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Flavanols: Catechins and Proanthocyanidins

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Natural Products

Abstract

Flavanols are a wide group of polyphenols that include flavan-3-ols (e.g., catechin and proanthocyanidins), flavan-4-ols, and flavan-3,4-diols. They arise from plant secondary metabolism through condensation of phenylalanine derived from the shikimate pathway with malonyl-CoA obtained from citrate that is produced by the tricarboxylic acid cycle, leading to the formation of the key precursor in the flavonoids biosynthesis: the naringenin chalcone. The exact nature of the molecular species that undergo polymerization and the mechanism of assembly in proanthocyanidins are still unknown. From a structural point of view, flavanols comprise a C15 (C6-C3-C6) general structure composed by a benzopyran moiety (A and C rings) with an additional aromatic ring (B ring) linked to carbon C-2 of C ring. Flavanols are present in nature in monomeric, oligomeric, and polymeric forms and differ from each other essentially in the configuration of carbon C-2, the hydroxylation/methoxylation pattern of the rings, the type of linkage between each unit, and the degree of galloylation. Flavanols in foods are described to present several beneficial effects such as antioxidant and anticarcinogenic properties and also contribute to the sensory properties of some food products, such as astringency and color. Some of these aspects are discussed herein.

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Abbreviations

4CL:

4-Coumarate:CoA ligase

ANR:

Anthocyanidin reductase

ANS:

Anthocyanidin synthase

C:

Catechin

C3G:

Catechin-3-O-gallate

C4H:

Cinnamate 4-hidroxylase

CGCC:

Catechin-gallocatechin-catechin

CHI:

Chalcone isomerase

CHS:

Chalcone synthase

DFR:

Dihydroxyflavonol 4-reductase

DP:

Degree of polymerization

E3G:

Epicatechin-3-O-glucoside

EC:

Epicatechin

EC3G:

Epicatechin-3-O-gallate

EGC:

Epigallocatechin

EEC:

Epicatechin-epicatechin-catechin

EGC3G:

Epigallocatechin-3-O-gallate

F3′5′H:

Flavonoid 3′,5′-hydroxylase

F3H:

Flavanone 3β-hydroxylase

F3′H:

Flavonoid 3′-hydroxylase

GC:

Gallocatechin

GC3G:

Gallocatechin-3-O-gallate

GCCC:

Gallocatechin-catechin-catechin

GCGCC:

Gallocatechin-gallocatechin-catechin

HCA-CoA:

Hydroxycinnamic acid-CoA

HMF:

Hydroxymethylfurfural

HPLC:

High-performance liquid chromatography

LAR:

Leucoanthocyanidin reductase

MW:

Molecular weight

PAL:

Phenylalanine ammonia lyase

PAs:

Proanthocyanidins

PCs:

Procyanidins

PDs:

Prodelphinidins

PPO:

Polyphenol oxidase

PRPs:

Proline-rich proteins

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Authors and Affiliations

  1. Departamento de Química, Faculdade de Ciências, Centro de Investigação em Química, Universidade do Porto, Rua do Campo Alegre, 687, 4169-007, Porto, Portugal

    Joana Oliveira & Dr. Victor de Freitas

  2. Department of Chemistry and Biochemistry, Chemistry Investigation Centre (CIQ), Universidade do Porto, Porto, Portugal

    Nuno Mateus

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  1. Joana Oliveira
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  2. Nuno Mateus
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  3. Dr. Victor de Freitas
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Correspondence to Victor de Freitas .

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  1. Botany Department, M.L. Sukhadia University, Durga Nursery Road, Udaipur, 313001, Rajasthan, India

    Kishan Gopal Ramawat

  2. Institute of Vine and Wine Sciences, Biological-Active Plant Substances Study, University of Bordeaux, 210 Chemin de Leysotte CS 50008, Villenave d'Ornon, 33882, France

    Jean-Michel Mérillon

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Oliveira, J., Mateus, N., de Freitas, V. (2013). Flavanols: Catechins and Proanthocyanidins. In: Ramawat, K., Mérillon, JM. (eds) Natural Products. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-22144-6_58

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