Piceid

Stilbenes have a 1,2-diphenylethylene as their basic structure (C6-C2-C6). Resve-ratrol, the most widely known compound, contains three hydroxyl groups in the basic structure and is called 3,4, 5-trihydroxystilbene. In plants, piceid, the glucoside of resveratrol, is the major derivative of resveratrol. Stilbenes are present in plants as cis or trans isomers. Trans forms can be isomerized to cis forms by UV radiation (Lamuela-Raventos and others 1995). 

Romero-Perez AI, Ibern-Gomez M, Lamuela-Raventos RM and de la Torre-Boronat MC. 1999. Piceid, the major resveratrol derivative in grape juices. J Agric Food Chem 47(4) 1533—1536. 

Romero-Perez AI, Lamuela-Raventos RM, Andres-Lacueva C and Torre-Boronat MC. 2001. Method for the quantitative extraction of resveratrol and piceid isomers in grape berry skins. Effect of powdery mildew on the stilbene content. J Agric Food Chem 49(1) 210-215. 

Waterhouse AL and Lamuela-Raventos RM. 1994. The occurrence of piceid, a stilbene glucoside, in grape berries. Phytochemistry 37 571-573. 

Decendit, A. et al., Anthocyanins, catechins, condensed tannins and piceid production in Vitis vinifera cell bioreactor cultures, Biotechnol. Lett., 18, 659, 1996. 

Table 7. Effects of 2,3,5,4 -tetrahydroxystiIbene-2-0-D-glucoside and piceid on cancer metastasis lu iung, spleen and thymus in LLC-bearing Mice...

Fig. 31. Effects of 2,3,5,4 -tetrahydroxystilbene-2-0-D-glueoside (a) and piceid (b) on tumor growth in LLC-bearing mice. 

Solid-type LLC was prepared by subcutaneous transplantation into the right hind paw on day 0. 2,3,5,4 -Tetrahydroxystilbene-2-0-D-glucoside or piceid was administered orally twice daily for 32 consecutive days, starting 12 h afler tumor implantation. 

R. M. Lamuela-Raventos et al., Direct HPLC Analysis of Cis- and 7>ans-resveratrol and Piceid Isomers in Spanish Red Vitis vinifera Wines, ... 

Yitrac X, Bornet A, Yanderlinde R, Vails JM, Richard T, Delaunay J-C, Merillon J-M, Teissedre P-L. 2005. Determination of stilbenes (8-viniferin, trans-astringin, trans-piceid, cis- and trans-resveratrol, e-viniferin) in Brazilian wines. J Agric Food Chem 53 5664-5669. 

Resveratrol and piceid are mainly present in grape and grape products, and its composition is affected by grape variety, maturity degree at harvest, fungal... 

Rimando et al., 2004 Sobolev and Cole, 1999 Tokusoglu et al., 2005]. In an adult Spanish cohort resveratrol and piceid, trans and czls-forms, were evaluated. Estimated median and mean of resveratrol and piceid were 100 and 933 pg/day, respectively, of which 98.4, 1.6, and less than 0.1% come from wines, grape and grape juice, and peanuts, pistachios, and berries, respectively [Zamora-Ros et al., 2008]. 

Caco-2 cells 150-300 pM t-Resv and t-piceid (0.03-0.5 h) i-Resv > t-piceid Henry et al., 2005... 

In summary, resveratrol absorption is higher as aglycon than piceid, although piceid can be hydrolyzed by (5-glucosidases in the enterocytes [Henry-Vitrac... 

The evaluation of pharmacokinetic analysis of resveratrol was carried out in different animal models such as rats, mice, and rabbits [Asensi et al., 2002 Chen et al., 2007 Juan et al., 2002 Marier et al., 2002 Sale et al., 2004] furthermore, pharmacokinetic analysis was also evaluated with other resveratrol derivatives such as piceid [Lv et al., 2006 Zhou et al., 2007], a Smilax china root extract [Huang et al., 2008], 3,4,5,4 -tetramethoxystilbene [Sale et al., 2004], piceatan-nol, pinosylvin, and rhapontigenin [Roupe et al., 2006] (Table 13.4). 

Various studies have focused on the metabolism of piceid, the glucoside of resveratrol. These studies are of great interest due to the higher amount of piceid compared to resveratrol in food. Therefore, bioavailability studies of this compound are required. In vitro studies have already observed the absorption of piceid in the enterocytes, but in vivo studies in animal models are still scarce. 

Zamora-Ros et al [2006] carried out the first work that assessed the bioavailability of resveratrol (provided by different wines) in a regular intervention during 28 day. The analyses were performed by LC-MS/MS. In the first study, 10 healthy males were recruited to consume 300 mL/day of sparkling wine (1.19 mg resveratrol/1). After 28 day of supplementation, urinary trans-and m-resveratrol-3-O-glucuronides were 75 and 38 nmol/g creatinine, respectively. In the second study, 10 healthy females were selected to consume 200 mL of white wine (1.99 mg resveratrol/L) or 200 mL of red wine (12.8 mg resveratrol/L) in a crossover clinical trial. Likewise after 28 days only resveratrol metabolites were detected in morning urine, trans- (205 and 473 nmol/g creatinine) and ra-resveratrol-3-O-glucuronidcs (58 and 140 nmol/g creatinine) were found after white and red wine intake, respectively. Those studies showed that urinary excretion was dose dependent. Furthermore, slight amounts of resveratrol metabolites were also detected at baseline periods. No free resveratrol or piceid were detected in any of the studies. 

Henry C, Vitrac X, Decendit A, Ennamany R, Krisa S, Merillon JM. 2005. Cellular uptake and efflux of trans-piceid and its aglycone traw-resveratrol on the apical membrane of human intestinal Caco-2 cells. J Agric Food Chem 53 798-803. 

Henry-Vitrac C, Desmouliere A, Girard D, Merillon JM, Krisa S. 2006. Transport, deglycosylation, and metabolism of trans-piceid by small intestinal epithelial cells. Eur J Nutr 45 376-382. 

Lv C, Zhang L, Wang Q, Liu W, Wang C, Jing X, Liu Y. 2006. Determination of piceid in rat plasma and tissues by high-performance liquid chromatographic method with UV detection. Biomed Chromatogr 20 1260-1266. 

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