Plant Polyphenols

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 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 bond dissociation energy (BDE) and the ionisation potential (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.

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.

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Further Reading

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