J. Agric. Food Chem. 1996, 44, 2124−2128
2124
Levels of cis- and trans-Resveratrol and Their Glucosides in White and Rose´ Vitis vinifera Wines from Spain Ana I. Romero-Pe´rez,† Rosa M. Lamuela-Ravento´s,*,† Andrew L. Waterhouse,‡ and M. C. de la Torre-Boronat† Nutricio´ i Bromatologia, Facultat de Farma`cia, Universitat de Barcelona, Av. Joan XXIII s/n, 08028-Barcelona, Spain, and Department of Viticulture and Enology, University of California, Davis, California 95616
The resveratrol monomers (trans-piceid, cis-piceid, trans-resveratrol, and cis-resveratrol) have been previously identified and quantified in red wines. Here, the levels of these compounds in Spanish white and rose´ wines are described. For white wines, a concentration step was needed to quantify the four resveratrol isomers. The recovery and reproducibility of this procedure were very good. These white wines had levels between 0.051 and 1.801 mg/L. Rose´ wines had an average level of 2.15 mg/L, in between those of red and white wines. Keywords: Resveratrol; piceid; glucosides; white wine; rose´ wine INTRODUCTION
trans-Resveratrol is one of the compounds present in wines that could be responsible for the decrease in coronary heart disease observed among wine drinkers. This potential effect could be due to resveratrol’s ability to inhibit LDL oxidation (Frankel et al., 1993), block platelet aggregation (Bertelli et al., 1995; Pace-Asciak et al., 1995), and inhibit eicosanoid synthesis (Kimura et al., 1985; Pace-Asciak et al., 1995). Piceid, the 3-βglucoside of trans-resveratrol, also shows antiplatelet aggregation properties (Kimura et al., 1985; Shan et al., 1990), and it may release trans-resveratrol by β-glucosidase hydrolysis in the intestine (Hackett,1986). Large differences in effective concentrations for antiaggregation activity have been reported. Pace-Asciak et al. (1995) reported that 129.9 ( 64.4 µmol/L transresveratrol can inhibit platelet aggregation by 50% when ADP is used as the inducer or 164.7 ( 67.3 µmol/L is sufficient when thrombin is the inducer, while Bertelli et al. (1995) found that 0.016 µmol/L inhibited platelet aggregation by 50.3% when collagen was the inducer. Similar disparities are reported with the inhibition of eicosanoid synthesis; the levels that have physiological effects according to Pace-Asciak et al. (1995) are 10 times higher than those reported by Kimura et al. (1985). These differences may be due to the different mechanism used by each inducer (ADP, thrombin, collagen) in the hemostatic process; the effectiveness of the inhibitor depends on which step in the platelet aggregation process is affected. However, in vivo all three inducers are employed in the platelet aggregation process. The cis isomers have potential anticancer activity, as do the trans isomers, by inhibiting protein-tyrosine kinase (Jayatilake et al., 1993), and cis-resveratrol also shows antiaggregation properties (Bertelli et al., 1996). However, the activity of the cis isomer in LDL oxidation has yet not been studied. Since Siemann and Creasy (1992) described the presence of the phytoalexin trans-resveratrol in wines, * Author to whom correspondence should be addressed (e-mail
[email protected]). † Universitat de Barcelona. ‡ University of California. S0021-8561(95)00765-5 CCC: $12.00
many different methods have been developed to determine this compound, including those based on HPLC (Lamuela and Waterhouse, 1993; Mattivi, 1993a; Roggero and Archie, 1994; Pezet et al., 1994; McMurtrey et al., 1994) and GC/MS (Jeandet et al., 1993; Soleas et al., 1993; Goldberg et al., 1994, 1995a). The quantification of the cis isomer of resveratrol in wines was achieved later by Jeandet et al. (1993, 1995), Soleas et al. (1995), and Goldberg et al. (1995a). Since the glycosides of these compounds are also present in red wines, HPLC methods that describe the separation of the four compounds have been published recently (Lamuela-Ravento´s et al., 1995; Mattivi et al., 1995). In grape berries, resveratrol synthesis is mainly located in the skin cells and is absent or low in the fruit flesh. Resveratrol requires a relatively long maceration time on the skins to be extracted (Creasy and Coffee, 1988; Jeandet et al., 1991, 1995). White wine is reported to have a much lower resveratrol content than red wine (Siemann and Creasy, 1992; Lamuela-Ravento´s and Waterhouse, 1993; McMurtrey et al., 1994; Pezet et al., 1994; Jeandet et al., 1993, 1995; Goldberg et al., 1995a,b), presumably due to minimal skin contact associated with white wine production. The levels of resveratrol isomers in white wines found in the literature are described in Table 1. Goldberg et al. (1995a) analyzed 100 white wines with concentrations of trans-resveratrol lower than 0.1 mg/L; however, they do not describe the varieties tested. Jeandet et al. (1995) noted that “white wines macerated with skins had higher resveratrol content, than nonmacerated ones, but is ca. 3 fold lower than in those made with red grapes”. In the only study on rose´ wines (Mattivi, 1993b), trans-resveratrol levels were between 0.005 and 1.19 mg/L, with the higher amounts than in white wines attributed to the longer maceration required to produce rose´ wines. Two reports have claimed that trans-resveratrol is unstable to rotary evaporation (Mattivi, 1993a; Pezet et al., 1994). Since this technique was utilized here in the analysis of white wines, the stability of these compounds under rotary evaporation was confirmed. Here, we describe the analysis of trans- and cis-piceid © 1996 American Chemical Society
J. Agric. Food Chem., Vol. 44, No. 8, 1996 2125
Resveratrols and Their Glucosides in White and Rose´ Wines Table 1. Amounts of trans- and cis-Resveratrol in White Wines
trans-resveratrol (mg/L) author Siemann and Creasy (1992)
Jeandet et al. (1993) Lamuela-Ravento´s and Waterhouse (1993) Mattivi (1993a)
Pezet et al. (1994) McMurtrey et al. (1994) Soleas et al. (1995)
a
variety
av
(min - max)
cis-resveratrol (mg/L) av
(min - max)
Chardonnay (n ) 13) Cayuga white (n ) 1) white blend (n ) 1) white Bordeaux (n ) 2) white Zinfandel (n ) 1) Aligote´ (n ) 2) Chardonnay (n ) 4) Chardonnay (n ) 1)
0.029 (0.006-0.100) 0.4 × 10-3 0.2 × 10-3 0.003 (0.002-0.004) 0.4 × 10-3 0.059 (0.036-0.083) 0.048 (0.019-0.062) not detected
0.089 0.106 -
(0.046-0.125) (0.088-0.124) -
white Bordeaux (n ) 1) Chardonnay (n ) 3) Mu¨ller Thurgau (n ) 1) Nosiola (n ) 3) Rhine Riesling (n ) 2) Chardonnay (n ) 1) Chasselas (n ) 1) Chardonnay (n ) 6) generic white (n ) 9) Sauvignon blanc (n ) 10) Chardonnay (n ) 1) Muscat (n ) 1) Seyval blanc (n ) 1) Vidal (n ) 1)
