Synthetic Resveratrol Derivatives and Their Biological Activities: A Review

Resveratrol, a naturally derived stilbene that exists in various foods and beverages, has attracted extensive exploration due to its multiple biological activities, such as anticancer, antioxidant, cardiovascular protection, anti-inflammatory, antiviral, chemopreventive effect, neuroprotective effect, immunomodulation and so on. However, owing to its poor oral bioavailability, the application of resveratrol is greatly restricted. Because of that, a large amount of efforts had been made by researchers on designing its derivatives to obtain compounds with improved efficiency and low toxicity for developing more active drugs for clinical application. In this report, we review the current development of studying on resveratrol derivatives including their properties and activities. Additionally, this article also presents the synthetic routes of correlative resveratrol derivatives.

[1]  C. Li,et al.  In vitro Antiviral Effects and 3D QSAR Study of Resveratrol Derivatives as Potent Inhibitors of Influenza H1N1 Neuraminidase , 2015, Chemical biology & drug design.

[2]  B. Sumegi,et al.  Anti-inflammatory effects of a triple-bond resveratrol analog: structure and function relationship. , 2015, European journal of pharmacology.

[3]  V. Krajka-Kuźniak,et al.  The effect of resveratrol and its methylthio-derivatives on NF-κB and AP-1 signaling pathways in HaCaT keratinocytes , 2014, Pharmacological reports : PR.

[4]  M. Adrian,et al.  Antimicrobial Activity of Resveratrol Analogues , 2014, Molecules.

[5]  Erbing Hua,et al.  Design and Synthesis of Resveratrol Analogs , 2014 .

[6]  P. R. Jenkins,et al.  Novel analogues of resveratrol: metabolism and inhibition of colon cancer cell proliferation , 2013 .

[7]  Hai-bin Luo,et al.  Design, synthesis, and evaluation of multitarget-directed resveratrol derivatives for the treatment of Alzheimer's disease. , 2013, Journal of medicinal chemistry.

[8]  J. Pezzuto,et al.  Resveratrol analogs: promising chemopreventive agents , 2013, Annals of the New York Academy of Sciences.

[9]  S. Manna,et al.  Synthesis and evaluation of resveratrol derivatives as new chemical entities for cancer. , 2013, Journal of molecular graphics & modelling.

[10]  Xiaojun Yan,et al.  From resveratrol to its derivatives: new sources of natural antioxidant. , 2013, Current medicinal chemistry.

[11]  Y. Taga,et al.  Resveratrol: French Paradox Revisited , 2012, Front. Pharmacol..

[12]  Qian Zhang,et al.  Synthesis of 3′-methoxy-E-diethylstilbestrol and its analogs as tumor angiogenesis inhibitors , 2012, Steroids.

[13]  D. Borderie,et al.  Antioxidant effects of resveratrol and other stilbene derivatives on oxidative stress and *NO bioavailability: Potential benefits to cardiovascular diseases. , 2012, Biochimie.

[14]  Hongxin Dong,et al.  Resveratrol, a neuroprotective supplement for Alzheimer's disease. , 2012, Current pharmaceutical design.

[15]  J. Fenoll,et al.  Comparative inhibitory activity of the stilbenes resveratrol and oxyresveratrol on African swine fever virus replication. , 2011, Antiviral research.

[16]  F. Mattivi,et al.  The immunomodulating activities of resveratrol glucosides in humans. , 2011, Recent patents on food, nutrition & agriculture.

[17]  T. Richard,et al.  Neuroprotective properties of resveratrol and derivatives , 2011, Annals of the New York Academy of Sciences.

[18]  T. Szekeres,et al.  Chemopreventive effects of resveratrol and resveratrol derivatives , 2011, Annals of the New York Academy of Sciences.

[19]  M. Diederich,et al.  Potential of the Dietary Antioxidants Resveratrol and Curcumin in Prevention and Treatment of Hematologic Malignancies , 2010, Molecules.

[20]  T. Tuccinardi,et al.  Synthesis of heterocycle-based analogs of resveratrol and their antitumor and vasorelaxing properties. , 2010, Bioorganic & medicinal chemistry.

[21]  Ying Yan,et al.  Resveratrol-induced cytotoxicity in human Burkitt's lymphoma cells is coupled to the unfolded protein response , 2010, BMC Cancer.

[22]  J. Pezzuto,et al.  Selective synthesis and biological evaluation of sulfate-conjugated resveratrol metabolites. , 2010, Journal of medicinal chemistry.

[23]  R. Borges,et al.  A theoretical antioxidant pharmacophore for resveratrol. , 2009, European journal of medicinal chemistry.

[24]  Xuyu Zu,et al.  The design, synthesis, and anti-tumor mechanism study of N-phosphoryl amino acid modified resveratrol analogues. , 2008, Bioorganic & medicinal chemistry.

[25]  C. Diniz,et al.  New insights on the anticancer properties of dietary polyphenols , 2006, Medicinal research reviews.

[26]  H. Ge,et al.  Synthesis and Cytotoxic Evaluation of a Series of Resveratrol Derivatives , 2006, Chemistry & biodiversity.

[27]  S. Vilar,et al.  Design, synthesis, and vasorelaxant and platelet antiaggregatory activities of coumarin-resveratrol hybrids. , 2006, Bioorganic & medicinal chemistry letters.

[28]  F. Orallo.  Comparative studies of the antioxidant effects of cis- and trans-resveratrol. , 2006, Current medicinal chemistry.

[29]  J. Gies,et al.  Heptahelical and other G-protein-coupled receptors (GPCRs) signaling. , 2006, Current medicinal chemistry.

[30]  Jinhua Dong,et al.  Synthesis and anti-inflammatory activity of resveratrol analogs. , 2005, Chemical & pharmaceutical bulletin.

[31]  S. Rapposelli,et al.  Synthesis of a resveratrol analogue with high ceramide-mediated proapoptotic activity on human breast cancer cells. , 2005, Journal of medicinal chemistry.

[32]  T. Walle,et al.  HIGH ABSORPTION BUT VERY LOW BIOAVAILABILITY OF ORAL RESVERATROL IN HUMANS , 2004, Drug Metabolism and Disposition.

[33]  F. Caruso,et al.  Structural basis for antioxidant activity of trans-resveratrol: ab initio calculations and crystal and molecular structure. , 2004, Journal of agricultural and food chemistry.

[34]  N. Seeram,et al.  Role of resveratrol in prevention and therapy of cancer: preclinical and clinical studies. , 2004, Anticancer research.

[35]  J. Thénot,et al.  Human hepatic cell uptake of resveratrol: involvement of both passive diffusion and carrier-mediated process. , 2004, Biochemical and biophysical research communications.

[36]  Zhong‐Li Liu,et al.  Inhibition of free radical-induced peroxidation of rat liver microsomes by resveratrol and its analogues. , 2003, Biochimica et biophysica acta.

[37]  G. Maga,et al.  Specific Structural Determinants Are Responsible for the Antioxidant Activity and the Cell Cycle Effects of Resveratrol* , 2001, The Journal of Biological Chemistry.

[38]  S. Manna,et al.  Resveratrol Suppresses TNF-Induced Activation of Nuclear Transcription Factors NF-κB, Activator Protein-1, and Apoptosis: Potential Role of Reactive Oxygen Intermediates and Lipid Peroxidation1 , 2000, The Journal of Immunology.

[39]  Jen-kun Lin,et al.  Suppression of nitric oxide synthase and the down‐regulation of the activation of NFκB in macrophages by resveratrol , 1999, British journal of pharmacology.

[40]  L. Barrier,et al.  Comparative study of radical scavenger and antioxidant properties of phenolic compounds from Vitis vinifera cell cultures using in vitro tests. , 1997, Life sciences.

[41]  M. Takaoka.  The Phenolic Substances of White Helleboro (Veratrum Grandiflorum Hoes. Fil.). III , 1940 .