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…

MODELLING THE AGEING POTENTIAL OF SYRAH RED WINES BY ACCELERATED AGEING TESTS: INFLUENCE OF ANTIOXIDANT ASSAYS AND PHENOLIC COMPOSITION

Red wine ageing is an important step in the red wine evolution and impacts its chemical and sensory characteristics through many chemicals and physico-chemical reactions. The kinetics of these evolutions depend on the wine studied and influence the wine ageing potential. Generally, high quality red wines require a longer period of bottle ageing before consumption¹. The ageing potential is an impor-tant parameter for wine quality and is related to the capacity of a wine to undergo oxidation over time². Phenolic compounds which are ones of the main substrates for oxidation can then potentially modulate ageing potential³.

Grouping Vitis vinifera grapevine varieties based on their aromatic composition

Climate change is likely to impact wine typicity across the globe, raising concerns in wine regions historically renowned for the quality of their terroir1. Amongst several changes in viticultural practices, replacing some of the planting material (i.e. clones, rootstocks and cultivars) is thought to be one of the most promising potential levers to be used for adapting to climate change. But the change of cultivars also involves the issue of protecting the region’s wine typicity. In Bordeaux (France), extensive research has been conducted on identifying meridional varieties that could be good candidates to help guard against the effects of climate change2 while less research has been done concerning their impacts on Bordeaux wine typicity.

EFFECTS OF LEAF REMOVAL AT DIFFERENT BUNCHES PHENOLOGICAL STAGES ON FREE AND GLYCOCONJUGATE AROMAS OF SKINS AND PULPS OF TWO ITALIAN RED GRAPES

Canopy-management practices are applied in viticulture to improve berries composition and quality, having a great impact on primary and secondary grape metabolism. Among these techniques, cluster zone leaf removal (defoliation) is widely used to manage air circulation, temperature and light radiation of grape bunches and close environment. Since volatiles are quantitatively and qualitatively influenced by the degree of fruit ripeness, the level of solar exposure, and the thermal environment in which grapes ripen, leaf removal has been shown to affect volatile composition of grape berries [1].

NEAR INFRARED SPECTROSCOPY FOR THE ESTIMATION OF TEMPRANILLO BLANCO VOLATILE COMPOSITION ALONG GRAPE MATURATION

Grape volatile compounds are mainly responsible for wine aroma, so it is important to know the va-rietal aromatic composition throughout ripening process. Currently, there are no tools that allow mea-suring the aromatic composition of grapes, in intact berries and periodically, throughout ripening, in the vineyard or in the winery. For this reason, this work evaluated the use of near infrared spectroscopy (NIR) to estimate the aromatic composition and total soluble solids (TSS) of Tempranillo Blanco berries during ripening. For this purpose, NIR spectra (1100-2100 nm) were acquired from 240 samples of in-tact berries, collected at different dates, from veraison to overripening.

INVESTIGATING TERROIR TYPICITY: A COMPREHENSIVE STUDY BASED ON THE AROMATIC AND SENSORIAL PROFILES OF RED WINES FROM CORBIÈRES APPELLATION

Volatile compounds play a significant role on the organoleptic properties defining wines quality. This particular role was exploited in several studies with the aim to differentiate wines from a more or less extensive production area, according to their sensory profile [1], as well as their chemical composition [2,3] (Di Paola-Naranjo et al., 2011; Kustos et al., 2020). Indeed, since aroma compounds development in grapes depends primarily on the environmental conditions of the vines and grapes (soil and climate), it is conceivable that these parameters craft the aromatic signature of the wine produced, in relation to its origin (Van Leeuwen et al., 2020). In this work, a general study on the aromatic and sensorial profile of wines produced in five sub-regions of the Corbières denomination, a renowned red grape varieties viticultural region in South France, was reported.