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…

IMPACT OF MINERAL AND ORGANIC NITROGEN ADDITION ON ALCOHOLIC FERMENTATION WITH S. CEREVISIAE

During alcoholic fermentation, nitrogen is one of essential nutrient for yeast as it plays a key role in sugar transport and biosynthesis of and wine aromatic compounds (thiols, esters, higher alcohols). The main issue of a lack in yeast assimilable nitrogen (YAN) in winemaking is sluggish or stuck fermentations promoting the growth of alteration species and leads to economic losses. Currently, grape musts are often characterized by low YAN concentration and an increase of sugars concentration due to global warming, making alcoholic fermentations even more difficult. YAN depletion can be corrected by addition of inorganic (ammonia) or organic (yeast derivatives products) nitrogen during alcoholic fermentation.

Read More

PHOTO OXIDATION OF LUGANA WINES: INFLUENCE OF YEASTS AND RESIDUAL NITROGEN ON VSCS PROFILE

Lugana wines are made from Turbiana grapes. In recent times, many white and rosé wines are bottled and stored in flint glass bottles because of commercial appeal. However, this practice could worsen the aroma profile of the wine, especially as regards the development of volatile sulfur compounds (VSCs). This study aims to investigate the consequences of exposure to light in flint bottles on VSCs profile of Lugana wines fermented with two different yeasts and with different post-fermentation residual nitrogen.

Read More

IDENTIFICATION AND LEVELS OF PHENOLIC COMPOUNDS (TANINS, ANTHO-CYANS) IN RED VARIETAL WINES (PROKUPAC AND BLACK TAMJANIKA) FROM SERBIA

The phenolic compounds of red wines represent a source of numerous benefits for human health, which is why they are a constant subject of scientific research. Winemaking in Serbia has a growing economic significance, with particularly autochthonous varieties included [1]. This research identifies and quantifies phenolic compounds of Serbian red varietal wines of Prokupac and Black Tamjanika varieties. Quantification of the level of phenolics has been conducted, including molecular tannins [(+)-catechin, (-)-epicatechin, procyanidin dimers B1, B2, B3, B4], molecular anthocyanins, and the mean degree of polymerization of tannins by HPLC by UV detection, total antioxidant capacity via spectrophotometric methods and chromatic characteristics via CIELAB.

Read More

PRODUCTION OF A FUNCTIONAL BEVERAGE FROM WINEMAKING BY-PRODUCTS: A NEW WAY OF VALORISATION

In the challenge of transforming waste into useful products that can be re-used in a circular economy perspective, winery by-products can be considered as a source of potentially bioactive molecules such as polyphenols. The wine industry generates each year 20 million tons of by-products. Kombucha fermentation is an ancestral process which allow to increase the biological properties of tea by the action of a microbial consortium formed by yeasts and bacteria called SCOBY. It belongs to the field of healthy food for which the interest of consumers is growing. The objective of this work was to propose a new functional beverage made from winemaking by-products fermented by a Kombucha SCOBY.

Read More

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.

Read More