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…

TANNINS AND ANTHOCYANINS KINETICS OF EXTRACTION FROM ARINARNOA, MARSELAN AND TANNAT UNDER DIFFERENT WINEMAKING TECHNIQUES

Marselan wines have an unusual high proportion of seed derived tannins from grapes having high proportions of skins, which are rich in tannins. But the causes behind this characteristic have not yet been identified. In vintage 2023 wines were made at experimental scale (9 kg by experimental unit) from Arinarnoa, Marselan and Tannat Vitis vinifera grape cultivars by traditional maceration, and by techniques aimed to increase the wine content in skin derived tannin: addition of extraction enzymes, addition at vatting of grape-skin enological tannins, or by extended maceration, known to increase the seed derived tannin contents of wines.

IMPACT OF ABIOTIC AND BIOTIC FACTORS ON BIOADHESION PROPERTIES OF BRETTANOMYCES BRUXELLENSIS

Brettanomyces bruxellensis is an ubiquitous yeast associated with different fermentation media such as beer and kombucha, where its presence is beneficial to bring an aromatic typicity. However, it is a main spoilage yeast in wines, in which it produces volatile phenols responsible for organoleptic deviations causing significant economic losses (Chatonnet et al., 1992). Cellar and winery equipment’s are considered as the first source of contamination, during fermentation and wine ageing process (Connel et al., 2002). Indeed, it is possible to find B. bruxellensis in the air, on walls and floors of the cellars, on small materials, vats and barrels.

HYDROXYTYROSOL PRODUCTION BY DIFFERENT YEAST STRAINS: SACCHAROMYCES AND NON-SACCHAROMYCES AND THE RELATION WITH THE NITROGEN CONSUMPTION

Hydroxytyrosol (HT) is a phenolic compound with extensive bioactive properties. It is present in olives, olive oil and wines. Its occurrence in wines is partly due to yeast synthetise tyrosol from tyrosine by the Ehrlich pathway, which is subsequently hydroxylated to .
The aim of the present work is to study how different yeast strains can influence in the HT production and, how the different nitrogen consumption of each strain can interfere the production of bioactive compounds.

STATISTICAL COMPARISON OF GROWTH PARAMETERS OF NINE BIOPROTECTION STRAINS IMPLEMENTED ON ARTIFICIALLY CONTAMINATED SYNTHETIC MUST

In recent years, consumer demand for products without chemical additives increased, becoming a priority for the wine sector. SO₂ is widely used for its multiple properties including antiseptics, antioxidants and antioxidasics and the strategy of bioprotection in winemaking represents now an alternative to this chemical additive. In oenology, results have highlighted the interest of bioprotection to limit the development of microorganisms like Hanseniaspora uvarum and thus reduce the doses of sulphite. Indeed, this species is considered because of its acetic acid and methyl butyl acetate production, the latter can cover the varietal character of wines.

CONTRIBUTION OF VOLATILE THIOLS TO THE AROMA OF RIESLING WINES FROM THREE REGIONS IN GERMANY AND FRANCE (RHEINGAU, MOSEL, AND ALSACE)

Riesling wines are appreciated for their diverse aromas, ranging from the fruity fresh characters in young vintages to the fragrant empyreumatic notes developed with aging. Wine tasters often refer to Riesling wines as prime examples showcasing terroir, with their typical aroma profiles reflecting the geographical provenance of the wine. However, the molecular basis of the distinctive aromas of these varietal wines from major Riesling producing regions in Europe have not been fully elucidated. In this study, new lights were shed on the chemical characterization and the sensory contribution of volatile thiols to Riesling wines from Rheingau, Mosel, and Alsace. First, Riesling wines (n = 46) from the three regions were collected and assessed for their aroma typicality by an expert panel.