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5 Polyphenols
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Polyphenols: Food, Nutraceutical, and Nanotherapeutic Applications, First Edition. Edited by Mithun Rudrapal.
© 2024 John Wiley & Sons, Inc. Published 2024 by John Wiley & Sons, Inc.
6
Polyphenols in Food Products – Nutraceutical Applications
André M. Oliveira
1,
* and Mithun Rudrapal
2
1
Federal Centre of Technological Education of Minas Gerais (CEFET-MG), Alameda das Perdizes, Contagem, MG, Brazil
2
Department of Pharmaceutical Sciences, School of Biotechnology and Pharmaceutical Sciences, Vignan’s Foundation for Science,
Technology & Research, Guntur, India
* Corresponding author
Polyphenols (PPHs) are compounds derived from the secondary metabolism of plants, and they
share a common structure moiety containing a benzene ring bound to multiple hydroxyl groups.
The metabolism of shikimic acid and polyacetate is the main biochemical source for the biosynthe-
sis of these compounds [1]. Secondary metabolism is not essential to the plant survival, and it is
responsible for the individuality of species [2].
Three principal kinds of secondary metabolites are biosynthesized by plants [3]: phenolic com-
pounds terpenoids/isoprenoids, alkaloids, and glucosinolates. Phenolic compound biosynthesis is
promoted by biotic and abiotic stresses such as herbivores, pathogens, temperature effects, pH,
saline stress, carbon dioxide, ozone, heavy metal stress, and ultraviolet radiation (Figure 6.1).
The production of phenolic compounds in plants involves a complex biosynthetic system that
starts with shikimic acid, leading to the formation of aromatic amino acids, such as L-tryptophan
(which is converted into alkaloids) and L-phenylalanine, which after being transformed into
L-tyrosine, enables the formation of the other compounds explained here.
6.1 Polyphenols: Concept and Classification
PPHs encompass a large and diverse group of compounds that contain aromatic rings bound to
hydroxyl groups. A general classification of them is summarized and illustrated in Table 6.1.
Despite the common phenolic substructure that characterizes this family of natural compounds,
the differences between the classes are also worth mentioning. Coumarins are lactones (cyclic
esters) that can be structurally related to phenolic acids. Flavonoids contain pyran-4-one rings
fused with a diphenol ring (or its methyl ethers). Some contain chiral centers such as hesperetin,
naringenin, eriodictyol, and epicatechin. Particularly interesting is the class of anthocyanins,
which contains an oxygen atom with a formal positive charge, that occurs in plants in the form of
salts that influence their solubility and bioavailability. Because of their pH-dependent colors, they
are used as colorants, food additives, and acid–base indicators.
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Figure 6.1 Phenolic compound biosynthesis promoted by biotic and abiotic stresses. Reproduced, by
permission CC BY 3.0, from Ref [3].
Table 6.1 Main classes of plant polyphenols and typical examples. Adapted from Ref [4, 5].
Polyphenol Class Examples
Gallic acid
OOH
OH
OH
O
H
Vanillic acid
CH
3
O
OH
O
OH
Protocatechuic acid
OOH
O
H
OH
Hydroxybenzoic acids
Phenolic acids and coumarins
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Polyphenol Class Examples
p-Hydroxybenzoic acid
HO O
OH
Caffeic acid
O
OH
OH
O
H
p-Coumaric acid
O
OH
O
H
Sinapic acid
CH
3
O
OH
OCH
3
O
OH
Ferulic acid
CH
3
O
O
HO
OH
Umbelliferone
O
OHO
Hydroxycinnamic acids
Table 6.1 (Continued)
(Continued)
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