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…

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.

SENSORY PROFILES AND EUROPEAN CONSUMER PREFERENCE RELATED TOAROMA AND PHENOLIC COMPOSITION OF WINES MADE FROM FUNGUSRESISTANT GRAPE VARIETIES (PIWI)

Planting grape varieties with several resistance loci towards powdery and downy mildew reduces the use of fungicides significantly. These fungus resistant or PIWI varieties (acronym of German Pilzwiderstandsfähig) contribute significantly to the 50% pesticide reduction goal, set by the European Green Deal for 2030. However, wine growers hesitate to plant PIWIs as they lack experience in vinification and are uncertain, how consumer accept and buy wines from these yet mostly unknown varieties. Grapes from four white and three red PIWI varieties were vinified in three vintages to obtain four diffe-rent white and red wine styles, respectively plus one rosé.

OPTIMIZATION OF EXTRACTION AND DEVELOPMENT OF AN LC-HRMS METHOD TO QUANTIFY GLUTATHIONE IN WHITE WINE LEES AND YEAST DERIVATIVES

Glutathione is a natural tripeptide composed of l-glutamate, l-cysteine and glycine, found in various foods and beverages. In particular, glutathione can be found in its reduced (GSH) or oxidized form (GSSG) in must, wine or yeasts¹. Numerous studies have highlighted the importance of GSH in wine quality and aging potential². During winemaking, especially during aging on lees, GSH helps prevent the harmful effects of oxidation on the aroma of the wine³. Nevertheless, the amounts of GSH/GSSG present in wine lees are often unknown and the choice of operating conditions (quantity of lees and aging time) remains empirical.

MONITOR SOME KEY PARAMETERS THROUGH THE IMPLEMENTATION OFCONTINUOUS CONTROL SYSTEMS OF THE MUST-WINE DURING MACERATION-FERMENTATION IN RED WINEMAKING TO MANAGE OPERATIONS IN “AUTOMATION”

This study is aimed to develop a complete tool for the winemaker with, complete and targeted “winemaking recipes” that can be adapted to criteria set by the winemaker, such as: grape variety, grape health status, degree of ripening, desired wine, redox status throughout the alcoholic fermentation.
To get such aim, specific sets of experiments using red grape juices from different varieties (Nebbiolo, Barbera, Pinot noir, etc.) collected at different technological and phenolic maturity points, will be held with “automatized 4.0 tanks” equipped with sensors for measuring: redox potential, dissolved oxygen, relative density, temperature, and color in order to collect a sufficient amount of data preparatory to the creation of operating models in the most widely winemaking situations in which the automatized 4.0 tanks “will be able to independently respond” with the right corrective actions (opening/closing aeration valve, execution/block pumping overs , etc.) if the key parameters exceed the limits of the recommended ranges set in the selected recipe.

UNCOVERING THE ROLE OF BERRY MATURITY STAGE AND GRAPE GENOTYPE ON WINE CHARACTERISTICS: INSIGHTS FROM CHEMICAL CHARACTERISTICS AND VOLATILE COMPOUNDS ANALYSIS

In a climate change context and aiming for sustainable, high-quality Bordeaux wine production, this project examines the impact of grape maturity levels in various cultivars chosen for their adaptability, genetic diversity, and potential to enhance wine quality. The study explores the effects on wine compo-sition and quality through sensory and molecular methods. We studied eight 14-year-old Vitis vinifera cv. grape varieties from the same area (VITADAPT plots 1 and 5): Cabernet Franc, Cabernet Sauvignon, Carmenère, Castets, Cot, Merlot, Petit Verdot, and Touriga Nacional.