Kinetics of lipid oxidation in the presence of cinnamic acid derivatives

Kortenska, Vessela D.; Velikova, Milena; Yanishlieva, N.; Totzeva, I. R.; Bankova, Vassya; Marcucci, María Cristina

doi:10.1002/1438-9312(200201)104:1<19::aid-ejlt19>3.0.co;2-q

Cited by 17 publications

(15 citation statements)

References 28 publications

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“…Lipid hydroperoxides (LOOH) may break down into free radicals, which are responsible for subsequent autoxidation reactions. In this regard, phenolic compounds and their derivatives are very efficient substances in avoiding autooxidation processes [128]. For instance, CGA was found to protect human erythrocytes from oxidative stress produced by low levels of lipid hydroperoxides in artificial liposomes [142].…”

Section: Amidationmentioning

confidence: 99%

“…For instance, CGA was found to protect human erythrocytes from oxidative stress produced by low levels of lipid hydroperoxides in artificial liposomes [142]. Kortenska et al [128] investigated the kinetics of lipid peroxidation in the presence of cinnamic acid derivatives. For this purpose, the triacylglycerols of sunflower oil were used as lipid samples in lipid oxidation model.…”

Section: Amidationmentioning

confidence: 99%

“…Similarly, the results of our group and others have demonstrated that esters of sinapic acid are more active than esters of ferulic acid in �-carotene-linoleic acid system [127] and in DPPH assay [126]. In a studty on the kinetics of lipid peroxidation in the presence of HCAs, sinapic acid ensured a longer oxidation stability of lipids when compared to ferulic and para-coumaric acid [128]. The higher stability of phenoxy radicals being surrounded by two methoxy groups rather than one, have been also exploited via combined kinetic and EPR studies [129].…”

Section: Introduction Of Electron Donating Substituentsmentioning

confidence: 99%

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

Razzaghi‐Asl¹,

Garrido²,

Khazraei³

et al. 2013

CMC

172

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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...

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Section: Amidationmentioning

confidence: 99%

Section: Amidationmentioning

confidence: 99%

Section: Introduction Of Electron Donating Substituentsmentioning

confidence: 99%

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

Razzaghi‐Asl¹,

Garrido²,

Khazraei³

et al. 2013

CMC

172

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“…Several studies establish a relationship between the antioxidant activity of ethanolic extracts of propolis and their contents of phenolic compounds, such as the flavonoids. 5,22,23 The analysis of variance revealed that the propolis concentration, the ethanol content, and their interaction are significant (P < 0.0500) for the content of total phenolic compounds: y = + 70.3855 + 2.4794 x 1 + 9.9669 x 2 -10.1251 x 1 x 2 , where y = content of total phenolic compounds, x 1 = ethanol content, x 2 = propolis concentration and x 1 x 2 = interaction between the propolis concentration and the ethanol content. The effect of the ethanol content was only 3%, while those of the propolis concentration and the "extract concentration × ethanol content" interaction were more important for the content of total phenolic compounds, with contributions of 46 and 48%, respectively (Figure 1c).…”

Section: Determination Of Antioxidant Activitymentioning

confidence: 99%

“…Studies report that mono-and diprenyl ortho-substituted phenolic acids (PHC and DPHC) show higher antioxidant activity in comparison with unsubstituted p-coumaric acid. 22 Such compounds are possibly detected as the ions of m/z 231, 299 and 163, respectively (Figure 3). In addition, other studies of the effects of various parameters on the propolis extraction yield 23 also observed increased yield for compounds derived from p-coumaric acid with increased ethanol content, such as mono-and diprenyl ortho-substituted phenol acids.…”

mentioning

confidence: 99%

Antioxidant activity and composition of propolis obtained by different methods of extraction

Cottica¹,

Sawaya²,

Eberlin³

et al. 2011

J. Braz. Chem. Soc.

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Extratos etanólicos de própolis obtidos a partir de diferentes concentrações de própolis e com álcool hidratado com diferentes teores de álcool/água foram analisados. A ação antioxidante destes extratos foi determinada através da captura do radical livre 1,1-difenil-2-picril-hidrazila (DPPH•) e do poder de redução férrico (FRAP) utilizando o complexo férrico-tripiridiltriazina (Fe 3+ -TPTZ). O teor de compostos fenólicos totais e a quantificação de flavonóides também foram verificados e obtidos por espectrometria de massas com ionização por electrospray (ESI(-)-MS) dos extratos. Observou-se que a composição química dos extratos de própolis e sua atividade antioxidante variam com a concentração de própolis e, principalmente, com o teor de álcool/água do etanol hidratado utilizado na extração. Foi possível perceber também que a atividade antioxidante dos extratos é significativamente dependente destes parâmetros de extração e que as composições de compostos fenólicos e flavonóides também variam muito. Os valores de FRAP não apresentaram, porém, boa correlação com o teor de flavonóides.Ethanolic extracts of propolis obtained with different concentrations of propolis and made using hydrous ethanol with various water/ethanol contents were analyzed. The antioxidant action of the extracts was determined by free radical 1,1-diphenyl-2-picryl-hydrazyl (DPPH•) scavenging and by ferric reducing ability power (FRAP), using the ferric-tripyridyl triazine (Fe 3+ -TPTZ) complex. The total phenolic and flavonoid contents were also determined, and the electrospray ionization mass spectrometry spectra (ESI(-)-MS) of the extracts were acquired. The chemical composition of propolis extracts and their antioxidant activity were observed to vary with the concentration of propolis, and especially with the water/ethanol contents of the hydrous ethanol used for extraction. The antioxidant activity of the extracts was also found to be significantly dependent on these extraction parameters, as well as on the composition of the phenolic compounds and flavonoids. FRAP values showed, however, poor correlation with the flavonoid content. Keywords: total phenolic contents, antioxidant activity, ESI(-)-MS fingerprint, propolis extraction, flavonoids IntroductionPropolis is a resin produced by honey bees by mixing wax, pollen, salivary secretions and collected natural resins. 1 The chemical composition of propolis is complex and varies with the vegetation visited by bees, as well as with bee species. [2][3][4][5][6] As propolis has characteristics that are beneficial to human health, such as antioxidant, anti-inflammatory, antifungal and anticancer activities, its chemical composition and properties have been extensively studied. [7][8][9][10] The antioxidant activity of ethanolic extracts of propolis has been evaluated by free radical 1,1-diphenyl-2-picrylhydrazyl (DPPH • ) scavenging, 8 by the ferric reducing ability power (FRAP) using the ferric-tripyridyltriazine Antioxidant Activity and Composition of Propolis Obtained by Different Methods o...

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Phenolic antioxidants – radical‐scavenging and chain‐breaking activity: A comparative study

Kancheva

2009

Euro J Lipid Sci & Tech

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Fifty phenolic antioxidants (AH) (42 individual compounds and 8 binary mixtures of two antioxidants) were chosen for a comparative analysis of their radical-scavenging (H-donating) and chain-breaking (antioxidant) activity. Correlations between experimental (antiradical and antioxidant) and predictable (theoretical) activities of 15 flavonoids, 15 hydroxy cinnamic acid derivatives, 5 hydroxy chalcones, 4 dihydroxy coumarins and 3 standard antioxidants (butylated hydroxytoluene, hydroquinone, DL-atocopherol) were summarized and discussed. The following models were applied to explain the structureactivity relationships of phenolic antioxidants of natural origin: (a) model 1, a DPPH assay used for the determination of the radical-scavenging capacity (AH 1 DPPH . ? A . 1 DPPH-H); (b) model 2, chemiluminescence of a model substrate RH (cumene or diphenylmethane) used for the determination of the rate constant of a reaction with model peroxyl radicals (AH 1 RO 2 . ? ROOH 1 A . ); (c) model 3, lipid autoxidation used for the determination of the chain-breaking antioxidant efficiency and reactivity (AH 1 LO 2 . ? LOOH 1 A . ; A . 1 LH (1O 2 ) ? AH 1 LO 2 . ); and (d) model 4, theoretical methods used for predicting the activity (predictable activity). The highest lipid oxidation stability was found for antioxidants with a catecholic structure and for their binary mixtures with DL-a-tocopherol, as a result of synergism between them.

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Kinetics of lipid oxidation in the presence of cinnamic acid derivatives

Cited by 17 publications

References 28 publications

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

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

Antioxidant activity and composition of propolis obtained by different methods of extraction

Phenolic antioxidants – radical‐scavenging and chain‐breaking activity: A comparative study

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