Antioxidant Versus Cytotoxic Properties of Hydroxycinnamic Acid Derivatives – A New Paradigm in Phenolic Research

Various triheterocyclic compounds containing benzimidazole, thiophene, and 1,2,4-triazole rings (3-6) were synthesized and screened for their antioxidant activities. The structures of the synthesized compounds (2-6) were judged by 1 H NMR, 13 C NMR, elemental analysis, and LC-MS spectral data. Antioxidant activities of the synthesized compounds (2-6) were determined with CUPric Reducing Antioxidant Capacity (CUPRAC), ABTS (2,2-azinobis(3-ethylbenzothiazoline-6-sulfonic acid)/persulfate, and DPPH (1,1-diphenyl-2-picrylhydrazyl) assays. Most of the compounds showed a significant antioxidant activity and especially, compound 5c showed very good SC 50 value for DPPH method and compound 5h exhibited very high scavenging activity to ABTS method.

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“…Antioxidant activity can be considered as an index of pharmacological usefulness 17 . Oxidants play role in many diseases.…”

Section: Antioxidant Activitymentioning

confidence: 99%

Synthesis and antioxidant activities of some new triheterocyclic compounds containing benzimidazole, thiophene, and 1,2,4-triazole rings

Menteşe

Yılmaz

Baltaş

et al. 2014

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…Our previous studies have uncovered the importance of this unsaturated side chain for the antioxidant activity [106], which could be ascribed to the participation of the double bond in stabilization of the phenoxy radicals via increased electron delocalization. However, its role is quite dependent of the type of HCAs, mainly of the substitution pattern of the aromatic moiety.…”

Section: Rational Design Of Antioxidants; Struc-ture-activity Relatiomentioning

confidence: 99%

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

Razzaghi‐Asl¹,

Garrido²,

Khazraei³

et al. 2013

CMC

167

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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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“…Transformation of side chain of safrole is a crucial step in achieving cancer prevention through induction of apoptosis and decreased proliferation of pre-malignant cells 11 . Such structural changes are directly related to free radical scavenging activity and the cytotoxic activity 12 . On the other hand, In vitro studies and experiments in animal models suggest that the pharmacological activities such as cytoprotective, antitumoral promoting, antiinflammatory, antipyretic and antiplatelet activities have been associated with the ability of fenolic compounds to scavenge highly reactive free radicals 13,14 .…”

Section: Introductionmentioning

confidence: 99%

Antioxidant and Toxicity Activity in Vitro of Twelve Safrole Derivatives

Madrid

Espinoza

Pavéz

et al. 2014

J. Chil. Chem. Soc.

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The aim of this study was to determine the influence of substituents in aromatic ring and the side chain of safrole on the antioxidant capacity and toxicity of twelve synthetic derivatives of safrole (S1-S12). Each compound was analyzed by two antioxidant methods: DPPH and bleaching of β-carotene (DBC). Among the derivates of safrol assayed, S5, S6, S9, S10 and S11 showed the strongest antioxidant capacity: DPPH method, first order specific rate constant (0.0152, 0.0211, 0.0432, 0.0317 and 0.0072) and DBC (22.41 + 0.13%, 10.71 + 0.05 %, 9.12 + 0.89 %, 30.97 + 0.92 % and 19.08 + 0.31 %), respectively. The toxicity of the active compounds was evaluated by means of two techniques, Artemia salina, LD 50 (4466 ± 1057 ppm, 630 ± 108 ppm, 1513 ± 797 ppm, 1585 ± 317 ppm, 1259 ± 242 ppm) and red cells, Haemolysis (1.58 + 0.98%, 4.02 + 2.03%, 8.42 + 1.38%, 2.59+ 2.31%, 2.92 + 0.52%), to provide preliminary information that can be used as a basis for further studies to contribute to the search for new antioxidants.

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Antioxidant Versus Cytotoxic Properties of Hydroxycinnamic Acid Derivatives – A New Paradigm in Phenolic Research

Cited by 50 publications

References 63 publications

Synthesis and antioxidant activities of some new triheterocyclic compounds containing benzimidazole, thiophene, and 1,2,4-triazole rings

Synthesis and antioxidant activities of some new triheterocyclic compounds containing benzimidazole, thiophene, and 1,2,4-triazole rings

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

Antioxidant and Toxicity Activity in Vitro of Twelve Safrole Derivatives

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