Plant Polyphenols

Stéphane Quideau, Université de Bordeaux, Pessac Cedex, France

Published online: April 2013

DOI: 10.1002/9780470015902.a0001913.pub2

Abstract

Polyphenols are plant secondary metabolites derived from the phenylpropanoid and polyketide biosynthetic pathways that feature more than one phenolic ring in their basic chemical structure. Interest in this wide family of structurally diverse natural products originally emerged from the exploitation of their capacity to interact with proteins in the conversion of animal skins into leather (tanning action). The inherent propensity of their phenolic functions to donate hydrogen atoms and/or electrons raised additional interest in their application as free radical scavengers (antioxidation). Such highly impacting physicochemical properties for compounds that are present in numerous plant‐derived foods and beverages continue to date to fuel multidisciplinary investigations on the role of polyphenols in plant biochemistry, physiology and ecology, and on their possible effects and applications in nutrition, food quality and preservation, food supplements, diseases prevention and curation, as well as in cosmetics and new materials.

Key Concepts:

  • All vegetable tannins are polyphenols, but plant polyphenols are not all capable of tanning actions.

  • The term ‘polyphenol’ should be restricted to define structures that display at least two phenolic rings, irrespective of the number of hydroxy groups they each bear.

  • Plant polyphenols can act either as protective antioxidants or toxic prooxidants, depending on their specific chemical structure and set of conditions under which they are used.

  • Pro‐oxidant plant polyphenols could be exploited in the development of DNA‐targeting chemotherapeutic agents in the treatment of diseases such as cancer.

  • Plant polyphenols are known to interact with proteins in a nonspecific manner, but some plant polyphenols can engage proteins via specific and intimate molecular recognition processes with high‐binding affinities.

  • The manner with which plant polyphenols interact (specifically or not) with proteins mutually depends on their physicochemical characteristics and those of their protein partners (i.e. chemical composition and structure, hydrophobic and hydrophilic characters, size, extended linear or packed globular shape, flexibility or rigidity).

Keywords: plant polyphenols; vegetable tannins; condensed tannins; tannic acid; gallotannins; ellagitannins; phlorotannins; resveratrol; antioxidation; prooxidation; polyphenol–protein interactions; astringency

Figure 1.

Proanthocyanidins or condensed tannins are oligomers and polymers of flavan‐3‐ols such as catechin, epicatechin and epigallocatechin.
Figure 10.

Space‐filling representation showing the intimate binding of resveratrol (central molecule in green with oxygen atoms in red) to mitochondrial F1‐ATPase.
Figure 11.

Stereoview of genistein (central molecule in green with oxygen atoms in red) bound to the oestrogen receptor α.
Figure 2.

Hydrolysable tannins include gallo‐ and ellagitannins that are all derived from the metabolism of gallic acid.
Figure 3.

Phlorotannins, red‐brown algal polyphenols derived from phenolic oxidative coupling of phloroglucinol.
Figure 4.

Representative examples of theatannins (theaflavin), caffeetannins (3,5‐di‐O‐caffeoylquinic acid) and labiataetannins (rosmarinic acid and rabdosiin).
Figure 5.

Other examples of plant polyphenols.
Figure 6.

The two main mechanisms, hydrogen‐atom transfer and single electron transfer, through which plant (poly)phenols can express their radical scavenging‐based antioxidant action. The phenolic (BDE) and the (IP) are the two basic physicochemical parameters that can be relied on to determine the potential efficacy of each process, respectively.
Figure 7.

The versatile basic physicochemical properties of the phenol functional group.
Figure 8.

Possible prooxidation mechanism for cupric ion‐promoted DNA damage by catecholic (or pyrogallolic) plant (poly)phenols.
Figure 9.

Multidentate cross‐linking of PRP molecules in the palate by polyphenolic molecules with the concomitant loss of lubrication and development of the astringent response.
close

References

Andersen ØM and Markham KR (2006) Flavonoids – Chemistry, Biochemistry and Applications. Boca Raton: CRC/Taylor & Francis.

Auzanneau C, Montaudon D, Jacquet R et al. (2012) The polyphenolic ellagitannin vescalagin acts as a preferential catalytic inhibitor of the alpha isoform of human DNA topoisomerasse II. Molecular Pharmacology 82: 134–141.

Baur JA and Sinclair DA (2006) Therapeutic potential of resveratrol: the in vivo evidence. Nature Reviews Drug Discovery 5: 493–506.

Bennick A (1982) Salivary proline‐rich proteins. Molecular and Cellular Biochemistry 45: 83–99.

Bernays EA, Cooper‐Driver G and Bilgener M (1989) Herbivores and plant tannins. Advances in Ecological Research 19: 263–302.

Butler LG (1992) Antinutritional effects of condensed and hydrolysable tannins. In: Hemingway RW and Laks PE (eds) Plant Polyphenols: Synthesis, Properties and Significance, pp. 693–698. New York: Plenum Press.

Cozza G, Bonvini P, Zorzi E et al. (2006) Identification of ellagic acid as potent inhibitor of protein kinase CK2: a successful example of a virtual screening application. Journal of Medicinal Chemistry 49: 2363–2366.

Crozier A, Jaganath IB and Clifford MN (2009) Dietary phenolics: chemistry, bioavailability and effects on health. Natural Product Reports 26: 1001–1043.

Dangles O (2012) Antioxidant activity of plant phenols: chemical mechanisms and biological significance. Current Organic Chemistry 16: 692–714.

Dangles O and Dufour C (2008) Flavonoid–protein binding processes and their potential impact on human health. In: Daayf F and Lattanzio V (eds) Recent Advances in Polyphenol Research, vol. 1, pp. 67–87. Oxford: Wiley–Blackwell.

Davies AP, Goodsall C, Cai Y et al. (1999) Black tea dimeric and oligomeric pigments – Structures and formation. In: Gross GG, Hemingway RW and Yoshida T (eds) Plant Polyphenols 2 – Chemistry, Biology, Pharmacology, Ecology, pp. 697–724. New York: Kluwer Academic/Plenum Publishers.

Dixon RA and Ferreira D (2002) Genistein. Phytochemistry 60: 205–211.

Douat‐Casassus C, Chassaing S, Di Primo C and Quideau S (2009) Specific or nonspecific protein–polyphenol interaction? Discrimination in real time by surface plasmon resonance. ChemBioChem 10: 2321–2324.

Ehrnhoefer DE, Bieschke J, Boeddrich A et al. (2008) EGCG redirects amyloidogenic polypeptides into unstructured, off‐pathway oligomers. Nature Structural and Molecular Biology 15: 558–566.

Fan G‐J, Jin X‐L, Qian Y‐P et al. (2009) Hydroxycinnamic acids as DNA‐cleaving agents in the presence of CuII ions: mechanism, structure–activity relationship, and biological implications. Chemistry 15: 12889–12899.

Ferreira D and Slade D (2002) Oligomeric Proanthocyanidins: naturally occurring O‐heterocycles. Natural Product Reports 19: 517–541.

de Freitas V and Mateus N (2012) Protein/polyphenol interactions: past and present contributions. Mechanisms of astringency perception. Current Organic Chemistry 16: 724–746.

Gledhill JR, Montgomery MG, Leslie AGW and Walker JE (2007) Mechanism of inhibition of bovine F1‐ATPase by resveratrol and related polyphenols. Proceedings of the National Academy of Sciences of the USA 104: 13632–13637.

Gomez‐Pinilla F and Nguyen TTJ (2012) Natural mood foods: the actions of polyphenols against psychiatric and cognitive disorders. Nutritional Neuroscience 15: 127–133.

Haddock EA, Gupta RK, Al‐Shafi SMK, Haslam E and Magnolato D (1982) The metabolism of gallic acid and hexahydroxydiphenic acid in plants. Part 1. Introduction. Naturally occurring galloyl esters. Journal of the Chemical Society, Perkin Transactions 1: 2515–2524.

Hagerman AE and Butler LG (1981) The specificity of proanthocyanidin–protein interactions. Journal of Biological Chemistry 256: 4494–4497.

Haslam E (1977) Symmetry and promiscuity in procyanidin biochemistry. Phytochemistry 16: 1625–1640.

Haslam E (1982) The metabolism of gallic acid and hexahydroxydiphenic acid in higher plants. Progress in the Chemistry of Organic Natural Products 41: 1–46.

Haslam E (1996) Natural polyphenols (vegetable tannins) as drugs: possible modes of action. Journal of Natural Products 59: 205–215.

Haslam E (1998) Practical Polyphenolics – From Structure to Molecular Recognition and Physiological Action. Cambridge: Cambridge University Press.

Haslam E (2007) Vegetable tannins – Lessons of a phytochemical lifetime. Phytochemistry 68: 2713–2721.

Haslam E and Cai Y (1994) Plant polyphenols (vegetable tannins): gallic acid metabolism. Natural Product Reports 11: 41–66.

Haslam E, Lilley TH, Cai Y, Martin R and Magnolato D (1989) Traditional herbal medicines – The role of polyphenols. Planta Medica 55: 1–7.

Hofmann T, Glabasnia A, Schwarz B et al. (2006) Protein binding and astringent taste of a polymeric procyanidin, 1,2,3,4,6‐penta‐O‐galloyl‐β‐D‐glucopyranose, castalagin, and grandinin. Journal of Agricultural and Food Chemistry 54: 9503–9509.

Kumamoto T, Fujii M and Hou D‐X (2009) Akt is a direct target for myricetin to inhibit cell transformation. Molecular and Cellular Biochemistry 332: 33–41.

Lin M and Yao C‐S (2006) Natural oligostilbenes. In: Atta‐ur‐Rahman (ed.) Studies in Natural Products Chemistry, vol. 33, pp. 601–644. Amsterdam: Elsevier.

Lu Y and Bennick A (1998) Interaction of tannin with human salivary proline‐rich proteins. Archives in Oral Biology 43: 717–728.

McManus JP, Davis KG, Beart JE et al. (1985) Polyphenol interactions. Part 1. Introduction: some observations on the reversible complexation of polyphenols with proteins and polysaccharides. Journal of the Chemical Society, Perkin Transactions 2: 1429–1438.

Nicotra S, Cramarossa MR, Mucci A et al. (2004) Biotransformation of resveratrol: synthesis of trans‐dehydrodimers catalyzed by laccases from Myceliophtora thermophyla and from Trametes pubescens. Tetrahedron 60: 595–600.

Nishizawa M, Yamagishi T, Nonaka G‐I and Nishioka I (1982) Tannins and related compounds. Part 5. Isolation and characterization of polygalloylglucoses from Chinese gallotannin. Journal of the Chemical Society, Perkin Transactions 1: 2963–2968.

Nishizawa M, Yamagishi T, Nonaka G‐I and Nishioka I (1983) Tannins and related compounds. Part 9. Isolation and characterization of polygalloylglucoses from Turkish galls (Quercus infectoria). Journal of the Chemical Society, Perkin Transactions 1: 961–965.

Okuda T, Yoshida T and Hatano T (1992) Pharmacologically active tannins isolated from medicinal plants. In: Hemingway RW and Laks PE (eds) Plant Polyphenols 1 – Synthesis, Properties, Significance, pp. 539–569. New York: Plenum Press.

Okuda T, Yoshida T and Hatano T (1995) Hydrolyzable tannins and related polyphenols. Progress in the Chemistry of Organic Natural Products 66: 1–117.

Porat Y, Abramowitz A and Gazit E (2006) Inhibition of amyloid fibril formation by polyphenols: structural similarity and aromatic interactions as a common inhibition mechanism. Chemical Biology & Drug Design 67: 27–37.

Quideau S and Feldman KS (1996) Ellagitannin chemistry. Chemical Reviews 96: 475–503.

Quideau S, Deffieux D, Douat‐Casassus C and Pouységu L (2011) Plant polyphenols: chemical properties, biological activities, and synthesis. Angewandte Chemie International Edition 50: 586–621.

Quideau S, Jourdes M, Lefeuvre D et al. (2005) The chemistry of wine polyphenolic C‐glycosidic ellagitannins targeting human topoisomerase II. Chemistry 11: 6503–6513.

Quideau S, Jourdes M, Lefeuvre D et al. (2010) Ellagitannins – An underestimated class of plant polyphenols: chemical reactivity of C‐glucosidic ellagitannins in relation to wine chemistry and biological activity. In: Santos‐Buelga C, Escribano‐Bailon MT and Lattanzio V (eds) Recent Advances in Polyphenol Research, vol. 2, pp. 81–137. Oxford: Wiley–Blackwell.

Richard T, Lefeuvre D, Descendit A, Quideau S and Monti J‐P (2006) Recognition characters in peptide–polyphenol complex formation. Biochimica et Biophysica Acta 1760: 951–958.

Saiko P, Szakmary A, Jaeger W and Szekeres T (2008) Resveratrol and its analogs: defense against cancer, coronary disease and neurodegenerative maladies or just a fad? Mutation Research 658: 68–94.

Sailler B and Glombitza K (1999) Phlorethols and fucophlorethols from the brown alga Cystophora retroflexa. Phytochemistry 50: 869–881.

Scalbert A, Manach C, Morand C and Rémésy C (2005) Dietary polyphenols and the prevention of diseases. Critical Reviews in Food Science and Nutrition 45: 287–306.

Stern JL, Hagerman AE, Steinberg PD and Mason PK (1996) Phlorotannin–protein interactions. Journal of Chemical Ecology 22: 1877–1899.

Swain T and Bate‐Smith EC (1962) Flavonoid compounds. In: Mason HS and Florkin AM (eds) Comparative Biochemistry, vol. 3, pp. 755–809. New York: Academic Press.

Tachibana H, Koga K, Fujimara Y and Yamada K (2004) A receptor for green tea polyphenol EGCG. Nature Structural and Molecular Biology 11: 380–381.

Tanaka T, Matsuo Y and Kouno I (2010) Chemistry of secondary polyphenols produced during processing of tea and selected foods. International Journal of Molecular Sciences 11: 14–40.

Tang HR, Covington AD and Hancock RA (2003) Structure‐activity relationships in the hydrophobic interactions of polyphenols with cellulose and collagen. Biopolymers 70: 403–413.

White T (1956) The scope of vegetable tannin chemistry. In: The Chemistry of Vegetable Tannins – A Symposium, pp. 7–29. Croydon: Society of Leather Trades' Chemists.

White T (1957) Tannins – Their occurrence and significance. Journal of the Science of Food and Agriculture 8: 377–385.

Yearley EJ, Zhurova EA, Zhurov VV and Pinkerton AA (2007) Binding of genistein to the estrogen receptor based on an experimental electron density study. Journal of the American Chemical Society 129: 15013–15021.

Further Reading

Asensi M, Ortega A, Mena S, Feddi F and Estrela JM (2011) Natural polyphenols in cancer therapy. Critical Reviews in Clinical Laboratory Sciences 48: 197–216.

Bandyopadhyay P, Ghosh AK and Ghosh C (2012) Recent developments on polyphenol–protein interactions: effects on tea and coffee taste, antioxidant properties and the digestive system. Food and Function 3: 592–605.

Cheynier V (2005) Polyphenols in foods are more complex than often thought. American Journal of Clinical Nutrition 81(Suppl): 223S–229S.

Haslam E (2001) Plant polyphenols: old wine in new bottles. Education in Chemistry 38: 17–20.

Quideau S (2009) Chemistry and Biology of Ellagitannins – An Underestimated Class of Bioactive Plant Polyphenols. Singapore: World Scientific Publishing.

Scalbert A (1991) Antimicrobial properties of tannins. Phytochemistry 30: 3875–3883.

Van Driel‐Murray C (2000) Leather work and skin products. In: Nicholson PT and Shaw I (eds) Ancient Egyptian Materials and Technology, pp. 299–319. Cambridge: Cambridge University Press.

Waterman PG and Mole S (1994) Analysis of Phenolic Plant Metabolites. Oxford: Blackwell Scientific Publications.

Zhu M, Phillipson D, Greengrass PM, Bowery NE and Cai Y (1997) Plant polyphenols: biologically active compounds or non‐selective binders to protein? Phytochemistry 44: 441–447.

Zucker WV (1983) Tannins: does structure determine function? An ecological perspective. American Naturalist 121: 335–365.

Related Sub-Topics:

Biomolecular Interactions | Plant Secondary Metabolism | Plant Stress Physiology | Other Biomolecules: Structure, Function, Metabolism | Plant Disease
Contact Editor close
Submit a note to the editor about this article by filling in the form below.

* Required Field

Article Title: Plant Polyphenols
 
How to Cite close
Quideau, Stéphane(Apr 2013) Plant Polyphenols. In: eLS. John Wiley & Sons Ltd, Chichester. http://www.els.net [doi: 10.1002/9780470015902.a0001913.pub2]