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…

Influence of agrophotovoltaic on vine and must in a cool climate

The current energy crisis means that interest in agrophotovoltaics has increased significantly. The reason behind this is that the system aims to combine agricultural production with energy production. During the three-year period from 2020 to 2022, the effects of photovoltaic panels on the vine, the yield and the quality of the must were studied in Walenstadt in northern Switzerland, an area with a cool, humid climate. 65 Pinot noir vines were planted in the 160m2 study area. Because of the large edge effects, only 3 repetitions with 4 vines each could be created. A significantly lower leaf infestation by Plasmopara viticola was observed among the panels in each of the three years.

Read More

MONOSACCHARIDE COMPOSITION AND POLYSACCHARIDE FAMILIES OF LYOPHILISED EXTRACTS OBTAINED FROM POMACES OF DIFFERENT WHITE GRAPE VARIETIES

The recovery of bioactive compounds from grape and wine by-products is currently an important and necessary objective for sustainability. Grape pomace is one of the main by-products and is a rich source of some bioactive compounds such as polyphenols, polysaccharides, fatty acids, minerals and seed oil. Polysaccharides contained in the grape cell wall can be rhamnogalacturonans type II (RG-II), polysaccharides rich in arabinose and galactose (PRAG), mannoproteins (MP), homogalacturonans (HG) and non pectic polysaccharides (NPP).

Read More

PROGRESS OF STUDIES OF LEES ORIGINATING FROM THE FIRST ALCOHOLIC FERMENTATION OF CHAMPAGNE WINES

Champagne wines are produced via a two-step process: the first is an initial alcoholic fermentation of grape must that produces a still base wine, followed by a second fermentation in bottle – the prise de mousse – that produces the effervescence. This appellation produces non-vintage sparkling wines composed of still base wines assembled from different vintages, varieties, and regions. These base wines, or “reserve wines,” are typically conserved on their fine lies and used to compensate for quality variance between vintages (1). Continuously blending small amounts of these reserve wines into newer ones also facilitates preserving the producer’s “house style.”

Read More

EVOLUTION OF CHEMICAL AND SENSORIAL PROFILE OF WINES ELABORATED WITH THEIR OWN TOASTED VINE-SHOOTS AND MICRO-OXYGENATION

The positive contribution of toasted vine-shoots (SEGs, Shoot from vines – Enological – Granule) used in winemaking to the chemical and sensory profile of wines has been widely proven. However, the combination of this new enological tool with other winemaking technologies, such as micro-oxygenation (MOX), has not been studied so far. It is known that micro-oxygenation is used in wineries to stabilizes color, improves structure or combining with oak alternatives products to achieve a more effective aroma integration of wines. For that, its implementation in combination with SEGs could result in differentiated wines.

Read More

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.

Read More