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…

MOUSY OFF-FLAVOURS IN WINES: UNVEILING THE MICROORGANISMS BEHIND IT

Taints and off-flavours are one of the major concerns in the wine industry and even if the issues provoked by them are harmless, they can still have a negative impact on the quality or on the visual perception of the consumer. Nowadays, the frequency of occurrence of mousy off-flavours in wines has increased.
The reasons behind this could be the significant decrease in sulphur dioxide addition during processing, the increase in pH or even the trend for spontaneous fermentation in wine. This off-flavour is associated with Brettanomyces bruxellensis or some lactic acid bacteria metabolisms.

Read More

TANNINS AND ANTHOCYANINS KINETICS OF EXTRACTION FROM ARINARNOA, MARSELAN AND TANNAT UNDER DIFFERENT WINEMAKING TECHNIQUES

Marselan wines have an unusual high proportion of seed derived tannins from grapes having high proportions of skins, which are rich in tannins. But the causes behind this characteristic have not yet been identified. In vintage 2023 wines were made at experimental scale (9 kg by experimental unit) from Arinarnoa, Marselan and Tannat Vitis vinifera grape cultivars by traditional maceration, and by techniques aimed to increase the wine content in skin derived tannin: addition of extraction enzymes, addition at vatting of grape-skin enological tannins, or by extended maceration, known to increase the seed derived tannin contents of wines.

Read More

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.

Read More

IMPACT OF GRAPE-ASSOCIATED MOLDS IN FRESH MUSHROOM AROMA PRODUCTION

Mycobiota encountered from vine to wine is a complex and diversified ecosystem that may impact grape quality at harvest and the sensorial properties of wines, thus leading to off-flavors [1-3]. Among known off-flavors in wine, fresh mushroom aroma (FMA) has been linked to some mold species, naturally pre-sent on grapes, producing specific volatile organic compounds (VOC) [4-5]. The most well-known are 1-octen-3-ol and 1-octen-3-one, although many other VOC are likely involved. To better understand the FMA defect, biotic and abiotic factors impacting growth kinetics and VOC production of selected fungal species in must media and on grapes were studied.

Read More

YEAST DERIVATIVE PRODUCTS: CHARACTERIZATION AND IMPACT ON RIBOFLAVIN RELEASE DURING THE ALCOHOLIC FERMENTATION

Light-struck taste (LST) is a wine fault that can occur in white and sparkling wines when exposed to light. This defect is mainly associated to the formation of methanethiol and dimethyl disulfide due to light-induced reactions involving riboflavin (RF) and methionine [1]. The presence of RF in wine is mainly due to the metabolism of yeast [2] which fermenting activity can be favoured by using yeast derivative products (YDPs) as nutrients. Nonetheless, a previous study showed the addition of YDPs before the alcoholic fermentation (AF) led to higher concentrations of RF in wines [3]. Due to the widespread use of YDPs in the winemaking process, this study aimed to understand the possible relation between the content of RF in wine and the YDP adopted as nutrient for AF.

Read More