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…

INVESTIGATION OF FILM COATINGS AS A PROTECTIVE LAYER IN REDUCING THE ABSORPTION OF SMOKE PHENOLS INTO PINOT NOIR GRAPES

Wine grapes exposed to wildfire smoke have resulted in wines with burnt and ashy sensory characteristics¹, that are undesirable qualities in wine. In extreme wildfire events, this can lead to total loss of grape crop. Currently there are no effective solutions in the market to prevent the uptake of smoke compounds into grapes. In this study, previously developed innovative film coatings were tested to analyze their effectiveness in reducing smoke phenol absorption². Four different cellulose nanofiber-based film types were investigated.

INFLUENCE OF THE THICKNESS OF OAK ALTERNATIVES ON THE COMPOSITION AND QUALITY OF RED WINES

Aging red wines in oak barrels is an expensive and laborious process that can only be applied to wines with a certain added value. For this reason, the use of oak alternatives coupled with micro-oxygenation has progressively increased over recent years, because it can reproduce the processes taking place in the barrels more economically and quickly [1]. Several studies have explored how oak alternatives [2-5] can contribute to wine composition and quality but little is known about the influence of their thickness.

LARGE SURVEY OF THE CHEMICAL COMPOSITION OF WINES RESULTING OF THE PRESSING OF RED WINE MARC. FIRST RESULTS

In the Bordeaux vineyards, press red wine represents about 15% of the volume of wines. Valuing this large volume of press wine is necessary from an economic point of view, of course, but also because of their organoleptic contribution to the blend. Nevertheless, there is a lack of recent knowledge on the composition of press wines. This work aims to establish an initial assessment of their composition (aromatic and polyphenolic) and to set up hypothesis on to the links with their sensorial identity.

A NEW TOOL TO QUANTIFY COMPOUNDS POTENTIALLY INVOLVED IN THE FRUITY AROMA OF RED WINES. DEVELOPMENT AND APPLICATION TO THE STU-DY OF THE FRUITY CHARACTER OF RED WINES MADE FROM VARIOUS GRAPE VARIETIES

A wide range of olfactory descriptors ranging from fresh and jammy fruit notes to cooked and oxidized fruit notes could describe the fruity aroma of red wines [1]. The fruity character of a wine is mainly related to the grape variety selected, to the terroir and the vinification process applied for its conception. In white wines, some volatile compounds confer directly their aroma to the wine while the question of “key” compound is more complex in red wines. According to many studies performed over the past decades, some fruity ethyl esters are directly involved in the fruity perception of red wines while others, present at subthreshold concentrations, participate indirectly to the fruity expression via perceptive interactions [2].

DETERMINATION OF FREE AMINO ACIDS, AMINO ACID POTENTIAL AND PROTEASE ACTIVITY IN THE LEES AND STILL WINES OF CHAMPAGNE

Prior to winemaking, organic or mineral nitrogen compound concentrations are usually measured in the vineyard and in grape musts. These indicators facilitate vine cultivation decisions, usually through yield or vigor. During vinification, yeast and bacteria metabolize nitrogen compounds in the musts in order to generate biomass. After fermentation, the microorganisms rerelease a part of this nitrogen as soluble compounds into the wines. Another part remains bound in the lees and can be lost during racking. The must’s natural nitrogen quantities, additional supplements during fermentation, and lees contact management enhance the release of nitrogen compounds to the wines. During ageing these nitrogen compounds – primarily the amino acids – are implicated in the generation of odorous compounds such as heterocycles(1).