Glycosides: Comparison
View Latest Version
Please note this is a comparison between Version 2 by Vicky Zhou and Version 1 by Andrew Caffrey.

Glycosides have been identified in almost every type of plant tissue including leaves, roots, stems, and reproductive organs (i.e., flowering and fruiting bodies). The direct role of glycosides in plants is still uncertain, but it is hypothesized that glycosides were a part of the “chemodiversity” necessary for plants to survive. The addition of sugar moieties onto hydrophobic aglycones changes the overall polarity and water solubility of the aglycone. The increased polarity of the glycoside allows for detoxification, storage, and transport within the plant.

  • glycosides
  • grapes
  • hops
  • analysis
  • aroma
  • fermentation
  • brewing
  • winemaking

1. Introduction

Through their association with aroma molecule aglycones, glycosides contribute to the aroma profile of fermented beverages such as wine and beer. Several cultivars of Vitis vinifera and Humulus lupulus have extensive glycosylation patterns that allow for the accumulation of glycosides in the plant tissues that can be released in their respective beverage products [1][2]. V. vinifera berries and H. lupulus hop cones contain their own unique glycotransferases within the VvGT and HlUGT protein families [3][4][5][6]. Glycosylation patterns and the role of glycosylated compounds on the sensory properties of beverages made with V. vinifera berries have been investigated over the last few decades, while research into H. lupulus glycosides and their effects on beer aroma and flavor is an emerging field [7][2][8]. The extent that glycosides affect wine aroma is still being investigated, but there is evidence that glycosides act as a reservoir for aroma compounds as they are hydrolyzed by enzymes or by acid-catalysis mechanisms during the fermentation and ageing process [9][10][11][12].
Grapes and hops have been found to contain several classes of volatile molecule aglycones that include: monoterpene alcohols, monoterpene polyols, norisoprenoids, sesquiterpenoids (not reported in hops), aliphatic alcohols, and volatile phenols [13][14][15][16]. A large breadth of research on aroma glycosides in plant materials has largely focused on grapes. There have been numerous studies on the impacts of external factors (i.e., growing and harvest year, ripening events, and vineyard practices) on grape glycosides [6][17][18][19][20]. For example, vineyard practices such as leaf removal as a part of canopy management have shown to increase the abundances of aroma glycosides in Riesling and Chardonnay varieties [19][20]. In addition to endogenous grape metabolites, it is also known that grapes can take in exogenous volatiles, such as volatile phenols produced during wildfires, and convert them to glycosides within the berry [21][22][23].
The extent of investigations into the glycoside composition of hop cones has focused largely on monoterpene alcohols, compounds often seen as driving factors for the aroma of several hop varieties, and norisoprenoids, such as β-damascenone [2][24][25][26]. However, less information into the development of these glycosides in hops is known, when compared to grapes, although it does appear that external factors such as soil, climate, and agricultural practices can influence glycoside abundances in hop plant materials [16]. It is possible that hops may undergo similar exogenous volatile uptake and glycosylation as grapes and other plants do, but future studies will be needed to investigate these ideas.
While there are several different aglycone classes found in grape and hops glycosides, the glycosylation pattern of glycosides follows specific patterns. In general, the first sugar bound to an aglycone by a UGT enzyme is a glucopyranose [7][4][27][28]. It was generally believed that a glucopyranose sugar was always the primary sugar bound to the aglycone; however, recent tentative identification of sesquiterpene glycosides in Muscat of Alexandria grapes and smoke taint glycosides in Cabernet Sauvignon grapes has shown that it is possible for non-glucosyl sugars to be bound directly to the aglycone [14][29]. Within the glycosylation process, up to three sugars in the glycone have been reported for grapes [18]. Although, there has not been full characterization of the glycone content of hop glycosides, evidence from hydrolysis studies suggests that hop glycosides may have one or two sugars in the glycone [2]. The potential sugars that may be found in the glycone are reported as glucopyranose, apiofuranose, xylopyranose, arabinofuranose, and rhamnopyranose sugars, in addition to malonylated glucosides [7][5][18][30][31]. The release of bound aglycones through enzyme hydrolysis is largely dependent on the sugars present in the glycoside, since specific enzymes are needed to cleave off each terminal sugar before the aglycone is released [7][30][31][32]. Some of these enzymes may not be present during winemaking or brewing, leaving glycosides with specific sugars intact [33][34]. Further discussion of these hydrolysis reactions in winemaking and brewing is included below.

2. Glycosides during Winemaking and Brewing

Both winemaking and brewing processes have several production steps that may influence the glycosidic profile in the finished beverage. Within this section, winemaking and brewing processes are discussed in separate sections with emphasis on the process itself in regard to glycosides. Microbial considerations for the winemaking and brewing sections are limited to Saccharomyces yeast as they are used for the majority of wine and beer fermentations. The production of wine and beer products with non-Saccharomyces microbes has been organized into its own section due to the large scope of yeast and bacteria that can be introduced into grape juice or wort systems. Outlines of winemaking and brewing processes with respect to glycoside hydrolysis may be found in Table 1.

Table 1.

Hydrolytic outline of the winemaking process and the brewing process.

Winemaking Stage Primary Hydrolysis References
Destemming and crushing Endogenous grape enzymes [31][35][36][37][38][39]
Fermentation—Saccharomyces Exogenous yeast enzymes [29][30][31][32][40][41][42][43][44][45][46][47][48][49][50]
Fermentation—non-Saccharomyces yeast and/or mixed fermentations Exogenous yeast enzymes [51][52][53][54][55]
Malolactic fermentation Exogenous bacterial enzymes [52][53][56][57][58][59][60][61][62][63][64][65][66]
Racking, bottling, and storage Spontaneous Acid Hydrolysis [34][67][68]
Brewing Stage Primary Hydrolysis References
Mashing N/A N/A
Lautering and sparging N/A N/A
Boiling and whirlpool Acid [2][26]
Fermentation—Saccharomyces Exogenous yeast enzymes [51][69][70]
Fermentation—non-Saccharomyces yeast and/or mixed fermentations Exogenous yeast or bacterial enzymes [51][54]
Dry hopping and hop creep Exogenous hops enzymes [71][72]
Storage Spontaneous Acid Hydrolysis [25]

3. Conclusions

Glycosylated aroma molecules are common metabolites found in the plant families Vitis vinifera and Humulus lupulus. The glycosylated molecules are of increasing interest due to their connection with free volatile molecules in wine and beer. Comparatively, there is a rich history of knowledge concerning the presence of glycosides and their respective aromas in grapes and wine, while the field of research is starting to develop for hops and beer. A large focus of winemaking has shown that microbial activity during the fermentation process is a key event in the hydrolysis of glycosides. Although much work has shown that microbial activity can trigger the hydrolytic release of glycosides from wine, there is still more work needed to understand how to control the process. Brewing is a complex process that offers several opportunities for hydrolysis such as the boiling and fermentation stages; however, the impact of glycosides from hops is frequently brought into question due to their low abundances. The development of liquid chromatography mass spectrometry methods has allowed for more in-depth and faster analysis of intact glycosides in both plant materials and fermented beverages when compared to traditional hydrolysis methods. More development is still needed for these methods as it can be difficult to distinguish isomeric aroma glycosides from one another through mass spectrometric methods alone.

References

  1. Mateo, J.J.; Jiménez, M. Monoterpenes in Grape Juice and Wines. J. Chromatogr. A 2000, 881, 557–567.
  2. Sharp, D.C.; Vollmer, D.M.; Qian, Y.P.; Shellhammer, T.H. Examination of Glycoside Hydrolysis Methods for the Determination of Terpenyl Glycoside Contents of Different Hop Cultivars. J. Am. Soc. Brew. Chem. 2017, 75, 101–108.
  3. Bönisch, F.; Frotscher, J.; Stanitzek, S.; Rühl, E.; Wüst, M.; Bitz, O.; Schwab, W. Activity-Based Profiling of a Physiologic Aglycone Library Reveals Sugar Acceptor Promiscuity of Family 1 UDP-Glucosyltransferases from Grape. Plant Physiol. 2014, 166, 23–29.
  4. Ono, E.; Tsuruoka, N. Monoterpene Glycosyltransferases Originating from Hop and Method for Using Same. US Patent 9,574,182 B2, 21 February 2017.
  5. Bönisch, F.; Frotscher, J.; Stanitzek, S.; Rühl, E.; Wüst, M.; Bitz, O.; Schwab, W. A UDP-Glucose:Monoterpenol Glucosyltransferase Adds to the Chemical Diversity of the Grapevine Metabolome. Plant Physiol. 2014, 165, 561–581.
  6. Li, X.Y.; Wen, Y.Q.; Meng, N.; Qian, X.; Pan, Q.H. Monoterpenyl Glycosyltransferases Differentially Contribute to Production of Monoterpenyl Glycosides in Two Aromatic Vitis vinifera Varieties. Front. Plant Sci. 2017, 8, 1–13.
  7. Winterhalter, P.; Skouroumounis, G.K. Glycoconjugated Aroma Compounds: Occurrence, Role and Biotechnological Transformation. In Biotechnology of Aroma Compounds; Springer: Berlin, Germany, 1997; Volume 55, pp. 78–81.
  8. Cibaka, M.L.K.; Ferreira, C.S.; Decourrière, L.; Lorenzo-Alonso, C.J.; Bodart, E.; Collin, S. Dry Hopping with the Dual-Purpose Varieties Amarillo, Citra, Hallertau Blanc, Mosaic, and Sorachi Ace: Minor Contribution of Hop Terpenol Glucosides to Beer Flavors. J. Am. Soc. Brew. Chem. 2017, 75, 122–129.
  9. Ristic, R.; Van Der Hulst, L.; Capone, D.L.; Wilkinson, K.L. Impact of Bottle Aging on Smoke-Tainted Wines from Different Grape Cultivars. J. Agric. Food Chem. 2017, 65, 4146–4152.
  10. Zoecklein, B.W.; Hackney, C.H.; Duncan, S.E.; Marcy, J.E. Effect of Fermentation, Aging and Thermal Storage on Total Glycosides, Phenol-Free Glycosides and Volatile Compounds of White Riesling (Vitis vinifera L.) Wines. J. Ind. Microbiol. Biotechnol. 1999, 22, 100–107.
  11. Loscos, N.; Hernández-Orte, P.; Cacho, J.; Ferreira, V. Evolution of the Aroma Composition of Wines Supplemented with Grape Flavour Precursors from Different Varietals during Accelerated Wine Ageing. Food Chem. 2010, 120, 205–216.
  12. Gunata, Y.Z.; Bayonove, C.L.; Baumes, R.L.; Cordonnier, R.E. Stability of Free and Bound Fractions of Some Aroma Components of Grapes Cv. Muscat during the Wine Processing: Preliminary Results. Am. J. Enol. Vitic. 1986, 37, 112–114.
  13. Ilc, T.; Werck-Reichhart, D.; Navrot, N. Meta-Analysis of the Core Aroma Components of Grape and Wine Aroma. Front. Plant Sci. 2016, 7, 1472.
  14. Caffrey, A.J.; Lerno, L.A.; Zweigenbaum, J.; Ebeler, S.E. Direct Analysis of Glycosidic Aroma Precursors Containing Multiple Aglycone Classes in Vitis vinifera Berries. J. Agric. Food Chem. 2020, 68, 3817–3833.
  15. Goldsein, H.; Ting, P.; Navarro, A.; Ryder, D. Water-Solluble Hop Flavor Precursors and Their Role in Beer Flavor. Proc. Congr. Brew. Conv. 1999, 27, 53–62.
  16. Morcol, T.B.; Negrin, A.; Matthews, P.D.; Kennelly, E.J. Hop (Humulus lupulus L.) Terroir Has Large Effect on a Glycosylated Green Leaf Volatile but Not on Other Aroma Glycosides. Food Chem. 2020, 321, 126644.
  17. Godshaw, J.; Hjelmeland, A.K.; Zweigenbaum, J.; Ebeler, S.E. Changes in Glycosylation Patterns of Monoterpenes during Grape Berry Maturation in Six Cultivars of Vitis vinifera. Food Chem. 2019, 297, 124921.
  18. Hjelmeland, A.K.; Zweigenbaum, J.; Ebeler, S.E. Profiling Monoterpenol Glycoconjugation in Vitis vinifera L. Cv. Muscat of Alexandria Using a Novel Putative Compound Database Approach, High Resolution Mass Spectrometry and Collision Induced Dissociation Fragmentation Analysis. Anal. Chim. Acta 2015, 887, 138–147.
  19. Zoecklein, B.W.; Wolf, T.K.; Duncan, S.E.; Marcy, J.E.; Jasinski, Y. Effect of Fruit Zone Leaf Removal on Total Glycoconjugates and Conjugate Fraction Concentration of Riesling and Chardonnay (Vitis vinifera L.) Grapes. Am. J. Enol. Vitic. 1998, 49, 259–265.
  20. Zoecklein, B.W.; Wolf, T.K.; Marcy, J.E.; Jasinski, Y. Effect of Fruit Zone Leaf Thinning on Total Glycosides and Selected Aglycone Concentrations of Riesling (Vitis vinifera L.) Grapes. Am. J. Enol. Vitic. 1998, 49, 35–43.
  21. 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.
  22. Landmann, C.; Fink, B.; Schwab, W. FaGT2: A Multifunctional Enzyme from Strawberry (Fragaria x Ananassa) Fruits Involved in the Metabolism of Natural and Xenobiotic Compounds. Planta 2007, 226, 417–428.
  23. Härtl, K.; Huang, F.C.; Giri, A.P.; Franz-Oberdorf, K.; Frotscher, J.; Shao, Y.; Hoffmann, T.; Schwab, W. Glucosylation of Smoke-Derived Volatiles in Grapevine (Vitis vinifera) Is Catalyzed by a Promiscuous Resveratrol/Guaiacol Glucosyltransferase. J. Agric. Food Chem. 2017, 65, 5681–5689.
  24. Takoi, K.; Itoga, Y.; Takayanagi, J.; Kosugi, T.; Shioi, T.; Nakamura, T.; Watari, J. Screening of Geraniol-Rich Flavor Hop and Interesting Behavior of β-Citronellol during Fermentation under Various Hop-Addition Timings. J. Am. Soc. Brew. Chem. 2014, 72, 22–29.
  25. Chevance, F.; Guyot-Declerck, C.; Dupont, J.; Collin, S. Investigation of the β-Damascenone Level in Fresh and Aged Commercial Beers. J. Agric. Food Chem. 2002, 50, 3818–3821.
  26. Kishimoto, T.; Wanikawa, A.; Kagami, N.; Kawatsura, K. Analysis of Hop-Derived Terpenoids in Beer and Evaluation of Their Behavior Using the Stir Bar-Sorptive Extraction Method with GC-MS. J. Agric. Food Chem. 2005, 53, 4701–4707.
  27. Takoi, K.; Itoga, Y.; Takayanagi, J.; Matsumoto, I.; Nakayama, Y. Control of Hop Aroma Impression of Beer with Blend-Hopping Using Geraniol-Rich Hop and New Hypothesis of Synergy among Hop-Derived Flavour Compounds. Brew. Sci. 2016, 69, 85–93.
  28. Takoi, K.; Koie, K.; Itoga, Y.; Katayama, Y.; Shimase, M.; Nakayama, Y.; Watari, J. Biotransformation of Hop-Derived Monoterpene Alcohols by Lager Yeast and Their Contribution to the Flavor of Hopped Beer. J. Agric. Food Chem. 2010, 58, 5050–5058.
  29. Caffrey, A.; Lerno, L.; Rumbaugh, A.; Girardello, R.; Zweigenbaum, J.; Oberholster, A.; Ebeler, S.E. Changes in Smoke-Taint Volatile-Phenol Glycosides in Wildfire Smoke-Exposed Cabernet Sauvignon Grapes throughout Winemaking. Am. J. Enol. Vitic. 2019, 70, 373–381.
  30. Gunata, Z.; Bitteur, S.; Brillouet, J.M.; Bayonove, C.; Cordonnier, R. Sequential Enzymic Hydrolysis of Potentially Aromatic Glycosides from Grape. Carbohydr. Res. 1988, 184, 139–149.
  31. Sarry, J.E.; Günata, Z. Plant and Microbial Glycoside Hydrolases: Volatile Release from Glycosidic Aroma Precursors. Food Chem. 2004, 87, 509–521.
  32. Brito-Arias, M. Synthesis and Characterization of Glycosides; Springer: New York, NY, USA, 2007.
  33. Delcroix, A.; Günata, Z.; Sapis, J.-C.; Salmon, J.-M.; Bayonove, C. Glycosidase Activities of Three Enological Yeast Strains during Winemaking: Effect on the Terpenol Content of Muscat Wine. Am. J. Enol. Vitic. 1994, 45, 291–296.
  34. Maicas, S.; Mateo, J.J. Hydrolysis of Terpenyl Glycosides in Grape Juice and Other Fruit Juices: A Review. Appl. Microbiol. Biotechnol. 2005, 67, 322–335.
  35. Aryan, A.R.; Wilson, B.; Strauss, C.R.; Williams, P.J. The Properties of Glycosidases of Vitis vinifera and a Comparison of Their Beta-Glycosidase Activity with That of Exogenous Enzymes. An Assessment of Possible Applications in Enology. Am. J. Enol. Vitic. 1987, 38, 182–188.
  36. Bayonove, C.; Gunata, Y.Z.; Cordonnier, R.E. Evidence of the Intervention of Enzymes in the Development of Muscat Flavor in Juice Prior to Fermentation. Bull. l’Organization Int. Vigne 1984, 57, 741–758.
  37. Günata, Y.; Biron, C.; Sapis, J.; Bayonove, C. Glycosidase Activities in Sound and Rotten Grapes in Relation to Hydrolysis of Grape Monoterpenyl Glycosides. VITIS-J. Grapevine Res. 1989, 28, 191–197.
  38. Gomez-Plaza, E.; Romero-Cascales, I.; Bautista-Ortin, A.B. Enzymes in Fruit and Vegetable Processing: Chemistry and Engineering Applications. In Enzymes in Fruit and Vegetable Processing: Chemistry and Engineering Applications; CRC: Boca Raton, FL, USA, 2010; pp. 225–227.
  39. Havkin-Frenkel, D.; Belanger, F.C. Biotechnology in Flavor Production; Publishing Ltd.: Oxford, UK, 2009.
  40. Mateo, J.J.; Di Stefano, R. Description of the β-Glucosidase Activity of Wine Yeasts. Food Microbiol. 1997, 14, 583–591.
  41. Fernández-González, M.; Di Stefano, R.; Briones, A. Hydrolysis and Transformation of Terpene Glycosides from Muscat Must by Different Yeast Species. Food Microbiol. 2003, 20, 35–41.
  42. Zea, L.; Moreno, J.; Ortega, J.M.; Medina, M. Content of Free Terpenic Compounds in Cells and Musts during Vinification with Three Saccharomyces cerevisiae Races. J. Agric. Food Chem. 1995, 43, 1110–1114.
  43. Bisotto, A.; Julien, A.; Rigou, P.; Schneider, R.; Salmon, J.M. Evaluation of the Inherent Capacity of Commercial Yeast Strains to Release Glycosidic Aroma Precursors from Muscat Grape Must. Aust. J. Grape Wine Res. 2015, 21, 194–199.
  44. Ganss, S.; Kirsch, F.; Winterhalter, P.; Fischer, U.; Schmarr, H.G. Aroma Changes Due to Second Fermentation and Glycosylated Precursors in Chardonnay and Riesling Sparkling Wines. J. Agric. Food Chem. 2011, 59, 2524–2533.
  45. Bell, S.J.; Henschke, P.A. Implications of Nitrogen Nutrition for Grapes, Fermentation and Wine. Aust. J. Grape Wine Res. 2005, 11, 242–295.
  46. Rosi, I.; Vinella, M.; Domizio, P. Characterization of b-glucosidase Activity in Yeasts of Oenological Origin. J. Appl. Bacteriol. 1994, 77, 519–527.
  47. Darriet, P.; Boidron, J.-N.; Dubourdieu, D. L’hydrolyse Des Hétérosides Terpéniques Du Muscat a Petits Grains Par Les Enzymes Périplasmiques de Saccharomyces cerevisiae. OENO One 1988, 22, 189–195.
  48. Noestheden, M.; Dennis, E.G.; Romero-Montalvo, E.; DiLabio, G.A.; Zandberg, W.F. Detailed Characterization of Glycosylated Sensory-Active Volatile Phenols in Smoke-Exposed Grapes and Wine. Food Chem. 2018, 259, 147–156.
  49. Ristic, R.; Osidacz, P.; Pinchbeck, K.A.; Hayasaka, Y.; Fudge, A.L.; Wilkinson, K.L. The Effect of Winemaking Techniques on the Intensity of Smoke Taint in Wine. Aust. J. Grape Wine Res. 2011, 17, S29–S40.
  50. Fia, G.; Giovani, G.; Rosi, I. Study of β-Glucosidase Production by Wine-Related Yeasts during Alcoholic Fermentation. A New Rapid Fluorimetric Method to Determine Enzymatic Activity. J. Appl. Microbiol. 2005, 99, 509–517.
  51. Daenen, L.; Saison, D.; Sterckx, F.; Delvaux, F.R.; Verachtert, H.; Derdelinckx, G. Screening and Evaluation of the Glucoside Hydrolase Activity in Saccharomyces and Brettanomyces Brewing Yeasts. J. Appl. Microbiol. 2008, 104, 478–488.
  52. McMahon, H.; Zoecklein, B.W.; Fugelsang, K.; Jasinski, Y. Quantification of Glycosidase Activities in Selected Yeasts and Lactic Acid Bacteria. J. Ind. Microbiol. Biotechnol. 1999, 23, 198–203.
  53. Mansfield, A.K.; Zoecklein, B.W.; Whiton, R.S. Quantification of Glycosidase Activity in Selected Strains of Brettanomyces bruxellensis and Oenococcus oeni. Am. J. Enol. Vitic. 2002, 53, 303–307.
  54. Daenen, L.; Sterckx, F.; Delvaux, F.R.; Verachtert, H.; Derdelinckx, G. Evaluation of the Glycoside Hydrolase Activity of a Brettanomyces Strain on Glycosides from Sour Cherry (Prunus cerasus L.) Used in the Production of Special Fruit Beers. FEMS Yeast Res. 2008, 8, 1103–1114.
  55. Maturano, Y.P.; Assaf, L.A.R.; Toro, M.E.; Nally, M.C.; Vallejo, M.; de Figueroa, L.I.C.; Combina, M.; Vazquez, F. Multi-Enzyme Production by Pure and Mixed Cultures of Saccharomyces and Non-Saccharomyces Yeasts during Wine Fermentation. Int. J. Food Microbiol. 2012.
  56. Pérez-Martín, F.; Seseña, S.; Izquierdo, P.M.; Martín, R.; Palop, M.L. Screening for Glycosidase Activities of Lactic Acid Bacteria as a Biotechnological Tool in Oenology. World J. Microbiol. Biotechnol. 2012, 28, 1423–1432.
  57. Ugliano, M.; Moio, L. The Influence of Malolactic Fermentation and Oenococcus oeni Strain on Glycosidic Aroma Precursors and Related Volatile Compounds of Red Wine. J. Sci. Food Agric. 2006, 86, 2468–2476.
  58. Boido, E.; Lloret, A.; Medina, K.; Carrau, F.; Dellacassa, E. Effect of β-Glycosidase Activity of Oenococcus oeni on the Glycosylated Flavor Precursors of Tannat Wine during Malolactic Fermentation. J. Agric. Food Chem. 2002, 50, 2344–2349.
  59. D’Incecco, N.; Bartowsky, E.; Kassara, S.; Lante, A.; Spettoli, P.; Henschke, P. Release of Glycosidically Bound Flavour Compounds of Chardonnay by Oenococcus oeni during Malolactic Fermentation. Food Microbiol. 2004, 21, 257–265.
  60. Michlmayr, H.; Nauer, S.; Brandes, W.; Schümann, C.; Kulbe, K.D.; Del Hierro, A.M.; Eder, R. Release of Wine Monoterpenes from Natural Precursors by Glycosidases from Oenococcus oeni. Food Chem. 2012, 135, 80–87.
  61. Grimaldi, A.; McLean, H.; Jiranek, V. Identification and Partial Characterization of Glycosidic Activities of Commercial Strains of the Lactic Acid Bacterium, Oenococcus oeni. Am. J. Enol. Vitic. 2000, 51, 362–369.
  62. Grimaldi, A.; Bartowsky, E.; Jiranek, V. A Survey of Glycosidase Activities of Commercial Wine Strains of Oenococcus oeni. Int. J. Food Microbiol. 2005, 105, 233–244.
  63. Ugliano, M.; Genovese, A.; Moio, L. Hydrolysis of Wine Aroma Precursors during Malolactic Fermentation with Four Commercial Starter Cultures of Oenococcus oeni. J. Agric. Food Chem. 2003, 51, 5073–5078.
  64. Pérez-Martín, F.; Izquierdo-Cañas, P.M.; Seseña, S.; García-Romero, E.; Palop, M.L. Aromatic Compounds Released from Natural Precursors by Selected Oenococcus oeni Strains during Malolactic Fermentation. Eur. Food Res. Technol. 2014, 240, 609–618.
  65. Rodríguez, M.E.; Lopes, C.A.; Barbagelata, R.J.; Barda, N.B.; Caballero, A.C. Influence of Candida pulcherrima Patagonian Strain on Alcoholic Fermentation Behaviour and Wine Aroma. Int. J. Food Microbiol. 2010, 138, 19–25.
  66. Zoecklein, B.W.; Marcy, J.E.; Williams, J.M.; Jasinski, Y. Effect of Native Yeasts and Selected Strains of Saccharomyces cerevisiae on Glycosyl Glucose, Potential Volatile Terpenes, and Selected Aglycones of White Riesling (Vitis vinifera L.) Wines. J. Food Compos. Anal. 1997, 10, 55–65.
  67. Skouroumounis, G.K.; Sefton, M.A. Acid-Catalyzed Hydrolysis of Alcohols and Their β-D-Glucopyranosides. J. Agric. Food Chem. 2000, 48, 2033–2039.
  68. Williams, P.J.; Strauss, C.R.; Wilson, B.; Massy-Westropp, R.A. Studies on the Hydrolysis of Vitis vinifera Monoterpene Precursor Compounds and Model Monoterpene β-D-Glucosides Rationalizing the Monoterpene Composition of Grapes. J. Agric. Food Chem. 1982, 30, 1219–1223.
  69. Sharp, D.C.; Steensels, J.; Shellhammer, T.H. The Effect of Hopping Regime, Cultivar and β-Glucosidase Activity on Monoterpene Alcohol Concentrations in Wort and Beer. J. Inst. Brew. 2017, 123, 185–191.
  70. Kanauchi, M.; Bamforth, C.W. β-Glucoside Hydrolyzing Enzymes from Ale and Lager Strains of Brewing Yeast. J. Am. Soc. Brew. Chem. 2012, 70, 303–307.
  71. Kirkpatrick, K.R.; Shellhammer, T.H. A Cultivar-Based Screening of Hops for Dextrin Degrading Enzymatic Potential. J. Am. Soc. Brew. Chem. 2018, 76, 247–256.
  72. Kirkpatrick, K.R.; Shellhammer, T.H. Evidence of Dextrin Hydrolyzing Enzymes in Cascade Hops (Humulus lupulus). J. Agric. Food Chem. 2018, 66, 9121–9126.
More
© Text is available under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/)
ScholarVision Creations
Feedback