  (Australia)

Author keywords

Aroma release; Glycosides; Grape; Headspace solid phase microextraction (HS SPME); Rapidase AR 2000; Wine

Indexed keywords

VITACEAE;

EID: 84908092951     PISSN: 13227130     EISSN: 17550238     Source Type: Journal    
DOI: 10.1111/ajgw.12087     Document Type: Article

References (64)

1. Allen, D., Bui, A.D., Cain, N., Rose, G. and Downey, M. (2013) Analysis of free and bound phenolics in wine and grapes by GC-MS after automated SPE. Analytical and Bioanalytical Chemistry 405, 9869-9877.
2. Arthur, C.L. and Pawliszyn, J. (1990) Solid phase microextraction with thermal desorption using fused silica optical fibers. Analytical Chemistry 62, 2145-2148.
3. Aryan, A.P., Wilson, B., Strauss, C.R. and Williams, P.J. (1987) The properties of glycosidases of Vitis vinifera and a comparison of their betaglucosidase activity with that of exogenous enzymes. An assessment of possible applications in enology. American Journal of Enology and Viticulture 38, 182-188.
4. Baek, H.H. and Cadwallader, K.R. (1999) Contribution of free and glycosidically bound volatile compounds to the aroma of muscadine grape juice. Journal of Food Science 64, 441-444.
5. Boulton, R.B., Singleton, V.L., Bisson, L.F. and Kunkee, R.E. (1996) Principles and practices of winemaking (Chapman & Hall: New York, NY, USA).
6. Boutou, S. and Chatonnet, P. (2007) Rapid headspace solid-phase microextraction/gas chromatographic/mass spectrometric assay for the quantitative determination of some of the main odorants causing offflavours in wine. Journal of Chromatography. A 1141, 1-9.
7. Buttery, R.G., Takeoka, G., Teranishi, R. and Ling, L.C. (1990) Tomato aroma components: identification of glycoside hydrolysis volatiles. Journal of Agricutural and Food Chemistry 38, 2050-2053.
8. Canuti, V., Conversano, M., Li Calzi, M., Heymann, H., Matthews, M.A. and Ebeler, S.E. (2009) Headspace solid-phase microextraction-gas chromatography-mass spectrometry for profiling free volatile compounds in Cabernet Sauvignon grapes and wines. Journal of Chromatography. A 1216, 3012-3022.
9. Doneva-Šapčeska, D., Dimitrovski, A., Bojadžiev, T., Milanov, G. and Vojnovski, B. (2006) Free and potentially volatile monoterpenes in grape varieties from the Republic of Macedonia. Bulletin of the Chemists and Technologists of Macedonia 25, 51-56.
10. Dungey, K.A., Hayasaka, Y. and Wilkinson, K.L. (2011) Quantitative analysis of glycoconjugate precursors of guaiacol in smoke-affected grapes using liquid chromatography tandem mass spectrometry based stable isotope dilution analysis. Food Chemistry 126, 801-806.
11. Dziadas, M. and Jelen, H.H. (2010) Analysis of terpenes in white wines using SPE-SPME-GC/MS approach. Analytic Chimica Acta 677, 43-49.
12. Francis, I.L., Tate, M.E. and Williams, P.J. (1996) The effect of hydrolysis conditions on the aroma released from Semillon grape glycosides. Australian Journal of Grape and Wine Research 2, 70-76.
13. Ganss, S., Kirsch, F., Winterhalter, P., Fischer, U. and Schmarr, H.-G. (2011) Aroma changes due to second fermentation and glycosylated precursors in Chardonnay and Riesling sparkling wines. Journal of Agricultural and Food Chemistry 59, 2524-2533.
14. Gil, J.V. and Valles, S. (2001) Effect of macerating enzymes on red wine aroma at laboratory scale: exogenous addition or expression by transgenic wine yeasts. Journal of Agricultural and Food Chemistry 49, 5515-5523.
15. Günata, Y.Z., Bayonove, C.L., Baumes, R.L. and Cordonnier, R.E. (1985) The aroma of grapes. I. Extraction and determination of free and glycosidically bound fractions of some grape aroma components. Journal of Chromatography. A 331, 83-90.
16. Günata, Z., Bitteur, S., Brillouet, J.-M., Bayonove, C. and Cordonnier, R. (1988) Sequential enzymic hydrolysis of potentially aromatic glycosides from grape. Carbohydrate Research 184, 139-149.
17. Hayasaka, Y., Baldock, G.A., Parker, M., Pardon, K.H., Black, C.A., Herderich, M.J. and Jeffery, D.W. (2010) Glycosylation of smoke-derived volatile phenols in grapes as a consequence of grapevine exposure to bushfire smoke. Journal of Agricultural and Food Chemistry 58, 10989-10998.
18. Herraiz, T. and Ough, C.S. (1993) Formation of ethyl esters of amino acids by yeasts during the alcoholic fermentation of grape juice. American Journal of Enology and Viticulture 44, 41-48.
19. Ibarz, M.J., Ferreira, V., Hernández-Orte, P., Loscos, N. and Cacho, J. (2006) Optimization and evaluation of a procedure for the gas chromatographicmass spectrometric analysis of the aromas generated by fast acid hydrolysis of flavor precursors extracted from grapes. Journal of Chromatography. A 1116, 217-229.
20. Iland, P.G., Cynkar,W., Francis, I.L.,Williams, P.J. and Coombe, B.G. (1996) Optimisation of methods for the determination of total and red-free glycosyl glucose in black grape berries of Vitis vinifera. Australian Journal of Grape and Wine Research 2, 171-178.
21. Jia, M., Zhang, Q.H. and Min, D.B. (1998) Optimization of solid-phase microextraction analysis for headspace flavor compounds of orange juice. Journal of Agricultural and Food Chemistry 46, 2744-2747.
22. Kalua, C.M. and Boss, P.K. (2009) Evolution of volatile compounds during the development of Cabernet Sauvignon grapes (Vitis vinifera L.). Journal of Agricultural and Food Chemistry 57, 3818-3830.
23. Kang, W., Xu, Y., Qin, L. and Wang, Y. (2010) Effects of different β-Dglycosidases on bound aroma compounds in Muscat grape determined by HS-SPME and GC-MS. Journal of the Institute of Brewing 116, 70-77.
24. Loscos, N., Hernandez-Orte, P., Cacho, J. and Ferreira, V. (2007) Release and formation of varietal aroma compounds during alcoholic fermentation from nonfloral grape odorless flavor precursors fractions. Journal of Agricultural and Food Chemistry 55, 6674-6684.
25. Loscos, N., Hernández-Orte, P., Cacho, J. and Ferreira, V. (2009) Comparison of the suitability of different hydrolytic strategies to predict aroma potential of different grape varieties. Journal of Agricultural and Food Chemistry 57, 2468-2480.
26. Loscos, N., Hernandez-Orte, P., Cacho, J. and Ferreira, V. (2010) Evolution of the aroma composition of wines supplemented with grape precursors from different varietals during accelerated wine ageing. Food Chemistry 120, 205-2016.
27. Lourens, K. and Pellerin, P. (2004) Enzymes in winemaking. Wynboer (November), 94-97.
28. Luan, F., Hampel, D., Mosandl, A. and Wüst, M. (2004) Enantioselective analysis of free and glycosidically bound monoterpene polyols in Vitis vinifera L. cvs. Morio Muscat and Muscat Ottonel: evidence for an oxidative monoterpene metabolism in grapes. Journal of Agricultural and Food Chemistry 52, 2036-2041.
29. Maicas, S. and Mateo, J.J. (2005) Hydrolysis of terpenyl glycosides in grape juice and other fruit juices: a review. Applied Microbiology and Biotechnology 67, 322-335.
30. Mateo, J.J. and Jiménez, M. (2000) Monoterpenes in grape juice and wines. Journal of Chromatography. A 881, 557-567.
31. Mathieu, S., Terrier, N., Procureur, J., Bigey, F. and Günata, Z. (2005) A carotenoid cleavage dioxygenase from Vitis vinifera L.: functional characterization and expression during grape berry development in relation to C13-norisoprenoid accumulation. Journal of Experimental Botany 56, 2721-2731.
32. Nakanishi, T., Konishi, M., Murata, H., Inada, A., Fujii, A., Tanaka, N. and Fujiwara, T. (1990) The structures of two new ionone glucosides from Melia toosendan and a novel type of selective bio-oxidation. Chemical and Pharmaceutical Bulletin 38, 830-832.
33. Nishimura, K., Ohnishi, M., Masuda, M., Koga, K. and Matsuyama, R. (1983) Reactions of wood components during maturation. Piggott, J.R., ed. Flavour of distilled beverages: origin and development (Ellis Horwood: Chichester, England) pp. 89-145.
34. Pedroza, M.A., Zalacain, A., Lara, J.F. and Salinas, M.R. (2010) Global grape aroma potential and its individual anaysis by SBSE-GC-MS. Food Research International 43, 1003-1008.
35. Polaskova, P., Herszage, J. and Ebeler, S.E. (2008) Wine flavor: chemistry in a glass. Chemical Society Reviews 37, 2478-2489.
36. Rapp, A. (1988) Wine aroma substances from gas chromatographic analysis. Linskens, H.-F. and Jackson, J.F., eds. Wine analysis. Modern methods of plant analysis, Vol. 6 (Springer-Verlag: Berlin, Germany) pp. 29-66.
37. Ravid, U., Elkabetz, M., Zamir, C., Cohen, K., Larkov, O. and Aly, R. (2010) Authenticity assessment of natural fruit flavour compounds in foods and beverages by auto-HS-SPME stereoselective GC-MS. Flavour and Fragrance Journal 25, 20-27.
38. Riou, C., Salmon, J.M., Vallier, M.J., Günata, Z. and Barre, P. (1998) Purification, characterization, and substrate specificity of a novel highly glucose-tolerant beta-glucosidase from Aspergillus oryzae. Applied and Environmental Microbiology 64, 3607-3614.
39. Riu-Aumatell, M., Castellari, M., López-Tamames, E., Galassi, S. and Buxaderas, S. (2004) Characterisation of volatile compounds of fruit juices and nectars by HS/SPME and GC/MS. Food Chemistry 87, 627-637.
40. Robinson, A.L., Ebeler, S.E., Heymann, H., Boss, P.K., Solomon, P.S. and Trengove, R.D. (2009) Interactions between wine volatile compounds and grape and wine matrix components influence aroma compound headspace partitioning. Journal of Agricultural and Food Chemistry 57, 10313-10322.
41. Rocha, S., Ramalheira, V., Barros, A., Delgadillo, I. and Coimbra, M.A. (2001) Headspace solid phase microextraction (SPME) analysis of flavor compounds in wines. Effect of the matrix volatile composition in the relative response factors in a wine model. Journal of Agricultural and Food Chemistry 49, 5142-5151.
42. Rodríguez-Bencomo, J.J., Selli, S., Muñoz-González, C., Martín-álvarez, P.J. and Pozo-Bayón, M.A. (2013) Application of glycosidic aroma precursors to enhance the aroma and sensory profile of dealcoholised wine. Food Research International 51, 450-457.
43. Sánchez Palomo, E., Díaz-Maroto Hidalgo, M.C., González-Viñas, M.á. and Pérez-Coello, M.S. (2005) Aroma enhancement in wines from different grape varieties using exogenous glycosidases. Food Chemistry 92, 627-635.
44. Sarry, J.-E. and Günata, Z. (2004) Plant and microbial glycoside hydrolases: volatile release from glycosidic aroma precursors. Food Chemistry 87, 509-521.
45. Schneider, R., Razungles, A., Augier, C. and Baumes, R. (2001) Monoterpenic and norisoprenoidic glycoconjugates of Vitis vinifera L. cv. Melon B. as precursors of odorants in Muscadet wines. Journal of Chromatography. A 936, 145-157.
46. Schneider, R., Charrier, F., Moutounet, M. and Baumes, R. (2004) Rapid analysis of grape aroma glycoconjugates using Fourier-transform infrared spectrometry and chemometric techniques. Analytica Chimica Acta 513, 91-96.
47. Schreier, P., Drawert, F. and Junker, A. (1976) Identification of volatile constituents from grapes. Journal of Agricultural and Food Chemistry 24, 331-336.
48. Schwab, W. and Schreier, P. (1988) Simultaneous enzyme catalysis extraction: a versatile technique for the study of flavor precursors. Journal of Agricultural and Food Chemistry 36, 1238-1242.
49. Sefton, M.A. and Williams, P.J. (1991) Generation of oxidation artifacts during the hydrolysis of norisoprenoid glycosides by fungal enzyme preparations. Journal of Agricultural and Food Chemistry 39, 1994-1997.
50. Sefton, M.A., Skouroumounis, G.K., Massy-Westropp, R.A. and Williams, P.J. (1989) Norisoprenoids in Vitis vinifera white wine grapes and the identification of a precursor of damascenone in these fruits. Australian Journal of Chemistry 42, 2071-2084.
51. Sefton, M.A., Francis, I.L. andWilliams, P.J. (1993) The volatile composition of Chardonnay juices: a study by flavor precursor analysis. American Journal of Enology and Viticulture 44, 359-370.
52. Sefton, M.A., Skouroumounis, G.K., Elsey, G.M. and Taylor, D.K. (2011) Occurrence, sensory impact, formation, and fate of damascenone in grapes, wines, and other foods and beverages. Journal of Agricultural and Food Chemistry 59, 9717-9746.
53. Setkova, L., Risticevic, S. and Pawliszyn, J. (2007) Rapid headspace solidphase microextraction-gas chromatographic-time-of-flight mass spectrometric method for qualitative profiling of ice wine volatile fraction: II: Classification of Canadian and Czech ice wines using statistical evaluation of the data. Journal of Chromatography. A 1147, 224-240.
54. Steffen, A. and Pawliszyn, J. (1996) Analysis of flavor volatiles using headspace solid-phase microextraction. Journal of Agricultural and Food Chemistry 44, 2187-2193.
55. Teranishi, R., Takeoka, G. and Güntert, M. (1992) Flavor precursors: thermal and enzymatic conversions. ACS Symposium Series No. 490 (American Chemical Society: Washington, DC, USA).
56. Torrens, J., Riu-Aumatell, M., López-Tamames, E. and Buxaderas, S. (2004) Volatile compounds of red and white wines by headspace-solid-phase microextraction using different fibers. Journal of Chromatographic Science 42, 310-316.
57. Varming, C., Andersen, M.L. and Poll, L. (2006) Volatile monoterpenes in black currant (Ribes nigrum L.) juice: effects of heating and enzymatic treatment by β-glucosidase. Journal of Agricultural and Food Chemistry 54, 2298-2302.
58. Voirin, S.G., Baumes, R.L., Bitteur, S.M., Günata, Z.Y. and Bayonove, C.L. (1990) Novel monoterpene disaccharide glycosides of Vitis vinifera grapes. Journal of Agricultural and Food Chemistry 38, 1373-1378.
59. Wang, Y., Zhang, C., Li, J. and Xu, Y. (2013) Different influences of β-glucosidases on volatile compounds and anthocyanins of Cabernet Gernischt and possible reason. Food Chemistry 140, 245-254.
60. Williams, P., Cynkar, W., Francis, I., Gray, J., Iland, P. and Coombe, B. (1995) Quantification of glycosides in grapes, juices, and wines through a determination of glycosyl glucose. Journal of Agricultural and Food Chemistry 43, 121-128.
61. Williams, P.J., Strauss, C.R., Wilson, B. and Massy-Westropp, R.A. (1982a) Use of C18 reversed-phase liquid chromatography for the isolation of monoterpene glycosides and nor-isoprenoid precursors from grape juice and wines. Journal of Chromatography. A 235, 471-480.
62. Williams, P.J., Strauss, C.R., Wilson, B. and Massy-Westropp, R.A. (1982b) Novel monoterpene disaccharide glycosides of Vitis vinifera grapes and wines. Phytochemistry 21, 2013-2020.
63. Williams, P.J., Sefton, M.A. and Wilson, B. (1989) Nonvolatile conjugates of secondary metabolites as precursors of varietal grape flavor components. Teranishi, R., Buttery, R.G. and Shahidi, F., eds. Flavor chemistry: trends and developments. ACS Symposium Series No. 388 (American Chemical Society: Washington, DC, USA) pp. 35-48.
64. Ximenes, E., Kim, Y., Mosier, N., Dien, B. and Ladisch, M. (2010) Inhibition of cellulases by phenols. Enzyme and Microbial Technology 46, 170-176.