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…

USE OF 13C CP/MAS NMR AND EPR SPECTROSCOPIC TECHNIQUES TO CHARACTERIZE MACROMOLECULAR CHANGES IN OAK WOOD(QUERCUS PETRAEA) DURING TOASTING

For coopers, toasting process is considered a crucial step in barrel production during which oak wood (Q. petraea) develops several aromatic nuances released to the wine during its maturation. Toasting consists of applying different degrees of heat to a barrel for a specific period. As the temperature increases, thermal degradation of oak wood structure produces a huge range of chemical compounds. Many studies have identified the main key aroma volatile compounds (whisky-lactone, furfural, eugenol, guaiacol, vanillin). However, detailed information on how the chemical structure of oak wood degrades with increasing toasting level is still lacking.

SENSORY EVALUATION OF WINE AROMA: SHOULD COLOR-DRIVEN DESCRIPTORS BE USED?

The vocabulary used to describe wine aroma is commonly organized according to color, raising the question of whether they reflect the reality of olfactory perception. Previous studies have assumed this convention of color-aroma matching, and have investigated color’s influence on the perception of aroma only in dyed white wine or in red wine from particular places of origin. Here 48 white and red varietal wines from around the world were evaluated in black glasses then in clear glasses by a panel of wine experts, who gave intensity ratings for aroma attributes commonly used by wine professionals. In black glasses, aromas conventionally associated with white wine were perceived in the red wines, and vice versa.

WHICH TERROIR-RELATED FACTORS INFLUENCE THE MOST VOLATILE COMPOUND PRODUCTION IN COGNAC BASE WINE?

Cognac is a famous spirit produced in southwest France in the region of the eponymous town from wines mainly from Vitis vinifera cv. Ugni blanc. This variety gives very acidic and poorly aromatic base wines for distillation which are produced according to a very specific procedure. Grapes are picked at low sugar concentrations ranging 13-21 °Brix and musts with high turbidity (>500 NTU) are fermented without sulphite addition [1]. Fermentative aromas, as esters and higher alcohols, are currently the main quality markers considered in Cognac spirits.

HYBRID GRAPEVINE CV BACO BLANC, BETWEEN TRADITION AND MODERNISM: FOCUS ON ENDOGENOUS EUGENOL AS RESISTANCE FACTOR TO BOTRYTIS CINEREA

The well-known antifungal and antibiotic molecule, eugenol, is widely spread in various plants including clove, basil and bay. It is also abundant in the hybrid grapevine cultivar (cv) Baco blanc (Vitis vi-nifera x Vitis riparia x Vitis labrusca), created by François Baco (19th century) in the Armagnac region. This study confirmed this cv as highly resistant to Botrytis cinerea by comparing fruit rot incidence and severity with two Vitis vinifera cultivars: Folle Blanche and Ugni Blanc. We have demonstrated the efficiency of eugenol in vitro, by further investigating the effect of small concentrations of eugenol, 3 to 4 ppm (corresponding to IC10), on B. cinerea. By comparing the two major modes of action (direct or volatile antibiosis), the vapour inhibiting effect of eugenol was more powerful. In the skin of Baco blanc berry, the total eugenol concentration reached a maximum at veraison, i.e. 1118 to 1478 μg/kg.

INFLUENCE OF GRAPE RIPENESS ON MACROMOLECULES EXTRACTABILITY FROM GRAPE SKIN TISSUES AND GRAPE SEEDS DURING WINEMAKING

A consequence of climate change is the modification of grape harvest quality and physico-chemical parameters of the obtained wine: increase in alcoholic degree, decrease in pH, and modification of the extractability of macromolecules, which leads to problems of microbiological, tartaric, colour and colloidal stability. In order to respond to these problems, the winemaking processes must be anticipated and adapted with a better knowledge of macromolecule extractability in grapes and their evolution, according to the grape variety, vintage and winemaking process. The purpose of this study was to understand 1) how the harvest date can influence the extractability of macromolecules, polysaccharides and phenolic compounds, which are responsible for wine stability 2) how to adapt the winemaking process to the harvest date in order to optimise wine quality.