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…

YEAST DERIVATIVE PRODUCTS: CHARACTERIZATION AND IMPACT ON RIBOFLAVIN RELEASE DURING THE ALCOHOLIC FERMENTATION

Light-struck taste (LST) is a wine fault that can occur in white and sparkling wines when exposed to light. This defect is mainly associated to the formation of methanethiol and dimethyl disulfide due to light-induced reactions involving riboflavin (RF) and methionine [1]. The presence of RF in wine is mainly due to the metabolism of yeast [2] which fermenting activity can be favoured by using yeast derivative products (YDPs) as nutrients. Nonetheless, a previous study showed the addition of YDPs before the alcoholic fermentation (AF) led to higher concentrations of RF in wines [3]. Due to the widespread use of YDPs in the winemaking process, this study aimed to understand the possible relation between the content of RF in wine and the YDP adopted as nutrient for AF.

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

FACTORS AFFECTING QUERCETIN SOLUBILITY IN SANGIOVESE RED WINE: FIRST RESULTS

Quercetin (Q) is present in grape in form of glycosides and as aglycone. These compounds are extracted from grape skins during winemaking. In wines, following the hydrolysis reactions, the amount of quercetin aglycon can exceed its solubility value. Unfortunately, a threshold solubility concentration for quercetin in wine is not easy to determine because it depends on wine matrix (Gambuti et al., 2020).

Read More

FLAVANOL COMPOSITION OF VARIETAL AND BLEND WINES MADE BEFORE AND AFTER FERMENTATION FROM SYRAH, MARSELAN AND TANNAT

Background: The Flavan-3-ol extraction from grape skin and seed during red-winemaking and their retention into wines depend on many factors, some of which are modified in the winemaking of blend wines. Recent research shows that Marselan, have grapes with high proportion of skins with high concentrations of flavanols, but produces red-wines with low proportion of skin derived flavanols, differently to the observed in Syrah or Tannat. But the factors explaining these differences are not yet understood.

Read More

SUB-CRITICAL WATER: AN ORIGINAL PROCESS TO EXTRACT ANTIOXIDANTS COMPOUNDS OF WINE LEES

Wine lees are quantitatively the second most important wine by-product after grape stems and marc [1]. In order to recycle, distilleries recovered ethanol and tartaric acid contained in wine lees but yeast biomass is often unused. It has already been demonstrated that this yeast biomass could be upcycled to produce yeast extracts of interest for wine chemical stabilization [2]. In addition, it is well known that lees, during aging, release compounds that preserve wine from oxidation.

Read More