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.

Read More

PROTEOMIC STUDY OF THE USE OF MANNOPROTEINS BY OENOCOCCUS OENI TO IMPROVE MALOLACTIC FERMENTATION

Malolactic fermentation (MLF) is a desired process to decrease acidity in wine. This fermentation, carried out mostly by Oenococcus oeni, is sometimes challenging due to the wine stress factors affecting this lactic acid bacterium. Wine is a harsh environment for microbial survival due to the presence of ethanol and the low pH, and with limited nutrients that compromise O. oeni development. This may result in slow or stuck fermentations. After the alcoholic fermentation the nutrients that remain in the medium, mainly released by yeast, can be used in a beneficial way by O. oeni during MLF.

Read More

Beyond liking scores: the importance of the drinking experience to understand our consumers

The presentation will approach the understanding of wine consumers´ perception based on the experiential model suggested by Warell (2008). In this framework, wine consumption gives rise to a
variety of experiences related to the perception, understanding, and judgment of the product. These
multidimensional facets of the drinking experience can be explored by measuring affective, cognitive,
and sensory responses of consumers, which are shown to be stable regardless of the social context.

Read More

INFLUENCE OF WINEMAKING VARIABLES AND VINEYARD LOCATIONS ON CHEMICAL AND SENSORY PROFILES OF SOUTH TYROLEAN PINOT BLANC

Pinot Blanc, an important grape variety grown in some mountain areas of Northern Italy such as South Tyrol over the last decades, with its cultivation covering 10.3% of the total vineyards, has compatible climatic conditions (e.g. heat requirements) which are normally found in the geographical areas of the mountain viticulture [1,2,3,4]. Climatic changes are hastening the growth of this variety at higher elevations, particularly for the production of high quality wine.

Read More

MODELLING THE AGEING POTENTIAL OF SYRAH RED WINES BY ACCELERATED AGEING TESTS: INFLUENCE OF ANTIOXIDANT ASSAYS AND PHENOLIC COMPOSITION

Red wine ageing is an important step in the red wine evolution and impacts its chemical and sensory characteristics through many chemicals and physico-chemical reactions. The kinetics of these evolutions depend on the wine studied and influence the wine ageing potential. Generally, high quality red wines require a longer period of bottle ageing before consumption¹. The ageing potential is an impor-tant parameter for wine quality and is related to the capacity of a wine to undergo oxidation over time². Phenolic compounds which are ones of the main substrates for oxidation can then potentially modulate ageing potential³.

Read More