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…

AGEING REVEALS THE TERROIR OF AGED RED BORDEAUX WINES REGARDLESS OF THE VINTAGES! TARGETED APPROACH USING ODOROUS COMPOUNDS LEVELS INCLUDING TERPENES AND C13 NORISOPRENOIDS

The chemistry of wine is notably complex and is modified by ageing of the bottles. The composition of wines is the result of vine production (under the influence of vintage, climate and soils); yeast production (under the influence of juice composition and fermentation management); lactic bacteria production (under the influence of young wine composition and malolactic fermentation management); and of the ageing process either in vats, barrels or bottles or both. The composition is linked to the quality perceived by consumers but also to their origin, sometimes associated to the “terroir” concept.

Read More

PRECISE AND SUSTAINABLE OENOLOGY THROUGH THE OPTIMIZED USE OF AD- JUVANTS: A BENTONITE-APPLIED MODEL OF STUDY TO EXPLOIT

As wine resilience is the result of different variables, including the wine pH and the concentration of wine components, a detailed knowledge of the relationships between the adjuvant to attain stability and the oenological medium is fundamental for process optimization and to increase wine durability till the time of consumption.

Read More

CHARACTERISTIC EXTRACTION OF THE PHENOL COMPOUNDS IN KOSHU (VITIS VINIFERA CV.) WINE DURING THE MACERATION

Koshu is one of the indigenous grape variety that has been grown in Japan for more than one thousand years. Recent research showed that it has 70% of Vitis vinifera genes. In 2010, the Koshu variety was included in ‘International List of Vine and Varieties and their Synonyms’ managed by the ‘International Organisation of Vine and Wine’ and has further fueled its popularity in Japan. It is the most cultivated variety for winemaking in Japan.
Koshu berries have light purple skins. The variety is mainly used to produce white wines such as an aromatic wine and a wine produced by sur lie method although various styles are produced.

Read More

ANALYZING THE ROLE OF ELEMENTAL SULFUR IN GRAPE JUICE ON THE DEVELOPMENT OF POLYFUNCTIONAL MERCAPTANS IN SAUVIGNON BLANC WINES

Sauvignon blanc is characterized by distinctive aromas, both fruity and herbaceous. The “green” character has been attributed to the methoxypyrazines, while the “fruity” character is associated with polyfunctional mercaptans . Polyfunctional mercaptans are of great significance due to their high impact on wines and associated low perception thresholds.
Elemental sulfur (S⁰) is widely used to protect grapevines from powdery mildew.

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