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…

HOW DO ROOTSTOCKS AFFECT CABERNET SAUVIGNON AROMATIC EXPRESSION?

Grape quality potential for wine production is strongly influenced by environmental parameters such as climate and agronomic factors such as rootstock. Several studies underline the effect of rootstock on vegetative growth of the scions [1] and on berry composition [2, 3] with an impact on wine quality. Rootstocks are promising agronomic tools for climate change adaptation and in most grape-growing regions the potential diversity of rootstocks is not fully used and only a few genotypes are planted. Little is known about the effect of rootstock genetic variability on the aromatic composition in wines; thus further investigations are needed.

THE POTENTIAL USE OF SOLUBLE POLYSACCHARIDES TO PREVENT THE OXIDATION OF ROSÉ WINES

Lately, rosé wine is rapidly increasing its popularity worldwide. Short-time macerations with the red skin of the grapes cause the partial extraction of anthocyanins, which are responsible for the pinki-sh-salmon hue of rosé wines. However, the low quantity of tannins (antioxidants) and richness in phenolic acids, which can be easily oxidized into yellowish pigments, tend to predispose rosé wines to an undesirable browning. Although the use of SO₂ for the prevention of oxidation is highly extended, this practice is expected to be reduced. Therefore, the search for alternative oenological adjuvants that prevent the oxidation and browning of rosé wines is highly desired.

FLOW CYTOMETRY, A POWERFUL AND SUSTAINABLE METHOD WITH MULTIPLE APPLICATIONS IN ENOLOGY

Flow cytometry (FCM) is a powerful technique allowing the detection, characterization and quantification of microbial populations in different fields of application (medical environment, food industry, enology, etc.). Depending on the fluorescent markers and specific probes used, FCM provides information on the physiological state of the cell and allows the quantification of a microorganism of interest within a mixed population. For 15 years, the enological sector has shown growing interest in this technique, which is now used to determine the populations present (of interest or spoilage) and the physiological state of microorganisms at the different stages of winemaking.

ABOUT THE ROLE PLAYED BY THE DIFFERENT POLYPHENOLS ON OXYGEN CONSUMPTION AND ON THE ACCUMULATION OF ACETALDEHYDE ANDSTRECKER ALDEHYDES DURING WINE OXIDATION

In a previous work1, it was suggested that the different contents in delphinidin and catechin of the grapes were determinant on the O2 consumption and Strecker aldehyde (SAs) accumulation rates. Higher delphinidin seemed to be related to a faster O2 consumption and a smaller SAs accumulation rate, and the opposite was observed regarding catechin.
In the present paper, these observations were fully corroborated by adding synthetic delphinidin to a wine model containing polyphenolic fractions (PFs) extracted from garnacha and synthetic catechin to a wine model containing PF extracted from tempranillo: The delphinin-containing garnacha model consumed O₂ significantly faster and accumulated significantly smaller amounts of SAs than the original garnacha model, and the catechin-containing tempranillo model, consumed O2 significantly slower and accumulated significantly higher amounts of SAs than the original tempranillo model.

PERCEPTUAL INTERACTIONS PHENOMENA INVOLVING VARIOUS VOLATILE COMPOUND FAMILIES LINKED TO SOME FRUITY NOTES IN BORDEAUX RED WINES

Fruity notes play a key role in the consumer’s appreciation of Bordeaux red wines. If literature provides a lot of knowledge about the nature of volatile compounds involved in this fruity expression, the sensory phenomena involving these compounds in mixture still need to be explored. Considering previous sensory works about the impact of esters and some overripening compounds, the goal of this work was to study the implication of perceptual interactions involving red wine odorant compounds of diverse origins and described as potentially affecting fruity aromatic expression.