Conversion of unsaturated fatty acids to precursors of γ-lactones by lactic acid bacteria during the production of malt whisky

Journal of the American Society of Brewing Chemists

Volumn 58, Issue 2, 2000, Pages 51-56

  Wanikawa, Akira ^a   Hosoi, Kenji ^a   Kato, Taro ^a  

^a Nikka Whisky Distilling Co Ltd   (Japan)

Author keywords

Decalactone; Dodecalactone; Brewer's yeast; Unsaturated fatty acids

Indexed keywords

10 HYDROXYPALMITIC ACID; 10 HYDROXYSTEARIC ACID; ALCOHOLIC BEVERAGE PRODUCTION; FATTY ACID METABOLISM; GAMMA DECALACTONE; GAMMA DODECALACTONE; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROXYLATION; LACTIC ACID BACTERIUM; LACTONE; MALT WHISKY; MASS SPECTROMETRY; OLEIC ACID; PALMITOLEIC ACID; UNSATURATED FATTY ACID; WHISKY;

EID: 0034097577     PISSN: 03610470     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (41)

1. Barbour, E. A., and Priest, F. G. Some effects of lactobacillus contamination in scotch whisky fermentation. J. Inst. Brew. 94:89-92, 1988.
2. Dolan, T. C. S. Some aspects of the impact of brewing science on scotch malt whisky production. J. Inst. Brew. 82:177-181, 1976.
3. Drost, B. R., von Eerde, P., Hoekstra, S. F., and Strating, J. Fatty acids and staling of beer. Proc. Congr. Eur. Brew. Conv. 13:451-458, 1971.
4. Drost, B. W., van den Berg, R., Freijee, F. J. M., van der Velde, E. G., and Hollemans, M. Flavor stability. J. Am. Soc. Brew. Chem. 48:124-131, 1990.
5. El-Sharkawy, S. H., Yang, W., Dostal, L., and Rosazza, J. P. N. Microbial oxidation of oleic acid. Appl. Environ. Microbiol. 58:2116-2122, 1992.
6. Esaki, N., Ito, S., Blank, W., and Soda, K. Biotransformation of oleic acid by Micrococcus luteus cells. Biosci. Biotech. Biochem. 58:319-321, 1994.
7. Frankel, E. N. Chemistry of free radical and singlet oxidation of lipids. Prog. Lipid Res. 23:197-221, 1985.
8. Furukawa, T., and Akiyama, Y. A microbiological control of sake brewing. Part IV. On the TTC-agar overlay method for grouping of yeast. Nippon Nogeikagaku Kaishi, 37:398-402, 1963.
9. Gatfield, I. I. Generation of flavor and aroma components by microbial fermentation and enzyme engineering technology. ACS Symp. Ser. 317:310-322, 1985.
10. Geddes, P. A., and Raffkin, H. L. Influence of lactic acid bacteria on aldehyde, ester and higher alcohol formation during Scotch whisky fermentations. Pages 93-199 in: Distilled Beverage Flavour. J. R. Piggott and A. Paterson, eds. Ellis Horwood Ltd., London, 1989.
11. Gocho, S., Tabogami, N., Inagaki, M., Kawabata, C., and Kornai, T. Biotransformation of oleic acid to optically active γ-dodecalactone. Biosci. Biotech. Biochem. 59:1571-1572, 1995.
12. Hagedorn, S., and Kaphammer, B. Microbial biocatalysis in the generation of flavour and fragrance chemicals. Annu. Rev. Microbiol. 48:773-800, 1994.
13. Hamberg, M. Trihydroxyoctadecenoic acids in beer. J. Agric. Food Chem. 39:1568, 1991.
14. Hashimoto, N., Aoyama, T., and Shioiri, T. New methods and reagents in organic synthesis. 14. A simple efficient preparation of methyl esters with trimethylsilyldiazomethane and its application to gas chromatographic analysis of fatty acids. Chem. Pharm. Bull. 29:1475-1478, 1981.
15. Heide, R. T. The flavour of distilled beverages. Pages 239-336 in: Food Flavours. I. D. Morton and A. J. Macleod, eds. Elsevier Science Publishers B.V., Amsterdam, 1986.
16. Hou, C. T. Production of 10-ketostearic acid from oleic acid by Flavobacterium sp. strain DS5 (NRRL B-14859). Appl. Environ. Microbiol. 60:3760-3763, 1994.
17. Imai, M., Sato, A., and Ishii, H. Study on the volatile compounds of 130-year-aged "Nukadoko" for picking. Agric. Biol. Chem. 55:2209-2220,1991.
18. Janssens, L., DePooter, H. L., Schamp, N. M., and Vandamme, E. J. Production of flavours by microorganisms. Process Biochem. 27:195-215, 1992.
19. Kahn, J. H., Shipley, P. A., LaRore, E. G., and Conner, H. A. Whisky composition: Identification of additional components by gas chromatography-mass spectrometry. J. Food Sci. 34:587-591, 1969.
20. Korhola, M., Harju, K., and Lehtonen, M. Fermentation. Pages 89-117 in: The Science and Technology of Whiskies. J. R. Piggott, R. Sharp, and R. E. B. Duncan, eds. Longman Scientific and Technical, Harlow, England, 1989.
21. Koritala, S., and Badgy, M. O. Microbial conversion of linoleic and linolenic acids to unsaturated hydroxy fatty acids. J. Am. Oil Chem. Soc. 69:575-578, 1992.
22. Lanser, A. C. Conversion of oleic acid to 10-ketostearic acid by a Staphylococcus species. J. .Am. Oil Chem. Soc. 70:543-545,1993.
23. Lanser, A. C., Plattner, R. D., and Bagby, M. O. Production of 15-, 16-and 17-hydroxy-9-octadecenoic acids by bioconversion of oleic acid with Bacillus pumilus. J. Am. Oil Chem. Soc. 69:363-366, 1992.
24. Lee, S.-L., Chou C.-C., and Wu, C.-M. Identification of volatile flavor constituents produced by Kluveromyces lactis, Ceratocystis moniliformis and Sporobomyces ordour. J. Cin. Agric. Chem. Soc. 29(1):43-53, 1991.
25. Lower, E. S. Hydroxy fatty acids. Riv. Ital. Sostanze Grasse 74:299-306, 1997.
26. Lower, E. S. Hydroxy fatty acids. Riv. Ital. Sostanze Grasse 74:359-378, 1997.
27. Maga, J. A. Oak lactones in alcoholic beverage. Food Rev. Int. 12(1):105-130, 1996.
28. Makanjuola, D. B., and Springham, D. G. Identification of lactic acid bacteria isolated from different stages of malt whisky distillery fermentations. J. Inst. Brew. 90(1):13-19, 1984.
29. Makanjuola, D. B., Tymon, A., and Springham, D. G. Some effects of lactic acid bacteria on laboratory-scale yeast fermentations. Enzyme Microb. Technol. 14:350-357, 1992.
30. Maume, K. A., and Cheetham, P. J. S. The production of γ-decalactone by fermentation of castor oil. Biocatalysis 5:79-97, 1991.
31. Miedaner, H., Narziss, L., and Eichhorn, P. Some aspects on flavour stability - A sensorial analytical evaluation. Proc. Congr. Eur. Brew. Conv. 23:401-408, 1991.
32. Nose, A, Ozaki, H., Takise, I., and Tanabe, M. Effects of using brewer's yeast on flavor components of whisky fermentation mash. J. Brew. Soc. Jpn. 89:983-988, 1994.
33. Palmer, G. H. Scientific review of Scotch malt whisky. Ferment 10:367-379.
34. Paterson, A., and Piggot, J. R. The contributions of the process to flavour in scotch malt whisky. Pages 51-169 in: Distilled Beverage Flavour. J. R. Piggott and A. Paterson, eds. Ellis Horwood Ltd., London, 1989.
35. Priest, F. G., and Pleasants, J. G. Numerical taxonomy of some leuconostocs and related bacteria isolated from Scotch whisky distilleries. J. Appl. Bacteriol. 64:379-387, 1988.
36. Ramsay, C. M., and Berry, D. R. Factors influencing the aroma and flavour of whisky. Brew. Distill. Int. 13:34-37, 1983.
37. Soumalainen, H., and Nykanen, L. Composition of whisky flavour. Process Biochem. 5:13-18, 1970.
38. Tahara, S., Fujiwara, K., and Mizutani, J. Neutral constituents of volatiles in cultured broth of Sporobomyces odorus. Agric. Biol. Chem. 37:2855-2861, 1973.
39. Tressl, R., Bahri, D., and Silwar, R. Formation of aldehydes by oxidation of lipids and their importance as "off-flavour" components in beer. Proc. Congr. Eur. Brew. Conv. 17:27-41, 1979.
40. Wanikawa, A., Hosoi, K., and Kato, T. Detection of γ-lactones in malt whisky. J. Inst. Brew. 106(1):39-43, 2 000.
41. Wilson, C. W., III, Shaw, P. E., and Knight, R. J., Jr. Importance of some lactones and 2,5-dimethyl-4-hydroxy-3 (2H)-furanone to mango aroma. J. Agric Food Chem. 38:1556-1559, 1990.