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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Hădărugă, NG., Hădărugă, DI. (2023). Hydroxycinnamic Acids. In: Jafari, S.M., Rashidinejad, A., Simal-Gandara, J. (eds) Handbook of Food Bioactive Ingredients. Springer, Cham. https://doi.org/10.1007/978-3-031-28109-9_3
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