terclim by ICS banner
IVES 9 IVES Conference Series 9 PHOTOCHEMICAL DEGRADATION OF TRYPTOPHAN IN MODEL WINE: IMPACT OF HEAVY METALS AND OXYGEN ON 2-AMINOACETOPHENONE FORMATION

PHOTOCHEMICAL DEGRADATION OF TRYPTOPHAN IN MODEL WINE: IMPACT OF HEAVY METALS AND OXYGEN ON 2-AMINOACETOPHENONE FORMATION

Abstract

The wine industry worldwide faces more and more challenges due to climate change, such as increased dryness in some areas, water stress, sunburn and early harvesting during hot summer temperatures¹. One of the resulting problems for the wine quality might be a higher prevalence of the untypical aging off-flavor (ATA)². A substance, which Rapp and Versini made responsible for ATA, is the 2-aminoace-tophenone (2-AAP)³. 2-AAP in wine causes a naphthalene, wet towels, wet wool, acacia flower or just a soapy note⁴. The formation of the substance occurs via the degradation of tryptophan and the trypto-phan metabolite indole-3-acetic acid. The formation of 2-AAP is promoted by abiotic stress factors such as drought, low nitrogen content and high temperature, and by microorganisms via riboflavin, known as a photosensitizer5. In this study, the influence of other abiotic factors, namely oxygen and heavy me-tals, on the light-induced degradation of tryptophan to 2-AAP was investigated. Model wine with 0.53 µmol/l riboflavin was treated with UV-C light to stimulate tryptophan degradation. A linear increase in the intensity of UV-C light exposure caused a linear increase of 2-AAP. Increasing oxygen in the model wine supported the production of 2-AAP verifying that tryptophan degradation via riboflavin follows an oxidative pathway. Indeed, 2-AAP production decreased by 81 % when oxygen was reduced from saturation to anoxic conditions. It was also found that the presence of heavy metals led to a significant reduction of 2-AAP: 0.1 mmol/l Fe²+ decreased 2-AAP by 63 %, and 0.1 mmol/l Cu²+ decreased 2-AAP by 32 %. This observation can be explained by the Fenton reaction which requires Fe²+ and/or Cu²+ to produce – in this case – acetaldehyde from ethanol. It is suggested that the Fenton reaction acts as a competitive reaction to the photosensitized production of 2-AAP. As a lateral observation, the model wine in this study turned yellow after being UV-C radiated. The LC-MS signal suggested the substance lumichrome; its signal increased with the more yellow color of the model wine. Accordingly, riboflavin could not only act as a photosensitizer but also degrade itself after exposure to light.

 

1. Santos, J. A. et al. (2020). A Review of the Potential Climate Change Impacts and Adaptation Options for European Viticulture. Applied Sciences, 10(9), 3092. https://doi.org/10.3390/app10093092
2. van Leeuwen, C. et al. (2020). Recent advancements in understanding the terroir effect on aromas in grapes and wines. OENO One, 54(2). https://doi.org/10.20870/oeno-one.2020.54.4.3983 
3. Rapp, A., Versini, V., Ullemeyer, H. (1993). 2-aminoacetophenone: Causal component of ‘untypical aging flavour’ (‘naphthale-ne note’, ‘hybrid note’) of wine. Vitis, 32(1), 61-62. https://doi.org/10.5073/vitis.1993.32.61-62
4. Alpeza, I. et al. (2021). Atypical aging off-flavour and relation between sensory recognition and 2-aminoacetophenone in Croatian wines. Journal of Central European Agriculture, 22(2), 408-419. https://doi.org/10.5513/JCEA01/22.2.3103
5. Hühn, T. et al. (1999). Release of undesired aroma compound from plant hormones during alcoholic fermentation. Vitiv. Enol. Sci., 54, 105-113.

DOI:

Publication date: February 9, 2024

Issue: OENO Macrowine 2023

Type: Article

Authors

Svetlana Cvetkova¹, Sarah Edinger¹, Daniel Zimmermann¹ und Dominik Durner¹

1. Weincampus Neustadt/DLR Rheinpfalz, Institute for Viticulture and Enology, Breitenweg 71, D-67435 Neustadt an der Weinstraße, Germany

Contact the author*

Keywords

2-aminoacetophenone, iron, oxygen, riboflavin

Tags

IVES Conference Series | oeno macrowine 2023 | oeno-macrowine

Citation

Related articles…

BORDEAUX RED WINES WITHOUT ADDED SULFITES SPECIFICITIES: COMPOSITIONAL AND SENSORY APPROACHES TOWARDS HIGHLIGHTING AND EXPLAI-NING THEIR SPECIFIC FRUITINESS AND COOLNESS

With the development of naturality expectations, wines produced without any addition of sulfur dioxide (SO₂) become very popular for consumers and such wines are increasingly present on the market. Recent studies also showed that Bordeaux red wines without added SO₂ could be differentiated from a sensory point of view from similar wines produced with SO₂¹. Thus, the aim of the current study was to characterize from a sensory point of view, specific aromas of wines without added SO₂ and to identify compounds involved.

Read More

REVEALING THE ORIGIN OF BORDEAUX WINES WITH RAW 1D-CHROMATOGRAMS

Understanding the composition of wine and how it is influenced by climate or wine-making practices is a challenging issue. Two approaches are typically used to explore this issue. The first approach uses chemical
fingerprints, which require advanced tools such as high-resolution mass spectrometry and multidimensional chromatography. The second approach is the targeted method, which relies on the widely available 1-D GC/MS, but involves integrating the areas under a few peaks which ends up using only a small fraction of the chromatogram.

Read More

SENSORY IMPROVEMENT OF DEALCOHOLISED WINES

Interest and willing-ness to buy alcohol-free wines by customers is increasing for several years [1]. Due to the rising relevance of dealcoholised wines it is the objective of this study to contribute to a better understanding of the flavor variation among dealcoholised wines and to explore enological measures, how to improve final quality.
First a range of commercial, alcoholfree white wines were analysed by the holistic sensory method projective mapping, including a question for hedonic acceptance. Based on the combination of a non-target-HS-SPME-GC/MS analysis with sensory analysis we obtained a clustering of the wines into three groups.

Read More

PRECISE AND SUSTAINABLE OENOLOGY THROUGH THE OPTIMIZED USE OF AD- JUVANTS: A BENTONITE-APPLIED MODEL OF STUDY TO EXPLOIT

As wine resilience is the result of different variables, including the wine pH and the concentration of wine components, a detailed knowledge of the relationships between the adjuvant to attain stability and the oenological medium is fundamental for process optimization and to increase wine durability till the time of consumption.

Read More

VOLATILE, PHENOLIC AND COLORIMETRIC CHARACTERIZATION OF THREE DIFFERENT LAMBRUSCO APPELLATIONS

Lambrusco is a commercially successful sparkling red and rosé wine. With 13.06 million litres sold in 2021 was the second best-selling Italian wine after Chianti. According to National Catalogue of Vine Varieties there are thirteen Lambrusco Varieties with which to date are produced seven PDO wines. Among these, “Lambrusco Salamino di Santa Croce”, “Lambrusco Grasparossa di Castelvetro” and “Lambrusco di Sorbara” are the only ones that can be considered mono-varietal appellations, all located in Modena area. The PDOs contemplate the possibility of producing wines by secondary fermentation either in tank (Charmat method), or in bottle (Classico method). Sur lie is a third method commonly employed for Lambrusco, similar to the Classico method, from which differs for the absence of disgorgement.

Read More