Novel monoterpene disaccharide glycosides of Vitis vinifera grapes

Voirin, Stéphane G.; Baumes, Raymond; Bitteur, Sylvaine; Günata, Ziya; Bayonove, Claude

doi:10.1021/jf00096a016

Cited by 108 publications

(57 citation statements)

References 17 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…S5 and S6). Enzyme activity studies were performed with UDP-[ 14 C]Glc and various putative substrates (terpenols, flavonoids, and different monoalcohols) that are known to be glycosidically bound and present in grape (Gunata et al, 1988;Voirin et al, 1990;Sefton et al, 1996;Ford and Hoj, 1998;Wirth et al, 2001). Recombinant VvGT14a, VvGT15a to VvGT15c, and VvGT16 converted several of the tested substrates (Fig.…”

Section: Metabolite Profilingmentioning

confidence: 99%

Activity-Based Profiling of a Physiologic Aglycone Library Reveals Sugar Acceptor Promiscuity of Family 1 UDP-Glucosyltransferases from Grape

et al. 2014

View full text Add to dashboard Cite

Monoterpenols serve various biological functions and accumulate in grape (Vitis vinifera), where a major fraction occurs as nonvolatile glycosides. We have screened the grape genome for sequences with similarity to terpene URIDINE DIPHOSPHATE GLYCOSYLTRANSFERASES (UGTs) from Arabidopsis (Arabidopsis thaliana). A ripening-related expression pattern was shown for three candidates by spatial and temporal expression analyses in five grape cultivars. Transcript accumulation correlated with the production of monoterpenyl b-D-glucosides in grape exocarp during ripening and was low in vegetative tissue. Targeted functional screening of the recombinant UGTs for their biological substrates was performed by activity-based metabolite profiling (ABMP) employing a physiologic library of aglycones built from glycosides isolated from grape. This approach led to the identification of two UDP-glucose:monoterpenol b-D-glucosyltransferases. Whereas VvGT14a glucosylated geraniol, R,S-citronellol, and nerol with similar efficiency, the three allelic forms VvGT15a, VvGT15b, and VvGT15c preferred geraniol over nerol. Kinetic resolution of R,S-citronellol and R,S-linalool was shown for VvGT15a and VvGT14a, respectively. ABMP revealed geraniol as the major biological substrate but also disclosed that these UGTs may add to the production of further glycoconjugates in planta. ABMP of aglycone libraries provides a versatile tool to uncover novel biologically relevant substrates of small-molecule glycosyltransferases that often show broad sugar acceptor promiscuity.Plant secondary metabolites are frequently decorated with Glc that is transferred from uridine diphosphoglucose by a so-called family 1 URIDINE DIPHOSPHATE GLUCOSYLTRANSFERASE (UGT; Caputi et al., 2012). Since the glucosylation process can be envisaged as a simple nucleophilic displacement reaction of Secondorder Nucleophilic Substitution type, the product is a b-glucoside. A remarkably large array of different small molecules is glucosylated in planta, including terpenoids, alkaloids, cyanohydrins, and glucosinolates, as well as flavonoids, isoflavonoids, anthocyanidins, and phenylpropanoids. In grape (Vitis vinifera) alone, more than 200 different glucosides have been identified, and there is special interest in those glucoconjugates, which can contribute to wine flavor after the hydrolytic release of volatiles during the biotechnological vinification sequence leading from grape to aged wine (Wirth et al., 2001). These flavorless glucoconjugates accumulate in grape berries during maturation and can be grouped according to their linked aglycones into monoterpenes, C13-norisoprenoids, aliphatic alcohols, and shikimatederived benzoids and phenylpropanoids (Sefton et al., 1996). It still remains an open question how this large number of structurally different flavor precursors is actually glucosylated in vivo, because the in vitro activities of single UGTs show large differences in the individual range of acceptors. Some UGTs are considered highly specific with respect to substrate ...

show abstract

Section: Metabolite Profilingmentioning

confidence: 99%

Activity-Based Profiling of a Physiologic Aglycone Library Reveals Sugar Acceptor Promiscuity of Family 1 UDP-Glucosyltransferases from Grape

et al. 2014

View full text Add to dashboard Cite

show abstract

“…The addition of other sugars to the glucose moiety will form disaccharide, trisaccharide, and higher order saccharide glycosides. In grapes, rhamnose and arabinose (Williams et al 1982a) along with apiose (Voirin et al 1990) have been identified as terminal sugars in disaccharide glycosides. Figure 4 shows the structures of identified glycones in grape, together with their names, and common names, when available.…”

Section: Structures Of Glycosidesmentioning

confidence: 99%

Glycosidically Bound Volatile Aroma Compounds in Grapes and Wine: A Review

Hjelmeland

Ebeler

2014

Am. J. Enol. Vitic.

142

114

View full text Add to dashboard Cite

Volatile aroma compounds in plants are typically found both as "free" and "bound" to a sugar moiety. When bound, these compounds are not odor active; however, upon hydrolysis of the glycoside, these compounds may then be volatilized. In grapes and wine, a large proportion of volatile aroma compounds are found in the bound form. A review of glycosides in grapes and in wine is presented with a focus on identified glycoside structures, their biosynthesis, their potential roles in the plant, and methods for their analysis. Studies of these compounds and their concentration changes during the winemaking process are discussed.

show abstract

“…The varietal flavour of a wine is mainly derived from glycosylated aroma precursors 33 . In wine grapes, the major precursors include structures such as β-D-glucopyranoside, β-apiosyl-β-D-glucopyranoside, α-L-arabinofuranosyl-β-D-glucopyranoside and α-L-rhamno-pyranosyl-β-D-glucopyranoside 16,36,40 . Numerous aglycones have been identified following hydrolysis of wine and grape juice glycosides, including terpenes, norisoprenoids, aliphatics and phenolic compounds 39 .…”

Section: Introductionmentioning

confidence: 99%

Effects of Different β-D-Glycosidases on Bound Aroma Compounds in Muscat Grape Determined by HS-SPME and GC-MS

Kang

Qin

et al. 2010

Journal of the Institute of Brewing

View full text Add to dashboard Cite

Important "floral" aromas naturally occur in grapes predominantly as flavourless glycoconjugate precursors. Since these aroma compounds can be released by hydrolysis, different glycosidase enzymes can potentially contribute different aromas to wines. In this paper, we first established a procedure for profiling the free and bound volatile compounds in grape using GC-MS combined with headspace solid-phase microextraction (HS-SPME). Comparison of the free and bound aroma compounds revealed that non-volatile glycosides, known as aroma precursors, occur in high concentrations in musts. Among all compounds identified, 11 were fully quantified according to established standard calibration curves, while others were semi-quantified. Using three different glycosidase enzymes, a total of 38 bound volatile compounds were identified in Muscat grape, including terpenes, higher alcohols, C-6 compounds, and phenols, among others. The different enzymes had significant effects on the varietal aroma. Principal component analysis indicated that the characteristic aroma hydrolyzed by the commercial enzyme AR2000 was clearly different from that produced by other enzymes.

show abstract

Novel monoterpene disaccharide glycosides of Vitis vinifera grapes

Cited by 108 publications

References 17 publications

Activity-Based Profiling of a Physiologic Aglycone Library Reveals Sugar Acceptor Promiscuity of Family 1 UDP-Glucosyltransferases from Grape

Activity-Based Profiling of a Physiologic Aglycone Library Reveals Sugar Acceptor Promiscuity of Family 1 UDP-Glucosyltransferases from Grape

Glycosidically Bound Volatile Aroma Compounds in Grapes and Wine: A Review

Effects of Different β-D-Glycosidases on Bound Aroma Compounds in Muscat Grape Determined by HS-SPME and GC-MS

Contact Info

Product

Resources

About