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…

EVALUATION OF A SEAWEED EXTRACT OF RUGULOPTERYX OKAMURAE AGAINST ERYSIPHE NECATOR IN GRAPEVINE

Powdery mildew, caused by Erysiphe necator, is a widespread disease that causes high economical losses in viticulture. The main strategy to control the disease is the recurrent application of sulphur based phytochemical compounds. However, in order to reduce their accumulation in the environment and promote the sustainability of the sector, the European Commission has applied restrictions to the number of pesticide treatments and the maximum quantity of fungicides to be applied in viticulture. Seaweeds, in particular macroalgae, are marine resources rich in sulphated polysaccharides with bio-protective potential for the plant, representing an environmentally-friendly alternative approach for sustainable wine production.

MAPPING THE CONCENTRATIONS OF GASEOUS ETHANOL IN THE HEADSPACE OF CHAMPAGNE GLASSES THROUGH INFRARED LASER ABSORPTION SPECTROSCOPY

Under standard wine tasting conditions, volatile organic compounds (VOCs) responsible for the wine’s bouquet progressively invade the glass headspace above the wine surface. Most of wines being complex water/ethanol mixtures (with typically 10-15 % ethanol by volume), gaseous ethanol is therefore undoubtedly the most abundant VOC in the glass headspace [1]. Yet, gaseous ethanol is known to have a multimodal influence on wine’s perception [2]. Of particular importance to flavor perception is the effect of ethanol on the release of aroma compounds into the headspace of the beverage [1].

CHEMICAL DRIVERS OF POSITIVE REDUCTION IN NEW ZEALAND CHARDONNAY WINES

According to winemakers, wine experts and sommeliers, aromas of wet stone, mineral, struck match and flint in white wines styles, such as those produced from Vitis vinifera L. cv. Chardonnay, are considered to be hallmarks of positive reduction.1,2 In recent years, the production of Chardonnay styles defined by aroma characteristics related to positive reduction has become more desirable among wine experts and consumers. The chemical basis of positive reduction is thought to originate from the concentration of specific volatile sulfur compounds (VSCs), including methanethiol (MeSH) imparting mineral and chalk notes,3 and benzenemethanethiol (BMT) responsible for struck match and flint.1,4

EFFECTIVENESS OF APPLIED MATERIALS IN REDUCING THE ABSORPTION OF SMOKE MARKER COMPOUNDS IN A SIMULATED WILDFIRE SCENARIO

Smoke taint (ST) is a grape-wine off-flavour that may occur when grapes absorb volatile phenols (VPs) originating from wildfire smoke (1). ST is associated with the negative sensory attributes such as smoky and ashy notes. VPs are glycosylated in the plant and thus present in both free and bound forms (2; 3). Wildfire smoke has resulted in a decline in grape and wine quality and financial losses which has become a prominent issue for the global wine industry.

IDENTIFYING POTENTIAL CHEMICAL MARKERS RESPONSIBLE FOR THE PERMISSIVENESS OF BORDEAUX RED WINES AGAINST BRETTANOMYCES BRUXELLENSIS USING UNTARGETED METABOLOMICS

All along the red winemaking process, many microorganisms develop in wine, some being beneficial and essential, others being feared spoilers. One of the most feared microbial enemy of wine all around the world is Brettanomyces bruxellensis. Indeed, in red wines, this yeast produces volatile phenols, molecules associated with a flavor described as “horse sweat”, “burnt plastic” or “leather”. To produce significant and detectable concentrations of these undesired molecules, the yeasts should first grow and become numerous enough. Even if the genetic group of the strain present and the cellar temperature may modulate the yeast growth rate¹ and thus the risk of spoilage, the main factor seems to be the wines themselves, some being much more permissive to B. bruxellensis development than others.