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Volume: 9, Issue: 7, July, 2019
DOI: 10.7324/JAPS.2019.90717

Review Article

Resveratrol and pterostilbene: A comparative overview of their chemistry, biosynthesis, plant sources and pharmacological properties

Eric Wei Chiang Chan1, Chen Wai Wong1, Yong Hui Tan1, Jenny Pei Yan Foo1, Siu Kuin Wong2, Hung Tuck Chan3

  Author Affiliations


Both resveratrol and pterostilbene are monomeric stilbenes having a 6−2−6 carbon skeleton with two phenyl rings linked by a double-bonded ethylene bridge. Resveratrol has three hydroxyl (−OH) groups, while pterostilbene has two methoxy (–OCH3) groups and one −OH group. They commonly occur in the trans form rather than the cis form. Red grapes and red wines are the main dietary sources of the resveratrol. Pterostilbene occurs in blueberries and grapes. Resveratrol and pterostilbene exhibit many similarities in pharmacological properties, including antioxidant, neuroprotective anti-cancer, cardioprotective, analgesic, anti-atherosclerosis, anti-aging, anti-diabetic, anti-inflammatory, and anti-obesity activities. The stronger pharmacological properties in pterostilbene than resveratrol have been attributed to its two –OCH3 groups. As a result, pterostilbene is more lipophilic which enhances its membrane permeability, bioavailability, and biological potency. Some future studies on resveratrol and pterostilbene are suggested. The sources of information cited in this comparative overview were from Science Direct, Google Scholar, and PubMed.


Resveratrol, pterostilbene, pharmacology, pharmacokinetics, future research.

Citation: Chan EWC, Wong CW, Tan YH, Foo JPY, Wong SK, Chan HT. Resveratrol and pterostilbene: A comparative overview of their chemistry, biosynthesis, plant sources and pharmacological properties. J Appl Pharm Sci, 2019; 9(07):124–129.

Copyright: The Author(s). This is an open access article distributed under the Creative Commons Attribution Non-Commercial License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.


Adrian M, Jeandet P, Douillet-Breuil AC, Tesson L, Bessis R. Stilbene content of mature Vitis vinifera berries in response to UV-C elicitation. J Agric Food Chem, 2000; 48:6103-5. https://doi.org/10.1021/jf0009910

Aguirre L, Milton-Laskibar I, Hijona E, Bujanda L, Rimando AM, Portillo MP. Effects of pterostilbene in brown adipose tissue from obese rats. J Physiol Biochem, 2016; 73:457-64. https://doi.org/10.1007/s13105-017-0556-2

Akinwumi B, Bordun KA, Anderson H. Biological activities of stilbenoids. Int J Mol Sci, 2018; 19:792. https://doi.org/10.3390/ijms19030792

Al Rahim M, Rimando AM, Silistreli K, El-Alfy AT. Anxiolytic action of pterostilbene: involvement of hippocampal ERK phosphorylation. Planta Med, 2013; 79:723-30. https://doi.org/10.1055/s-0032-1328553

Anisimova NY, Kiselevsky MV, Sosnov AV, Sadovnikov SV, Stankov IN, Gakh AA. Trans-, cis- and dihydro-resveratrol: a comparative study. Chem Central J, 2011; 5:88. https://doi.org/10.1186/1752-153X-5-88

Asensi M, Medina I, Ortega A, Carretero J, Baño MC, Obrador E, Estrela JM. Inhibition of cancer growth by resveratrol is related to its low bioavailability. Free Radic Biol Med, 2002; 33:387-98. https://doi.org/10.1016/S0891-5849(02)00911-5

Ballabh P, Braun A, Nedergaard M. The blood-brain barrier: an overview-structure, regulation and clinical implications. Neurobiol Dis, 2004; 16:1-3. https://doi.org/10.1016/j.nbd.2003.12.016

Bastianetto S, Ménard C, Quirion R. Neuroprotective action of resveratrol. Biochim Biophys Acta-Mol Basis Dis, 2015; 1852: 1195-201. https://doi.org/10.1016/j.bbadis.2014.09.011

Baur JA, Sinclair DA. Therapeutic potential of resveratrol: the in vivo evidence. Nat Rev Drug Discov, 2006; 5:493-506. https://doi.org/10.1038/nrd2060

Berman AY, Motechin RA, Wiesenfeld MY, Holz MK. The therapeutic potential of resveratrol: a review of clinical trials. NPJ Precis Oncol, 2017; 1:35. https://doi.org/10.1038/s41698-017-0038-6

Bhullar KS, Hubbard BP. Lifespan and health-span extension by resveratrol. Biochim Biophys Acta-Mol Basis Dis, 2015; 1852:1209-18. https://doi.org/10.1016/j.bbadis.2015.01.012

Bonnefont-Rousselot D. Resveratrol and cardiovascular diseases. Nutrients, 2016; 8:250. https://doi.org/10.3390/nu8050250

Brown VA, Patel KR, Viskaduraki M, Crowell JA, Perloff M, Booth TD, Vasilinin G, Sen A, Schinas AM, Piccirilli G, Brown K. Repeat dose study of the cancer chemopreventive agent resveratrol in healthy volunteers: safety, pharmacokinetics, and effect on the insulin-like growth factor axis. Cancer Res, 2010; 70:9003-11. https://doi.org/10.1158/0008-5472.CAN-10-2364

Burns J, Yokota T, Ashihara H, Lean MEJ, Crozier A. Plant foods and herbal sources of resveratrol. J Agric Food Chem, 2002; 50:3337-40. https://doi.org/10.1021/jf0112973

Catalgol B, Batirel S, Taga Y, Ozer NK. Resveratrol: French paradox revisited. Front Pharmacol, 2012; 3:141. https://doi.org/10.3389/fphar.2012.00141

Cavallini G, Straniero S, Donati A, Bergamini E. Resveratrol requires red wine polyphenols for optimum antioxidant activity. J Nutr Health Aging, 2016; 20:540-5. https://doi.org/10.1007/s12603-015-0611-z

Chakraborty S, Kumar A, Butt NA, Zhang L, Williams R, Rimando AM, Biswas PK, Levenson AS. Molecular insight into the differential anti-androgenic activity of resveratrol and its natural analogs: in silico approach to understand biological actions. Mol BioSyst, 2016; 12:1702-9. https://doi.org/10.1039/C6MB00186F

Chang J, Rimando A, Pallas M, Camins A, Porquet D, Reeves J, Shukitt-Hale B, Smith MA, Joseph JA, Casadesus G. Low-dose pterostilbene, but not resveratrol, is a potent neuro-modulator in aging and Alzheimer's disease. Neurobiol Aging, 2012; 33:2062-71. https://doi.org/10.1016/j.neurobiolaging.2011.08.015

Chatterjee K, AlSharif D, Mazza C, Syar P, Al Sharif M, Fata JE. Resveratrol and pterostilbene exhibit anticancer properties involving the downregulation of HPV oncoprotein E6 in cervical cancer cells. Nutrients, 2018; 10:243. https://doi.org/10.3390/nu10020243

Choo QY, Yeo SC, Ho PC, Tanaka Y, Lin HS. Pterostilbene surpassed resveratrol for anti-inflammatory application: potency consideration and pharmacokinetics perspective. J Funct Foods, 2014; 11:352-62. https://doi.org/10.1016/j.jff.2014.10.018

Cottart CH, Nivet-Antoine V, Laguillier-Morizot C, Beaudeux JL. Resveratrol bioavailability and toxicity in humans. Mol Nutr Food Res, 2010; 54:7-16. https://doi.org/10.1002/mnfr.200900437

de Ligt M, Timmers S, Schrauwen P. Resveratrol and obesity: can resveratrol relieve metabolic disturbances? Biochim Biophys Acta- Mol Basis Dis, 2015; 1852:1137-44. https://doi.org/10.1016/j.bbadis.2014.11.012

de Sá Coutinho D, Pacheco M, Frozza R, Bernardi A. Anti-inflammatory effects of resveratrol: mechanistic insights. Int J Mol Sci, 2018; 19:1812. https://doi.org/10.3390/ijms19061812

Dvorakova M, Landa P. Anti-inflammatory activity of natural stilbenoids: a review. Pharmacol Res, 2017; 124:126-45. https://doi.org/10.1016/j.phrs.2017.08.002

El Khawand T, Courtois A, Valls J, Richard T, Krisa S. A review of dietary stilbenes: sources and bioavailability. Phytochem Rev, 2018; 17:1007-29. https://doi.org/10.1007/s11101-018-9578-9

Langcake P, Cornford CA, Pryce RJ. Identification of pterostilbene as a phytoalexin from Vitis vinifera leaves. Phytochemistry, 1979; 18:1025-7. https://doi.org/10.1016/S0031-9422(00)91470-5

Hsieh TC, Wu JM. 2018. Unraveling and trailblazing cardioprotection by resveratrol. In: Wu JM, Hsieh TC, editors. Resveratrol: State-of-the-Art Science and Health Applications. World Publishing, Singapore, pp. 1-28, 2018. https://doi.org/10.1142/9789813270916_0001

Jang M, Cai L, Udeani GO, Slowing KV, Thomas CF, Beecher CW, Fong HH, Farnsworth NR, Kinghorn AD, Mehta RG, Moon RC. Cancer chemopreventive activity of resveratrol, a natural product derived from grapes. Science, 1997; 275:218-20. https://doi.org/10.1126/science.275.5297.218

Jeandet P, Delaunois B, Conreux A, Donnez D, Nuzzo V, Cordelier S, Clément C, Courot E. Biosynthesis, metabolism, molecular engineering, and biological functions of stilbene phytoalexins in plants. Biofactors, 2010; 36:331−41. https://doi.org/10.1002/biof.108

Jeandet P, Douillet-Breuil AC, Bessis R, Debord S, Sbaghi M, Adrian M. Phytoalexins from the Vitaceae: biosynthesis, phytoalexin gene expression in transgenic plants, antifungal activity, and metabolism. J Agric Food Chem, 2002; 50:2731-41. https://doi.org/10.1021/jf011429s

Kanwar JR, Sriramoju B, Kanwar RK. Neurological disorders and therapeutics targeted to surmount the blood-brain barrier. Int J Nanomed, 2012; 7:3259-78. https://doi.org/10.2147/IJN.S30919

Kapetanovic IM, Muzzio M, Huang Z, Thompson TN, McCormick DL. Pharmacokinetics, oral bioavailability, and metabolic profile of resveratrol and its dimethylether analog, pterostilbene, in rats. Cancer Chemother Pharmacol, 2011; 68:593-601. https://doi.org/10.1007/s00280-010-1525-4

Kosuru R, Rai U, Prakash S, Singh A, Singh S. Promising therapeutic potential of pterostilbene and its mechanistic insight based on preclinical evidence. Eur J Pharmacol, 2016; 789:229-43. https://doi.org/10.1016/j.ejphar.2016.07.046

Lange KW, Li S. Resveratrol, pterostilbene, and dementia. BioFactors, 2018; 44:83-90. https://doi.org/10.1002/biof.1396

Li YR, Li S, Lin CC. Effect of resveratrol and pterostilbene on aging and longevity. Biofactors, 2018; 44:69-82. https://doi.org/10.1002/biof.1400

Lopez MS, Dempsey RJ, Vemuganti R. Resveratrol neuroprotection in stroke and traumatic CNS injury. Neurochem Int, 2015; 89:75-82. https://doi.org/10.1016/j.neuint.2015.08.009

Manickam M, Ramanathan M, Jahromi MA, Chansouria JP, Ray AB. Anti-hyperglycemic activity of phenolics from Pterocarpus marsupium. J Nat Prod, 1997; 60:609-10. https://doi.org/10.1021/np9607013

Marier JF, Vachon P, Gritsas A, Zhang J, Moreau JP, Ducharme MP. Metabolism and disposition of resveratrol in rats: extent of absorption, glucuronidation, and enterohepatic recirculation evidenced by a linked-rat model. J Pharmacol Exper Ther, 2002; 302:369-73. https://doi.org/10.1124/jpet.102.033340

Maurya R, Ray AB, Duah FK, Slatkin DJ, Schiff PL. Constituents of Pterocarpus marsupium. J Nat Prod. 1984; 47:179-81. https://doi.org/10.1021/np50031a029

McCormack D, McFadden D. Pterostilbene and cancer: current review. J Surg Res, 2012; 173:53-61. https://doi.org/10.1016/j.jss.2011.09.054

McCormack D, McFadden D. A review of pterostilbene antioxidant activity and disease modification. Oxid Med Cell Longev, 2013; Article ID 575482, 15 p. https://doi.org/10.1155/2013/575482

Meng XL, Yang JY, Chen GL, Wang LH, Zhang LJ, Wang S, Li J, Wu CF. Effects of resveratrol and its derivatives on lipopolysaccharide-induced microglial activation and their structure-activity relationships. Chem Biol Interact, 2008; 174:51-9. https://doi.org/10.1016/j.cbi.2008.04.015

Messina F, Guglielmini G, Curini M, Orsini S, Gresele P, Marcotullio MC. Effect of substituted stilbenes on platelet function. Fitoterapia, 2015; 105:228-33. https://doi.org/10.1016/j.fitote.2015.07.009

Mikstacka R, Rimando AM, Ignatowicz E. Antioxidant effect of trans-resveratrol, pterostilbene, quercetin and their combinations in human erythrocytes in vitro. Plant Foods Hum Nutr, 2010; 65:57-63. https://doi.org/10.1007/s11130-010-0154-8

Niesen DB, Hessler C, Seeram NP. Beyond resveratrol: a review of natural stilbenoids identified from 2009-2013. J Berry Res, 2013; 3: 181-96.

Nonomura S, Kanagawa H, Makimoto A. Chemical constituents of polygonaceous plants. I. Studies on the components of Ko-jo-kon (Polygonum cuspidatum Sieb. et Zucc.). Yakugaku Zasshi, 1963; 83: 988-90. https://doi.org/10.1248/yakushi1947.83.10_988

Nutakul W, Sobers HS, Qiu P, Dong P, Decker EA, McClements DJ, Xiao H. Inhibitory effects of resveratrol and pterostilbene on human colon cancer cells: a side-by-side comparison. J Agric Food Chem, 2011; 59:10964-70. https://doi.org/10.1021/jf202846b

Pan MH, Wu JC, Ho CT, Lai CS. Anti-obesity molecular mechanisms of action: resveratrol and pterostilbene. BioFactors, 2018; 44:50-60. https://doi.org/10.1002/biof.1409

Paul S, Rimando AM, Lee HJ, Ji Y, Reddy BS, Suh N. Anti-inflammatory action of pterostlbene is mediated through the p38 mitogen-activated protein kinase pathway in colon cancer cells. Cancer Prev Res, 2009; 2:650−7. https://doi.org/10.1158/1940-6207.CAPR-08-0224

Poulose SM, Thangthaeng N, Miller MG, Shukitt-Hale B. Effects of pterostilbene and resveratrol on brain and behavior. Neurochem Int, 2015; 89:227−33. https://doi.org/10.1016/j.neuint.2015.07.017

Rauf A, Imran M, Butt MS, Nadeem M, Peters DG, Mubarak MS. Resveratrol as an anti-cancer agent: a review. Crit Rev Food Sci Nutr, 2018; 58:1428−47. https://doi.org/10.1080/10408398.2016.1263597

Rege SD, Geetha T, Griffin GD, Broderick TL, Babu JR. Neuroprotective effects of resveratrol in Alzheimer disease pathology. Front Aging Neurosci, 2014; 6:218. https://doi.org/10.3389/fnagi.2014.00218

Remsberg CM, Yáñez JA, Ohgami Y, Vega-Villa KR, Rimando AM, Davies NM. Pharmacometrics of pterostilbene: preclinical pharmacokinetics and metabolism, anticancer, anti-inflammatory, antioxidant and analgesic activity. Phytother Res, 2008; 22:169−79. https://doi.org/10.1002/ptr.2277

Renaud SD, de Lorgeril M. Wine, alcohol, platelets, and the French paradox for coronary heart disease. Lancet, 1992; 339:1523-6. https://doi.org/10.1016/0140-6736(92)91277-F

Riche DM, McEwen CL, Riche KD, Sherman JJ, Wofford MR, Deschamp D, Griswold M. Analysis of safety from a human clinical trial with pterostilbene. J Toxicol, 2013; Article ID 463595: 5 p. https://doi.org/10.1155/2013/463595

Rimando AM, Cuendet M, Desmarchelier C, Mehta RG, Pezzuto JM, Duke SO. Cancer chemopreventive and antioxidant activities of pterostilbene, a naturally occurring analogue of resveratrol. J Agric Food Chem, 2002; 50:3453-7. https://doi.org/10.1021/jf0116855

Rimando AM, Nagmani R, Feller DR, Yokoyama W. Pterostilbene, a new agonist for the peroxisome proliferator-activated receptor α-isoform, lowers plasma lipoproteins and cholesterol in hyper-cholesterolemic hamsters. J Agric Food Chem, 2005; 53:3403-7. https://doi.org/10.1021/jf0580364

Rimando AM, Kalt W, Magee JB, Dewey J, Ballington JR. Resveratrol, pterostilbene, and piceatannol in Vaccinium berries. J Agric Food Chem, 2004; 52:4713-9. https://doi.org/10.1021/jf040095e

Roberti M, Pizzirani D, Simoni D, Rondanin R, Baruchello R, Bonora C, Buscemi F, Grimaudo S, Tolomeo M. Synthesis and biological evaluation of resveratrol and analogs as apoptosis-inducing agents. J Med Chem, 2003; 46:3546-54. https://doi.org/10.1021/jm030785u

Rossi M, Caruso F, Antonioletti R, Viglianti A, Traversi G, Leone S, Basso E, Cozzi R. Scavenging of hydroxyl radical by resveratrol and related natural stilbenes after hydrogen peroxide attack on DNA. Chem Biol Interact, 2013; 20:175-85. https://doi.org/10.1016/j.cbi.2013.09.013

Schoonen WM, Salinas CA, Kiemeney LAL, Stanford JL. Alcohol consumption and risk of prostate cancer in middle-aged men. Int J Cancer, 2005; 113:133-40. https://doi.org/10.1002/ijc.20528

Seshadri TR. Polyphenols of Pterocarpus and Dalbergia woods. Phytochemistry, 1972; 11:881-98. https://doi.org/10.1016/S0031-9422(00)88430-7

Siemann EH, Creasy LL. Concentration of the phytoalexin resveratrol in wine. Am J Eno Vitic, 1992; 43:49-52.

Silva CG, Monteiro J, Marques RR, Silva AM, Martínez C, Canle M, Faria JL. Photochemical and photocatalytic degradation of trans-resveratrol. Photochem Photobiol Sci, 2013; 12:638-44. https://doi.org/10.1039/C2PP25239B

Sobolev VS, Khan SI, Tabanca N, Wedge DE, Manly SP, Cutler SJ, Coy MR, Becnel JJ, Neff SA, Gloer JB. Biological activity of peanut (Arachis hypogaea) phytoalexins and selected natural and synthetic stilbenoids. J Agric Food Chem, 2011; 59:1673-82. https://doi.org/10.1021/jf104742n

Sun AY, Simonyi A, Sun GY. The "French paradox" and beyond: neuroprotective effects of polyphenols. Free Radic Biol Med, 2002; 32:314−8. https://doi.org/10.1016/S0891-5849(01)00803-6

Szkudelski T, Szkudelska K. Anti-diabetic effects of resveratrol. Ann N Y Acad Sci, 2011; 1215:34-9. https://doi.org/10.1111/j.1749-6632.2010.05844.x

Tastekin B, Pelit A, Polat S, Tuli A, Sencar L, Alparslan MM, Daglioglu YK. Therapeutic potential of pterostilbene and resveratrol on biomechanic, biochemical, and histological parameters in streptozotocin-induced diabetic rats. Evid Based Complement Alternat Med, 2018; Article ID 9012352: 10 p. https://doi.org/10.1155/2018/9012352

Tellone E, Galtieri A, Russo A, Giardina B, Ficarra S. Resveratrol: a focus on several neurodegenerative diseases. Oxidat Med Cell Longevity, 2015; Article ID 392169:14 p. https://doi.org/10.1155/2015/392169

Timmers S, Auwerx J, Schrauwen P. The journey of resveratrol from yeast to human. Aging, 2012; 4:146-58. https://doi.org/10.18632/aging.100445

Tou JC. Evaluating resveratrol as a therapeutic bone agent: preclinical evidence from rat models of osteoporosis. Ann N Y Acad Sci, 2015; 1348:75−85. https://doi.org/10.1111/nyas.12840

Tsai HY, Ho CT, Chen YK. Biological actions and molecular effects of resveratrol, pterostilbene and 3'-hydroxypterostilbene. J Food Drug Anal, 2017; 25:134−47. https://doi.org/10.1016/j.jfda.2016.07.004

Varoni EM, Lo Faro AF, Sharifi-Rad J, Iriti M. Anticancer molecular mechanisms of resveratrol. Front Nutr, 2016; 3:8. https://doi.org/10.3389/fnut.2016.00008

Wang B, Liu H, Yue L, Li X, Zhao L, Yang X, Wang X, Yang Y, Qu Y. Neuroprotective effects of pterostilbene against oxidative stress injury: involvement of nuclear factor erythroid 2-related factor 2 pathway. Brain Res, 2016; 1643:70−9. https://doi.org/10.1016/j.brainres.2016.04.048

Wang P, Sang S. Metabolism and pharmacokinetics of resveratrol and pterostilbene. BioFactors, 2018; 44:16-25. https://doi.org/10.1002/biof.1410

Wang Q, Xu J, Rottinghaus GE, Simonyi A, Lubahn D, Sun GY, Sun AY. Resveratrol protects against global cerebral ischemic injury in gerbils. Brain Res, 2002; 958:439-47. https://doi.org/10.1016/S0006-8993(02)03543-6

Williams LD, Burdock GA, Edwards JA, Beck M, Bausch J. Safety studies conducted on high-purity trans-resveratrol in experimental animals. Food Chem Toxicol, 2009; 47:2170-82. https://doi.org/10.1016/j.fct.2009.06.002

Zhao RZ, Liu S, Zhou LL. Rapid quantitative HPTLC analysis, on one plate, of emodin, resveratrol and polydatin in the Chinese herb Polygonum cuspidatum. Chromatographia, 2005; 61:311-4. https://doi.org/10.1365/s10337-005-0514-y

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