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

ASSESSMENT OF ‘DOLCETTO’ GRAPES AND WINES FROM DIFFERENT AREAS OF OVADA DOCG

Dolcetto (Vitis vinifera L.) is one of the traditionally cultivated varieties in Piedmont (north-east Italy). Dolcetto wines have long been associated with local consumption and they are little known internationally. In particular, the Ovada area (south-east Piedmont), even if it represents a small share of the regional PDO Dolcetto production, is one of the oldest and vocated territory, giving wine also suitable for aging. In this study, the basic composition and phenolic content of Dolcetto grapes for Ovada DOCG wines have been investigated in three different vintages (2020-2022), as well as the main aspects of the derived commercial and experimental wines (basic parameters, phenolics, volatile compounds, sensory properties).

Read More

BORDEAUX RED WINES WITHOUT ADDED SULFITES SPECIFICITIES: COMPOSITIONAL AND SENSORY APPROACHES TOWARDS HIGHLIGHTING AND EXPLAI-NING THEIR SPECIFIC FRUITINESS AND COOLNESS

With the development of naturality expectations, wines produced without any addition of sulfur dioxide (SO₂) become very popular for consumers and such wines are increasingly present on the market. Recent studies also showed that Bordeaux red wines without added SO₂ could be differentiated from a sensory point of view from similar wines produced with SO₂¹. Thus, the aim of the current study was to characterize from a sensory point of view, specific aromas of wines without added SO₂ and to identify compounds involved.

Read More

IMPACT OF METSCHNIKOWIA PULCHERRIMA DURING FERMENTATION ON AROMATIC PROFILE OF VIDAL BLANC ICEWINE

Non-Saccharomyces yeasts not only increase microbial diversity during wine fermentation, but also have a positive effect on improving wine aroma. Among these non-Saccharomyces yeast species, Metschnikowia pulcherrima is often studied and used in winemaking in recent years, but its application in icewine has been rarely reported. In this study, indigenous M. pulcherrima strains and Saccharomyces cerevisiae strains (commercial and indigenous strains) were sequentially inoculated for icewine fermentations; meanwhile, pure S. cerevisiae fermentations were used as the control; indigenous strains used above were screened from spontaneous fermentations of Vidal blanc icewine.

Read More

SIP and save the planet: a sensory and consumer exploration of australian wines made from potentially drought-tolerant white wine grapes

In order to attenuate the effects of climate change on the ability to cultivate quality wine grape vines in Australia, it is essential to adapt to the projected less favourable Australian climate scenarios. One response may be to convert a portion of the current grapevine plantings to those varieties that demand less water and can tolerate increased heat. This investigation aimed to (i) generate sensory profiles and (ii) obtain knowledge about Australian wine consumers’ preferences and opinions of Australian wines made from potentially drought tolerant, white wine grape varieties not traditionally cultivated in Australia. A Rate-All-That-Apply (RATA) sensory panel (n = 49) generated sensory profiles of 44 commercial white wines made from 7 different white grape varieties (Arinto, Fiano, Garganega, Greco, Verdejo, Verdelho and Vermentino), plus two benchmark examples each of an Australian Riesling, Pinot Gris and Chardonnay wine.

Read More