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…

THE EFFECT OF BENTONITE FINING ON THE VOLATILE AND NON-VOLATILE PROFILE OF ITALIAN WHITE WINES

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. Macerations were of 7 days, except in the extended macerations that were of 15 days.

PINKING PHENOMENA ON WHITE WINES: RELATION BETWEEN PINKING SUSCEPTIBILITY INDEX (PSI) AND WINE ANTHOCYANINS CONTENT

Pinking is the emergence of pink tones in white wines exclusively produced from white grape varieties, known as pinking phenomena for many years. Pinking is essentially appeared when white wines are produced under reducing conditions [1,2,3]. Pinking usually occurs after bottling and storage of white wines, but its appearance has also been described after alcoholic fermentation or even as soon as the grape must is extracted [4]. Therefore, the purpose of this work was to investigate the existence of an-thocyanins in white wines made from different white grape varieties and grown locations and critically evaluate the most common method used for predicting pinking appearance in white wines: the Pinking Susceptibility Index (PSI).

WINE SWIRLING: A FIRST STEP TOWARDS THE UNLOCKING OF THE WINE’STASTER GESTURE

Right after the pouring of wine in a glass, a myriad of volatile organic compounds, including ethanol, overwhelm the glass headspace, thus causing the so-called wine’s bouquet [1]. Otherwise, it is worth noting that during wine tasting, most people automatically swirl their glass to enhance the release of aromas in the glass headspace [1]. About a decade ago, Swiss researchers revealed the complex fluid mechanics underlying wine swirling [2]. However, despite mechanically repeated throughout wine tasting, the consequences of glass swirling on the chemical space found in the headspace of wine glasses are still barely known.

MODULATION OF YEAST-DERIVED AROMA COMPOUNDS IN CHARDONNAY WINES USING ENCAPSULATED DIAMMONIUM PHOSPHATE TO CONTROL NUTRIENT RELEASE

Yeast-derived aroma compounds are the result of different and complex biochemical pathways that mainly occur during alcoholic fermentation. Many of them are related -but not limited- to the availability of nutrients in the fermentation medium and linked to nitrogen metabolism and biomass produced. Besides, the metabolic phase of yeast also regulates the expression of many enzymes involved in the formation of aroma active compounds. The work investigates the overall effect of continuous supplementation of nutrients during alcoholic fermentation of a grape must on the volatile composition of wines.

Beyond liking scores: the importance of the drinking experience to understand our consumers

The presentation will approach the understanding of wine consumers´ perception based on the experiential model suggested by Warell (2008). In this framework, wine consumption gives rise to a
variety of experiences related to the perception, understanding, and judgment of the product. These
multidimensional facets of the drinking experience can be explored by measuring affective, cognitive,
and sensory responses of consumers, which are shown to be stable regardless of the social context.