Occurrence and contribution of alkyl methoxypyrazines in wine tainted by Harmonia axyridis and Coccinella septempunctata.

BACKGROUND: Ladybug taint (LBT) is a wine fault caused by the inadvertent incorporation of ladybeetles to the wine during the winemaking process. Harmonia axyridis, also known as the multicolored Asian lady-beetle (MALB), was the only species considered responsible for causing the taint. A second species, Coccinella septempunctata (7 Spot), has recently also been implicated. The main objectives of this study were to identify and quantify the compounds associated with ladybug taint of white and red wine from these two Coccinellidae species (Harmonia axyridis and Coccinella septempunctata), and determine the most odor-active compounds in LBT-affected wines. RESULTS: Results show that Coccinellidae can contribute dimethyl, isopropyl, secbutyl and isobutyl methoxypyrazine to wine when they are processed with grapes, and that the methoxypyrazine composition varies between MALB and 7 Spot. Isopropyl methoxypyrazine is the major contributor to LBT in wines produced with these ladybeetle species, although secbutyl and isobutyl methoxypyrazine may contribute in MALB- and 7 Spot-affected wines, respectively. Finally, dimethyl methoxypyrazine is reported for the first time in wines not affected by Coccinellidae; the global significance and prevalence of this compound in wine remains to be determined. CONCLUSION: 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.

Effect of closure and packaging type on 3-alkyl-2-methoxypyrazines and other impact odorants of Riesling and Cabernet Franc wines.

3-Alkyl-2-methoxypyrazines (MPs) represent an important and potent class of grape- and insect-derived odor-active compounds associated with wine quality. Thirty nanograms per liter each of 3-isobutyl-2-methoxypyrazine (IBMP), 3-isopropyl-2-methoxypyrazine (IPMP), and 3-sec-butyl-2-methoxypyrazine (SBMP) was added to Riesling and Cabernet Franc wines and monitored with headspace solid-phase microextraction and gas chromatography-mass spectrometry over 18 months to investigate the effects of various closure and packaging options on MPs. Changes in MP concentrations during bottle aging varied with closure/packaging option, with the greatest decrease evident in Tetrapak cartons. After 18 months, IBMP, IPMP, and SBMP in both Tetrapak-stored wines decreased by approximately 45, 32, and 26%, respectively. Similar changes were observed in other impact odorants to previous studies, including a greater decrease in odorant concentrations in wines closed with synthetic corks compared to natural corks and screw caps. These differences are thought to be due to the differential sorptive capacities of the various closure types. Overall, the data suggest that differences in gas permeability/contribution from the different closure and packaging options strongly associate with changes in wine composition during aging.