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…

EVIDENCE OF THE INTERACTION OF ULTRASOUND AND ASPERGILLOPEPSINS I ON UNSTABLE GRAPE PROTEINS

Most of the effects of ultrasound (US) result from the collapse of bubbles due to cavitation. The shockwave produced is associated with shear forces, along with high localised temperatures and pressures. However, the high-speed stream, radical species formation, and heat generated during sonication may also affect the stability of some enzymes and proteins, depending on their chemical structure. Recently, Ce-lotti et al. (2021) reported the effects of US on protein stability in wines. To investigate this further, the effect of temperature (40°C and 70°C; 60s), sonication (20 kHz and 100 % amplitude, for 20s and 60s, leading to the same temperatures as above, respectively), in combination with Aspergillopepsins I (AP-I) supplementation (100 μg/L), was studied on unstable protein concentration (TLPs and chitinases) using HPLC with an UV–Vis detector in a TLPs-supplemented model system and in an unstable white wine.

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.

MICROFLUIDIC PLATFORM FOR SORTING YEAST CELLS ACCORDING TO THEIR MORPHOLOGY

In this work we briefly present a microfluidic device aiming to sort yeast cells according to their morphology. The technology is based upon microfluidic chips made out of Polydimethylsiloxane and glass using soft lithography processes and replica molding. The microfluidic device was used for encapsulating single yeast cells in liquid droplets containing growth medium. Liquid droplet containing yeast cells were sorted using a real time imaging and decision-making process.

NOVEL BENZENETHIOLS WITH PHENOLS CAUSE ASHY, SMOKE FLAVOR PERCEPTION IN RED WINES

Smoke impacts on wines are becoming a worldwide problem; the size and severity of wildfires increasing due to influences from changing climates.¹ For over a century, wines have been known to have a unique issue of absorbing chemical compounds derived from wildfire smoke wherein the flavor of the subsequent wine becomes ashy, rubbery, campfire-like, and smoky.² The economic impacts of a smoke-impacted wine can last for years depending on the grape varietal, costing Oregon and Washington states in the United States over a billion dollars from the 2020 wildfires, as an example.³ While years of research have indicated elevated concentrations of smoke-related compounds, such as guaiacol and syringol, in wines after smoke events, unfortunately, replicating the sensory experience using smoke-associated phenols has not had much success.⁴

OPTIMIZATION, VALIDATION AND APPLICATION OF THE EPR SPIN-TRAPPING TECHNIQUE TO THE DETECTION OF FREE RADICALS IN CHARDONNAY WINES

The aging potential of Burgundy chardonnay wines is considered as quality indicator. However, some of them exhibit higher oxidative sensitivity and premature oxidative aging symptoms, which are potentially induced by no-enzymatic oxidation such as Fenton-type reaction (Danilewicz, 2003). This chemical mechanism involves the action of transition metal, native phenolic compounds and oxygen which promote the generation of highly reactive oxygen species (ROS) such as hydroxyl radicals (OH) or 1-hydroxyethyl radicals (1-HER) from oxidation of ethanol. Such mechanism is involved in the radical oxidation occurring during bottle aging. According to Elias et al.,(2009a), the 1-HER is the most abundant radical in forced oxidation treated wines. Consequently, understanding its evolution kinetic in dry white wines is of great importance.