Abstract
Stilbenoids are naturally occurring polyphenols, found in several edible plants, such as berries, peanuts, and grapes, which have been attracting increasing interest owing to their potential benefits for human health, namely, to prevent and treat chronic diseases related with aging. They can be constitutively expressed or biosynthesized as phytoalexins. Structurally characterized by a C6–C2–C6 scaffold, they can be found as monomers, dimers, trimers, or very complex oligomers. In this chapter, the focus will be on dietary stilbenoids found in the Vitis vinifera, namely, in grapes and wine, which are the principal dietary source of stilbenes. Among them, trans-resveratrol is the most extensively investigated stilbene. The main bioactive constituents, bioavailability and metabolism, the in vivo biological properties of the major constituents, and their role in human health, application in food, as well as issues related with safety and marketed and patented products will be also discussed.
References
Akinwumi B, Bordun K, Anderson H (2018) Biological activities of stilbenoids. Int J Mol Sci 19(3):792. https://doi.org/10.3390/ijms19030792
Beres C, Costa GNS, Cabezudo I et al (2017) Towards integral utilization of grape pomace from winemaking process: a review. Waste Manag 68:581–594
Boocock DJ, Faust G, Patel K et al (2007) Phase I dose escalation pharmacokinetic study in healthy volunteers of resveratrol, a potential cancer chemopreventive agent. Cancer Epidemiol Biomark Prev 16:1246–1252. https://doi.org/10.1158/1055-9965.EPI-07-0022
Braga A, Ferreira P, Oliveira J et al (2018) Heterologous production of resveratrol in bacterial hosts: current status and perspectives. World J Microbiol Biotechnol 34:122. https://doi.org/10.1007/s11274-018-2506-8
Calvo-Castro L, Schiborr C, David F et al (2018) The oral bioavailability of trans-resveratrol from a grapevine-shoot extract in healthy humans is significantly increased by micellar solubilization. Mol Nutr Food Res 62:1–8
Dewick PM (2009) Medicinal natural products: a biosynthentic approach. John Wiley and Sons, Ltd. West Sussex. United Kingdon
Dvorakova M, Landa P (2017) Anti-inflammatory activity of natural stilbenoids: a review. Pharmacol Res 124:126–145
Edwards J, Beck M, Riegger C et al (2011) Safety of resveratrol with examples for high purity, trans-resveratrol, res Vida®. Ann N Y Acad Sci 1215:131–137
Gabaston J, Cantos-Villar E, Biais B et al (2017) Stilbenes from Vitis vinifera L. waste: a sustainable tool for controlling Plasmopara viticola. J Agric Food Chem 65:2711–2718
Georgiev V, Ananga A, Tsolova V (2014) Recent advances and uses of grape flavonoids as nutraceuticals. Nutrients 6:391–415
Georgiev V, Ananga A, Tsolova V (2016) Dietary supplements/nutraceuticals made from grapes and wines. In: Moreno-Arribas MV, Suáldea BB (eds) Wine safety, consumer preference, and human health, 1st edn. Springer, Cham, pp 201–227
ISVV – Polyphenols reference database (2017) Stilbenes, Viniferin, Resveratrol and derivatives. https://mib-polyphenol.eu/plant/vitis/vitis-vinifera-l/. Accessed 19 Jan 2019
Kershaw J, Kim K (2017) The therapeutic potential of piceatannol, a natural stilbene, in metabolic diseases: a review. J Med Food 20:427–438
Khawand T, Courtois A, Valls J et al (2018) A review of dietary stilbenes: sources and bioavailability. Phytochem Rev 17:1007–1029
Kuo H, Wang R, Lin Y et al (2017) Pilot scale repeated fed-batch fermentation processes of the wine yeast Dekkera bruxellensis for mass production of resveratrol from Polygonum cuspidatum. Bioresour Technol 243:986–993
Li C, Xu X, Tao Z et al (2016) Resveratrol derivatives: an updated patent review (2012–2015). Expert Opin Ther Pat 26:1–12
Merryvital AG (2018) Cosmetic or pharmaceutical preparation for the care of the skin and improve the skin condition. German Patent DE201820105288
Motta S, Guaita M, Petrozziello M et al (2017) Comparison of the physicochemical and volatile composition of wine fractions obtained by two different dealcoholization techniques. Food Chem 221:1–10
Navarro G, Martínez Pinilla E, Ortiz R et al (2018) Resveratrol and related stilbenoids, nutraceutical/dietary complements with health-promoting actions: industrial production, safety, and the search for mode of action. Compr Rev Food Sci Food Saf 17:808–826
Nguyen A, Martinez M, Stamos M et al (2009) Results of a phase I pilot clinical trial examining the effect of plant-derived resveratrol and grape powder on Wnt pathway target gene expression in colonic mucosa and colon cancer. Cancer Manag Res 1:25–37
Pawlus A, Waffo-Teguo P, Saver J et al (2012) Stilbenoid chemistry from wine and the genus vitis, a review. J Int Sci Vigne Vin 46:57–111
Peng R, Lin G, Ting Y et al (2018) Oral delivery system enhanced the bioavailability of stilbenes: resveratrol and pterostilbene. Biofactors 44:5–15
Pezzuto J, Kondratyuk T, Ogas T (2013) Resveratrol derivatives: a patent review (2009 – 2012). Expert Opin Ther Pat 23:1529–1546
Piver B, Fer M, Vitrac X et al (2004) Involvement of cytochrome P450 1A2 in the biotransformation of trans-resveratrol in human liver microsomes. Biochem Pharmacol 68:773–782
Pixabay (2019) https://pixabay.com/pt/bagas-de-vinho-uvas-bagas-azul-694196/. Accessed 20 Feb 2019
Queipo-Ortuño M, Boto-Ordóñez M, Murri M et al (2012) Influence of red wine polyphenols and ethanol on the gut microbiota ecology and biochemical biomarkers. Am J Clin Nutr 95:1323–1334
Ramírez-Garza S, Laveriano-Santos E, Marhuenda-Muñoz M et al (2018) Health effects of resveratrol: results from human intervention trials. Nutrients. pii: E1892. https://doi.org/10.3390/nu10121892
Riche D, McEwen C, Riche K et al (2013) Analysis of safety from a human clinical trial with pterostilbene. J Toxicol 463595. https://doi.org/10.1155/2013/463595
Riche D, Riche K, Blackshear C et al (2014) Pterostilbene on metabolic parameters: a randomized, double-blind, and placebo-controlled trial. Evid Based Complement Altern Med 459165. https://doi.org/10.1155/2014/459165
Rivière C, Pawlus A, Mérillon J (2012) Natural stilbenoids: distribution in the plant kingdom and chemotaxonomic interest in Vitaceae. Nat Prod Rep 29:1317–1333
Rocha-Parra D, Chirife J, Zamora C et al (2018) Chemical characterization of an encapsulated red wine powder and its effects on neuronal cells. Molecules 23:842. https://doi.org/10.3390/molecules23040842
Rossi D, Guerrini A, Bruni R et al (2012) Trans-resveratrol in nutraceuticals: issues in retail quality and effectiveness. Molecules 17:12393–12405. https://doi.org/10.3390/molecules171012393
Salehi B, Mishra AP, Nigam M et al (2018) Resveratrol: a double-edged sword in health benefits. Biomedicine 6:91. https://doi.org/10.3390/biomedicines6030091
Shen T, Wang X, Lou H (2009) Natural stilbenes: an overview. Nat Prod Rep 26:916–935
Shen J, Zhou Q, Li P et al (2017) Update on phytochemistry and pharmacology of naturally occurring resveratrol oligomers. Molecules 22:2050. https://doi.org/10.3390/molecules22122050
Siddiqui I, Sanna V, Ahmad N et al (2015) Resveratrol nanoformulation for cancer prevention and therapy. Ann N Y Acad Sci 1348:20–31
Singh C, Ndiaye M, Ahmad N (2015) Resveratrol and cancer: challenges for clinical translation. Biochim Biophys Acta Mol basis Dis 1852:1178–1185
Sotheeswaran S, Pasupathy V (1993) Distribution of resveratrol oligomers in plants. Phytochemistry 32:1083–1092
Summerlin N, Soo E, Thakur S et al (2015) Resveratrol nanoformulations: challenges and opportunities. Int J Pharm 479:282–290
Teixeira A, Baenas N, Dominguez-Perles R et al (2014) Natural bioactive compounds from winery by-products as health promoters: a review. Int J Mol Sci 15:15638–15678
Thomas B, Thomas M, Sinclair D (2016) Process for stimulating hyaluronic acid synthesis. World Patent WO/2016/193791
Tomé-Carneiro J, Gonzálvez M, Larrosa M et al (2012a) Consumption of a grape extract supplement containing resveratrol decreases oxidized LDL and ApoB in patients undergoing primary prevention of cardiovascular disease: a triple-blind, 6-month follow-up, placebo-controlled, randomized trial. Mol Nutr Food Res 56:810–821
Tomé-Carneiro J, Gonzálvez M, Larrosa M et al (2012b) One-year consumption of a grape nutraceutical containing resveratrol improves the inflammatory and fibrinolytic status of patients in primary prevention of cardiovascular disease. Am J Cardiol 110:356–363
Tomé-Carneiro J, Gonzálvez M, Larrosa M et al (2013a) Grape resveratrol increases serum adiponectin and downregulates inflammatory genes in peripheral blood mononuclear cells: a triple-blind, placebo-controlled, one-year clinical trial in patients with stable coronary artery disease. Cardiovasc Drugs Ther 27:37–48
Tomé-Carneiro J, Larrosa M, Yáñez-Gascón MJ et al (2013b) One-year supplementation with a grape extract containing resveratrol modulates inflammatory-related microRNAs and cytokines expression in peripheral blood mononuclear cells of type 2 diabetes and hypertensive patients with coronary artery disease. Pharmacol Res 72:69–82
Tsai H, Ho C, Chen Y (2017) Biological actions and molecular effects of resveratrol, pterostilbene, and 3′-hydroxypterostilbene. J Food Drug Anal 25:134–147. https://doi.org/10.1016/j.jfda.2016.07.004
Tsuchiya H (2015) Membrane interactions of phytochemicals as their molecular mechanism applicable to the discovery of drug leads from plants. Molecules 20:18923–18966. https://doi.org/10.3390/molecules201018923
Vercauteren J, Castagnino C, Dalaunay J-C, Caudalie (1999) Composition based on resveratrol. World Patent WO/1999/003816
Vitaglione P, Sforza S, Galaverna G et al (2005) Bioavailability of trans-resveratrol from red wine in humans. Mol Nutr Food Res 49:495–504
Waffo-Téguo P, Hawthorne ME, Cuendet M, Mérillon JM, Kinghorn AD, Pezzuto JM, Mehta RG (2001) Potential cancer-chemopreventive activities of wine stilbenoids and flavans extracted from grape (Vitis vinifera) cell cultures. Nutr Cancer 40(2):173–179
Wahab A, Gao K, Jia C et al (2017) Significance of resveratrol in clinical management of chronic diseases. Molecules 22:1329. https://doi.org/10.3390/molecules22081329
Walle T, Hsieh F, DeLegge M et al (2004) High absorption but very low bioavailability of oral resveratrol in humans. Drug Discov Today 32:1377–1382
Wang P, Sang S (2018) Metabolism and pharmacokinetics of resveratrol and pterostilbene. Biofactors 44:16–25
Wikimedia commons (2019) https://commons.wikimedia.org/wiki/File:K%C3%B6hler%27s_Medizinal-Pflanzen_in_naturgetreuen_Abbildungen_mit_kurz_erl%C3%A4uterndem_Texte_(Plate_51)_(7118324671).jpg. Accessed 28 Mar 2019
Williams L, Burdock G, Edwards J et al (2009) Safety studies conducted on high-purity trans-resveratrol in experimental animals. Food Chem Toxicol 47:2170–2182
Xiao K, Zhanga H, Xuan L et al (2008) Stilbenoids: chemistry and bioactivities. In: Atta-ur-Rahman (ed) Studies in Natural Products Chemistry, Elsevier. Amsterdam, Netherlands. vol 34, pp 453–646
Yamakoshi J, Saito M, Kataoka S, Kikuchi M (2002) Safety evaluation of proanthocyanidin-rich extract from grape seeds. Food Chem Toxicol 40:599–607
Yu L, Wang S, Kogure Y et al (2013) Modulation of TRP channels by resveratrol and other stilbenoids. Mol Pain 9(3). https://doi.org/10.1186/1744-8069-9-3
Zha W (2018) Transporter-mediated natural product–drug interactions for the treatment of cardiovascular diseases. J Food Drug Anal 26:S32–S44. https://doi.org/10.1016/j.jfda.2017.11.008
Zhu F, Du B, Zheng L et al (2015) Advance on the bioactivity and potential applications of dietary fibre from grape pomace. Food Chem 186:207–212
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Duarte, N., Ramalhete, C., Rijo, P., Reis, M.A., Ferreira, MJ.U. (2020). Stilbenoids in Grapes and Wine. In: Xiao, J., Sarker, S., Asakawa, Y. (eds) Handbook of Dietary Phytochemicals. Springer, Singapore. https://doi.org/10.1007/978-981-13-1745-3_21-1
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