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…

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.

MICROFLUIDIC PLATFORM FOR SORTING YEAST CELLS ACCORDING TO THEIR MORPHOLOGY

In this work we briefly present a microfluidic device aiming to sort yeast cells according to their morphology. The technology is based upon microfluidic chips made out of Polydimethylsiloxane and glass using soft lithography processes and replica molding. The microfluidic device was used for encapsulating single yeast cells in liquid droplets containing growth medium. Liquid droplet containing yeast cells were sorted using a real time imaging and decision-making process.

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.

ABOUT THE ROLE PLAYED BY THE DIFFERENT POLYPHENOLS ON OXYGEN CONSUMPTION AND ON THE ACCUMULATION OF ACETALDEHYDE ANDSTRECKER ALDEHYDES DURING WINE OXIDATION

In a previous work1, it was suggested that the different contents in delphinidin and catechin of the grapes were determinant on the O2 consumption and Strecker aldehyde (SAs) accumulation rates. Higher delphinidin seemed to be related to a faster O2 consumption and a smaller SAs accumulation rate, and the opposite was observed regarding catechin.
In the present paper, these observations were fully corroborated by adding synthetic delphinidin to a wine model containing polyphenolic fractions (PFs) extracted from garnacha and synthetic catechin to a wine model containing PF extracted from tempranillo: The delphinin-containing garnacha model consumed O₂ significantly faster and accumulated significantly smaller amounts of SAs than the original garnacha model, and the catechin-containing tempranillo model, consumed O2 significantly slower and accumulated significantly higher amounts of SAs than the original tempranillo model.

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.