Resveratrol in grapes

Wang Y, Catana F, Yang Y, Roderick R, Breemen RB. 2002. An LC-MS method for analyzing total resveratrol in grape juice, cranberry juice, and wine. J Agric Food Chem 50 431 435. 

One of the most relevant and extensively studied stilbene is trani-resveratrol (3,5,4 -trihydroxystilbene), a phytoalexin produced by grapevines in response to fungal infection, particularly Botrytis cinerea. Synthesis of resveratrol in grape berries is mainly located in the skin cells and is absent or low in the fruit flesh. In nature, resveratrol exists in two isomeric forms (cis- and frani -conflgured) in the free as well as in 6-glucoconjugated form. The 3-0-6-D-glucosides of cis- and trans-resveratrol cis-and trans-conflgured are called piceids. The chemical structures of resveratrol and further stilbenes are depicted in Fig. 9C.6. 

For determination of free and glucoside fnws-resveratrol in grape, 20 berries are separated from seeds and extracted for lh by 30 mL of methanol. After homogenization and centrifugation, the supernatant is separated from the solid parts and methanol is removed under vacuum. 

Due to the beneficial health effects of trans-resveratrol in grape wine, many methods have been developed for its detection and quantification.1 In our laboratory, a MIP-based CL imaging sensor for determination of tram-resveratro 1 in grape wine has been developed. The MIP of trans-resveratro 1 was prepared by a precipitation polymerization using trans-resveratrol as the target molecule,... 

Post-harvest elicitation of resveratrol in grapes by external agents... 

As described in the previous subsection, the rather unspecific antifungal character and the selective accumulation of tranr-resveratrol in grape skin make it a good candidate to serve as a natural pesticide against pathogen attack and, therefore, to improve the natural resistance of grapes to fungal infection. 

The PEE technique has so far been used almost exclusively as a first step in methods for analyzing several polyphenols from fresh grapes. Thus, Pineiro et al. [204] determined frani-resveratrol in grapes by using a method involving a triple-discrete PEE step with methanol as cosolvent. Also, Ju and Howard [205,206] examined the effect of various solvents and temperature conditions on the PLE of... 

Pineiro, Z., Palma, M. and Barroso, C.G., Determination of franj-resveratrol in grapes by pressurized liquid extraction and fast high-performance liquid chromatography, J. Chromatogr. A, 1110, 61, 2006. 

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. 

A similar effect was observed in other fruits and vegetables, where UV-C treated strawberries showed a higher increment of phenols and PAL activity 12 hours after treatment than unirradiated (control)(Pan and others 2004), which could be the reason for the increment in total phenol constituents (Lancaster and others 2000). UV-C and UV-B caused a two- and threefold increase in content of resveratrol (a grape phenol constituent). Thus, mature Napoleon grapes that had been irradiated with UV-C light can provide up to 3 mg of resveratrol per serving (Cantos and others 2001). Therefore, UV-C treatments clearly cause a benefit effect, increasing total phenol content, which can be mainly attributed to the increment of PAL activity. 

Aside from being UV-protectants, in a number of species certain stilbenes act as phytoalexins. Resveratrol (6.24 trans-3,5,4 -trihydroxy-stilbene), its cA-isomer, as well as their glucosides and dehydrodimer mm-e- iniferin (6.25) are present in grape leaves and berries and play a role in the defense against gray rot caused by the fungal pathogen Botrytis cinerea. 

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

Chan MM, Mattiacci JA, Hwang HS, Shah A, Fong D. 2000. Synergy between ethanol and grape polyphenols, quercetin, and resveratrol, in the inhibition of the inducible nitric oxide synthase pathway. Biochem Pharmacol 60 1539-1548. 

Gehm BD, McAndrews JM, Chien PY, Jameson JL. 1997. Resveratrol, a polyphenolic compound found in grapes and wine, is an agonist for the estrogen receptor. Proc Natl Acad Sci USA 94 14138-14143. 

Martin AR, Villegas I, La Casa C, de la Lastra CA. 2004. Resveratrol, a polyphenol found in grapes, suppresses oxidative damage and stimulates apoptosis during early colonic inflammation in rats. Biochem Pharmacol 67 1399-1410. 

Among polyphenols, resveratrol and its derivatives are thought to play a special role. Resveratrol occurs naturally in grapes in both cis-and trans-isomers, and in their respective glucosides (cis- and trans-piceids). All forms inhibit the oxidation of low density lipoprotein (LDL) and additional benefits. Resveratrol occurs in most red wines but is undetectable or occurs in negligible amounts in dry white wines (Pour Nikfardjam, 2002). 

Gebhardt, R. and Beck, H. 1996. Differential inhibitory effects of garlic-derived organosulfur compounds on cholesterol biosynthesis in primary rat hepatocyte culture. Lipids 31, 1269-1276. Gehm, B.D., McAndrews, J.M., Chien, P.Y., and Jameson, J.L. 1997. Resveratrol, a polyphenolic compound found in grapes and wine, is an agonist for estrogen receptor. Proc. Natl Acad. Sci. 94, 14138-14143. 

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