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Physiology and Metabolism of Dekkera/Brettanomyces Yeast in Relation to Mousy Taint Production

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Physiology and Metabolism of Dekkera/Brettanomyces Yeast in Relation to Mousy Taint Production ?o'ì'c{g t, i{ Physiology and metabolism of Dekkera/Brettanomyces yeast in relation to mousy taint production by PAUL R. GRBIN BSc. (Adel.), Grad. Dip. Wine (Roseworthy) A thesis submitted for the degree of Doctor of Philosophy in the Faculty of Agricultural and Natural Resources Sciences Department of Horticulture, Viticulture, and Oenology The Univeróity of Raelaide March 1998 'a flavour often left on the tongue as an aftertaste, reminiscent of the odour from mice kept in a confined space' (Erckmann, 1898) Table of Contents SUMMARY 1V DECLARATION .............. vlll ACKNO\ilLEDGMENTS IX ABBREYIATIONS.. x CHAPTER 1 Introduction and Literature Review............ .1 1.1 Introduction .1 1.2 The chemical nature of mousy taint............. 4 1.2. I 2-ethyltetahydropyridine 4 1.2.2 2-acetyltetrahyd¡opyridine ...... 4 1.2.3 2-acetylpynoline 7 1.3 Dekkeral Brettanomyces and beverage production ... 8 1.3.I T axonomy of D ekkeral BrettsnomJ)ces I l.3.2DekkeralBrettanomltcesspoilageotherfh?nmousytaint.. t2 l.3.3Positiveconfübutionsof De.kkgral&rettanomycesinbevetageproduction............ 15 1.3.4 Incidence of Dekkeral Brettanom]¡ces in wine production l6 1 .3 .5 D e kker a I B r ett an o m]¡ c e s and mottsy taint pro duction .. .' ., t7 1.4 Factors affecting mousy taint production by DekkeralBrettanomyces........ l8 1.4. I Lvsine catabolism ..... 18 1.4.2 Ethanol and mous]¡ taint .....25 1.4.3 The role of air/ox)¡gen... .....26 1.5 Proposed pathway for mousy taint production .....28 1.6 Research aims ..... 30 CHAPTER 2 Method Development for the Analysis of Mousy Taint Compounds 32 2.1 Introduction 32 2.2 Materials and methods........ 33 2.2.1 Chemicals and reagents.. 33 2.2.2 Mousy wine samples ........ 34 2,2,3 ACTPY.... 34 2.2.4BTPY...... .. 38 2.2.5 ACPY...... 39 2.3 Results and Discussion 40 2.3.1ACTPY 40 2.3.2ETPY 50 2.3.3 ACPY. 53 2.3.4 Mousv wine analvsis .... 54 CHAPTER 3 Mousy Taint Production by D ekkeral B rettanomyce s ............ 58 3.1 Introduction 58 3.2 Materials and methods... 60 3.2.1 Yeast strains ...... 60 3.2.2 Yeast growth and mousy taint formation in wine 61 3.2.3 T]¡pe strain screening trial for mousy taint formation 64 3.2.4 Identification and quantification gf mousy taint compounds ... 66 67 3.3.1 Yeast growth and mous]¡ taint formation in wine 67 3.3.2 Type stuain screening trial for mousy taint formation ......72 3.3.3 Identification and quantification of mousy taint compounds....... ......76 3.4 DÍscussion ...... 80 3.4.I Growth and mousy taint production ...... 80 3.4.2 Culture conditions ......84 3.4.3 Mousy taint compounds ...... 86 CHAPTER 4 Physiotogical Influences on Mousy Taint Production by DekkeralBrettanomyces 88 4.1 Introduction 88 4.2 Mzterials and methods... 90 4.2.1 Mousy taint production and stage of growth 90 4.2.2 Influence of air onmousy taintproduction.,..... 91 u 4.3 Results................. 101 4.3.1 Mousy taint production and stagE of growth ... 101 4.3.2 Influence of air on mous)¡ taint production ... 104 4.4 DÍscussion t07 CHAPTER 5 Metabolism of Mousy Taint Compounds: the Role of Amino Nitrogen 113 5.1 Introduction 113 5.2 Materials and methods.......... .. tt4 5.2.1 Sole nitrogen source .. tt4 5.2.2 Dose response to L-lysine 116 5.2.3 L-L]¡sine derivatives tt7 5.2.4 D-Lysine 118 5.2.5 Stable isotopes of L-lysine.. 118 5.3 Results.............. r20 5.3.1 Sole nitrogen source r20 5.3.2 Dose response to L-lysine t22 5.3.3 L-Lvsine derivatives. 126 5.3.4 D-Lysine 727 5.3.5 Stable isotopes of L-lysine 129 5.4 Discussion ................ r37 CHAPTER 6 General Discussion and Proposed Pathway of Mousy Taint Biosynthesis....... 144 6.1 General discussion.... t44 6.2 Proposed pathway(s) for the biosynthesis of mousy taint compounds t46 6.2.1 Pathway A t49 6.2.2 Pathway B 153 6.2.3 Which oathwav? 155 6.3 Model for mousy taint production by DekkeralBrettanomyces ................. 157 6.4 Future research... 159 REFERENCES 160 u1 Thesis Summary Mousy taint is an insidious spoilage characteristic of wine and other fermented beverages. Its origin is reputedly due to the growth of certain strains of lactic acid bacteria and yeasts of the genus Dekkera, more often described by the asexual form, Brettanomyces. Tainted wines are rendered unpalatable and this is economically disastrous for the wine producer. The compounds considered responsible for mousy taint in wine are the tautomers 2-acetyl- 1,4,5,6-tetrahydropyridine and 2-acetyl-3,4,5,6 tetrahydropyridine (described together as ACTPY). The lack of a sensitive analytical method for the measurement of the compounds associated with mousy taint, which only occur at low concentrations (¡rgll range), has constrained research in this area. In the present work a reliable analytical method was developed to examine the chemical basis of mousy taint and to investigate the role of DekkeralBrettanomyces yeast in the formation of mousy taint. A method for the extraction, analysis and quantification of ACTPY was developed, incorporating a continuous liquid/liquid extraction procedure and analysis by gas chromatography/mass spectrometry (GC/ÏVIS). The procedure was validated by a spiking trial and was shown to be reliable and highly sensitive. This enabled a detailed analysis of mousy taint compounds in wine and culture media extracts. Detection and analysis of other compounds which reputedly had a mousy character was undertaken; 2-acetyl-l-pynoline (ACPY) and 2-ethyl-3,4,5,6-tetrahydropyridine (ETPY) were identified as important constituents of mousy taint. The very sensorily potent ^CPY was detected in mousy wines and in some experimental fermentations carried out by DekkeralBrettanomyces species. This was the first report of the production of this compound by yeast. Its identity was confirmed by comparison of mass spectral data with lv that of an authentic reference sample. The mousy impact of ACPY was confirmed by GC effluent sniffing (GC-sniff). The compound ETPY was also detected in mousy wines and fermentation media, and synthesis of an authentic reference and comparison of mass spectral data confirmed its identity. Confirmation \Mas also shown with co-injection analysis by GC/IMS of an authentic sample and an extract containing tentatively identified ETPY. This analysis indicated the detection of ETPY by the symmetrical peak enhancement of the target compound with no significant change in relative ratios of the component ions. This compound was detected below its reported taste threshold in wine, indicating that it may have a limited impact on mousy taint in wine. However, it was always detected in association with ACTPY and to a smaller extent with ACPY. This suggests a possible route for its formation, but does not discount any additive sensory effect. Two surveys of mousy taint production by the type strains of DekkeralBrettanomyces cultured under different conditions were ca:ried out. A rapid and simple method was used initially. The yeasts were grown in a grape juice medium and mousy taint detected by sensory evaluation. A large proportion of the yeasts, representing all species, produced taint under these conditions. A more detailed analytical study in which all the known type strains of DekkeralBrettanomyces were cultured in a chemically defined medium was undertaken. This showed that all DekkeralBrettanomyces tested, including the recently classified B. nana, could produce ACTPY and to a lesser extent ETPY. No ACPY was detected under these conditions. A practical consequence of these data is that mousy taint formation in wine could arise from the presence in wine of any strain or species of these yeasts, depending on the conditions and availability of appropriate precursors. This work confirmed the previously reported observations that the amino acid r-lysine is an important precursor for the formation mousy taint, as a marked reduction in ACTPY and ETPY concentration was observed in its absence. This finding suggests that the intracellular pool of r-lysine is v enlarged by the presence of extracellular L-lysine, thereby increasing the flux of tetrahydropyridine formation. These data also indicated that L-lysine is not the precursor of ACPY. Substantial concentrations of ACPY were produced by the DekkeralBrettanomyces species tested only when r-ornithine was the sole nitrogen source. The production of mousy taint compounds can therefore be considered a characteristic of the genera Dekkeral Brettanomyces. The origin of the nitrogen heterocycle ACTPY (and ETPY) was investigated by the use of stable isotopes. In a feeding experiment, uniformly labelled L-lysine l36u-15¡, was found to be the primary precursor to ACTPY and ETPY, as labelled C and N were incorporated into these compounds. Further investigations using 15N label at the either o-amino or e- amino groups of r-lysine, showed that the e-N contributed to ACTPY and ETPY. These data indicate a novel route of L-lysine catabolism in DekkeralBrettanomyces. The accumulation of ACTPY in culture media was strongly linked to the growth phase, with the amount of ACTPY increasing as the culture progressed from early to middle stationary phase. The formation of ACTPY coincided with the uptake of r-lysine from the medium, providing further evidence that the catabolism of this amino acid was important to tetrahydropyridine formation. In contrast to ACTPY, the production of ETPY was delayed until the middle stationary phase. This suggests that ETPY is a product of further metabolism of ACTPY. The strong link to growth indicates that mousy taint compounds are a product of general cell metabolism. The role of oxygen in mousy taint formation was investigated in a grape juice medium.
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