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…

PHENOLICS DYNAMICS OF BERRIES FROM VITIS VINIFERA CV SYRAH GRAFTED ON TWO CONTRASTING ROOTSTOCKS UNDER COMBINED SALINITY AND WATER STRESSORS AND ITS EFFECT ON WINE QUALITY

Wine regions are getting warmer as average temperatures continue raising affecting grape growth, berry composition and wine production. Berry quality was evaluated in plants of Vitis vinifera cv Syrah grafted on two rootstocks, Paulsen (PL1103) and SO4, and grown under two salinity concentrations (LS:0.7dS/m and HS:2.5dSm-1) in combination with two irrigation regimes (HW:133% and CW:100%), being the seasonal water application 483mm (control, 100%). Spectrophotometer measurements from berry skin during veraison and harvest stages and from “young” wine samples, were indicative of the stressors effect and the mediation of the rootstocks. At veraison (i) total phenolics content were high under LSHW (0.7dSm-1 and high water conditions) for SO4 and PL1103.

NEW PLANT BIOPOLYMERS FOR THE COLLOIDAL STABILITY OF THE COLORING MATTER OF RED WINES

The color as well as the “clarity” of red wines are ones of the qualities required by the consumers. Red wines must have colloidal stability from its bottling to its consumption. The supplementation of red wines with additives, and especially Acacia senegal gum, contributes to its organoleptic properties such as the colloidal stabilization of the coloring matter. In a global perspective of limitation of additives in the field of enology, one of the objectives is notably (i) to reduce the use of additives in wines, by their number and/or their quantity, and (ii) to favor the use of natural additives while preserving the organoleptic and sensory qualities of wines.

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.

A NEW SPECIFIC LINEAGE OF OENOCOCCUS OENI IN COGNAC APPELLATION WINES

Oenococcus oeni is the main lactic acid bacteria (LAB) species which conducts the malolactic fermentation (MLF) in wine. During MLF, O. oeni converts malic acid into lactic acid, which modulates wine aroma composition leading to better balanced organoleptic properties. O. oeni is a highly specialized species only detected in environments containing alcohol such as wine, cider or kombucha. Genome analysis of more than 240 strains showed that they form at least 4 main phylogenetic lineages and several sublineages, which are associated with different beverages or types of wines.

CONSENSUS AND SENSORY DOMINANCE ARE DEPENDENT ON QUALITY CONCEPT DEFINITIONS

The definition of the term “quality” in sensory evaluation of food products does not seem to be consensual. Descriptive or liking methods are generally used to differentiate between wines (Lawless et al., 1997). Nevertheless, quality evaluation of a product such as wine can also relate to emotional aspects. As exposed by Costell (2002), product quality is defined as an integrated impression, like acceptability, pleasure, or emotional experiences during tasting. According to the ‘modality appropriateness’ hypothesis which predicts that wine tasters weigh the most suitable sensory inputs for a specific assess- ment (Freides, 1974; Welch & Warren, 1980), the nature of the quality definitions may modulate sensory influences.