Synthesis and antioxidant activity of long chain alkyl hydroxycinnamates

Menezes, José C. J. M. D. S.; Kamat, Shrivallabh P.; Cavaleiro, José A. S.; Gaspar, Alexandra; Garrido, Jorge; Borges, Fernanda

doi:10.1016/j.ejmech.2010.12.016

Cited by 102 publications

(70 citation statements)

References 27 publications

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“…Addition of the second methoxy group (as in the structure of sinapic acid Fig. 1) further increases the activity, as deducted from the comparison of sinapic acid with ferulic acid in hypochlorite scavenging [47] and DPPH scavenging assays [125,126]. 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].…”

Section: Introduction Of Electron Donating Substituentssupporting

confidence: 60%

“…The effect of esterification on the antioxidant activity of HCAs seems to be dependent on the type of cinnamic acid as well as the ester [126]. It has been found that ester derivatives of caffeic acid possessed stronger biological activity as compared to caffeic acid, ferulic acid and even synthetic Trolox compound in AAPH-induced lipid peroxidation of Tween-emulsified linolenic acid [35].…”

Section: Modifications Of the Carboxylic Func-tion Esterificationmentioning

confidence: 99%

“…1) further increases the activity, as deducted from the comparison of sinapic acid with ferulic acid in hypochlorite scavenging [47] and DPPH scavenging assays [125,126]. 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].…”

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: Introduction Of Electron Donating Substituentssupporting

confidence: 60%

Section: Modifications Of the Carboxylic Func-tion Esterificationmentioning

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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“…It was proposed that phenolipids (lipophilized phenolic compound) efficacy may improve by increasing the length of unbranched fatty alcohols to a critical chain length. [17] Several studies on synthesized alkyl caffeates, coumarates and ferulates, caffeic acid phenethyl esters, and long chain alkyl hydroxycinnamates using esterification reactions have 0.0 ppm using TMS as internal reference. FT-IR spectra were recorded on a FTIR nicolet 5700 spectrophotometer using two KBr plates with a drop of compound between them for liquid samples and thin film (50-100 μm) for grafted polymers.…”

Section: Introductionmentioning

confidence: 99%

Polyolefin elastomer grafted unsaturated hindered phenol esters: synthesis and antioxidant behavior

Manteghi

Ahmadi

Arabi

2016

Designed Monomers and Polymers

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Monomeric antioxidants are synthesized from esterification of 3,5-di-tert-butyl-4-hydroxybenzoic acid and 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid with unsaturated fatty alcohols. The antioxidant activity is evaluated both in blending and radical grafting processes. The effect of chain length and phenolic group is investigated on efficiency of antioxidants. It is demonstrated that the esters of 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionic acid exhibit significantly longer induction time. The results of radical grafting reaction shows synthesized antioxidants can be successfully grafted onto polymer chains and the phenolic moiety is functional after extraction process, while pure and commercially stabilized samples are degraded instantaneously. Also, different initiator systems are utilized to enhance the extent of grafting. Among MEK, DCP, and DHBP peroxides, DHBP can be more effective in increasing the antioxidant grafted onto polymer. In addition, possibility of rising in graft content is investigated in presence of redox initiator. Using this approach, polymerbound antioxidant with prolonged thermal stability can be achieved.

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“…Emerging clinical and experimental evidence now supports the identifi cation of phytochemicals with the potential to inhibit the processes of carcinogenesis. Sinapic acid (SA) is a phenolic acid and a natural hydrophilic antioxidant which occurs in fruits, vegetables, oil seeds, spices and herbs (11) (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Effect of sinapic acid on 1,2 dimethylhydrazine induced aberrant crypt foci, biotransforming bacterial enzymes and circulatory oxidative stress status in experimental rat colon carcinogenesis

Chilukuri¹,

Jayachandran²,

Nalini³

2015

BLL

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AIM: This study was aimed to investigate the effect of sinapic acid (SA) on 1,2-dimethylhydrazine (DMH) induced experimental rat colon carcinogenesis. MATERIALS AND METHODS: Rats were assorted into six groups, group 1 served as control, group 2 received SA (80 mg/kg b.w.) post orally every day until the end of the experimental period of 16 weeks, groups 3-6 rats were injected DMH (20 mg/kg b.w.) subcutaneously once a week for fi rst four weeks. In addition, groups 4-6 rats received different doses of SA (20, 40 and 80 mg/kg b.w.). RESULTS: Our results showed that DMH induced rats revealed signifi cantly increased ACF development and multiplicity, which were signifi cantly inhibited on supplementation with SA. Moreover, elevated levels/activities of circulatory oxidative stress markers, faecal and colonic mucosal bacterial enzymes were observed in DMH exposed rats, which were diminished on supplementation with SA. CONCLUSION: Overall, our fi ndings revealed that supplementation with SA offers signifi cant protection against DMH induced rat colon carcinogenesis and the effect of SA at the dose of 40 mg/kg b.w. was more pronounced as compared to the other two doses (Tab. 5, Fig. 3, Ref. 46). Text in PDF www.elis.sk.

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Synthesis and antioxidant activity of long chain alkyl hydroxycinnamates

Cited by 102 publications

References 27 publications

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

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

Polyolefin elastomer grafted unsaturated hindered phenol esters: synthesis and antioxidant behavior

Effect of sinapic acid on 1,2 dimethylhydrazine induced aberrant crypt foci, biotransforming bacterial enzymes and circulatory oxidative stress status in experimental rat colon carcinogenesis

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