“Untypical Aging Off-Flavor” in Wine:  Synthesis of Potential Degradation Compounds of Indole-3-acetic Acid and Kynurenine and Their Evaluation as Precursors of 2-Aminoacetophenone

Hoenicke, Katrin; Borchert, Ole; Grüning, Kai; Simat, T. J.

doi:10.1021/jf011672r

Cited by 53 publications

(52 citation statements)

References 18 publications

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“…Sodium acetate-2-13 C, deuteroacetic acid, DHQ, and all other chemicals were from Sigma-Aldrich (Oakville, ON, Canada). N-Formylacetophenone was synthesised according to Hoenicke et al (2002).…”

Section: Methodsmentioning

confidence: 99%

PqsA is required for the biosynthesis of 2,4-dihydroxyquinoline (DHQ), a newly identified metabolite produced by Pseudomonas aeruginosa and Burkholderia thailandensis

Lépine¹,

Dekimpe²,

Lesic

et al. 2007

BCHM

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A new metabolite, 2,4-dihydroxyquinoline (DHQ), was identified in cultures of the bacteria Pseudomonas aeruginosa and Burkholderia thailandensis. We found that the biosynthesis of DHQ correlates with the presence of a functional PqsA, which is a product of the pqsABCDE operon responsible for the synthesis of 4-hydroxy-2-alkylquinolines (HAQs) in P. aeruginosa. However, DHQ is not a degradation product or precursor of HAQs. This finding sheds some light on the poorly understood biosynthesis pathway of HAQs, which includes important communication signals regulating the expression of virulence factors.

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Section: Methodsmentioning

confidence: 99%

PqsA is required for the biosynthesis of 2,4-dihydroxyquinoline (DHQ), a newly identified metabolite produced by Pseudomonas aeruginosa and Burkholderia thailandensis

Lépine¹,

Dekimpe²,

Lesic

et al. 2007

BCHM

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“…But, in light of the findings of Escudero et al (2002), namely that acetaldehyde does not seem to influence the oxidised aroma, this should be investigated further. Hoenicke et al (2002) showed that 2-amino-acetophenone, which imparts an untypical aged off-flavour (acacia, soapy) to wine, is formed via the intermediates 2-formamidoacetophenone and 3-(2-formylaminophenyl)-3-oxopropionic acid after oxidative degradation of indole-3-acetic acid. More research is necessary on wine parameters that affect white wine aroma in combination with O2, especially under South African conditions.…”

Section: Effect Of Oxygen On Wine Aromamentioning

confidence: 99%

Oxygen in Must and Wine: A review

Toit

Marais

Pretorius

et al. 2017

SAJEV

107

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The atmosphere consists of approximately 21% oxygen (O2). It plays a crucial role in many metabolic and chemical reactions on earth, thus it is of little surprise that it plays a very important role in the winemaking process. Wine can never be completely protected from it. The general use of sulphur dioxide as an anti-oxidant dates back to the early 18th century and the protection of wine from unwanted oxidative spoilage has been recognised . Oxygen can influence the composition and quality of wine drastically, either positively or negatively, and this will be the focus of this review. This review will also focus on the basic steps involved in oxidation, substrates for oxidation in wine and the evolution of wine constituents during the wine production process when in contact with different concentrations of O2. Basic reactions of oxygen in wineOxidation is the process where electron transfer takes place between reductive and oxidative partners. In wine, O 2 is predominantly responsible for this, with it being reduced to certain intermediates and eventually to hydrogen peroxide and then water. Molecular O2 exists as a diradical and is thus in a triplet ground state. This limits the reactivity of O2 and it cannot form bonds by accepting electron pairs. However, the addition of a single electron, originating from reduced transitional metal ions, can overcome this limitation. This leads to an unpaired electron in the resulting negatively-charged superoxide radical, with a second electron transfer resulting in a peroxide anion (Miller et al., 1990;Danilewicz, 2003). This phenomenon results in O2 being involved in various reactions in wine. Substrates for oxidation in winePhenolic molecules originating from grapes can basically be divided into the non-flavonoids and the flavonoids. The nonflavonoids, which are hydroxybenzoic and hydroxycinnamic derivatives, originate from the grape juice, and are normally the principal phenolic molecules in white wines at concentrations ranging from 50-250 mg/L, depending on the cultivar, winemaking techniques, etc. Examples of non-flavonoids are the tartaric esters of caffeic acid, p-coutaric acid and furanic acids. These molecules have been shown to be the main phenolic molecules in white wine that did not receive prolonged periods of skin contact, because they occur at higher concentrations in the grape juice (Margalit, 1997;Monagas et al., 2005).The second main group of grape-derived phenolics is the flavonoids. This group of molecules basically consists of two phenolic rings attached to a pyran ring. The flavanoids have a more complex structure than the non-flavonoids. In a young wine they are normally in a more unpolymerised state, but as wine matures they undergo different polymerisation reactions in which O 2 plays an important role. The most important flavonoids in wine are the anthocyanins, flavanols and flavonols. Anthocyanins occur mainly in the skins of red grape cultivars and are responsible for the colour of red wine. In young red wines their concentrations can range fr...

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“…In fermentation media containing IAA as in natural musts, however, l-kynurenine was ruled out as a precursor of AAP (Hoenicke et al 2002a). Under these conditions, IAA was considered the relevant precursor.…”

Section: Microbiological Formation Of Aapmentioning

confidence: 99%

“…As a consequence, for average concentrations of nonbound IAA in white wine of ~100 µg/L at the time point of sulfiting, the formation of sensorially relevant concentrations of greater than 1 µg/L AAP is possible within a few weeks after SO 2 addition. Intermediate products of the tryptophan metabolism other than IAA are far less able to produce AAP (Christoph et al 1998, Hoenicke et al 2002a.…”

Section: Metabolism Of the Precursor Iaamentioning

confidence: 99%

“…By decarboxylation before or after pyrrole oxidation and cleavage of the indole ring, a reaction sequence comprising 3-methylindole (skatole) and 2-formyl acetophenone gives rise to the appearance of AAP. Compound structure and reaction pathways have been described (Christoph et al 1999, Hoenicke et al 2002a, 2002b. Without addition of sulfites, the reaction does not take place.…”

Section: Factors In the Conversion Of Iaa Into Aapmentioning

confidence: 99%

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Atypical Aging Defect: Sensory Discrimination, Viticultural Causes, and Enological Consequences. A Review

Schneider

2014

Am. J. Enol. Vitic.

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Atypical aging is an off-flavor that can occur in white wines within a period of a few weeks to one year after the first addition of sulfur dioxide postfermentation. Its sensory characterization is varied and controversial, including a premature loss of varietal aroma combined with an increase in off-flavors that comprise various attributes such as mothballs, furniture varnish, acacia blossom, wet wool, and dirty dish rag. Most research agrees on 2-aminoacetophenone and other less well-identified compounds generated by degradation of indole-3-acetic acid as the causal agents. This chemical pathway is controlled by the oxygen radical scavenging capacity of the wine, which, in turn, is highly influenced by viticultural stress factors as the ultimate cause. Although oxygen is involved, atypical aging is distinct from premature oxidative aging with its own set of sensory and chemical descriptors.

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“Untypical Aging Off-Flavor” in Wine: Synthesis of Potential Degradation Compounds of Indole-3-acetic Acid and Kynurenine and Their Evaluation as Precursors of 2-Aminoacetophenone

Cited by 53 publications

References 18 publications

PqsA is required for the biosynthesis of 2,4-dihydroxyquinoline (DHQ), a newly identified metabolite produced by Pseudomonas aeruginosa and Burkholderia thailandensis

PqsA is required for the biosynthesis of 2,4-dihydroxyquinoline (DHQ), a newly identified metabolite produced by Pseudomonas aeruginosa and Burkholderia thailandensis

Oxygen in Must and Wine: A review

Atypical Aging Defect: Sensory Discrimination, Viticultural Causes, and Enological Consequences. A Review

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