Biosynthesis of 4-Hydroxy-2,5-dimethyl-3(2<i>H</i>)-furanone by <i>Zygosaccharomyces rouxii</i>

Hecquet, Laurence; Sancelme, Martine; Bolte, Jean; Demuynck, Colette

doi:10.1021/jf950435j

Cited by 54 publications

(39 citation statements)

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“…It has been reported that HEMF and HDMF were secondary metabolites of Z. rouxii, involving different precursor sugars. 32,33) Compared with HDMF, more HEMF was found in our study. In particular, a relatively high level of HEMF was observed in the YE sample inoculated with Z. rouxii (2.1 mg/L), this being followed by the NT control level (1.7 mg/L).…”

Section: )mentioning

confidence: 55%

Comparative Volatile Profiles in Soy Sauce According to Inoculated Microorganisms

Lee

Choi³

et al. 2013

Bioscience, Biotechnology, and Biochemistry

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We compared the volatile profiles in soy sauce according to inoculation with Tetragenococcus halophilus and/or Zygosaccharomyces rouxii. Totals of 107 and 81 volatiles were respectively identified by using solidphase microextraction and solvent extraction. The various volatile compounds identified included acids, aldehydes, esters, ketones, furans and furan derivatives, and phenols. The major volatiles in the samples treated with T. halophilus were acetic acid, formic acid, benzaldehyde, methyl acetate, ethyl 2-hydroxypropanoate, 2-hydroxy-3-methyl-2-cyclopenten-1-one, and 4-hydroxy-3-methoxybenzaldehyde, while those in the samples inoculated with Z. rouxii were mainly ethanol, acetaldehyde, ethyl propanoate, 2/3-methylbutanol, 1-butanol, 2-phenylethanol, ethyl 2-methylpropanoate, and 4-hydroxy-2-ethyl-5-methyl-3(2H)-furanone. The results indicate that T. halophilus produced significant acid compounds and could affect the Z. rouxii activity, supporting the notion that yeasts and lactic acid bacteria respectively have different metabolic pathways of alcoholic fermentation and lactic acid fermentation, and produce different dominant volatile compounds in soy sauce.Key words: soy sauce; volatile compound; volatile profile; Zygosaccharomyces rouxii; Tetragenococcus halophilus Soy sauce, a soybean-based fermented food, is used in the cooking and seasoning of many Asian foods. Its popularity is increasing worldwide, mainly due to its characteristic flavor and umami taste.1) The industrial manufacturing process for soy sauce generally consists of three main steps: making koji, fermenting brine, and refining. Making koji involves inoculating cooked soybeans with Aspergillus oryzae (A. sojae) which produces such extracellular enzymes as proteases and amylases that hydrolyze proteins and polysaccharides in the soybeans. A brine mixture is then made by steeping the obtained koji in a salt solution. The brine mixture can be inoculated at this point with such a pure cultured lactic acid bacterium as Tetragenococus halophilus and such yeast as Zygosaccharomyces rouxii. Since these salt-tolerable lactic acid bacteria and yeasts are the predominant microorganisms during brine fermentation, adding pure cultured T. halophilus and Z. rouxii can accelerate and develop the formation of flavor in soy sauce.2,3) The high salt concentration also prevents the growth of undesirable microorganisms. The enzymes from the koji continuously break down the macromolecules in soybeans into smaller molecules such as sugars, peptides, and amino acids. During the growth of T. halophilus and Z. rouxii, diverse secondary metabolites, including the volatile flavor components, are formed via different metabolic pathways during lactic acid fermentation and alcoholic fermentation.3) The objective of brine fermentation is consequently to maximize both flavor production and hydrolysis of the macromolecules in soybeans.4) Nearly 300 volatile flavor compounds in soy sauce have been identified by many studies.5-7) The various volatiles identified in soy sauce...

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Section: )mentioning

confidence: 55%

Comparative Volatile Profiles in Soy Sauce According to Inoculated Microorganisms

Lee

Choi³

et al. 2013

Bioscience, Biotechnology, and Biochemistry

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“…For Q1 the NMR data showed the presence of a 1-phospho-2,3,4-trihydroxybutyl moiety, and for Q2 the data showed the presence of a 1-phospho-2,3-dihydroxypropyl moiety at C-2Ј. The linkage of the phosphate group to C-1 was proved by the split signals in the 13 C spectra due to the phosphorus-carbon coupling and the corresponding coupling constants ( 2 J C-1,P ϭ 5.2 Hz and 3 J C-2,P ϭ 7.5 Hz for Q1, 2 J C-1,P ϭ 5.5 Hz and 3 J C-2,P ϭ 7.5 Hz for Q2) (36). The presence of phosphorus was additionally confirmed by 31 P NMR (data not shown).…”

Section: Detection Of ␣-Dicarbonyl Compounds Derived From Fbpmentioning

confidence: 93%

“…D-Xylulose-5-phosphate, D-ribulose-5-phosphate, and D-sedoheptulose-7-phosphate were determined as potential precursors of homofuraneol and norfuraneol (31). Hecquet et al (13) demonstrated that HDMF is produced by Z. rouxii from D-fructose-1,6-bisphosphate (FBP), and results from Roscher et al (30) confirmed FBP as the most effective precursor in ripe strawberry fruits. Z. rouxii produced approximately 80 ppm of HDMF after 11 days of incubation in nutrient solutions containing 10% FBP and 5% D-glucose (carbon source).…”

Section: -Hydroxy-3[2h]mentioning

confidence: 99%

“…Three nutrient solutions were prepared according to the method of Hecquet et al (13). Two media were supplemented with FBP, and one of the phosphohexose-containing media was inoculated with Z. rouxii cells.…”

Section: Detection Of ␣-Dicarbonyl Compounds Derived From Fbpmentioning

confidence: 99%

“…Q1, Q2, and Q3 were isolated from a culture medium containing FBP and Z. rouxii cells for structure elucidation. Identification was achieved by NMR spectroscopy including 1 H, 13 C, distortionless enhancement by polarization transfer, homonuclear correlation spectroscopy, heteronuclear multiple-bond connectivity, and 1 H-detected heteronuclear multiple-quantum coherence experiments. All three substances showed similar signals in the 1 H and 13 C NMR spectra arising from the protons H-5Ј and H-8Ј and from the carbons C-4aЈ, C-5Ј, C-6Ј, C-7Ј, C-8Ј, and C-8aЈ of the quinoxaline skeletal structure (9,16,20,42).…”

Section: Detection Of ␣-Dicarbonyl Compounds Derived From Fbpmentioning

confidence: 99%

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Formation of 4-Hydroxy-2,5-Dimethyl-3[2H]-Furanone by Zygosaccharomyces rouxii : Identification of an Intermediate

Hauck

Brühlmann

Schwab

2003

Appl Environ Microbiol

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13 C]FBP to the nutrient medium revealed that only exogenously supplied FBP was transformed to HDMF (6). It was assumed that at least one metabolic step takes place in the cell wall or membrane of the yeast. However, the biosynthesis in plants and microorganisms is still unclear since no enzyme or intermediate involved in HDMF formation has been identified so far. Recently, the chemical formation of HDMF from FBP in the presence of NAD(P)H was reported (11). The authors proposed the dicarbonyl compound 1-deoxy-2,3-hexodiulose-6-phosphate as a possible intermediate which is subsequently reduced by NAD(P)H to the final product, HDMF. A similar biosynthetic pathway is anticipated in plants and microorganisms.Prior to the usage of Z. rouxii for the biotechnological production of the economically important flavor compound HDMF, it is of utmost significance to know the biosynthetic pathway of HDMF. The objective of this study was to obtain detailed information about HDMF formation from FBP by the yeast Z. rouxii. Here, we report on potential intermediates, such as ␣-dicarbonyls in the culture medium. Employment of the ␣-dicarbonyl-trapping reagent o-phenylenediamine revealed three highly reactive ␣-dicarbonyl structures derived from FBP in the nutrient medium. Structure elucidation of the corresponding quinoxaline derivatives demonstrated the chemical formation of the often postulated but never identified intermediate * Corresponding author. Present address: Biomolekulare Lebensmitteltechnologie,

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The importance of the furanones HDMF and HEMF in the flavour profile of Japanese barley miso and their production during fermentation

Hayashida

Nishimura

Slaughter

1998

J. Sci. Food Agric.

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Biosynthesis of 4-Hydroxy-2,5-dimethyl-3(2H)-furanone by Zygosaccharomyces rouxii

Cited by 54 publications

References 14 publications

Comparative Volatile Profiles in Soy Sauce According to Inoculated Microorganisms

Comparative Volatile Profiles in Soy Sauce According to Inoculated Microorganisms

Formation of 4-Hydroxy-2,5-Dimethyl-3[2H]-Furanone by Zygosaccharomyces rouxii : Identification of an Intermediate

The importance of the furanones HDMF and HEMF in the flavour profile of Japanese barley miso and their production during fermentation

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