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Resveratrol and Its Derivatives as Phytoalexins

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Bioactive Polyphenols from Wine Grapes

Part of the book series: SpringerBriefs in Cell Biology ((SBCB))

Abstract

Phytoalexins are plant metabolites produced in response to biotic and abiotic stressors. Stilbenes are a class of phytoalexins produced in particularly high levels in the grapevine Vitis vinifera that are of biomedical interest for their activities in mammalian cells. In this chapter we review the biochemistry of stilbene synthesis and briefly outline the role of these compounds in plant physiology. We summarize the steps involved in the synthesis of resveratrol, the most well studied stilbene produced by Vitis vinifera in the context of human health, and show how this molecule serves as the precursor to a variety of structurally similar molecules found in grapevines and red wines. We then discuss current strategies used to enhance stilbene production in the grapevine, and the concentrations of resveratrol and related stilbenes in red wines.

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References

  • Adrian M, Jeandet P, Breuil AC, Levite D, Debord S, Bessis R (2000a) Assay of resveratrol and derivative stilbenes in wines by direct injection high performance liquid chromatography. Am J Enol Viticult 51:37–41

    CAS  Google Scholar 

  • Adrian M, Jeandet P, Douillet-Breuil AC, Tesson L, Bessis R (2000b) Stilbene content of mature Vitis vinifera berries in response to UV-C elicitation. J Agric Food Chem 48:6103–6105

    Article  PubMed  CAS  Google Scholar 

  • Ahuja I, Kissen R, Bones AM (2012) Phytoalexins in defense against pathogens. Trends Plant Sci 17:73–90

    Article  PubMed  CAS  Google Scholar 

  • Bavaresco L, Pezzutto S, Gatti M, Mattivi F (2007) Role of the variety and some environmental factors on grape stilbenes. Vitis 46:57–61

    Google Scholar 

  • Boso S, Alonso-Villaverde V, Martinez M-C, Kassemeyer H-H (2012) Quantification of stilbenes in Vitis genotypes with different levels of resistance to Plasmopara viticola infection. Am J Enol Viticult 63:419–423

    Article  Google Scholar 

  • Boue SM, Cleveland TE, Carter-Wientjes C, Shih BY, Bhatnagar D, McLachlan JM, Burow ME (2009) Phytoalexin-enriched functional foods. J Agric Food Chem 57:2614–2622

    Article  PubMed  CAS  Google Scholar 

  • Boutegrabet L, Fekete A, Hertkorn N, Papastamoulis Y, Waffo-Téguo P, Mérillon JM, Jeandet P, Gougeon RD, Schmitt-Kopplin P (2011) Determination of stilbene derivatives in Burgundy red wines by ultra-high-pressure liquid chromatography. Anal Bioanal Chem 401:1513–1521

    Article  PubMed  Google Scholar 

  • Chong J, Poutaraud A, Hugueney P (2009) Metabolism and roles of stilbenes in plants. Plant Sci 177:143–155

    Article  CAS  Google Scholar 

  • Coutos-Thevenot P, Poinssot B, Bonomelli A, Yean H, Breda C, Buffard D, Esnault R, Hain R, Boulay M (2001) In vitro tolerance to Botrytis cinerea of grapevine 41B rootstock in transgenic plants expressing the stilbene synthase Vst1 gene under the control of a pathogen-inducible PR10 promoter. J Exp Bot 52:901–910

    Article  PubMed  CAS  Google Scholar 

  • Douillet-Breuil AC, Jeandet P, Adrian M, Bessis R (1999) Changes in the phytoalexin content of various Vits spp. In response to ultraviolet C elicitation. J Agric Food Chem 47:4456–4461

    Article  PubMed  CAS  Google Scholar 

  • Dourtoglou VG, Makris DP, Bois-Dounasand F, Zonas C (1999) Trans-resveratrol concentration in wines produced in Greece. J Food Comps Anal 12:227–233

    Article  CAS  Google Scholar 

  • Gaudette NJ, Pickering GJ (2011) Sensory and chemical characteristics of trans-resveratrol fortified wine. Aust J Grape Wine Res 17:249–257

    Article  CAS  Google Scholar 

  • Gonzalez Urena A, Orea JM, Montero C, Jimenez JB, Gonzalez JL, Sanchez A, Dorado M (2003) Improving the post-harvest resistance in fruits by external application of trans-resveratrol. J Agric Food Chem 51:82–89

    Article  PubMed  CAS  Google Scholar 

  • Hurst WJ, Glinski JA, Miller KB, Apgar J, Davey MH, Stuart DA (2008) Survey of the trans-­resveratrol and trans-piceid content of cocoa-containing and chocolate products. J Agric Food Chem 56:8374–8378

    Article  PubMed  CAS  Google Scholar 

  • Ingrosso I, Bonsegna S, De Demonico S, Laddomada B, Blando F, Santino A, Giovinazzo G (2011) Over-expression of a grape stilbene synthase gene in tomato induces parthenocarpy and causes abnormal pollen development. Plant Physiol Biochem 49:1092–1099

    Article  PubMed  CAS  Google Scholar 

  • Jeandet P, Douillet-Breuil A-C, Bessis R, Debord S, Sbaghi M, Adrian M (2002) Phytoalexins from the Vitaceae: biosynthesis, phytoalexin gene expression in transgenic plants, antifungal activity, and metabolism. J Agric Food Chem 50:2731–2741

    Article  PubMed  CAS  Google Scholar 

  • Jimenez JB, Orea JM, Urena AG, Escribano P, de la Osa PL, Guadarrama A (2007) Short anoxic treatments to enhance trans-resveratrol content in grapes and wine. Eur Food Res Technol 224:373–378

    Article  CAS  Google Scholar 

  • Larronde F, Gaudilliere JP, Krisa S, Decendit A, Deffieux G, Merillon JM (2003) Airborne methyl jasmonate induces stilbene accumulation in leaves and berries of grapevine plants. Am J Enol Viticult 54:63–66

    CAS  Google Scholar 

  • Lijavetzky D, Almagro L, Belchi-Navarro S, Martinez-Zapater JM, Bru L, Pedreno MA (2008) Synergistic effect of methyljasmonate and cyclodextrin on stilbene biosynthesis pathway gene expression and resveratrol production in Monastrell grapevine cell cultures. BMC Res Notes 1:132

    Article  PubMed  Google Scholar 

  • Liu SJ, Hu YL, Wang XL, Zhong J, Lin ZP (2006) High content of resveratrol in lettuce transformed with a stilbene synthase gene of Parthenocissus henryana. Journal of Agricultural and Food Chemistry 54:8082–8085

    Article  PubMed  Google Scholar 

  • Liu Z, Zhuang C, Sheng S, Shao L, Zhao W, Zhao S (2011) Overexpression of a resveratrol synthase gene (PcRS) from Polygonum cuspidatum in transgenic Arabidopsis causes the accumulation of trans-piceid with antifungal activity. Plant Cell Rep 30:2027–2036

    Article  PubMed  CAS  Google Scholar 

  • Malacarne G, Vrhovsek U, Zulini L, Cestaro A, Stefanini M, Mattivi F, Delledonne M, Velasco R, Moser C (2011) Resistance to Plasmopara viticola in a grapevine segregating population is associated with stilbenoid accumulation and with specific host transcriptional responses. BMC Plant Biol 11:114

    Article  PubMed  CAS  Google Scholar 

  • Mark L, Nikfardjam MS, Avar P, Ohmacht R (2005) A validated HPLC method for the analysis of trans-resveratrol and trans-piceid in Hungarian wines. J Chromatogr Sci 43:445–449

    PubMed  CAS  Google Scholar 

  • Moreno-Labanda JF, Mallavia R, Pérez-Fons L, Lizama V, Saura D, Micol V (2004) Determination of piceid and resveratrol in Spanish wines deriving from Monastrell (Vitis vinifera L.) grape variety. J Agric Food Chem 52:5396–5403

    PubMed  CAS  Google Scholar 

  • Montero C, Cristescu SM, Jime’nez JB, Orea JM, te Lintel Hekkert S, Harren FJM, Gonza’lez Uren A (2003) Trans-resveratrol and grape disease resistance. A dynamical study by high-­resolution laser-based techniques. Plant Physiol 131:129–138

    Article  PubMed  CAS  Google Scholar 

  • Naugler C, McCallum JL, Klassen G, Strommer J (2007) Concentrations of trans-resveratrol and related stilbenes in Nova Scotia wines. Am J Enol Vit 58:117–119

    CAS  Google Scholar 

  • Pan Q-H, Wang L, Li J-M (2009) Amounts and subcellular localization of stilbene synthase in response of grape berries to UV irradiation. Plant Sci 176:360–366

    Article  CAS  Google Scholar 

  • Parage C, Tavares R, Rety S, Baltenweck-Guyot R, Poutaraud A, Renault L, Heintz D, Lugan R, Marais G, Aubourg S, Hugueney P (2012) Structural, functional and evolutionary analysis of the unusually large stilbene synthase gene family in grapevine (Vitis vinifera). Plant Physiol 160(3):1407–1419

    Article  PubMed  CAS  Google Scholar 

  • Rimando AM, Pan Z, Polashock JJ, Dayan FE, Mizuno CS, Snook ME, Liu C-J, Baserson SR (2012) In planta production of the highly potent resveratrol analogue pterostilbene via stilbene synthase and O-methyltransferase co-expression. Plant Biotech J 10:269–283

    Article  CAS  Google Scholar 

  • Romero-Pérez AI, Ibern-Gómez M, Lamuela-Raventós RM, de La Torre-Boronat MC (1999) Piceid, the major resveratrol derivative in grape juices. J Agric Food Chem 47:1533–1536

    Article  PubMed  Google Scholar 

  • Romero-Pérez AI, Lamuela-Raventós RM, Andrés-Lacueva C, de La Torre-Boronat MC (2001) Method for the quantitative extraction of resveratrol and piceid isomers in grape berry skins. Effect of powdery mildew on the stilbene content. J Agric Food Chem 49:210–215

    Article  PubMed  Google Scholar 

  • Schmidlin L, Poutaraud A, Claudel P, Mestre P, Prado E, Santos-Rosa M, Wiedemann-Merdinoglu S, Karst F, Merdinolglu D, Hugueney P (2008) A stress-inducible resveratrol O-methyltransferase involved in the biosynthesis of pterostilbene in grapevine. Plant Physiol 148:1630–1639

    Article  PubMed  CAS  Google Scholar 

  • Schnee S, Viret O, Gindro K (2008) Role of stilbenes in the resistance of grapevine to powdery mildew. Physiol Mol Plant Pathol 72:128–133

    Article  CAS  Google Scholar 

  • Stervbo U, Vang O, Bonnesen C (2007) A review of the content of the putative chemopreventive phytoalexin resveratrol in red wine. Food Chem 101:449–457

    Article  CAS  Google Scholar 

  • Thomzik JE, Stenzel K, Stocker R, Schreier PH, Hain R, Stahl DJ (2001) Synthesis of a grapevine phytoalexin in transgenic tomatoes (Lycopersicon Esculentum Mill.) conditions resistance against Phytophthora infestans. Physiol Mol Plant Pathol 51:265–278

    Article  Google Scholar 

  • Vezzulli S, Civardi S, Ferrari F, Bavaresco L (2007) Methyl jasmonate treatment as a trigger of resveratrol synthesis in cultivated grapevine. Am J Enol Viticult 58:530–533

    CAS  Google Scholar 

  • Wang W, Tang K, Yang HR, Wen PF, Zhang P, Wang HL, Huang WD (2010) Distribution of resveratrol and stilbene synthase in young grape plants (Vitis vinifera L. cv. Cabernet Sauvignon) and the effect of UV-C on its accumulation. Plant Physiol Biochem 48:142–152

    Article  PubMed  CAS  Google Scholar 

  • Xu Y, Xu TF, Zhao XC, Zou Y, Li ZQ, Xiang J, Li FJ, Wang YJ (2012) Co-expression of VpROMT gene from Chinese wild Vitis pseudoreticulata with VpSTS in tobacco plants and its effects on the accumulation of pterostilbene. Protoplasma 249:819–833

    Article  PubMed  CAS  Google Scholar 

  • Zamboni A, Gatto P, Cestaro A, Pilati S, Viola R, Mattivi F, Moser C, Velasco R (2009) Grapevine cell early activation of specific responses to DIMEB, a resveratrol elicitor. BMC Genomics 10:363

    Article  PubMed  Google Scholar 

  • Zhu YJ, Agbayani R, Jackson MC, Tang CS, Moore PH (2004) Expression of the grapevine stilbene synthase gene VST1 in papaya provides increased resistance against diseases caused by Phytophthora palmivora. Planta 220:241–250

    Article  PubMed  CAS  Google Scholar 

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Stuart, J.A., Robb, E.L. (2013). Resveratrol and Its Derivatives as Phytoalexins. In: Bioactive Polyphenols from Wine Grapes. SpringerBriefs in Cell Biology. Springer, New York, NY. https://doi.org/10.1007/978-1-4614-6968-1_1

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