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…

A NEW STRATEGY AND METHODOLOGY FOR THE CHARACTERIZATION OF POLYPHENOLS IN FINING PRECIPITATE

Polyphenols are secondary metabolite widely distributed in plant kingdom such as in fruits, in grapes and in wine. During the winemaking process, polyphenols are extract from the skin and seed of the berries. Fining is an important winemaking step just before bottling which has an impact on wine stabilization and clarification. Most the time, fining agent are animal or vegetal protein while some of them can be synthetic polymer like PVPP or natural origin like bentonite.

‘TROPICAL’ POLYFUNCTIONAL THIOLS AND THEIR ROLE IN AUSTRALIAN RED WINES

Following anecdotal evidence of unwanted ‘tropical’ character in red wines resulting from vineyard interventions and a subsequent yeast trial observing higher ‘red fruit’ character correlated with higher thiol concentrations, the role of polyfunctional thiols in commercial Australian red wines was investigated.
First, trials into the known tropical thiol modulation technique of foliar applications of sulfur and urea were conducted in parallel on Chardonnay and Shiraz.1 The Chardonnay wines showed expected results with elevated concentrations of 3-sulfanylhexanol (3-SH) and 3-sulfanylhexyl acetate (3-SHA), whereas the Shiraz wines lacked 3-SHA. Furthermore, the Shiraz wines were described as ‘drain’ (known as ‘reductive’ aroma character) during sensory evaluation although they did not contain thiols traditionally associated with ‘reductive’ thiols (H2S, methanethiol etc.).

METHYL SALICYLATE, A COMPOUND INVOLVED IN BORDEAUX RED WINES PRODUCED WITHOUT SULFITES ADDITION

Sulfur dioxide (SO₂) is the most commonly used additive during winemaking to protect wine from oxidation and from microorganisms. Thus, since the 18th century, SO₂ was almost systematically present in wines. Recently, wines produced without any addition of SO₂ during all the winemaking process including bottling became more and more popular for consumers. A recent study dedicated to sensory characterization of Bordeaux red wines produced without added SO₂, revealed that such wines were perceived differently from similar wines produced with using SO₂ and were characterized by specific fruity aromas and coolness1,2.

ALCOHOLIC FERMENTATION AND COLOR OF ROSÉ WINES: INVESTIGATIONS ON THE MECHANISMS RESPONSIBLE FOR SUCH DIVERSITY

Color is one of the key elements for the marketing of rosé wines due to their packaging in transparent bottles. Their broad color range is due to the presence of pigments belonging to phenolic compounds extracted from grapes or formed during the wine-making process. However, the mechanisms responsible for such diversity are poorly understood. The few investigations performed on rosé wines showed that their phenolic composition is highly variable, close to that of red wines for the darkest rosés but very different for light ones [1]. Moreover, large variations in the extent of color loss taking place during fermentation have been reported but the mechanisms involved and causes of such variability are unknown.

MOVING FROM SULFITES TO BIOPROTECTION: WHICH IMPACT ON CHARDONNAY WINE?

Over the last few years, several tools have been developed to reduce the quantity of sulfites used during winemaking, including bioprotection. Although its effectiveness in preventing the development of spoilage microorganisms has been proven, few data are available on the impact of sulfite substitution by bioprotection on the final product. The objective of this study was therefore to characterize Chardonnay wines with the addition of sulfite or bioprotection in the pre-fermentation stage. The effects of both treatments on resulting matrices was evaluated at several scales: analysis of classical oenological parameters, antioxidant capacity, phenolic compounds, non-volatile metabolome and sensory profile.