Identification of Impact Odorants Contributing to Fresh Mushroom Off-Flavor in Wines: Incidence of Their Reactivity with Nitrogen Compounds on the Decrease of the Olfactory Defect

Abstract

Analysis of wines from different grape varieties marked by sometimes intense aromatic nuances of fresh mushroom was performed by gas chromatography coupled with olfactometry. This analysis has led to the identification of several odoriferous zones, which were recalling a fresh mushroom odor. Two trace compounds responsible for these odoriferous zones, 1-nonen-3-one and 1-octen-3-one, have been identified and their content has been determined by using either a multidimensional gas chromatography technique coupled to olfactometry and mass spectrometry detection (in the case of 1-nonen-3-one) or the preparation of the derivative with O-2,3,4,5,6-pentafluorobenzylhydroxylamine hydrochloride in the presence of the deuterated form, as the internal standard (in the case of 1-octen-3-one), then gas chromatography coupled to mass spectrometry detection. The assays allowed the quantification of these compounds at concentration levels sometimes well above their detection and recognition olfactory threshold. We show that adding nitrogen compounds to the altered wines, such as an amino acid (glycine) or a tripeptide (glutathione), led to lower concentrations of 1-octen-3-one in wines and diminished smell of fresh mushrooms. The study of the reaction in a model medium, whose composition is close to wine, by liquid chromatography coupled to mass spectrometry demonstrated the formation of adducts between 1-octen-3-one and glycine, and 1-octen-3-one and glutathione characterized by NMR.

A <i>Basidiomycete Fungus</i> Responsible for Fresh Mushroom Off-Flavour in Wines: <i>Crustomyces subabruptus</i>, (Bourdot & Galzin) Jülich 1978

“…1-octen-3-one and 1-octen-3-ol are well-known metabolites of various ascomycetes and basidiomycetes (Tressl et al, 1982). The concentrations of 1-octen-3-ol are almost lower than the olfactory perception thresholds for this compound, whereas 1-octen-3-one, and occasionally 1-nonen-3-one, are detected, in wines which have a mushroom flavour, at concentrations over their olfactory perception threshold and recognition threshold (Pons et al, 2011). The olfactory perception threshold for 1-octene-3-one is around 3 ng/L in water, 30 ng/L in model solution and 70 ng/L in red wine (La Guerche et al, 2006).…”

Interactions between Polyphenols and Volatile Compounds in Wine: A Literature Review on Physicochemical and Sensory Insights

“…Thus, considering the observed negative impact at increasing levels and the polymerization of PPhs on the release of esters and β-damascenone [62], it can be argued that this could correspond to a significant diminution of the fruity character of red wines, especially in aged and/or woody ones. Concerning 1-octen-3-one, a compound involved in the cork taint [77,78], it could be interesting to test if the concentration and the nature of PPhs could be useful in managing the sensory impact of this off-flavor.…”

Roles of microbiota in the formation of botrytized grapes and wines

“…The compounds 1-octen-3-one, fenchol, and fenchone are frequently detected in grape wines and juices contaminated with filamentous fungi (La Guerche et al, 2006). The compound 1-octen-3-one was reported to originate from Penicillium brevicompactum and U. necator, whereas fenchol originated from Penicillium spp., Aspergillus spp., or Rhizopus nigricans (Darriet et al, 2002;La Guerche et al, 2006;M. Pons et al, 2011).…”