Alkylmethoxypyrazines (MPs) are a class of compounds that can elicit undesirable aroma and flavor characteristics in wine, and resist remediation using traditional wine making approaches. MPs are grape-derived constituents as well as contaminants from Coccinellidae beetles present during wine processing; the latter eliciting an off-flavor referred to as 'ladybug taint'. In this study we investigated the capacity of two plastic polymers-one silicone-based, the other polylactic acid-based-applied with varying surface areas to reduce concentrations of isopropylmethoxypyrazine (IPMP), sec-butylmethoxypyrazine (SBMP) and isobutylmethoxypyrazine (IBMP) in a Merlot wine using multi-dimensional gas chromatography coupled with mass spectrometry and headspace solid phase microextraction (SPME-MDGCMS). The impact of treatments on the sensory characteristics of the wine (descriptive analysis) and volatile aroma compounds (VOCs) (SPME-MDGCMS) was also investigated. Results showed substantial reductions for all of the target odorants: up to 38%, 44% and 39% for IPMP, SBMP and IBMP, respectively, for the silicone polymer, and up to 75%, 78% and 77% for IPMP, SBMP and IBMP, respectively, for the polylactic acid polymer. These polymers had no or minimal effect on VOCs at applications of 200 cm 2 /L for silicone or for all polylactic acid treatments. Sensory impacts were less clear, but generally showed minimal effect from the treatments. Taken overall, the data confirm the utility of both polylactic acid and silicone polymers in reducing elevated levels of grape-derived MPs, as well as potentially improving wine contaminated by ladybug taint.

Both Harmonia axyridis and Coccinella septempunctata can contribute alkyl methoxypyrazines, and particularly isopropyl methoxypyrazine, to wine at concentrations that can have a negative impact on wine quality. These findings will allow grape growers and winemakers to be more aware of the risks posed by 7 Spot beetles, and to take the appropriate preventative and remedial actions. Furthermore, this is the first time dimethyl methoxypyrazine is reported in wine, either as an endogenous or Coccinellidae-derived odorant.

2,5-Dimethyl-3-methoxypyrazine (DMMP) has been recently identified in both Coccinellidae-tainted (by either Coccinella septempunctata or Harmonia axyridis beetles) and untainted wines; however, little is known regarding its impact on wine aroma and flavor. The aims of this study were to obtain an accurate estimate of both the ortho- and retronasal detection thresholds of DMMP in red wine and to understand how DMMP contributes to the aroma profile of red wine. In the first study, thresholds were determined for 21 individuals using the ASTM E679 ascending forced choice method of limits. The orthonasal group best estimate threshold (BET) was 31 ng/L and the retronasal group BET was 70 ng/L. A moderate variation in individual thresholds was observed for the orthonasal modality (standard deviation (SD) = 19.8) and a larger variation was noted for retronasal thresholds (SD = 111.8). In the second study, a panel of 8 assessors performed descriptive sensory analysis on 3 red wines containing various concentrations of added DMMP (0, 50, and 120 ng/L). Results show significant changes in aroma characteristics in the 120 ng/L wine and smaller effects at the 50 ng/L level. Overall, wines spiked with DMMP generated lower intensity ratings for cherry and red berry descriptors and higher ratings for earthy/musty and green/vegetal descriptors. When considered with other recent results on DMMP concentrations found in wine, DMMP can be considered a hitherto undescribed impact odorant in some wine styles.

3-Alkyl-2-methoxypyrazines (MPs) are odour-active compounds that elicit atypical green aromas and flavours in some wines, and are resilient to removal using traditional wine-making approaches. They originate either as contaminants from Coccinellidae beetles inadvertently introduced during wine processing ("ladybug taint") or as grape-derived constituents that are undesirable at elevated levels. In this study we investigated the capacity of a selection of plastic polymers to reduce concentrations of three MPs: isopropyl methoxypyrazine (IPMP), secbutyl methoxypyrazine (SBMP) and isobutyl methoxypyrazine (IBMP). In Trial 1, red wine was spiked with IPMP (20 ng/l), SBMP (20 ng/l) and IBMP (20 ng/l), then separately treated with 13 plastic polymers (surface area 350 cm(2)/l). Three polymers were then identified for further testing based on the results from Trial 1: silicone, ethylene and vinyl acetate (EVA) and a poly-lactic acid-based biodegradable polymer. In Trial 2, the efficacy of these selected polymers to reduce MP levels in red wine was tested as a function of contact time. Solid-phase micro-extraction multi-dimensional GC-MS was used to measure MP levels before and after treatment with the polymers. Results showed significant reductions in all target odorants after 24 h treatment: silicone reduced IPMP and IBMP by 96% and 100%, respectively, while the biodegradable polymer decreased IPMP and IBMP concentrations by 52% and 36%, respectively. EVA was less effective in lowering MP levels (7% IPMP and 23% IBMP after 24 h). Taken overall, the data suggest the potential for the use of poly-lactic acid and silicone in treating wines contaminated by ladybug taint, as well as in reducing high levels of grape-derived MPs.

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These results provide direction for more targeted treatments aimed at remediating musts/wines affected by Coccinellidae and indicate that winegrowers do not need to differentiate between H. axyridis and C. septempunctata when making action threshold decisions in the vineyard or winery.

Ladybug taint (also known as ladybird taint) is a relatively recently recognized fault that has been identified in wines from a wide range of terroirs. Alkyl-methoxypyrazines—particularly 2-isopropyl-3-methoxypyrazine—have been determined as the causal compounds, and these are introduced into grape must during processing, when specific species of vineyard-dwelling Coccinellidae are incorporated into the harvested fruit. Coccinella septempunctata, and especially the invasive Harmonia axyridis, are the beetles implicated, and climate change is facilitating wider dispersal and survivability of H. axyridis in viticultural regions worldwide. Affected wines are typically characterized as possessing excessively green, bell pepper-, and peanut-like aroma and flavor. In this paper, we review a range of vineyard practices that seek to reduce Coccinellidae densities, as well as both “standard” and novel wine treatments aimed at reducing alkyl-methoxypyrazine load. We conclude that while prevention of ladybug taint is preferable, there are several winery interventions that can remediate the quality of wine affected by this taint, although they vary in their relative efficacy and specificity.