C13 norisoprenoids

Mathieu, S., N. Terrier et al. (2005). A carotenoid cleavage dioxygenase from Vitis vinifera L. Functional characterization and expression during grape berry development in relation to C13-norisoprenoid accumulation. J. Exp. Bot. 56(420) 2721-2731. 

The aglycon part of glycoside is often represented by monoterpenes, C13-norisoprenoids, benzene derivatives, and long-chain aliphatic alcohols (Fig. 18) [74, 75]. 

In order to expand the worldwide market, considerable efforts are being devoted to improve the image of Madeira wine. Consequently, their characteristics have to be well defined. So, in order to define and describe the particular characteristics and the authenticity of the product, secondary metabolites of grape and wines mainly linked to a specific variety, must be deeply studied. In Madeira wine, these compounds are mainly included in the chemical classes of mono and sesquiterpenoids C13 norisoprenoid higher alcohols, ethyl esters, volatile fatty acids, carbonyl compounds, sulfur compounds, furanic compounds, lactones, and polyphenols. 

Natural Precursors of Thermally Induced C13 Norisoprenoids in Quince... 

The release of glycosidically-bound aroma compounds, such as monoterpenes, C13 norisoprenoids, and aliphatic alcohols, can be achieved by the action of glycosi-dase enzymes. 3-Glycosidase activity has not been much studied in wine LAB. McMahon et al. (1999) detected a low p-glycosidase activity in O. oeni OSU and a... 

Winterhalter, P. (1991). 1,1,6-trimethyl-1,2-dihydronaphtalene (TDN) formation in wine. 1. Studies on the hydrolysis of 2,6,10,10-tetramethyl-l-oxaspiro-[4,5] -dec-6-ene-2,8-diol rationalizing the origin of TDN and related C13 norisoprenoids in RiesUng wine. J. Agric. Food Chem., 39, 1825-1829. 

Winterhalter, R, Sefton, M. A. P.J. Williams. (1991). Volatile C13 norisoprenoids are generated from multiple precursors. Am. J. Enol. Vitic., 41, 277-283. 

Carotenoids are regarded as part of the aroma potential of grape, as they are the biogenetic precursors of C13-norisoprenoids, a chemical family with many powerful odorants, which are mainly found as glycoconjugates in grape (Baumes et al. 2002 Enzell 1985 Mathieu et al. 2005 Winterhalter 1993). Sunshine favors the biosynthesis of carotenoids in the berry, from the first stage of fruit formation... 

Gunata, Z., Wirth, J.L., Guo, W. and Baumes, R.L. (2002) C13-norisoprenoid aglycon composition of leaves and grape berries from Muscat of Alexandria and Shiraz culti-vars, In Carotenoid-derived aroma compounds, ACS Symp. Series 802, Am. Chem. Soc., Washington DC. 

Marais, J., Versini, G., van Wyk, C.J. and Rapp, A. (1992) Effect of region on free and bound monoterpene and C13-norisoprenoids in Weisser Riesling wines, S. Afric. J. Enol. Vitic., 13, 71-77. 

Strauss, C.R., Dimitriadis, E., Wilson, B., and Williams, RJ. (1986). Studies on the hydrolysis of two megastigma-3,6,9-triols rationalizing the origins of some volatile C13 norisoprenoids of Vitis vinifera grapes, J. Agric. Food. Chem., 34,145-149. 

GRAPE AROMA COMPOUNDS TERPENES, C13-NORISOPRENOIDS, BENZENE COMPOUNDS, AND 3-ALKYL-2-METHOXYPYRAZINES... 

The subsequent recognition of glycosides of C13 norisoprenoid compounds and of shikimic acid-derived metabolites as precursors of non-floral grape flavor, was a later development (6). Further aspects of the involvement of glycosides in the flavor of grapes and wines have been recently discussed (7-9). 

Grape variety Free terpenols (hg/1) Terpene glycosides (qgd) C13 -norisoprenoid glycosides (qg/l) Reference... 

Fig. 7.2. The various forms of terpene glycosides (or norisoprenoids) identified in grapes R = terpenol or C13 -norisoprenoid...

Terpenes and C13 norisoprenoids. Terpene compounds are characteristic of aromatic varieties such as Muscat, have a low olfactory threshold and are generally associated with floral and citric aromas (Etievant, 1991 Guth, 1997). Linalool, P-citronellol and frflws-geraniol were detected in wines from four vintages. 

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