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…

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.

HOW TO EVALUATE THE QUALITY OF NATURAL WINES?

The movement of Natural wines has clearly increased in the last few years, to reach a high demand from consumers nowadays. Switzerland has not been left out of this movement and has created a dedicated association in 2021. This association has the ambition to develop a specific tasting sheet for natural wines. The study of the tasting notes shows that the olfactory description of wines is recent but predominant today. But wine is a product makes to be drunk and not (just) to smell it. Based on these findings, a new 100-point tasting sheet has been developed. The main characteristics are 1) an evaluation in the mouth before the description of the olfaction, 2) to give 50% of the points on the judgment for the mouth characteristics, 3) to pejorate the visual aspects only if the wine is judged as “not drinkable” and 4) to express personal emotions.

THE POTENTIAL USE OF SOLUBLE POLYSACCHARIDES TO PREVENT THE OXIDATION OF ROSÉ WINES

Lately, rosé wine is rapidly increasing its popularity worldwide. Short-time macerations with the red skin of the grapes cause the partial extraction of anthocyanins, which are responsible for the pinki-sh-salmon hue of rosé wines. However, the low quantity of tannins (antioxidants) and richness in phenolic acids, which can be easily oxidized into yellowish pigments, tend to predispose rosé wines to an undesirable browning. Although the use of SO₂ for the prevention of oxidation is highly extended, this practice is expected to be reduced. Therefore, the search for alternative oenological adjuvants that prevent the oxidation and browning of rosé wines is highly desired.

METABOLIC INTERACTIONS OF SACCHAROMYCES CEREVISIAE COCULTURES: A WAY TO EXTEND THE AROMA DIVERSITY OF CHARDONNAY WINE

Yeast co-inoculations in winemaking have been investigated in various applications, but most often in the context of modulating the aromatic profiles of wines. Our study aimed to characterize S. cerevisiae interactions and their impact on wine by taking an integrative approach. Three cocultures and corresponding pure cultures of S. cerevisiae were characterized according to their fermentative capacities, the chemical composition and aromatic profile of the associated Chardonnay wines. The various strains studied within the cocultures showed different behaviors regarding their development.

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.