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…

CHARACTERIZATION AND ANTIBACTERIAL ACTIVITY OF A POLYPHENOLIC EXTRACT OBTAINED BY GREEN SUPERCRITICAL CO₂ EXTRACTION FROM RED GRAPE POMACE

Upgrading wine industry solid wastes is considered as one of the main strategies to support the circular economy. Red grape pomaces constitute a rich source of polyphenols, which have been shown to possess antioxidant properties and to provide benefits for human and animal health. The objective of this work was to obtain and characterise polyphenolic extracts from red grape pomaces via green supercritical CO₂ extraction using ethanol as a co-solvent, and to evaluate their antibacterial activity against susceptible and multidrug-resistant Escherichia coli strains of animal intestinal origin.

MAPPING OF GAS-PHASE CO₂ IN THE HEADSPACE OF CHAMPAGNE GLASSES BY USING AN INFRARED LASER SENSOR UNDER STATIC TASTING CONDITIONS

From the chemical angle, Champagne wines are complex hydro-alcoholic mixtures supersaturated with dissolved carbon dioxide (CO₂). During the pouring process and throughout the several minutes of tasting, the headspace of a champagne glass is progressively invaded by many chemical species, including gas-phase CO₂ in large majority. CO₂ bubbles nucleated in the glass and collapsing at the champagne surface act indeed as a continuous paternoster lift for aromas throughout champagne or sparkling wine tasting [1]. Nevertheless, inhaling a gas space with a concentration of gaseous CO₂ close to 30% and higher triggers a very unpleasant tingling sensation, the so-called “carbonic bite”, which might completely perturb the perception of the wine’s bouquet.

UNTARGETED METABOLOMICS ANALYSES TO IDENTIFY A NEW SWEET COMPOUND RELEASED DURING POST-FERMENTATION MACERATION OF WINE

The gustatory balance of dry wines is centered on three flavors, sourness, bitterness and sweetness. Even if certain compounds were already identified as contributing to sweetness, some taste modifications remain largely unexplained1,2. Some empirical observations combined with sensory analyzes have shown that an increase of wine sweetness occurs during post-fermentation maceration³. This step is a key stage of red winemaking during which the juice is left in contact with the marc, that contains the solid parts of the grape (seeds, skins and sometimes stems). This work aimed to identify a new taste-active compound that contributes to this gain of sweetness.

EFFECT OF MICRO-OXYGENATION IN COLOR OF WINES MADE WITH TOASTED VINE-SHOOTS

The use of toasted vine-shoots (SEGs) as an enological tool is a new practice that seeks to improve wines, differentiating them and encouraging sustainable wine production. The micro-oxygenation (MOX) technique is normally combined with alternative oak products with the aim to simulate the oxygen transmission rate that takes place during the traditional barrel aging. Such new use for SEGs implies a reduction in color due to the absorption by the wood of the responsible compounds, therefore, given the known effect that MOX has shown to have on the modification of wine color, its use together with the SEGs could result in an interesting implementation with the aim to obtain final wines with more stable color over time.

SENSORY PROFILES AND EUROPEAN CONSUMER PREFERENCE RELATED TOAROMA AND PHENOLIC COMPOSITION OF WINES MADE FROM FUNGUSRESISTANT GRAPE VARIETIES (PIWI)

Planting grape varieties with several resistance loci towards powdery and downy mildew reduces the use of fungicides significantly. These fungus resistant or PIWI varieties (acronym of German Pilzwiderstandsfähig) contribute significantly to the 50% pesticide reduction goal, set by the European Green Deal for 2030. However, wine growers hesitate to plant PIWIs as they lack experience in vinification and are uncertain, how consumer accept and buy wines from these yet mostly unknown varieties. Grapes from four white and three red PIWI varieties were vinified in three vintages to obtain four diffe-rent white and red wine styles, respectively plus one rosé.