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…

FERMENTATION POTENTIAL OF INDIGENOUS NON-SACCHAROMYCES YEASTS ISOLATED FROM MARAŠTINA GRAPES OF CROATIAN VINEYARDS

The interest in indigenous non-Saccharomyces yeast for use in wine production has increased in recent years because they contribute to the complex character of the wine. The aim of this work was to investigate the fermentation products of ten indigenous strains selected from a collection of native yeasts established at the Institute for Adriatic Crops and Karst Reclamation in 2021, previously isolated from Croatian Maraština grapes, belonging to Hypopichia pseudoburtonii, Metschnikowia pulcherrima, Metschnikowia sinensis, Metschnikowia chrysoperlae, Lachancea thermotolerans, Pichia kluyveri, Hanseniaspora uvarum, Hanseniaspora guillermondii, Hanseniaspora pseudoguillermondii, and Starmerella apicola species, and compare it with commercial non-Saccharomyces and Saccharomyces strains.

SIP and save the planet: a sensory and consumer exploration of australian wines made from potentially drought-tolerant white wine grapes

In order to attenuate the effects of climate change on the ability to cultivate quality wine grape vines in Australia, it is essential to adapt to the projected less favourable Australian climate scenarios. One response may be to convert a portion of the current grapevine plantings to those varieties that demand less water and can tolerate increased heat. This investigation aimed to (i) generate sensory profiles and (ii) obtain knowledge about Australian wine consumers’ preferences and opinions of Australian wines made from potentially drought tolerant, white wine grape varieties not traditionally cultivated in Australia. A Rate-All-That-Apply (RATA) sensory panel (n = 49) generated sensory profiles of 44 commercial white wines made from 7 different white grape varieties (Arinto, Fiano, Garganega, Greco, Verdejo, Verdelho and Vermentino), plus two benchmark examples each of an Australian Riesling, Pinot Gris and Chardonnay wine.

IMPACT OF RHIZOPUS AND BOTRYTIS ON WINE FOAMING PROPERTIES

A lot of work has been done on the impact of Botrytis on the foam of sparkling wines. This work often concerns wines produced in cool regions, where Botrytis is the dominant fungal pathogen. However, in southern countries such as Spain, in particularly hot years such as 2022, the majority fungal pathogen is sometimes Rhizopus. Like Botrytis, Rhizopus is a fungus that produces an aspartic protease.

MICROFLUIDIC PLATFORM FOR SORTING YEAST CELLS ACCORDING TO THEIR MORPHOLOGY

In this work we briefly present a microfluidic device aiming to sort yeast cells according to their morphology. The technology is based upon microfluidic chips made out of Polydimethylsiloxane and glass using soft lithography processes and replica molding. The microfluidic device was used for encapsulating single yeast cells in liquid droplets containing growth medium. Liquid droplet containing yeast cells were sorted using a real time imaging and decision-making process.

IDENTIFYING POTENTIAL CHEMICAL MARKERS RESPONSIBLE FOR THE PERMISSIVENESS OF BORDEAUX RED WINES AGAINST BRETTANOMYCES BRUXELLENSIS USING UNTARGETED METABOLOMICS

All along the red winemaking process, many microorganisms develop in wine, some being beneficial and essential, others being feared spoilers. One of the most feared microbial enemy of wine all around the world is Brettanomyces bruxellensis. Indeed, in red wines, this yeast produces volatile phenols, molecules associated with a flavor described as “horse sweat”, “burnt plastic” or “leather”. To produce significant and detectable concentrations of these undesired molecules, the yeasts should first grow and become numerous enough. Even if the genetic group of the strain present and the cellar temperature may modulate the yeast growth rate¹ and thus the risk of spoilage, the main factor seems to be the wines themselves, some being much more permissive to B. bruxellensis development than others.