Qualitative profiling of mono- and sesquiterpenols in aglycon libraries from Vitis vinifera L. Gewürztraminer using multidimensional gas chromatography–mass spectrometry

Abstract

In grape berries (Vitis vinifera L.), sesquiterpenes are mainly accumulated as hydrocarbons in the epicuticular wax layer of grapes, whereas monoterpenes, which are predominantly present as alcohols, are glycosylated and are stored as glycosides in the vacuoles of grape berry cells. In this study, extensive analysis of grape berry hydrolysates by means of comprehensive two-dimensional gas chromatography–time-of-flight–mass spectrometry demonstrated that glycosylated sesquiterpene alcohols show very little structural diversity when compared to the sesquiterpene hydrocarbon fraction in the cuticle and are glycosylated to a rather low extent when compared to monoterpenols. Twenty-four enzymatically released terpenols were found in hydrolysates of the aromatic white wine variety Gewürztraminer (V. vinifera subsp. vinifera) after previous solid-phase extraction and headspace solid-phase microextraction. The detection of only three sesquiterpene alcohols, namely farnesol, nerolidol and drimenol, shows that most sesquiterpene hydrocarbons do not have a related hydroxylated structure in grapes. Nevertheless, the presence of the acyclic aglycone farnesol and nerolidol may be of importance for the wine aroma, since these structural isomers can be converted into numerous sesquiterpenes by nonenzymatic acid-catalyzed reactions during wine production. Grape-derived glycosidically bound sesquiterpene alcohols, therefore, represent, in addition to free sesquiterpene hydrocarbons, another pool of compounds that may influence the aroma profile of wines.

Effects of Cabya (Piper retrofractum Vahl.) Fruit Developmental Stage on VOCs

“…Two particular alcohols, nerolidol and apitol, were only present in these periods. These structural isomers can be converted into many sesquiterpenes by non-enzymatic acid-catalyzed reactions [ 21 ], and thereby contributed to the observed increase in alkenes in phase D and the aroma of ripe fruits. It is important to note that the most prevalent component of the B phase, -eudesmol, has been found to be an appropriate raw material for natural products with anti-disease, anti-Alzheimer’s, and anti-spasmodic qualities [ 22 ].…”

Foods and Contaminants Analysis Using Multidimensional Gas Chromatography: An Update of Recent Studies, Technology, and Applications

“…Some applications focus on chiral volatiles using H/C MDGC 142,145−147 or GC×GC with a chiral column as the 1 D column 148 (also referred to as eGC×GC). Other reported specific compound groups are sulfur-containing compounds, 139,149 sesquiterpenols, 150 lactones, 151 and sesquiterpenes. 152 Noting that sample preparation can have an impact on the quality of the analysis, different drinks among alcoholic beverage class may be suitable to various sample preparation techniques.…”

“…Some applications focus on chiral volatiles using H/C MDGC ,− or GC×GC with a chiral column as the 1 D column (also referred to as e GC×GC). Other reported specific compound groups are sulfur-containing compounds, , sesquiterpenols, lactones, and sesquiterpenes …”

Effect of Agronomic Techniques on Aroma Composition of White Grapevines: A Review

“…Terpenes are present as free volatiles and as sugar-bound precursors [81]. Monoterpenes (C10) and sesqui-(C15) are formed in plastids, via the cytosolic mevalonate-dependent metabolic pathway (MVA) and the mevalonate-independent 1-deoxy-d-xylulose 5-phosphate/2-C-methyl-d-erythritol 4-phosphate biosynthesis pathway (DOXP/MEP) [82,83]. The presence of monoterpene glycosides by hydrolytic cleavage of the glycosidic bond was confirmed, identifying both acyclic monoterpene alcohols, such as linalool, nerol, and geraniol, and monocyclic terpenes such as α-terpineol as released aglycones [84].…”