Cis-resveratrol

Fig. 2.77. Chromatogram of a reverse-phase HPLC of Azorean (Basalto) red wine monitored at 306 nm. Peaks 1 = frans-pieceid 2 = cw-pieceid 3 = /nms-resvcralrol 4 = cis-resveratrol 5 = quercetin. Reprinted with permission from J. A. B. Baptista et al. [194].

Aumont V, Krisa S, Battaglia E, Netter P, Richard T, Merillon JM, Magdalou J, Sabolovic N. 2001. Regioselective and stereospecific glucuronidation of trans- and cis-resveratrol in human. Arch Biochem Biophys 393 281-289. 

Bertelli AA, Giovannini L, Stradi R, Bertelli A, Tillement JP. 1996. Plasma, urine and tissue levels of trans- and cis-resveratrol (3,4, 5-trihydroxystilbene) after short-term or prolonged administration of red wine to rats. Int J Tissue React 18 67-71. 

Moreno A, Castro M, Falque E. 2008. Evolution of trans- and cis-resveratrol content in red grapes (Vitis vinifera L. cv Mencia, Albarello and Merenzao) during ripening. 

Trans-conflgured stilbenes such as /rani-resveratrol, /rani-pterostilbene and /ran -e-viniferin show two characteristic bands corresponding to high absorbances from 308 to 336 nm and from 281 to 313 nm. Cis-configured stilbenes like cis-resveratrol, c/x-pterostilbene and c/x-e-viniferin exhibit a UV maximum at 285nm (Jeandet et al. 1997). 

Figure 2.26 Chromatogram relative to the hydroxystilbenes analysis in a grape skins extract recorded at wavelength 285 nm. 1. ds-resveratrol glucoside 2. cis-resveratrol (F. Grippi, personal communication)...

Figure 2.27 Chromatograms recorded at 307nm before (a) and after (b) UV irradiation at 254 nm of a 16mg/L fraws-resveratrol methanolic standard solution. 1. fraws-resveratrol (max absorbance at 307nm) 2. cis-resveratrol (max absorbance at 285nm). Percentage of trans/cis transformation 79% (Flamini et coll., unpublished data)...

Dinan L. reported that three resveratrol trimers, suffruticosols A (100), B (101), C (102), and one monomer cis resveratrol from Paeonia suffruticosa are active as ecdysteroids (antagonists (EDso) 10-50 pM vs. 5xlO 8pM of 20-hydroxyecdyson), but inactive as agonists in the Drosophila melanogaster BII cell bioassay for ecdysteroids agonists/ antagonists [75]. 

Bertelli AA, Giovannini L, Bernini W, Migliori M, Lregoni M, Bavaresco L, BertelU A. Antiplatelet activity of cis-resveratrol. Drugs Exp Clin Res 1996 22 61-63. 

In order to evaluate their potential individual contributions to TAP, phenohc antioxidants were analysed as pure solutions in the same concentration. The order of contributions of individual phenolic antioxidants to TAP determined according to spectrophotometric method was different than those determined with cherniliuninometric method. Generalised, cis-resveratrol has the biggest contribution to TAP, following by trans-iesveratrol, (-)-... 

Fig. 1. Comparison between natural logarithm of sum of gallic acid, (+)-catechin, (-)-epicatechin, irans-resveratrol, ci resveratrol and quercetin, determined using HPLC and TAPcl. All wine samples included.

In this work, we compared two routinely used methods of determination of the following wine phenolic antioxidants gallic acid, (H-)-catechin, (-)-epicatechin, fraws-resveratrol, cis-resveratrol and quercetin. We used liquid chromatographic method with UV-vis detection, the conventional Folin-Ciocalteu spectrophotometric method and chemiluminometric method. The comparisons led us to the following conclusions ... 

Determinations of the total antioxidant potential determined with chemiluminometric method correlate well with the sum of individual contents of geJHc acid, (-i-)-catechin, (-)-epttcatechin, frans-resveratrol, cis-resveratrol and quercetin as obtained using HPLC method in all wine samples. 

PCA was applied to investigate the correlations between TAPsp, TAPcl and individual phenolic antioxidants and especially good co-correlation was found with TAPcl and cis-resveratrol. TAPsp and amount of gallic acid, determined with HPLC method are very strongly co-correlated and most strongly affected by quercetin content. 

The presence of and relationship between trans- and cis-resveratrol monomers in the varietal wines from Dalmatia (Croatia), produced according to the Croatian appellation of origin system, were reported [19]. Standard methods of analysis for general wine components were used for a preliminary control of the selected wines. Resveratrol monomers in wine were measured by HPLC. Significant differences... 

On the other hand, Cai et al. [75] examined the effect of hydrostatic pressure on the extracellular production of stUbenes using V. vinifera cv Camay Freaux cell cultures. They observed that the pressure treatment of 40 MPa for 10 min provoked an increase in cis-resveratrol 3-0-p-glucoside (identified as cis-piceid by Waffo-Teguo et al. [27]) of 2.20 pg g FW on the second day of the treatment. 

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