Resveratrol chemical structure

Figure 14.1 (a) Chemical structure of resveratrol. (b) Chemical structure of stilbene... 

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. 

Fig. 9C.6 Chemical structures of stilbenes trani-resveratrol (1), ais-resveratrol (2), froni-piceid (3), cii-piceid (4), ironi-piceatannol (5), frani-pterostilbene (6), trani-5-viniferin (7), trans- s-vinifeiin (8), a-viniferin (9), hopeaphenol (10)...

Figure 6.3 Chemical structures of curcuminoids, resveratrol, and gallates.

The difference in the chemical structure of fraws-resveratrol and cis-piceid is that the latter has a glucose at the Rj position while the former has a hydroxyl group. This implies that the presence of the hydroxyl substituent is necessary for antitumor activity of the stilbene. The difference in activity may also be due to geometric stereochemical differences between the cis and trans double bonds and/or the poor solubility of the glucoside derivative in water which inhibits the interaction of this compound with cellular components. 

Figure 2 Chemical structures of selected plant polyphenols. Structures include a flavonol (quercetin), isoflavone (daidzein), cinnamic acid (chlorogenic acid), flavan-3-ol (catechin), a lignan microbial metabolite (enterodiol), and a stilbene (resveratrol).

FIGURE 26.1 Chemical structures of resveratrol isoforms found in natural products. 

Fig. 3.11 Chemical structure of anti-aging remedies that should be included in diet to prevent stroke. Cucurmin (a) resveratrol (b) green tea catechm (epigaliocatechin geiilate) (c) and ferulic acid (d)...

FIGURE 35.2 Chemical structure of fatty acids, vitamins, cholesterol, protoporphyrin IX, and resveratrol. 

Fig. 2.18 Chemical structures of estradiol and /raw-resveratrol. (Authors own work)...

Fig. 82.3 Chemical structures of some important molecules (a) glucosinolates, (b) caffeine, (c) beta carotene, (d) beta sitosterol, (e) isoflavones, and (f) resveratrol...

Fig. 5.1 Chemical structures reporting examples of natural compounds with different biological effects, a a-Linolenic acid, an essential omega-3 fatty acid. Omega-3 is known to decrease the risk of cardiovascular diseases b a-amantine is a deadly natural compound found in the Amanita phalloides mushrooms c resveratrol, a polyphenolic stilbenoid produced in plants with several reported pharmacological actions...

Fig. 7.4 Chemical structures and DPP-IV inhibitory activity for the most relevant natural compounds of non-peptide nature a sulphostin b berberine c trigonelline d compound 4 e curcumin f resveratrol g luteolin h apigenin i flavone j naringin and kZINC02132035...

Figure 3. Chemical structures of daidzein, genistein, resorcinol and resveratrol. All agents have a common resorcin moiety, except for daidzein,...

In this article, we have reviewed the literatures available for the mechanism of action and anti-inflammatory properties of selected nutraceuticals such as curcumin, resveratrol, green tea polyphenols and diarylheptanoids (chemical structures in Figure 1). In addition we have also shown the antiinflammatory properties of a diarylheptanoids from Alpinia galanga and different possible targets in inflammation. 

The H and I3C NMR data for the majority of the resveratrol dimers are presented in Tables (3) and (4), respectively. The data presented in these tables represent the typical range of chemical shift values and coupling constants that are encountered with all known resveratrol oligomers. Since most resveratrol oligomers can be considered as a dimer to which additional resveratrol monomers are fused (i.e. the trimer, leachianol D (34b), is the dimer pallidol fused with a third resveratrol moiety), these tables can be used to quickly help identify which structural moieties may be present in a new resveratrol oligomer. 

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