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…

EXPLORING RED WINE TYPICITY OF CORBIÈRES: EVALUATION OF THE DEGREE OF IMPACT OF VINIFICATION PROCESS ON THE CHEMICAL COMPOSITION AND ORGANOLEPTIC PROPERTIES OF WINES FROM DIFFERENT TERROIR

It is important nowadays for wine producers to create a product that is an expression of their terroir, a concept including the interaction between a place (topography, climate, soil), the people (tradition, winemaking and viticultural practices) and the resulting product (grape varieties, wines) [1]. Nonetheless, wine’s typicity linked to those terroirs must be easily recognizable by consumers thanks to distinctive sensory characters and composition [2]. Among the compounds of interest, aromatic compounds and polyphenols play an important role in the quality of red wines, by impacting on the odour, color and astringency. To explore the influence of terroir factors, including climate, soil and human practices, on the chemical and sensory profile of wines, red wines from five terroirs of the Corbières appellation were subjected to a general study approach.

WINE CONSUMER TRADE-OFF BETWEEN ORGANOLEPTIC CHARACTERISTICS AND SUSTAINABLE CLAIMS. AN EXPERIMENT ON RED WINES FROM BORDEAUX REGION

In economics, the perception of wine quality is not limited to sensorial characteristics: an indication of the region of production significantly affects the perception of quality and consumers’ WTP ([1]; [2]). However, [3] or more recently [4] show that even if a wine has an organic label, the taste of wine remains the predominant criterion in consumer preferences. The contribution of our experiment is to evaluate the impact of responsible attributes (organic label, Non Added Sulfites, HVE certification) on the appreciation of several red wines on the market. More than 280 consumers participated to the present study and they perform 25 tastings divided into 5 different sessions. 20 different red wines from Bordeaux Area are tasted.

INVESTIGATION OF FILM COATINGS AS A PROTECTIVE LAYER IN REDUCING THE ABSORPTION OF SMOKE PHENOLS INTO PINOT NOIR GRAPES

Wine grapes exposed to wildfire smoke have resulted in wines with burnt and ashy sensory characteristics¹, that are undesirable qualities in wine. In extreme wildfire events, this can lead to total loss of grape crop. Currently there are no effective solutions in the market to prevent the uptake of smoke compounds into grapes. In this study, previously developed innovative film coatings were tested to analyze their effectiveness in reducing smoke phenol absorption². Four different cellulose nanofiber-based film types were investigated.

PERCEPTUAL INTERACTIONS PHENOMENA INVOLVING VARIOUS VOLATILE COMPOUND FAMILIES LINKED TO SOME FRUITY NOTES IN BORDEAUX RED WINES

Fruity notes play a key role in the consumer’s appreciation of Bordeaux red wines. If literature provides a lot of knowledge about the nature of volatile compounds involved in this fruity expression, the sensory phenomena involving these compounds in mixture still need to be explored. Considering previous sensory works about the impact of esters and some overripening compounds, the goal of this work was to study the implication of perceptual interactions involving red wine odorant compounds of diverse origins and described as potentially affecting fruity aromatic expression.

THE EFFECT OF BENTONITE FINING ON THE VOLATILE AND NON-VOLATILE PROFILE OF ITALIAN WHITE WINES

Marselan wines have an unusual high proportion of seed derived tannins from grapes having high proportions of skins, which are rich in tannins. But the causes behind this characteristic have not yet been identified. In vintage 2023 wines were made at experimental scale (9 kg by experimental unit) from Arinarnoa, Marselan and Tannat Vitis vinifera grape cultivars by traditional maceration, and by techniques aimed to increase the wine content in skin derived tannin: addition of extraction enzymes, addition at vatting of grape-skin enological tannins, or by extended maceration, known to increase the seed derived tannin contents of wines. Macerations were of 7 days, except in the extended macerations that were of 15 days.