The Cysteine Reaction with Diacetyl under Wine‐Like Conditions: Proposed Mechanisms for Mixed Origins of 2‐Methylthiazole, 2‐Methyl‐3‐thiazoline, 2‐Methylthiazolidine, and 2,4,5‐Trimethyloxazole

Marchand, Stéphanie; Almy, John; Revel, Gilles de

doi:10.1111/j.1750-3841.2011.02261.x

Cited by 18 publications

(23 citation statements)

References 36 publications

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“…It has been reported that diacetyl can react with ARPs, although at a much slower rate than acetaldehyde (Blanco-Vega et al, 2011 ). It can also react to thiols, such as cysteine, producing a wide range of subproducts (Marchand et al, 2000 , 2011 ). Remarkably, one of the reactions suffered by diacetyl and other α-dicarbonyls is Maillard reaction with amino acids, one of whose possible outcomes is the Strecker degradation to form the corresponding Strecker aldehydes (Oliveira et al, 2011a ).…”

Section: Resultsmentioning

confidence: 99%

Formation and Accumulation of Acetaldehyde and Strecker Aldehydes during Red Wine Oxidation

et al. 2018

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The main aim of the present work is to study the accumulation of acetaldehyde and Strecker aldehydes (isobutyraldehyde, 2-methylbutanal, isovaleraldehyde, methional, phenylacetaldehyde) during the oxidation of red wines, and to relate the patterns of accumulation to the wine chemical composition. For that, eight different wines, extensively chemically characterized, were subjected at 25°C to three different controlled O2 exposure conditions: low (10 mg L−1) and medium or high (the stoichiometrically required amount to oxidize all wine total SO2 plus 18 or 32 mg L−1, respectively). Levels of volatile aldehydes and carbonyls were then determined and processed by different statistical techniques. Results showed that young wines (<2 years-old bottled wines) hardly accumulate any acetaldehyde regardless of the O2 consumed. In contrast, aged wines (>3 years-old bottled wines) accumulated acetaldehyde while their content in SO2 was not null, and the aged wine containing lowest polyphenols accumulated it throughout the whole process. Models suggest that the ability of a wine to accumulate acetaldehyde is positively related to its content in combined SO2, in epigallocatechin and to the mean degree of polymerization, and negatively to its content in Aldehyde Reactive Polyphenols (ARPs) which, attending to our models, are anthocyanins and small tannins. The accumulation of Strecker aldehydes is directly proportional to the wine content in the amino acid precursor, being the proportionality factor much higher for aged wines, except for phenylacetaldehyde, for which the opposite pattern was observed. Models suggest that non-aromatic Strecker aldehydes share with acetaldehyde a strong affinity toward ARPs and that the specific pattern of phenylacetaldehyde is likely due to a much reduced reactivity toward ARPs, to the possibility that diacetyl induces Strecker degradation of phenyl alanine and to the potential higher reactivity of this amino acid to some quinones derived from catechin. All this makes that this aldehyde accumulates with intensity, particularly in young wines, shortly after wine SO2 is depleted.

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Section: Resultsmentioning

confidence: 99%

Formation and Accumulation of Acetaldehyde and Strecker Aldehydes during Red Wine Oxidation

et al. 2018

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“…Cys and Met can play an important role in wine aroma since they are usually related with the formation of several volatile compounds with low olfactory threshold, namely, off-odours such as methional [24,27]. Cys has been pointed out as the most interesting sulphur amino acid that through Maillard and Strecker reactions is transformed into many products including heterocyclic groups in their structure revealing strong-smelling notes, namely, of sulphur, popcorn, hazelnut, toasted, roasted, and ripe fruits [28,29]. In turn, the oxidative degradation of Phe and Thr is associated with the formation of phenylacetaldehyde and sotolon, respectively, both oxidation wine markers [30,31].…”

Section: Resultsmentioning

confidence: 99%

Amino Acids and Biogenic Amines Evolution during theEstufagemof Fortified Wines

Pereira

Pereira²,

Trujillo³

et al. 2015

Journal of Chemistry

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The current study was focused on the impact of accelerated ageing (heating step) on the amino acid and biogenic amine profiles of fortified wines. In this sense, three Madeira wines from two commonly used grape varieties (one red and the other white) were analysed during the heating, at standard (45°C, 3 months) and overheating (70°C, 1 month) conditions, following a precolumn derivatization procedure using iodoacetic acid,o-phthaldialdehyde, and 2-mercaptoethanol, carried out in the injection loop prior to RP-HPLC-FLD detection. Eighteen amino acids were identified, with arginine being the most abundant. An important decrease of the amino acid levels was detected during the standard heating (up to 30%), enhanced up to 61% by the temperature increase. Cysteine, histidine, and asparagine revealed the greatest decreases at 45°C. Conversely, some amino acids, such as asparagine, slightly increased. Four biogenic amines were identified but always in trace amounts. Finally, it was observed that the accelerated ageing did not favour the biogenic amine development. The results also indicate that the heating process promotes the amino acid transformation into new ageing products.

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“…2,4,5-trimethyl oxazole (nutty-like flavor), an aroma compound resulting from the reactions between diacetyl and aminoacids (Marchand et al, 2011), was also increased by prolonged aerated growth. 2,4,5-trimethyl oxazole contributes to the aroma profile of roasted foods (e.g., potato, peanuts, coffee), but is also a powerful odorant in wine (Marchand et al, 2000, 2011) and Chinese traditional vinegars (Yu et al, 2012; Zhu et al, 2016). As this compound has not been previously identified among the metabolites produced by respiration-competent LAB, this aspect deserves further investigation.…”

Section: Discussionmentioning

confidence: 99%

Effect of Respiratory Growth on the Metabolite Production and Stress Robustness of Lactobacillus casei N87 Cultivated in Cheese Whey Permeate Medium

et al. 2019

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Cheese whey permeate (WP) is a low-cost feedstock used for the production of biomass and metabolites from several lactic acid bacteria (LAB) strains. In this study, Lactobacillus casei N87 was cultivated in an optimized WP medium (WPM) to evaluate the effect of anaerobic and respiratory conditions on the growth performances (kinetics, biomass yield), consumption of sugars (lactose, galactose, glucose) and citrate, metabolite production [organic acids, volatile organic compounds (VOCs)] and stress survival (oxidative, heat, freezing, freeze-drying). The transcription of genes involved in the main pathways for pyruvate conversion was quantified through Real Time-PCR to elucidate the metabolic shifts due to respiratory state. Cultivation in WPM induced a diauxic growth in both anaerobic and respiratory conditions, and L. casei N87 effectively consumed the lactose and galactose present in WPM. Genomic information suggested that membrane PTS system and tagatose-6-P pathway mediated the metabolism of lactose and galactose in L. casei N87. Respiration did not affect specific growth rate and biomass production, but significantly altered the pyruvate conversion pathways, reducing lactate accumulation and promoting the formation of acetate, acetoin and diacetyl to ensure the redox balance. Ethanol was not produced under either cultivation. Pyruvate oxidase ( pox ), acetate kinase ( ack ), α-acetolactate decarboxylase ( ald ), acetolactate synthase ( als ) and oxaloacetate decarboxylase ( oad ) genes were up-regulated under respiration, while L-lactate dehydrogenase ( ldh ), pyruvate formate lyase ( pfl ), pyruvate carboxylase ( pyc ), and phosphate acetyltransferase ( pta ) were down regulated by oxygen. Transcription analysis was consistent with metabolite production, confirming that POX-ACK and ALS-ALD were the alternative pathways activated under aerobic cultivation. Respiratory growth affected the production of volatile compounds useful for the development of aroma profile in several fermented foods, and promoted the survival of L. casei N87 to oxidative stresses and long-term storage. This study confirmed that the respiration-based technology coupled with cultivation on low-cost medium may be effectively exploited to produce competitive and functional starter and/or adjunct cultures. Our results, additionally, provided further information on the activation and regulation of metabolic pathways in homofermentative LAB grown under respiratory promoting conditions.

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The Cysteine Reaction with Diacetyl under Wine‐Like Conditions: Proposed Mechanisms for Mixed Origins of 2‐Methylthiazole, 2‐Methyl‐3‐thiazoline, 2‐Methylthiazolidine, and 2,4,5‐Trimethyloxazole

Cited by 18 publications

References 36 publications

Formation and Accumulation of Acetaldehyde and Strecker Aldehydes during Red Wine Oxidation

Formation and Accumulation of Acetaldehyde and Strecker Aldehydes during Red Wine Oxidation

Amino Acids and Biogenic Amines Evolution during theEstufagemof Fortified Wines

Effect of Respiratory Growth on the Metabolite Production and Stress Robustness of Lactobacillus casei N87 Cultivated in Cheese Whey Permeate Medium

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