New insights into the antioxidant activity of hydroxycinnamic acids: Synthesis and physicochemical characterization of novel halogenated derivatives

Gaspar, Alexandra; Garrido, Eduardo; Esteves, M. de Fátima; Quezada, Elías; Milhazes, Nuno; Garrido, Jorge; Borges, Fernanda

doi:10.1016/j.ejmech.2008.10.027

Cited by 79 publications

(70 citation statements)

References 41 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…We have also observed that methoxylation of ferulic acid leads to an increase in redox potential and a decrease in the antioxidant activity [82]. Other investigators…”

Section: [183] Cape and 5 Of Its Derivativesmentioning

confidence: 58%

“…AAPH: 2,2'-azobis(2-amidinopropane) dihydrochloride; ABTS •+ : 2,2'-azinobis- (3-ethylbenzthiazoline-6- O activity of different molecules [146]. Studies performed by our group and others on synthesized and natural HCAs have demonstrated that redox potential is closely related with the in vitro antioxidant activity of HCAs [82,135]. Differential pulse and cyclic voltammetry techniques have revealed that the structural characteristics of HCAs may influence the reduction-oxidation potential [121].…”

Section: [183] Cape and 5 Of Its Derivativesmentioning

confidence: 99%

“…3-Nitro-4-hydroxycinnamic acid has been found as a secondary metabolite of marine Vibrio strain from the Red Sea [131]. However, some preliminary studies have shown that the presence of bromine electron withdrawing group at the ortho position to the hydroxy group of HCAs has no effect on the antioxidant activity [82].…”

Section: Introduction Of Electron Withdrawing Substituentsmentioning

confidence: 99%

“…There are several reports which emphasize on the role of physicochemical variables in radical scavenging activity of HCAs [35,52,82,109,143]. Some of the most important physicochemical parameters will be discussed here.…”

Section: Effect Of Physicochemical Properties On the Antioxidant Actimentioning

confidence: 99%

“…HCAs have been shown to be phytochemicals with remarkable antioxidant outlines they are able; a) to increase the resistance of low density lipoprotein (LDL) to lipid peroxidation [56,79,80]; b) to protect proteins against oxida-tion [81]; c) to chelate transition metals that catalyze oxida-tive reactions [82]; d) to scavenge a variety of ROS [47,[83][84][85][86]; e) to inhibit enzymes that are involved in oxidative stress [48,87].…”

Section: Coo Hmentioning

confidence: 99%

See 4 more Smart Citations

Antioxidant Properties of Hydroxycinnamic Acids: A Review of Structure- Activity Relationships

Razzaghi‐Asl¹,

Garrido²,

Khazraei³

et al. 2013

CMC

167

View full text Add to dashboard Cite

Hydroxycinnamic acids (HCAs) are important phytochemicals possessing significant biological properties. Several investigators have studied in vitro antioxidant activity of HCAs in detail. In this review, we have gathered the studies focused on the structure-activity relationships (SARs) of these compounds that have used medicinal chemistry to generate more potent antioxidant molecules. Most of the reports indicated that the presence of an unsaturated bond on the side chain of HCAs is vital to their activity. The structural features that were reported to be of importance to the antioxi-dant activity were categorized as follows: modifications of the aromatic ring, which include alterations in the number and position of hydroxy groups and insertion of electron donating or withdrawing moieties as well as modifications of the car-boxylic function that include esterification and amidation process. Furthermore, reports that have addressed the influence of physicochemical properties including redox potential, lipid solubility and dissociation constant on the antioxidant activ-ity were also summarized. Finally, the pro-oxidant effect of HCAs in some test systems was addressed. Most of the investigations concluded that the presence of ortho-dihydroxy phenyl group (catechol moiety) is of significant importance to the antioxidant activity, while, the presence of three hydroxy groups does not necessarily improve the activity. Optimiza-tion of the structure of molecular leads is an important task of modern medicinal chemistry and its accomplishment relies on the careful assessment of SARs. SAR studies on HCAs can identify the most successful antioxidants that could be use-ful for management of oxidative stress-related diseases.Keywords: Antioxidant, hydroxycinnamic acids, in vitro, ROS, structure-activity relationships. OXIDATIVE STRESS AND ANTIOXIDANTSReactive oxygen species (ROS) are oxygen derived molecules that readily react with other compounds and macromolecules and oxidize them. Some representative exam-ples of these species include superoxide (O2•-), hydroxy (HO • ) and peroxy (ROO • ) radicals, hydrogen peroxide (H2O2) and singletROS are involved in important physiological processes such as immune response, gene expression, signal transduc-tion and growth regulation [5,6]; however if they are not kept under tight control by physiological antioxidant systems they will be able to oxidize and damage various biological molecules leading to a condition called oxidative stress [1,7,8]. In this regard, oxidative stress has been reported to be in-volved in the pathogenesis of diseases such as cancer [9], neurodegenerative diseases [10], stroke [11], and others [12,13].Since an important source of ROS comes from environment [14], with the industrial development and the change in life style, oxidative stress related diseases need a special attention [15].Antioxidants operate by preventing or slowing the progression of oxidative damage reactions [16,17]. An antioxidant has been defined as "any substance that delays, p...

show abstract

“…We have also observed that methoxylation of ferulic acid leads to an increase in redox potential and a decrease in the antioxidant activity [82]. Other investigators…”

Section: [183] Cape and 5 Of Its Derivativesmentioning

confidence: 58%

Section: [183] Cape and 5 Of Its Derivativesmentioning

confidence: 99%

Section: Introduction Of Electron Withdrawing Substituentsmentioning

confidence: 99%

Section: Effect Of Physicochemical Properties On the Antioxidant Actimentioning

confidence: 99%

Section: Coo Hmentioning

confidence: 99%

See 3 more Smart Citations

Antioxidant Properties of Hydroxycinnamic Acids: A Review of Structure- Activity Relationships

Razzaghi‐Asl¹,

Garrido²,

Khazraei³

et al. 2013

CMC

167

View full text Add to dashboard Cite

show abstract

Attenuation of sinapic acid and sinapine‐derived flavor‐active compounds using a factorial‐based pressurized high‐temperature processing

Nandasiri

Zago

Thiyam‐Holländer

et al. 2021

J Americ Oil Chem Soc

View full text Add to dashboard Cite

De‐oiled canola meals are sources of protein‐containing flavor‐active phenolic compounds. Conventional canola oil processing utilizes an excess amount of solvents and is associated with the release of high‐intensity bitter flavor‐active phenolic compounds, limiting the use of the canola meal. Recent advances in the extraction and isolation of the bitter favor‐active phenolic compounds from canola by‐products produce protein isolates, however, would benefit the industry by producing a side‐stream ingredient rich in phenolics. High temperature and pressure‐aided processing, namely the accelerated solvent extraction (ASE) was investigated to extract the flavor‐active bitter molecules from the canola meal. The extractability of flavor‐active phenolic compounds including the major sinapates, kaempferol derivatives, and other thermo‐generative compounds including thomasidioc acid (TA) was evaluated. The effects of temperature, solvent extractant and concentration, and the particle size of the meal were examined on the extraction efficiency of these phenolic compounds. Extraction temperature (180°C) was the primary determinant (p < 0.05) for the attenuation of major sinapates including sinapine and sinapic acid. Both ethanol and methanol extractants at a concentration of 70% (v/v) significantly (p < 0.05) extracted the flavor‐active phenolic compounds. The pressurized high temperature through optimized ASE conditions attenuated the bitter undesirable flavor‐active phenolic molecules from canola meal, thereby facilitating a potential value‐added phenolic‐rich by‐product.

show abstract

Fast, Simple and Sensitive Determination of Coumaric Acid in Fruit Juice Samples by Magnetite Nanoparticles‐zeolitic Imidazolate Framework Material

Şenocak

2020

Electroanalysis

View full text Add to dashboard Cite

In this work, magnetic iron nanoparticle (Fe 3 O 4) was functionalized a zeolitic imidalozate framework (ZIF-4) material by co-precipitation process to provide a magnetic hybrid nanomaterial, viz. Fe 3 O 4 @ZIF-4. The structural characterization was performed different spectroscopic, thermal and microscopic techniques. Moreover, voltammetric sensor properties of Fe 3 O 4 @ZIF-4 nanohybrid material for determination of p-coumaric acid (CA) were performed by differential pulse (DPV) and cyclic voltammetry (CV). A reliable and selective electroanalytical method exhibited for the detection of CA. It was found that the deposition of Fe 3 O 4 @ZIF-4 nanohybrid on a glassy carbon electrode (GCE) brought about 2.3, 3.5 and 5.0 fold more sensitive than Fe 3 O 4 /GCE, ZIF-4/GCE and unmodified GCE responses to CA in Britton-Robinson (BÀ R) buffer solution (a pH of 4). The detection, quantification limits and linear range of CA were determined as 0.18, 0.60 μM and 0.50-12.00 μM. The stability, repeatability and selectivity of the suggested Fe 3 O 4 @ZIF-4 modified GCE sensor was fully investigated. In addition, an application of orange juices samples was performed on modified electrode for determination of CA, which was showed by a standard addition method with verifying of High Performance Liquid Chromatography (HPLC) analysis. Besides the ease of synthesis and low price, the suggested Fe 3 O 4 @ZIF-4/GCE sensor offers repeatability, selectivity, stability and easy to apply to real samples.

show abstract

New insights into the antioxidant activity of hydroxycinnamic acids: Synthesis and physicochemical characterization of novel halogenated derivatives

Cited by 79 publications

References 41 publications

Antioxidant Properties of Hydroxycinnamic Acids: A Review of Structure- Activity Relationships

Antioxidant Properties of Hydroxycinnamic Acids: A Review of Structure- Activity Relationships

Attenuation of sinapic acid and sinapine‐derived flavor‐active compounds using a factorial‐based pressurized high‐temperature processing

Fast, Simple and Sensitive Determination of Coumaric Acid in Fruit Juice Samples by Magnetite Nanoparticles‐zeolitic Imidazolate Framework Material

Contact Info

Product

Resources

About