The Formation Mechanism by Yeast of 4-Hydroxy-2(or 5)-ethyl-5(or 2)-methyl-3(2<i>H</i>)-furanone in Miso

Ohata, Motoko; Kohama, Keiko; Morimitsu, Yasujiro; Kubota, Kikue; Sugawara, Etsuko

doi:10.1271/bbb.60466

Cited by 52 publications

(33 citation statements)

References 8 publications

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“…They contribute a caramel-like odour to soy sauce aroma. The 4-HDMF and 4-HEMF in soy sauce can be formed through a Maillard reaction of pentoses during heating or by a biosynthetic pathway involving yeasts 4,10,22 . In addition, furfural and 5-methylfurfural could also be very important because of their presence in 11 brand soy sauces, respectively.…”

Section: Furansmentioning

confidence: 99%

Profile of Volatile Compounds in 12 Chinese Soy Sauces Produced by a High-Salt-Diluted State Fermentation

Sun

Jiang²,

Zhao

2010

Journal of the Institute of Brewing

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There have been limited studies on the flavour compounds in Chinese soy sauces. In order to obtain wider information about the chemical composition of the volatile fractions in 12 brands of Chinese soy sauces produced by high-salt-diluted state fermentation (HSDSF) and to compare them, a headspace solid microextraction method coupled to gas chromatography-mass spectrometry (HS-SPME-GC-MS) method was proposed and developed. A 50/30μm Divinylbenzene/Carboxen/Polydimethylsiloxane (DVB/CAR/PDMS) fibre was used for extraction of volatiles. The adsorption time and temperature of the SPME fibre were optimized separately for various aroma compounds in the soy sauce (50°C and 40 min for alcohols and esters; 40°C and 50 min for ketones, aldehydes and pyrazines; 60°C and 50 min for acids, phenols and furans). From the study, a total of 80 compounds were identified in the 12 samples, of which 34 volatiles were in common. Alcohols and acids were the main volatiles present in the soy sauces. Dominant volatile alcohols were ethanol, 2/3-methyl butanol and β-phenylethyl alcohol; and important acids were acetic acid, butanoic acid, and 3-methylbutanoic acid. Miscellaneous, esters, furans and phenols also made large contributions to the total volatiles of the soy sauces. According to the scatter point plot obtained from principal component analysis, the 12 soy sauces could be classified into four groups.

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Section: Furansmentioning

confidence: 99%

Profile of Volatile Compounds in 12 Chinese Soy Sauces Produced by a High-Salt-Diluted State Fermentation

Sun

Jiang²,

Zhao

2010

Journal of the Institute of Brewing

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“…Biologically or abiologically formed acetaldehyde has been reported to be an effective C 2 precursor for HEMF (19,20). Subsequently, we examined the acetaldehyde contents of the mutants with high-level HEMF production to determine whether acetaldehyde accumulation caused the high-level HEMF production in these gene deletion mutants.…”

Section: Resultsmentioning

confidence: 99%

“…However, Sugawara et al and Hayashida et al demonstrated that HEMF formation was promoted by cultivating halotolerant yeast in the medium, including the Maillard reaction products formed from ribose and amino acids, such as glycine (16), alanine (17), and glutamic acid (18), during heat sterilization. Furthermore, Ohata et al demonstrated that the five-member ring and the methyl group on the HEMF side chain were formed from a 5-carbon chemical compound generated by the amino-carbonyl reaction of ribose and glycine (the C 5 precursor) and that the ethyl group on the HEMF side chain was formed from a 2-carbon chemical compound generated by the glucose metabolism of yeast (the C 2 precursor) (19). Ohata et al also assumed that acetaldehyde is effective as the C 2 precursor and that the C 5 and C 2 precursors were most likely enzymatically combined by yeast (19).…”

Section: H Emf [4-hydroxy-2 (Or 5)-ethyl-5 (Or 2)-methyl-3(2h)-furanone]mentioning

confidence: 99%

“…Furthermore, Ohata et al demonstrated that the five-member ring and the methyl group on the HEMF side chain were formed from a 5-carbon chemical compound generated by the amino-carbonyl reaction of ribose and glycine (the C 5 precursor) and that the ethyl group on the HEMF side chain was formed from a 2-carbon chemical compound generated by the glucose metabolism of yeast (the C 2 precursor) (19). Ohata et al also assumed that acetaldehyde is effective as the C 2 precursor and that the C 5 and C 2 precursors were most likely enzymatically combined by yeast (19). This assumption was supported by the fact that HEMF was formed by a chemical reaction between Maillard reaction products from pentose and acetaldehyde, which are the Strecker degradation products of alanine (20).…”

Section: H Emf [4-hydroxy-2 (Or 5)-ethyl-5 (Or 2)-methyl-3(2h)-furanone]mentioning

confidence: 99%

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Screening of High-Level 4-Hydroxy-2 (or 5)-Ethyl-5 (or 2)-Methyl-3(2 H )-Furanone-Producing Strains from a Collection of Gene Deletion Mutants of Saccharomyces cerevisiae

Uehara

Watanabe

Akao

et al. 2015

Appl Environ Microbiol

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4-Hydroxy-2 (or 5)-ethyl-5 (or 2)-methyl-3(2H)-furanone (HEMF)is an important flavor compound that contributes to the sensory properties of many natural products, particularly soy sauce and soybean paste. The compound exhibits a caramel-like aroma and several important physiological activities, such as strong antioxidant activity. HEMF is produced by yeast species in soy sauce manufacturing; however, the enzymes involved in HEMF production remain unknown, hindering efforts to breed yeasts with high-level HEMF production. In this study, we identified high-level HEMF-producing mutants among a Saccharomyces cerevisiae gene deletion mutant collection. Fourteen deletion mutants were screened as high-level HEMF-producing mutants, and the ADH1 gene deletion mutant (adh1⌬) exhibited the maximum HEMF production capacity. Further investigations of the adh1⌬ mutant implied that acetaldehyde accumulation contributes to HEMF production, agreeing with previous findings. Therefore, acetaldehyde might be a precursor for HEMF. The ADH1 gene deletion mutant of Zygosaccharomyces rouxii, which is the dominant strain of yeast found during soy sauce fermentation, also produces HEMF effectively, suggesting that acetaldehyde accumulation might be a benchmark for breeding industrial yeasts with excellent HEMF production abilities.is an aromatic component that produces a sweet caramel-like odor with a very low threshold value, which is below 20 ppb in water (1); the compound exists in two tautomeric forms in a 1:3 to 1:2 ratio through keto-enol isomerization: 4-hydroxy-2-ethyl-5-methyl-3(2H)-furanone and 4-hydroxy-5-ethyl-2-methyl-3(2H)-furanone (2, 3, 4). HEMF was isolated for the first time from soy sauce (2), and it has also been detected in roasted coffee (5), soybean paste (6, 7), melons (1), and beer (8, 9). HEMF, in particular, is a very important characteristic component of Japanese traditional fermented foods, such as soy sauce and soybean paste, and it occurs at high levels in soy sauce (10). In addition to its contribution to the sensory characteristics of foods, HEMF exhibits strong antioxidant properties: anticarcinogenic effects (11), anticataract effects (12), inhibition of lipid peroxidation (13), and prevention of radiation-based hazard (14). Therefore, HEMF exhibits characteristic aromatic properties while performing several important physiological functions.Sasaki et al. proposed that the HEMF in soy sauce is biosynthesized by soy sauce yeasts from the sugar phosphates found in the pentose-phosphate cycle, such as D-xylulose 5-phosphate (10, 15). However, Sugawara et al. and Hayashida et al. demonstrated that HEMF formation was promoted by cultivating halotolerant yeast in the medium, including the Maillard reaction products formed from ribose and amino acids, such as glycine (16), alanine (17), and glutamic acid (18), during heat sterilization. Furthermore, Ohata et al. demonstrated that the five-member ring and the methyl group on the HEMF side chain were formed from a 5-carbon chemical compound generated by the amin...

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“…Ohata et al (2007) have recently reported on the formation mechanism of HEMF by yeast during the aging of moromi. We consider that there is likely to be another important component of soy sauce in the unidentified odorant formed by the Maillard reaction and/or yeast.…”

Section: Introductionmentioning

confidence: 99%

Quantification and Odor Contribution of Volatile Thiols in Japanese Soy Sauce

Kakuta

Sugawara

2012

FSTR

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Three compounds of volatile thiols, 2-furanmethanethiol (2FM) with a strong roast coffee aroma, benzenemethanethiol (BM) with a strong empyreumatic aroma reminiscent of smoke and ethyl 2-mercaptopropionate (ET2MP) with a tropical fruit-like aroma, were identified for the first time in four types of heat-treated soy sauce and raw soy sauce. 2FM, BM and ET2MP were present in these soy sauce samples at considerably higher concentrations than their perception thresholds. Their concentrations also increased when the raw soy sauce was heated for pasteurization. A triangle test on the raw soy sauce and heat-treated soy sauce showed that the aroma of the raw soy sauce became similar to that of the heattreated soy sauce after the addition of the three volatile thiols to the raw soy sauce. The volatile thiols thus contributed to the aroma of heat-treated soy sauce.

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The Formation Mechanism by Yeast of 4-Hydroxy-2(or 5)-ethyl-5(or 2)-methyl-3(2H)-furanone in Miso

Cited by 52 publications

References 8 publications

Profile of Volatile Compounds in 12 Chinese Soy Sauces Produced by a High-Salt-Diluted State Fermentation

Profile of Volatile Compounds in 12 Chinese Soy Sauces Produced by a High-Salt-Diluted State Fermentation

Screening of High-Level 4-Hydroxy-2 (or 5)-Ethyl-5 (or 2)-Methyl-3(2 H )-Furanone-Producing Strains from a Collection of Gene Deletion Mutants of Saccharomyces cerevisiae

Quantification and Odor Contribution of Volatile Thiols in Japanese Soy Sauce

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