Synthesis of fruity ethyl esters by acyl coenzyme A: Alcohol acyltransferase and reverse esterase activities in Oenococcus oeni and Lactobacillus plantarum

Journal of Applied Microbiology

Volumn 114, Issue 3, 2013, Pages 797-806

  Costello, P J ^a   Siebert, T E ^a   Solomon, M R ^a   Bartowsky, E J ^a  

^a AUSTRALIAN WINE RESEARCH INSTITUTE   (Australia)

Author keywords

Alcohol acyltransferase; Ester biosynthesis; Esterase; Lactobacillus plantarum; Malolactic fermentation; Oenococcus oeni

Indexed keywords

BACILLI; BIOCHEMISTRY; COENZYMES; DEUTERIUM; FERMENTATION; LABORATORIES; LACTIC ACID; STRAIN; WINE;

ACYL-COENZYMES; ALCOHOL ACYLTRANSFERASE; COENZYME A; ESTER BIOSYNTHESIS; ESTERASE; ETHYL ESTERS; LACTIC ACID BACTERIA; LACTOBACILLUS PLANTARUM; MALOLACTIC FERMENTATION; OENOCOCCUS OENI;

ESTERS;

ACYL COENZYME A; ACYL COENZYME A ALCOHOL ACYLTRANSFERASE; ALCOHOL; BUTYRIC ACID; ESTERASE; FATTY ACID ESTER; HEXANOIC ACID; OCTANOIC ACID; PROPANOL; REVERSE ESTERASE; UNCLASSIFIED DRUG;

BACTERIUM; BREWING INDUSTRY; ENZYME ACTIVITY; ESTER; FATTY ACID; FERMENTATION;

ANAEROBIC GROWTH; ARTICLE; BACTERIAL GROWTH; BACTERIAL STRAIN; BIOSYNTHESIS; CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME SYNTHESIS; FLAVOR; LACTOBACILLUS PLANTARUM; MASS FRAGMENTOGRAPHY; NONHUMAN; OENOCOCCUS OENI; ORGANOLEPTIC PROPERTY; PH; PRECURSOR; SCREENING; WINE;

LACTOBACILLUS PLANTARUM; OENOCOCCUS OENI;

EID: 84873987389     PISSN: 13645072     EISSN: 13652672     Source Type: Journal    
DOI: 10.1111/jam.12098     Document Type: Article

References (43)

1. Abeijón-Mukdsi, M.C., Medina, R.B., Alvarez, M.D. and Gonzalez, S.N. (2009) Ester synthesis by lactic acid bacteria isolated from goat's and ewe's milk and cheeses. Food Chem 117, 241-247.
2. Abrahamse, C.E. and Bartowsky, E.J. (2012) Timing of malolactic fermentation inoculation in Shiraz grape must and wine: influence on chemical composition. World J Microb Biot 28, 255-265.
3. Bradford, M.M. (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72, 248-254.
4. Costantini, A., García-Moruno, E. and Moreno-Arribas, M.V. (2009) Biochemical transformations produced by malolactic fermentation. In Wine Chemistry and Biochemistry ed. Moreno-Arribas, M.V. and Polo, M.C. pp. 27-57. New York: Springer Science+Business Media.
5. Costello, P.J., Francis, I.L. and Bartowsky, E. (2012) Variations in the effect of malolactic fermentation on the chemical and sensory properties of Cabernet Sauvignon wine: interactive influences of Oenococcus oeni strain and wine matrix composition. Aust J Grape Wine R 18, 287-301.
6. Cristiani, G. and Monnet, V. (2001) Food micro-organisms and aromatic ester synthesis. Sci Aliments 21, 211-230.
7. Davis, C.R., Wibowo, D., Fleet, G.H. and Lee, T.H. (1988) Properties of wine lactic acid bacteria: their potential enological significance. Am J Enol Viticult 39, 137-142.
8. D'Incecco, N., Bartowsky, E., Kassara, S., Lante, A., Spettolli, P. and Henschke, P. (2004) Release of glycosidically bound flavour compounds of Chardonnay by Oenococcus oeni during malolactic fermentation. Food Microbiol 21, 257-265.
9. Dols-Lafargue, M., Gindreau, E., Le Marrec, C., Chambat, G., Heyraud, A. and Lonvaud-Funel, A. (2007) Changes in red wine soluble polysaccharide composition induced by malolactic fermentation. J Agric Food Chem 55, 9592-9599.
10. Dufour, J.P., Malcorps, P. and Silcock, P. (2003) Control of ester synthesis during brewery fermentation. In Brewing Yeast Fermentation Performance ed. Smart, K. pp. 213-233. Oxford: Blackwell Science.
11. Escudero, A., Campo, E., Farina, L., Cacho, J. and Ferreira, V. (2007) Analytical characterization of the aroma of five premium red wines. Insights into the role of odor families and the concept of fruitiness of wines. J Agric Food Chem 55, 4501-4510.
12. Gámbaro, A., Boido, E., Zlotejablko, A., Medina, K., Lloret, A., Dellacassa, E. and Carrau, F. (2001) Effect of malolactic fermentation on the aroma properties of Tannat wine. Aust J Grape Wine R 7, 27-32.
13. Guilloux-Benatier, M., Pageault, O., Man, A. and Feuillat, M. (2000) Lysis of yeast cells by Oenococcus oeni enzymes. J Ind Microbiol Biot 25, 193-197.
14. Henick-Kling, T. (1993) Malolactic fermentation. In Wine Microbiology and Biotechnology ed. Fleet, G.H. pp. 289-326. Chur, Switzerland: Harwood Academic Publishers.
15. Holland, R., Liu, S.Q., Crow, V.L., Delabre, M.L., Lubbers, M., Bennett, M. and Norris, G. (2005) Esterases of lactic acid bacteria and cheese flavour: milk fat hydrolysis, alcoholysis and esterification. Int Dairy J 15, 711-718.
16. Hosono, A. and Elliott, J.A. (1974) Properties of crude ethylester-forming enzyme preparations from some lactic acid and psychrotrophic bacteria. J Dairy Sci 57, 1432-1437.
17. Hosono, A., Elliott, J.A. and McGugan, W.A. (1974) Production of ethylesters by some lactic acid and psychrotrophic bacteria. J Dairy Sci 57, 535-539.
18. Knoll, C., du Toit, M., Schnell, S., Rauhut, D. and Irmler, S. (2011a) Cloning and characterisation of a cystathionine beta/gamma-lyase from two Oenococcus oeni oenological strains. Appl Microbiol Biot 89, 1051-1060.
19. Knoll, C., Fritsch, S., Schnell, S., Grossmann, M., Rauhut, D. and du Toit, M. (2011b) Influence of pH and ethanol on malolactic fermentation and volatile aroma compound composition in white wines. LWT-Food Sci Technol 44, 2077-2086.
20. Knoll, C., Fritsch, S., Schnell, S., Grossmann, M., Krieger-Weber, S., du Toit, M. and Rauhut, D. (2012) Impact of different malolactic fermentation inoculation scenarios on Riesling wine aroma. World J Microb Biot 28, 1143-1153.
21. Liu, S.Q., Holland, R. and Crow, V.L. (1998) Ethyl butanoate formation by dairy lactic acid bacteria. Int Dairy J 8, 651-657.
22. Liu, S.Q., Holland, R. and Crow, V.L. (2003) Ester synthesis in an aqueous environment by Streptococcus thermophilus and other dairy lactic acid bacteria. Appl Microbiol Biotechnol 63, 81-88.
23. Liu, S.Q., Baker, K., Bennett, M., Holland, R., Norris, G. and Crow, V.L. (2004a) Characterisation of esterases of Streptococcus thermophilus ST1 and Lactococcus lactis subsp. cremoris B1079 as alcohol acyltransferases. Int Dairy J 14, 865-870.
24. Liu, S.Q., Holland, R. and Crow, V.L. (2004b) Esters and their biosynthesis in fermented dairy products: a review. Int Dairy J 14, 923-945.
25. López, R., López-Alfaro, I., Gutiérrez, A.R., Tenorio, C., Garijo, P., González-Arenzana, L. and Santamaría, P. (2011) Malolactic fermentation of Tempranillo wine: contribution of the lactic acid bacteria inoculation to sensory quality and chemical composition. Int J Food Sci Technol 46, 2373-2381.
26. Malherbe, S., Tredoux, A.G.J., Nieuwoudt, H.H. and du Toit, M. (2012) Comparative metabolic profiling to investigate the contribution of O. oeni MLF starter cultures to red wine composition. J Ind Microbiol Biot 39, 477-494.
27. Matthews, A., Grbin, P.R. and Jiranek, V. (2006) A survey of lactic acid bacteria for enzymes of interest to oenology. Aust J Grape Wine R 12, 235-244.
28. Matthews, A., Grbin, P.R. and Jiranek, V. (2007) Biochemical characterisation of the esterase activities of wine lactic acid bacteria. Appl Microbiol Biot 77, 329-337.
29. Nardi, M., Fiez-Vandal, C., Tailliez, P. and Monnet, V. (2002) The EstA esterase is responsible for the main capacity of Lactococcus lactis to synthesize short chain fatty acid esters in vitro. J Appl Microbiol 93, 994-1002.
30. Pineau, B., Barbe, J.C., Van Leeuwen, C. and Dubourdieu, D. (2009) Examples of perceptive interactions involved in specific "Red-" and "Black-berry" aromas in red wines. J Agric Food Chem 57, 3702-3708.
31. du Plessis, H.W., Steger, C.L.C., du Toit, M. and Lambrechts, M.G. (2002) The occurrence of malolactic fermentation in brandy base wine and its influence on brandy quality. J Appl Microbiol 92, 1005-1013.
32. Pripis-Nicolau, L., de Revel, G., Bertrand, A. and Lonvaud-Funel, A. (2004) Methionine catabolism and production of volatile sulphur compounds by Oenococcus oeni. J Appl Microbiol 96, 1176-1184.
33. Saerens, S.M.G., Verstrepen, K.J., Van Laere, S.D.M., Voet, A.R.D., Van Dijck, P., Delvaux, F.R. and Thevelein, J.M. (2006) The Saccharomyces cerevisiae EHT1 and EEB1 genes encode novel enzymes with medium-chain fatty acid ethyl ester synthesis and hydrolysis capacity. J Biol Chem 281, 4446-4456.
34. Saerens, S.M.G., Delvaux, F., Verstrepen, K.J., Van Dijck, P., Thevelein, J.M. and Delvaux, F.R. (2008) Parameters affecting ethyl ester production by Saccharomyces cerevisiae during fermentation. Appl Environ Microbiol 74, 454-461.
35. Saerens, S.M.G., Delvaux, F.R., Verstrepen, K.J. and Thevelein, J.M. (2010) Production and biological function of volatile esters in Saccharomyces cerevisiae. Microb Biotechnol 3, 165-177.
36. Siebert, T.E., Smyth, H.E., Capone, D.L., Neuwohner, C., Pardon, K.H., Skouroumounis, G.K., Herderich, M., Sefton, M.A. etal. (2005) Stable isotope dilution analysis of wine fermentation products by HS-SPME-GC-MS. Anal Bioanal Chem 381, 937-947.
37. Sumby, K.M., Matthews, A.H., Grbin, P.R. and Jiranek, V. (2009) Cloning and characterization of an intracellular esterase from the wine-associated lactic acid bacterium Oenococcus oeni. Appl Environ Microbiol 75, 6729-6735.
38. Sumby, K.M., Grbin, P.R. and Jiranek, V. (2010) Microbial modulation of aromatic esters in wine: current knowledge and future prospects. Food Chem 121, 1-16.
39. Swiegers, J.H., Bartowsky, E.J., Henschke, P.A. and Pretorius, I.S. (2005) Yeast and bacterial modulation of wine aroma and flavour. Aust J Grape Wine R 11, 139-173.
40. Versari, A., Parpinello, G.P. and Cattaneo, M. (1999) Leuconostoc oenos and malolactic fermentation in wine: a review. J Ind Microbiol Biot 23, 447-455.
41. Verstrepen, K.J., Derdelinckx, G., Dufour, J.P., Winderickx, J., Thevelein, J.M., Pretorius, I.S. and Delvaux, F.R. (2003) Flavor-active esters: adding fruitiness to beer. J Biosci Bioeng 96, 110-118.
42. Wibowo, D., Eschenbruch, R., Davis, C.R., Fleet, G.H. and Lee, T.H. (1985) Occurrence and growth of lactic-acid bacteria in wine - a review. Am J Enol Viticult 36, 302-313.
43. Yamauchi, H., Hasuo, T., Amachi, T., Akita, O., Hara, S. and Yoshizawa, K. (1989) Cell-free synthesis of ethyl hexanoate by extract from Neurospora sp., containing novel acyl coenzyme A: alcohol acyltransferase. Agric Biol Chem 53, 821-825.