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The glycosidic aroma precursors in wine: occurrence, characterization and potential biological applications

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Abstract

Wine aroma is defined as the cumulative effect of smell, taste and mouth-feel. Free and glycosidically bound aroma compounds (GBAC) were found in wine. The glycosidic aroma precursors are non-odorous. Most advances have been made in free aroma compounds from wine in recent decades. However, the glycosidically bound aroma compounds have received much less consideration than free aroma compounds. Acids and enzymes are responsible for transferring these glycosidic aroma precursors to aromatic compounds. This review provides an overview of recent developments in isolation, hydrolysis and characterization for glycosidic aroma precursors in wines, as well as their biological applications. It looks like that the GBAC had important biological applications, such as, genetic engineering, immobilization, aroma enhancement and biosynthesis. It will help to better understand the GBAC and free aroma compounds of wines.

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Abbreviations

CCC:

Counter-current chromatography

FTIR:

Fourier transform infrared spectroscopy

GBAC:

Glycosidically bound aroma compounds

GC–FID:

Gas chromatography-flame ionization detector

GC–MS:

Gas chromatography-mass spectrometer

HPLC:

High performance liquid chromatography

HRGC:

High resolution gas chromatography

LC:

Liquid chromatography

MLF:

Malolactic fermentation

NMR:

Nuclear magnetic resonance

RP:

Reversed phase

SEC:

Size-exclusion chromatography

References

  • Baek HH, Cadwallader KR (1999) Contribution of free and glycosidically bound volatile compounds to the aroma of muscadine grape juice. J Food Sci 64(3):441–444

    Article  CAS  Google Scholar 

  • Bartowsky DJ, Henschke PA, Hoj PB, Pretorius IS (2004) Chasing wine aroma-Dose Oenococcus oeni have the potential to release aroma compounds from authentic grape precursors? Wine Ind J 19(2):24–31

    Google Scholar 

  • Bisotto A, Julien A, Rigou P, Schneider R, Salmon JM (2015) Evaluation of the inherent capacity of commercial yeast strains to release glycosidic aroma precursors from Muscat grape must. Aust J Gr Wine Res 21(2):194–199

    Article  CAS  Google Scholar 

  • Bothlho G, Paulino C, Mendes-Fala A, Climaco MC (2007) A method to analyse bound aroma compounds in non-aromatic red grape juices. Cienc Tec Vitiv 22:21–26

    Google Scholar 

  • Colagrande O, Silva A, Fumi MD (1994) Recent application of biotechnology in wine production-review. Biotechnol Progr 10:2–18

    Article  CAS  Google Scholar 

  • D’Ambrosio M, Harghel P, Guantieri V, D’Ambrosio M, Harghel P, Guantieri V (2014) Isolation of intact glycosidic aroma precursors from grape juice by hydrophilic interaction liquid chromatography. Aust J Grape Wine Res 19(1):189–192

    Google Scholar 

  • D’Incecco N, Bartowsky E, Kassara S (2004) Release of glycosidically bound flavour compounds of chardonnay by oenococcus oeni during malolactic fermentation. Food Microbiol 21(3):257–265

    Article  Google Scholar 

  • Gil JV, Manzanares P, Genovés S, Vallés S, González-Candelas L (2005) Over-production of the major exoglucanase of Saccharomyces cereviside leads to an increase in the aroma of wine. Int J Food Microbiol 103(1):57–68

    Article  CAS  PubMed  Google Scholar 

  • González-Barreiro C, Rial-Otero R, Cancho-Grande B, Simal-Gándara J (2015) Wine aroma compounds in grapes: a critical review. Crit Rev Food Sci 55(2):202–218

    Article  Google Scholar 

  • Gunata Z, Dugelay I, Sapis JC, Baumes R, Bayonove C (1993) Role of the enzymes in the use of the flavour potential from grape glycosides in winemaking. In: Schreier P, Winterhalter P (eds) Progress in flavour precursor studies. Alured, Carol Stream, pp 219–234

    Google Scholar 

  • Hampel D, Robinson AL, Johnson AJ, Ebeler SE (2014a) Direct hydrolysis and analysis of glycosidically bound aroma compounds in grapes and wines: comparison of hydrolysis conditions and sample preparation methods. Aust J Gr Wine Res 20(3):361–377

    Article  CAS  Google Scholar 

  • Hampel D, Robinson AL, Johnson AJ, Ebeler SE (2014b) Direct hydrolysis and analysis of glycosidically bound aroma compounds in grapes and wines: comparison of hydrolysis conditions and sample preparation methods. Aust J Gr Wine R 20(3):361–377

    Article  CAS  Google Scholar 

  • Hayasaka Y, Dungey KA, Baldock GA, Kennison KR, Wilkinson KL (2010) Identification of a β-d-glucopyranoside precursor to guaiacol in grape juice following grapevine exposure to smoke. Anal Chim Acta 660(1–2):143–148

    Article  CAS  PubMed  Google Scholar 

  • Hjelmeland AK, Ebeler SE (2014) Glycosidically bound volatile aroma compounds in grapes and wine: a review. Am J Enol Viticult 66:1–11

    Article  Google Scholar 

  • Ikemoto T, Okabe BI, Mimura K, Kitahara T (2002) Formation of fragrant materials from odourless glycosidically-bound volatiles on skin microflora (part 1). Flavour Fragr J 17(6):452–455

    Article  CAS  Google Scholar 

  • Lasanta C, Caro I, Pérez L (2009) β-Glucosidase immobilization on ion exchange resins for using as aromatic enhancement of wines. Chem En Trans 17:1–6

    Google Scholar 

  • López S, Mateo JJ, Maicas S (2014) Characterisation of Hanseniaspora isolates with potential aroma-enhancing properties in muscat wines. S Afr J Enol Vitic 35:292–303

    Google Scholar 

  • Manzanares P, Gil JV, Orejas M, Graaff LH, Visser J, Graaff LH (2003) Construction of a genetically modified wine yeast strain expressing the Aspergillus aculeatus rhaA gene, encoding an α-l-rhamnosidase of enological interest. Appl Environ Microbiol 69(12):7558–7562

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Muñoz-González C, Sémon E, Martín-Álvarez PJ, Guichard E, Moreno-Arribas MV, Feron G, Pozo-Bayón MÁ (2015) Wine matrix composition affects temporal aroma release as measured by proton transfer reaction- time-of-flight- mass spectrometry. Aust J Gr Wine Res 21(3):367–375

    Article  Google Scholar 

  • Oliveira JM, Oliveira P, Baumes RL, Maia MO (2008) Volatile and glycosidically bound composition of “loureiro” and “alvarinho” wines. Food Sci Technol Int 14(4):341–353

    Article  CAS  Google Scholar 

  • Ono E, Homma Y, Horikawa M, Kunikane-Doi S, Imai H, Takahashi S, Kawai Y, Ishiguro M, Fukui Y, Nakayama T (2010) Functional differentiation of the glycosyl transferases that contribute to the chemical diversity of bioactive flavonol glycosides in grapevines (vitis vinifera). Plant Cell 22(8):2856–2871

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Palmeri R, Spagna G (2007) β-Glucosidase in cellular and acellular form for winemaking application. Enzyme Microb Technol 40:382–389

    Article  CAS  Google Scholar 

  • Palomo ES, Pérez-Coello MS, Díaz-Maroto MC, Viñas MAG, Cabezudo MD (2006) Contribution of free and glycosidically-bound volatile compounds to the aroma of muscat “a petit grains” wines and effect of skin contact. Food Chem 95(2):279–289

    Article  CAS  Google Scholar 

  • Pedroza MA, Zalacain A, Lara JF, Salinas MR (2010) Global grape aroma potential and its individual analysis by SBSE-GC-MS. Food Res Int 43(4):1003–1008

    Article  CAS  Google Scholar 

  • Perestrelo R, Caldeira M, Câmara JS (2012) Solid phase microextraction as a reliable alternative to conventional extraction techniques to evaluate the pattern of hydrolytically released components in vitis vinifera, l. grapes. Talanta 95(12):1–11

    Article  CAS  PubMed  Google Scholar 

  • Polásková P, Herszage J, Ebeler SE (2008) Wine flavor: chemistry in a glass. Chem Soc Rev 37(11):2478–2489

    Article  PubMed  Google Scholar 

  • Querol A, Ramon D (1996) The application of molecular techniques in wine microbiology. Trends Food Sci Technol 7(3):73–78

    Article  CAS  Google Scholar 

  • Rusjan D (2010) Aromas in grape and wine. In: Delrot S, Medrano H, Or E, Bavaresco L, Grando S (eds) Methodologies and results in grapevine research. Springer, Berlin

    Google Scholar 

  • Sánchezpalomo E, Alonsovillegas R, González Viñas MA (2015) Characterisation of free and glycosidically bound aroma compounds of la mancha verdejo white wines. Food Chem 173(173):1195–1202

    Article  Google Scholar 

  • Sasaki K, Takase H, Tanzawa F, Kobayashi H, Saito H, Matsuo H, Takata R (2015) Identification of furaneol glucopyranoside, the precursor of strawberry-like aroma, furaneol, in Muscat Bailey A. Am J Enol Viticult 66(1):91–94

    Article  CAS  Google Scholar 

  • Schievano E, D’Ambrosio M, Mazzaretto I, Ferrarini R, Magno F, Mammi S, Favaro G (2013) Identification of wine aroma precursors in Moscato Giallo grape juice: a nuclear magnetic resonance and liquid chromatography-mass spectrometry tandem study. Talanta 116(22):841–851

    Article  CAS  PubMed  Google Scholar 

  • Schneider R, Charrier F, Moutounet M, Baumes R (2004) Rapid analysis of grape aroma glycoconjugates using fourier-transform infrared spectrometry and chemometric techniques. Anal Chim Acta 513(1):91–96

    Article  CAS  Google Scholar 

  • Sefton MA, Francis IL, Williams PJ (1993) The volatile composition of chardonnay juices: a study by flavor precursor analysis. Am J Enol Viticult 44(4):359–370

    CAS  Google Scholar 

  • Williams PJ, Sefton MA, Wilson B (1989) Nonvolatile conjugates of secondary metabolites as precursors of varietal grape flavour components. In: Teranishi R, Buttery RG, Shahide R (eds) Flavour chemistry, trends and developments, ACS symposium series N0 388, pp 35–48. American Chemical Society, Washington, DC

  • Williams PJ, Cynkar W, Francis IL, Gray JD, Iland PG, Coombe BG (1995) Quantification of glycosides in grapes, juices, and wines through a determination of glycosyl glucose. J Agric Food Chem 43(1):121–128

    Article  CAS  Google Scholar 

  • Winterhalter P, Skouroumounis GK (1997) Glycoconjugated aroma compounds: occurrence, role and biotechnological transformation. In: Sheper T (ed) Advances in biochemical engineering/biotechnology. Springer, Berlin, pp 74–99

    Google Scholar 

  • Wirth J, Guo W, Baumes R, Günata Z (2001) 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(6):2917–2923

    Article  CAS  PubMed  Google Scholar 

  • Zhu FM, Du B, Li J (2014) Aroma enhancement and enzymolysis regulation of grape wine using β-glycosidase. Food Sci Nutr 2(2):139–145

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Zhu FM, Du B, Li J (2016) Aroma compounds in wine, in name (1st), grape and wine biotechnology. In: Morata A (ed) InTech. ISBN: 978-953-51-2692-8

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Acknowledgements

This research was supported by National Natural Science Foundation of China (Project code: 31470542 and 31570374) and Natural Science Foundation of Hebei Province, P.R. China (Project code: C2014407059 and 2015407059).

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Authors and Affiliations

  1. College of Food Science and Technology, Hebei Normal University of Science and Technology, Qinhuangdao, 066600, People’s Republic of China

    Fengmei Zhu, Yange Ma & Jun Li

  2. Analysis and Testing Center, Hebei Normal University of Science and Technology, Qinhuangdao, 066600, People’s Republic of China

    Bin Du

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  1. Fengmei Zhu
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Correspondence to Jun Li.

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Zhu, F., Du, B., Ma, Y. et al. The glycosidic aroma precursors in wine: occurrence, characterization and potential biological applications. Phytochem Rev 16, 565–571 (2017). https://doi.org/10.1007/s11101-016-9487-8

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  • DOI: https://doi.org/10.1007/s11101-016-9487-8

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