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A comprehensive review of the classification, sources, biosynthesis, and biological properties of hydroxybenzoic and hydroxycinnamic acids

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Abstract

Simple phenolic acids are considered the most common and widely studied bioactive compounds belonging to plants’ secondary metabolites. The simple phenolic acids can be classified as hydroxybenzoic (gallic, protocatechuic, p-hydroxybenzoic, and syringic acids) and hydroxycinnamic acids (p-coumaric, caffeic, ferulic, and sinapic acids) and present high commercial value. This review comprehensively discussed the trends, classification, sources, biosynthesis, and biological properties of hydroxybenzoic and hydroxycinnamic acids, focusing on the antioxidant, anticancer, antitumor, anti-diabetic, anti-inflammatory, antimicrobial, anticholesterolemic, antimutagenic, and antihypertensive activities. The findings obtained support the application of simple phenolic acids in the cosmetic, food, pharmaceutical, and health industries and provide future perspectives and guidance for the exploration of simple phenolic acids from plants and fruit sources.

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Abbreviations

PEP:

Phosphoenolpyruvate

E4P:

Erythrose 4-phosphate

DAHP:

3-Deoxy-D-arabino-heptulosonate 7-phosphate

DAHPS:

DAHP synthase

DHQ:

3-Dehydroquinate

DHQS:

3-Dehydroquinate synthase

DHS:

3-Dehydroshikimate

DHQD/SDH:

3-Dehydroquinate dehydratase/shikimate dehydrogenase

SK:

Shikimate kinase

S3P:

Shikimate 3-phosphate

EPSP:

5-Enolpyruvylshikimate 3-phosphate

EPSPS:

EPSP synthase

CS:

Chorismate synthase

Tyr:

Tyrosine

Trp:

Tryptophan

ICS:

IC synthase

SA:

Salicylic acid

O-COU:

o-Coumaric acid

HQT:

Hydroxycinnamoyl-CoA quinate: hydroxycinnamoyl transferase

HPP:

3-Hydroxy-3-phenylpropionic acid

CHD:

CIN-CoA hydratase/CIN-CoA dehydratase

HPP-CoA:

3-Hydroxy-3-phenylpropionyl-CoA

OPP-CoA:

3-Oxo-3-phenylpropanoyl-CoA

KAT:

3-Ketoacyl-CoA thiolase

BZL:

Benzoyl-CoA ligase

EC-hydratase:

Enoyl-CoA hydratase

EC-lyase:

Enoyl-CoA

AAO:

Aldehyde oxidase

BA2H:

Benzoic acid 2-hydroxylase

BEN-Glu:

Benzoyl–glucose

ALDH:

Aldehyde dehydrogenase

CNL:

Cinnamoyl-CoA ligase

CIN-CoA:

Cinnamoyl-CoA

PAL:

Phenylalanine ammonia lyase

4CL:

4-Coumarate-CoA: ligase

F5H:

Ferulate (coniferil aldehyde/alcohol) 5-hydroxylase

COMT:

Cinnamyl (caffeate) O-methyltransferase

S:

Syringyl

G:

Guaiacyl

H:

p-Hydroxyphenyl

ROS:

Reactive oxygen species

RNS:

Reactive nitrogen species

DPHH:

Antioxidant method by DPPH method

FRAP:

Antioxidant method by FRAP method

GSH:

Glutathione

MDA:

Malonaldehyde

NO:

Nitric oxide

H2O2 :

Hydrogen peroxide

GPx:

Glutathione peroxidase

CAT:

Catalase

NPT:

Nonprotein thiol

SOD:

Superoxide dismutase

GST:

Glutathione-S-transferase

HO-1:

Heme oxygenase-1

GCLC:

Glutamate ligase catalytic subunit

GCLM:

Glutamate-cysteine ligase modifier subunit

NADPH:

Nicotinamide adenine dinucleotide phosphate

NQO1:

NAD(P)H Quinone Dehydrogenase 1quinone oxidoreductase 1

MSG:

Monosodium glutamate

NF-κB:

Nuclear factor kappa B

ABTS:

Antioxidant capacity by ABTS method

CUPRAC:

Antioxidant capacity by CUPRAC method

FCA:

Ferulic acid

MMP-9:

Matrix Metalloproteinase-9

PARP:

Poly (ADP-ribose) polymerase

NSCLC H1299:

Non-small-cell lung cancer

CAPE:

Caffeic acid phenethyl ester

BCL-2:

B-cell lymphoma 2

NOX:

NADPH oxidase

EGFR:

Epidermal growth factor receptor

Nox2:

NADPH oxidase 2

AMPK:

AMP-activated protein kinase

PGC1 alpha:

Proliferator-activated receptor-alpha coactivator1 alpha

PPAR-γ:

Peroxisome proliferator-activated receptor gamma

PRDX1:

Peroxiredoxin 1

IL:

Interleukins

COX-2:

Inferferon-γ (IFN- γ), tumor necrosis factor-α (TNF- α), cyclooxygenase-2

PGE-2:

Prostaglandin E2

MCP-1:

Monocyte chemoattractant protein-1

DSS:

Dextran sulfate sodium

SMEDDS:

Acid-self-micro emulsifying drug delivery system

SLRL:

Sex-linked recessive lethal

DOCA:

Deoxycorticosterone acetate

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Correspondence to Aline Priscilla Gomes da Silva.

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da Silva, A.P.G., Sganzerla, W.G., John, O.D. et al. A comprehensive review of the classification, sources, biosynthesis, and biological properties of hydroxybenzoic and hydroxycinnamic acids. Phytochem Rev (2023). https://doi.org/10.1007/s11101-023-09891-y

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  • DOI: https://doi.org/10.1007/s11101-023-09891-y

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