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…

MODULATION OF YEAST-DERIVED AROMA COMPOUNDS IN CHARDONNAY WINES USING ENCAPSULATED DIAMMONIUM PHOSPHATE TO CONTROL NUTRIENT RELEASE

Yeast-derived aroma compounds are the result of different and complex biochemical pathways that mainly occur during alcoholic fermentation. Many of them are related -but not limited- to the availability of nutrients in the fermentation medium and linked to nitrogen metabolism and biomass produced. Besides, the metabolic phase of yeast also regulates the expression of many enzymes involved in the formation of aroma active compounds. The work investigates the overall effect of continuous supplementation of nutrients during alcoholic fermentation of a grape must on the volatile composition of wines.

Read More

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.

Read More

IMPACT OF ABIOTIC AND BIOTIC FACTORS ON BIOADHESION PROPERTIES OF BRETTANOMYCES BRUXELLENSIS

Brettanomyces bruxellensis is an ubiquitous yeast associated with different fermentation media such as beer and kombucha, where its presence is beneficial to bring an aromatic typicity. However, it is a main spoilage yeast in wines, in which it produces volatile phenols responsible for organoleptic deviations causing significant economic losses (Chatonnet et al., 1992). Cellar and winery equipment’s are considered as the first source of contamination, during fermentation and wine ageing process (Connel et al., 2002). Indeed, it is possible to find B. bruxellensis in the air, on walls and floors of the cellars, on small materials, vats and barrels.

Read More

REDUCING NITROGEN FERTILIZATION ALTERS PHENOLIC PROFILES OF VITIS VINIFERA L. CV. CABERNET GERNISCHT WINE OF YANTAI, CHINA

Nitrogen (N) fertilizer is important for grape growth and the quality of wine. It is essential to address the mismatch between N application and wine composition. Cabernet Gernischt (Vitis vinifera L.), as one of the main wine-grape cultivars in China, was introduced to Yantai wine region in 1892. This grape cultivar is traditionally used for quality dry red wine with fruit, spices aroma, ruby red and full-bodied wines. In order to regulate vine growth and improve grape and wine quality, Cabernet Gernischt grapevines were subjected to decreased levels of N treatments, compared to normal N supply treatment, during grape growing seasons of 2019 and 2020.

Read More

Molecular approaches for understanding and modulating wine taste

Wine consumers generally demand wines having a perception of softer tannins and less ripe, having a heaviness and richness on palate (full-body wine) with a limpid and stable color. However, polyphenol
(tannins)-rich wines have been also correlated with unpleasant taste properties such as astringency and
bitterness when perceived at high intensities. Modulating these unpleasant properties could be important for consumer’s approval of wines.

Read More