Factors influencing the formation of histaminol, hydroxytyrosol, tyrosol, and tryptophol in wine: Temperature, alcoholic degree, and amino acids concentration

Bordiga, Matteo; Lorenzo, Cándida; Pardo, Francisco; Salinas, M. Rosario; Travaglia, Fabiano; Arlorio, Marco; Coïsson, J. D.; Garde‐Cerdán, Teresa

doi:10.1016/j.foodchem.2015.11.112

Cited by 40 publications

(22 citation statements)

References 25 publications

(27 reference statements)

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“…[1][2][3] The ability of S. cerevisiae to synthesize higher alcohols was discoveredb yF elix Ehrlich more than 100 years ago, [4] and characteristics and consequences of the "Ehrlich pathway" are being revealed still today. [5,6] Amino acids that undergo this pathwaya re mainly the branched-chain amino acids valine, leucine, and isoleucine and the aromatic amino acids phenylalanine, tyrosine, and tryptophan. [1,7,8] The transamination of an a-aminoa cid of type 1 to produce an a-keto acid of type 2 is the first step in the reaction (Scheme1).…”

Section: Introductionmentioning

confidence: 99%

Transformation of Free and Dipeptide‐Bound Glycated Amino Acids by Two Strains of Saccharomyces cerevisiae

et al. 2016

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The yeast Saccharomyces cerevisiae transforms branched-chain and aromatic amino acids into higher alcohols in the Ehrlich pathway. During microbiological culturing and industrial fermentations, this yeast is confronted with amino acids modified by reducing sugars in the Maillard reaction (glycation). In order to gain some preliminary insight into the physiological "handling" of glycated amino acids by yeasts, individual Maillard reaction products (MRPs: fructosyllysine, carboxymethyllysine, pyrraline, formyline, maltosine, methylglyoxal-derived hydroimidazolone) were administered to two strains of S. cerevisiae in a rich medium. Only formyline was converted into the corresponding α-hydroxy acid, to a small extent (10 %). Dipeptide-bound pyrraline and maltosine were removed from the medium with concomitant emergence of several metabolites. Pyrraline was mainly converted into the corresponding Ehrlich alcohol (20-60 %) and maltosine into the corresponding α-hydroxy acid (40-60 %). Five specific metabolites of glycated amino acids were synthesized and characterized. We show for the first time that S. cerevisiae can use glycated amino acids as a nitrogen source and transform them into new metabolites, provided that the substances can be transported across the cell membrane.

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Section: Introductionmentioning

confidence: 99%

Transformation of Free and Dipeptide‐Bound Glycated Amino Acids by Two Strains of Saccharomyces cerevisiae

et al. 2016

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“…The histaminol analysis was performed according to the method previously validated and reported (Bordiga et al ., ). A high‐performance liquid chromatography HPLC‐PDA‐MS/MS (Thermo Scientific, fitted with quaternary pump, autosampler, column oven, PDA detector ACCELA and TSQ Quantum Access Max) equipped with Thermo Hypersil GOLD column (50 mm × 2.1 mm, 1.9 μm) was used.…”

Section: Methodsmentioning

confidence: 97%

“…Alternatively, according to the Ehrlich pathway, histidine is potentially converted into histaminol during alcoholic fermentation (Lopez‐Rituerto et al ., ). However, concerning a well‐known fermented product such as wine, the analysis of the corresponding alcohol derived from catabolism of L‐histidine has not been extensively studied even though its presence in wine has been detected in our previous studies conducted on a set of several wines (Bordiga et al ., , ). However, a study describing the characteristics of this process, applying different selected yeast strains, is not reported in literature.…”

Section: Introductionmentioning

confidence: 99%

Influence of different commercial active dry yeasts on histaminol production during wine alcoholic fermentation

Bordiga

Guzzon

Larcher

et al. 2017

Int J of Food Sci Tech

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The performance of different selected yeast strains regarding the capacity to convert histidine into histaminol during fermentation has been described and discussed in a model grape must (Chardonnay). First, the activity of 10 commercial active dry yeast strains (ADY) in the native grape must both with and without a nitrogen supplementation has been compared. In the second set of fermentations, after selecting the four best-performing strains, their performances using four different nitrogen sources have been tested. During fermentation process it was not possible to identify a common trend. In some cases, histaminol content appeared related to the nutrient supplementation, however, in other cases a different behaviour emerged. However, as shown by the experimental evidences, among the two variables considered the nature of yeast strain was slightly prevalent.

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“…It is possible that production of OH-TYL proceeds from TYL, but in practice, the relevant hydrolase was not isolated in yeast but in bacteria [35]. OH-TYL was detected in wine, and recently, it was demonstrated that it can be produced by yeast [10,36]. Since the highest concentration quantified in pinot gris must was about 90 times higher than that of chardonnay while the maximum differences in the three fermentations (QA, RF and Td+QA) were less than 20%, it can be hypothesized that OH-TYL production depends mainly on must/grape cultivar composition.…”

Section: Extracellular Metabolitesmentioning

confidence: 99%

Modulating Wine Aromatic Amino Acid Catabolites by Using Torulaspora delbrueckii in Sequentially Inoculated Fermentations or Saccharomyces cerevisiae Alone

et al. 2020

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Yeasts are the key microorganisms that transform grape juice into wine, and nitrogen is an essential nutrient able to affect yeast cell growth, fermentation kinetics and wine quality. In this work, we focused on the intra- and extracellular metabolomic changes of three aromatic amino acids (tryptophan, tyrosine, and phenylalanine) during alcoholic fermentation of two grape musts by two Saccharomyces cerevisiae strains and the sequential inoculation of Torulaspora delbrueckii with Saccharomyces cerevisiae. An UPLC-MS/MS method was used to monitor 33 metabolites, and 26 of them were detected in the extracellular samples and 8 were detected in the intracellular ones. The results indicate that the most intensive metabolomic changes occurred during the logarithm cellular growth phase and that pure S. cerevisiae fermentations produced higher amounts of N-acetyl derivatives of tryptophan and tyrosine and the off-odour molecule 2-aminoacetophenone. The sequentially inoculated fermentations showed a slower evolution and a higher production of metabolites linked to the well-known plant hormone indole acetic acid (auxin). Finally, the production of sulfonated tryptophol during must fermentation was confirmed, which also may explain the bitter taste of wines produced by Torulaspora delbrueckii co-fermentations, while sulfonated indole carboxylic acid was detected for the first time in such an experimental design.

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Factors influencing the formation of histaminol, hydroxytyrosol, tyrosol, and tryptophol in wine: Temperature, alcoholic degree, and amino acids concentration

Cited by 40 publications

References 25 publications

Transformation of Free and Dipeptide‐Bound Glycated Amino Acids by Two Strains of Saccharomyces cerevisiae

Transformation of Free and Dipeptide‐Bound Glycated Amino Acids by Two Strains of Saccharomyces cerevisiae

Influence of different commercial active dry yeasts on histaminol production during wine alcoholic fermentation

Modulating Wine Aromatic Amino Acid Catabolites by Using Torulaspora delbrueckii in Sequentially Inoculated Fermentations or Saccharomyces cerevisiae Alone

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