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…

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.

Read More

CHARACTERIZATION OF THE VOLATILE COMPOUNDS PROFILE OF COMMERCIAL GRAPPAS OBTAINED FROM THE POMACE OF AMARONE WINES

Grappa is a traditional Italian alcoholic beverage, with an alcohol content generally between 40-60% vol., obtained from the distillation of grape pomace used for the production of wine. Grappa are often aged in wooden barrels. There are various types of grappa: young, aromatic, aged, extra-aged depending on whether the distillate comes from aromatic vines or is aged in wooden barrels for shorter or longer periods. There is also flavored grappa if herbs, fruit or roots are added. All this makes it an extremely heterogeneous product both from an organoleptic and compositional point of view.

Read More

ANTI-TRANSPIRANT MODULATION OF GRAPE RIPENING: EFFECTS ON MERLOT VINE DEVELOPMENT AND ROSÉ WINE PHENOLIC AND AROMATIC PROFILES

Climate changes are impacting viticultural regions throughout the world with temperature increases being most prevalent.1 These changes will not only impact the regions capable of growing grapes, but also
the grapes that can be grown.2 As temperatures rise the growing degree days increase and with it the sugar accumulation within the berries and subsequent alcohol levels in wine. Consequently, viticultural
practices need to be examined to decrease the levels of sugars.

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

EFFECT OF FUMARIC ACID ON SPONTANEOUS FERMENTATION IN GRAPE MUST

Malolactic fermentation (MLF)¹, the decarboxylation of L-malic acid into L-lactic acid, is performed by lactic acid bacteria (LAB). MLF has a deacidifying effect that may compromise freshness or microbiological stability in wines² and can be inhibited by fumaric acid [E297] (FA). In wine, can be added at a maximum allowable dose of 0.6 g/L³. Its inhibition with FA is being studied as an alternative strategy to minimize added doses of SO₂⁴. In addition, wine yeasts are capable of metabolizing and storing small amounts of FA and during alcoholic fermentation (AF).

Read More