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Resveratrol is a stilbenoid polyphenol, possessing two phenol rings linked to each other by an ethylene bridge. The chemical structure of resveratrol (trans-3,5,4′-trihydroxystilbene) is identified in two isomeric forms, cis- and trans-resveratrol. trans form is dominant in terms of its prevalence and different biological activities are attributed, namely in inducing cellular responses such as cell cycle arrest, differentiation, apoptosis, and to enhance cancer cells anti-proliferation.
Formal chemical name (IUPAC name) of resveratrol is E-5-(4-hydroxystyryl)benzene-1,3-diol. Various aspects on resveratrol chemistry are currently being studied. It exists as two geometric isomers: cis-(Z) and trans-(E). trans form can undergo to cis form isomerization when exposed to UV irradiation. trans-resveratrol powder was found to be stable under “accelerated stability” conditions of 75% humidity and 40 °C in the presence of air. The low resveratrol bioavailability was encumbered its therapeutic application. Therefore, modification of resveratrol structure has received special attention from researchers and many resveratrol derivatives have been synthesized such as methoxylated, hydroxylated and halogenated derivatives, all of them exhibiting favorable therapeutic potential. Resveratrol is present in dietary products as glycosylated forms, known as piceid. Though, plants and pathogens, and even human digestive tract possess enzymes able to triggers polyphenols oxidation (and subsequent inactivation), the glycosylation prevents enzymatic oxidation of resveratrol, thereby preserving its biological effects and increasing its overall stability and bioavailability [18]. Furthermore, since intestinal cells can absorb only resveratrol aglycone form, absorption process requires glycosidases. Therefore, the relative aglycone and glycosylated resveratrol amounts in foods and beverages may modulate its absorption rate.
Three glycosylated resveratrol analogues, piceid, piceatannol glucoside, and resveratroloside isolated from the invasive plant species Polygonum cuspidatum were identified as the major antibacterial compounds. Glycosylated resveratrol analogues have comparable biological effects after transepitelial passage, as they can be hydrolyzed into deglycosylated forms, resveratrol in the intestine. However, in vitro studies have shown that the glycosylated analogues even show more powerful bioactivities. For example, resveratrol and piceid have similar antioxidant capacity, but piceid appears to be more efficacious than resveratrol due to its reaction with its radical form. Indeed, resveratrol-glycoside was more effective than resveratrol against hepatitis B virus. Piceatannol, with one more hydroxyl group, was already reported as having stronger anti-inflammatory, immunomodulatory, anti-proliferative, anti-leishmanial, anti-leukemic, and protein-tyrosine kinase inhibitory effects.
Pterostilbene, a natural methoxylated resveratrol analogue, was first isolated from Pterocarpus santalinus (red sandalwood), a plant used in traditional medicine for diabetes treatment. This Pterocarpus marsupium active constituent is mainly found in blueberries, grapes, and several plant woods. Pterostilbene has a similar structure to resveratrol except that in A ring 3 and 5 position was replaced by a methoxyl group. This compound pro-lipophilicity, greater than that of resveratrol, increases its bioavailability resulting in stronger bioactivities, including anticancer, anti-lipidemic, antidiabetic, and cardioprotective effects than those of resveratrol.
In the same line, resveratrol nanoformulation have been conceived as a promising approach for biological function retaining, where polycaprolactone form the hydrophobic core, whereas polyethylene glycol form the hydrophilic shell of the encapsulated resveratrol micelles. Solid lipid nanoparticles and nanostructured lipid carriers are two unique resveratrol nanodelivery systems that were developed to enhance resveratrol’ oral bioavailability for nutraceutical purposes. Indeed, resveratrol nanoparticles led to an improvement in its solubility and enhances its antioxidant potential than free form. For example, resveratrol nanoformulation exhibited an in vivo absorption raise, length of action extension and bioavailability improvement by 3.516 times more, when compared with raw form. In addition, the hydrophobic nature of resveratrol considerably contributes to its limited bioavailability, which results from its poor water solubility. Thus, resveratrol encapsulated in methylated-β-cyclodextrins (in a ratio 1:1) improved its water solubility (about 400-fold), and consequently its bioavailability, maintaining its antioxidant and antibacterial effects (against Campylobacter), at same time that encourages its further application in food industry, aiming at foodborne pathogens control, as well as for nutraceuticals purposes.
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Author Info
1Medical Ethics and Law Research Center, Shahid Beheshti University of Medical Sciences, Tehran 88777539, Iran;
2Student Research Committee, Shahid Beheshti University of Medical Sciences, Tehran 22439789, Iran
3Department of Pharmaceutical Chemistry, H. N. B. Garhwal (A Central) University, Srinagar Garhwal 246174, Uttarakhand, India;
4Department of Biochemistry, H. N. B. Garhwal (A Central) University, Srinagar Garhwal 246174, Uttarakhand, India;
5Gazi University Faculty of Pharmacy Department of Pharmacognosy, Ankara 06330, Turkey; (B.S.);(M.K.)
6Department of Medical Parasitology, Zabol University of Medical Sciences, Zabol 61663335, Iran
7Antimicrobial and Biocontrol Agents Unit, Department of Biochemistry, Faculty of Science, University of Yaounde 1, Ngoa Ekelle, Annex Fac. Sci, P.O. Box. 812, Yaounde-Cameroon.
8Faculty of Medicine, University of Porto, Alameda Prof. Hernâni Monteiro, Porto 4200-319, Portugal
9Institute for Research and Innovation in Health (i3S), University of Porto, Porto 4200-135, Portugal
10Phytochemistry Research Center, Shahid Beheshti University of Medical Sciences, Tehran 11369, Iran
11Department of Chemistry, Richardson College for the Environmental Science Complex, The University of Winnipeg, Winnipeg, MB R3B 2G3, Canada
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6164842/
(All these Articles can be read from this URL: )
https://markethive.com/group/ama/blog/the-role-of-resveratrol-in-achieving-optimal-health-p5
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