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…

EFFECT OF DIFFERENT VITICULTURAL AND ENOLOGICAL PRACTICES ON THE PHENOLIC COMPOSITION OF RED WINES

Global climate change is exerting a notable influence on viticulture sector and grape composition. The increase in temperature and the changes in rainfall pattern are causing a gap between phenolic and technological grape maturities [1]. As a result, the composition of grapes at harvest time and, consequently, that of wines are being affected, especially with regards to phenolic composition. Hence, wine quality is decreasing due to changes in the organoleptic properties, such as color and astringency, making necessary to implement new adaptive technologies in wineries to modulate these properties in order to improve wine quality.

MOUSY OFF-FLAVOURS IN WINES: UNVEILING THE MICROORGANISMS BEHIND IT

Taints and off-flavours are one of the major concerns in the wine industry and even if the issues provoked by them are harmless, they can still have a negative impact on the quality or on the visual perception of the consumer. Nowadays, the frequency of occurrence of mousy off-flavours in wines has increased.
The reasons behind this could be the significant decrease in sulphur dioxide addition during processing, the increase in pH or even the trend for spontaneous fermentation in wine. This off-flavour is associated with Brettanomyces bruxellensis or some lactic acid bacteria metabolisms.

EVALUATION OF A SEAWEED EXTRACT OF RUGULOPTERYX OKAMURAE AGAINST ERYSIPHE NECATOR IN GRAPEVINE

Powdery mildew, caused by Erysiphe necator, is a widespread disease that causes high economical losses in viticulture. The main strategy to control the disease is the recurrent application of sulphur based phytochemical compounds. However, in order to reduce their accumulation in the environment and promote the sustainability of the sector, the European Commission has applied restrictions to the number of pesticide treatments and the maximum quantity of fungicides to be applied in viticulture. Seaweeds, in particular macroalgae, are marine resources rich in sulphated polysaccharides with bio-protective potential for the plant, representing an environmentally-friendly alternative approach for sustainable wine production.

EFFECT OF MANNOPROTEIN-RICH EXTRACTS FROM WINE LEES ON PHENOLICCOMPOSITION AND COLOUR OF RED WINE

In 2022, wine production was estimated at around 260 million hl. This high production rate implies to generate a large amount of by-products, which include grape pomace, grape stalks and wine lees. It is estimated that processing 100 tons of grapes leads to ~ 22 tons of by-products from which ~ 6 tons are lees [1]. Wine lees are a sludge-looking material mostly made of dead and living yeast cells, yeast debris and other particles that precipitate at the bottom of wine tanks after alcoholic fermentation. Unlike grape pomace or grape stalks, few strategies have been proposed for the recovery and valorisation of wine less [2].

FERMENTATION POTENTIAL OF INDIGENOUS NON-SACCHAROMYCES YEASTS ISOLATED FROM MARAŠTINA GRAPES OF CROATIAN VINEYARDS

The interest in indigenous non-Saccharomyces yeast for use in wine production has increased in recent years because they contribute to the complex character of the wine. The aim of this work was to investigate the fermentation products of ten indigenous strains selected from a collection of native yeasts established at the Institute for Adriatic Crops and Karst Reclamation in 2021, previously isolated from Croatian Maraština grapes, belonging to Hypopichia pseudoburtonii, Metschnikowia pulcherrima, Metschnikowia sinensis, Metschnikowia chrysoperlae, Lachancea thermotolerans, Pichia kluyveri, Hanseniaspora uvarum, Hanseniaspora guillermondii, Hanseniaspora pseudoguillermondii, and Starmerella apicola species, and compare it with commercial non-Saccharomyces and Saccharomyces strains.