Hydroxycinnamic Acids

Hădărugă, Nicoleta-Gabriela; Hădărugă, Daniel-Ioan

doi:10.1007/978-3-030-81404-5_3-1

Nicoleta-Gabriela Hădărugă⁴ &
Daniel-Ioan Hădărugă⁵

74 Accesses
1 Citations

Abstract

The “Hydroxycinnamic Acids” chapter focuses on the occurrence, separation, properties, food, and other applications of the main antioxidant compounds from this chemical class. An up-to-date review on the cinnamic acid as the reference compound, as well as on p-coumaric, caffeic, ferulic, sinapic, chlorogenic, and rosmarinic acids was presented. The recent identified hydroxycinnamic acid derivatives were also highlighted. A comprehensive biosynthetic approach for the above-mentioned hydroxycinnamic acids was discussed. An important part of this chapter was dedicated to the food applications of these antioxidants and the corresponding extracts as well as their interactions with other ingredients from food matrices. Cinnamic acid has no antioxidant activity, but it was investigated, together with cinnamaldehyde, as antimicrobial and preservative in food nanoemulsions and products. Many food applications were found for simple hydroxycinnamic acids and their derivatives. p-Coumaric, caffeic, ferulic, and sinapic acids were discussed in relation with their interactions with food biomacromolecules (proteins and oligo- and polysaccharides), antioxidant properties against degradation of some vegetable and food constituents such as anthocyanins, and even covalent binding to food biopolymers for novel ingredients and functional foods. Biotechnological aspects related to enhancing the hydroxycinnamic acid production and optimized extraction techniques were also investigated. These aspects were considered for hydroxycinnamic acid esters, such as mono- and di-p-coumaroyl/caffeoyl/feruloyl/sinapoylquinic acids, and the corresponding mixed esters, known as chlorogenic acids, rosmarinic, chicoric, or aldaric acids. Chlorogenic and rosmarinic acids are valuable natural antioxidants with many food applications even through the natural sources such as green coffee beans and rosemary, or concentrated formulations. Generally, chlorogenic and rosmarinic acids-based extracts, obtained by optimized production and extraction from various sources, are used. Finally, a comprehensive conclusion and future perspectives point out the main directions on hydroxycinnamic acids research and applications are presented.

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Abbreviations

¹H/¹³C-NMR:: ¹H/¹³C-nuclear magnetic resonance
4CL:: 4-coumarate:CoA ligase
ABTS·⁺:: 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid radical cation
AFM:: Atomic force microscopy
BHA:: tertbutylated hydroxyanisole
BSA:: Bovine serum albumin
C3’H:: p-coumaroyl shikimate 3′-hydroxlase
CD:: Circular dichroism
CE:: Capillary electrophoresis
CG-CTA:: 2-(S-cysteinylglycyl)-trans-caftaric acid
CoA:: Coenzyme A
COA-H:: Coumaric acid hexose derivatives
COMT:: Caffeoyl-CoA O-methyl transferase
CPC:: Centrifugal partition chromatography
CQA:: Caffeoylquinic acid
DLS:: Dynamic light scattering
DPPH·:: 2,2-diphenyl-1-pycrylhydrazyl radical
DSC:: Differential scanning calorimetry
DW:: Dry weight
FA-H:: Ferulic acid hexose derivatives
FAME:: Fatty acid methyl ester
Far-UV CD:: Far-ultraviolet circular dichroism spectroscopy
FQA:: Feruloylquinic acid
FRAP:: Ferric reducing antioxidant power
FT:: Fourier transform
FT-IR:: Fourier transform infrared spectroscopy
FW:: Fresh weight
GC-FID/MS:: Gas chromatography coupled with flame ionization detector/mass spectrometry detector
GT-CA:: 2-(S-Glutathionyl)-trans-caffeic acid
GT-CTA:: 5-(S-Glutathionyl)-trans-caftaric acid
HCGQT:: Hydroxycinnamoyl d-glucose:quinate hydroxycinnamoyl transferase
HCT:: Hydroxycinnamoyl-CoA:shikimate hydroxycinnamoyl transferase
HPLC-DAD/FLD/MS/RI/UV-Vis:: High pressure liquid chromatography coupled with diode array detector/fluorescence detector/mass spectrometry detector/refractive index detector/ultraviolet-visible spectrophotometric detector
HPLC-MS/MS/MSⁿ/MRM-MS:: Liquid chromatography coupled with tandem mass spectrometry (MS/MS or MSⁿ)/multiple reaction monitoring-mass spectrometry detector
HPTLC:: High performance thin layer chromatography
HQT:: Hydroxycinnamoyl-CoA:quinate hydroxycinnamoyl transferase
HS:: Headspace
HS-SPME:: Headspace-solid-phase microextraction
IUPAC:: International Union of Pure and Applied Chemistry
LC × LC:: Two-dimensional liquid chromatography
LC:: Liquid chromatography
MIC:: Minimum inhibitory concentration
NADP⁺/NADPH:: Nicotinamide adenine dinucleotide phosphate/reduced form
NIR:: Near infrared spectroscopy
ORAC:: Oxygen radical absorbance capacity
PBAT:: Poly(butylene-adipate-co-terephthalate)
PLA:: Poly(lactide)
SARS-CoV-2:: Severe acute respiratory syndrome coronavirus 2
SEM:: Scanning electron microscopy
SIFT-MS:: Selected ion flowtube mass spectrometry
SPE:: Solid-phase extraction
SPLET:: Sequential proton loss electron transfer
SPME:: Solid-phase microextraction
TAL:: Tyrosine ammonia lyase
TE:: Trolox equivalent
TEAC:: Trolox equivalent antioxidant capacity
TEM:: Transmission electronic microscopy
TG:: Thermogravimetry
TLC:: Thin layer chromatography
UDP-GT:: Uridine diphosphate glucosyltransferase
UHPLC(UPLC)-MS/MS/UV-Vis:: Ultrahigh pressure liquid chromatography coupled with tandem mass spectrometry detector/ultraviolet-visible spectrophotometry detector
UV-Vis:: Ultraviolet-visible spectrophotometry
XRD:: X-ray diffractometry

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Department of Food Science, Banat’s University of Agricultural Sciences and Veterinary Medicine “King Michael I of Romania” – Timişoara, Timişoara, Romania
Nicoleta-Gabriela Hădărugă
Department of Applied Chemistry, Organic and Natural Compounds Engineering, Polytechnic University of Timişoara, Timişoara, Romania
Daniel-Ioan Hădărugă

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Nicoleta-Gabriela Hădărugă
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Daniel-Ioan Hădărugă
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Correspondence to Nicoleta-Gabriela Hădărugă .

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International Iberian Food Laboratory, University of Vigo, Vigo, Spain
Seid Mahdi Jafari
Massey University, Riddet Institute, Palmerston North, New Zealand
Ali Rashidinejad
Nutrition and Food Science Group, University of Vigo, Vigo, Spain
Jesus Simal-Gandara

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Massey University, Riddet Institute, Palmerston North, New Zealand
Ali Rashidinejad

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Hădărugă, NG., Hădărugă, DI. (2022). Hydroxycinnamic Acids. In: Jafari, S.M., Rashidinejad, A., Simal-Gandara, J. (eds) Handbook of Food Bioactive Ingredients. Springer, Cham. https://doi.org/10.1007/978-3-030-81404-5_3-1

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DOI: https://doi.org/10.1007/978-3-030-81404-5_3-1
Received: 28 December 2021
Accepted: 03 February 2022
Published: 29 December 2022
Publisher Name: Springer, Cham
Print ISBN: 978-3-030-81404-5
Online ISBN: 978-3-030-81404-5
eBook Packages: Springer Reference Biomedicine and Life SciencesReference Module Biomedical and Life Sciences

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