New 1,3,5-Triazine Derivatives Incorporating Aminobenzenesulfonamide, Aminoalcohol, Piperazine, Chalcone or Stilbene Structural Motifs and Evaluation of Their Antioxidative Activity

A series of 1,3,5-triazine derivatives, incorporating aminobenzenesulfonamide, aminoalcohol/phenol, piperazine, chalcone, or stilbene structural motifs, were evaluated as potential antioxidants. The compounds were prepared by using step by step nucleophilic substitution of chlorine atoms in starting 2,4,6-trichloro-1,3,5-triazine. Reactions were catalyzed by Cu(I)-supported on a weakly acidic resin. The radical scavenging activity was determined in terms of %inhibition activity and IC50, using the ABTS method. Trolox and ascorbic acid (ASA) were used as standards. In the lowest used concentration 1 × 10−4 M, the %inhibition activity at time 0 min was comparable with both standards at least for 10 compounds. After 60 min compounds 1, 2, 9 and 25 showed nearly twice %inhibition (73.44–87.09%) in comparison with standards (Trolox = 41.49%; ASA = 31.07%). Values of IC50 correlated with %inhibition activity. For compounds 1, 2, 9 and 25 values of IC50 in time 60 min (17.16–27.78 μM) were 5 times lower than IC50 of both standards (Trolox = 178.33 μM; ASA = 147.47 μM). Based on these results, the presented 1,3,5-triazine derivatives and their analogs have a high potential in the treatment of illnesses caused or related to oxidative stress.

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Antioxidative Activity of 1,3,5-Triazine Analogues Incorporating Aminobenzene Sulfonamide, Aminoalcohol/Phenol, Piperazine, Chalcone, or Stilbene Motifs

Molecules ◽

10.3390/molecules25081787 ◽

2020 ◽

Vol 25 (8) ◽

pp. 1787 ◽

Cited By ~ 1

Author(s):

Eva Havránková ◽

Nikola Čalkovská ◽

Tereza Padrtová ◽

Jozef Csöllei ◽

Radka Opatřilová ◽

...

Keyword(s):

Oxidative Stress ◽

Ascorbic Acid ◽

Nucleophilic Substitution ◽

Antioxidative Activity ◽

Radical Scavenging Activity ◽

Radical Scavenging ◽

High Potential ◽

Scavenging Activity ◽

Inhibition Activity ◽

Acidic Resin

A series of 1,3,5-triazine analogues, incorporating aminobenzene sulfonamide, aminoalcohol/phenol, piperazine, chalcone, or stilbene structural motifs, were evaluated as potential antioxidants. The compounds were prepared by using step-by-step nucleophilic substitution of chlorine atoms in starting 2,4,6-trichloro-1,3,5-triazine. Reactions were catalyzed by Cu(I)-supported on a weakly acidic resin. The radical scavenging activity was determined in terms of %inhibition activity and EC50, using the ABTS method. Trolox and ascorbic acid (ASA) were used as standards. In the lowest concentration 1 × 10−4 M, the %inhibition activity values at 0 min were comparable with both standards at least for 10 compounds. After 60 min, compounds 5, 6, 13, and 25 showed nearly twice %inhibition (73.44–87.09%) in comparison with the standards (Trolox = 41.49%; ASA = 31.07%). Values of EC50 at 60 min (17.16–27.78 μM) were 5 times lower for compounds 5, 6, 13, and 25 than EC50 of both standards (trolox = 178.33 μM; ASA = 147.47 μM). Values of EC50 correlated with %inhibition activity. Based on these results, the presented 1,3,5-triazine analogues have a high potential in the treatment of illnesses caused or related to oxidative stress.

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Effect of Metal Ions (Cu2+/Fe2+) on the Antioxidant Activity of L-Ascorbic Acid-Glycine Model System

Advanced Materials Research ◽

10.4028/www.scientific.net/amr.396-398.28 ◽

2011 ◽

Vol 396-398 ◽

pp. 28-31

Author(s):

Cheng Yi Lei ◽

Da Zhai Zhou ◽

Rong Zhao ◽

Qi Hui Deng ◽

Ai Nong Yu ◽

...

Keyword(s):

Antioxidant Activity ◽

Ascorbic Acid ◽

Maillard Reaction ◽

Antioxidative Activity ◽

Radical Scavenging Activity ◽

Radical Scavenging ◽

Model System ◽

Model Systems ◽

Scavenging Activity ◽

Metal Concentrations

The influence of Cu2+, Fe2+ on the Maillard reaction were studied by heating L-ascorbic(ASA) and glycine (Gly) solutions adjusted to pH 5 at 120±2°C for 140 min in an oil bath. The presence of metals affected the intensity of browning and intermediate products, as monitored by absorbance at 420 nm and absorbance at 294 nm, sharply increased with the increase of metal concentrations applied (0.000M, 0.005M, 0.010M, 0.015M, 0.020M). Thereafter, slight increases were observed up to 0.020M. Antioxidative activity of all MRPs derived from ASA-Gly model systems sharply increased at 0.015M (P < 0.05) and slightly changes in activity were found with increasing metal concentrations up to 0.020M. Moreover, radical-scavenging activity correlated well with browning intensity and absorbance at 294 nm.

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Comparison of Total Carotenoid Content, Ascorbic Acid and Radical Scavenging Activity of Three Indian Mango Varieties

International Journal of Scientific Research ◽

10.15373/22778179/dec2012/34 ◽

2012 ◽

Vol 1 (7) ◽

pp. 86-87 ◽

Cited By ~ 1

Author(s):

Manju Nehra ◽

◽

Alka Sharma

Keyword(s):

Ascorbic Acid ◽

Radical Scavenging Activity ◽

Radical Scavenging ◽

Carotenoid Content ◽

Scavenging Activity ◽

Total Carotenoid ◽

Total Carotenoid Content

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Synthesis and Biological Activities of Hydroxytyrosol Ester Derivatives

Journal of the chemical society of pakistan ◽

10.52568/000610 ◽

2020 ◽

Vol 42 (1) ◽

pp. 109-109

Author(s):

Hao Zang Hao Zang ◽

Qian Xu Qian Xu ◽

Luyun Zhang Luyun Zhang ◽

Guangqing Xia Guangqing Xia ◽

Jiaming Sun and Junyi Zhu Jiaming Sun and Junyi Zhu

Keyword(s):

Ascorbic Acid ◽

Antioxidant Activities ◽

Biological Activities ◽

Radical Scavenging Activity ◽

Radical Scavenging ◽

Acetylcholinesterase Inhibition ◽

Hydroxyl Group ◽

Scavenging Activity ◽

Antioxidant Power ◽

Better Than

A series of hydroxytyrosol (HT) derivatives were synthesized by modification of alcohol hydroxyl group of HT, twenty-five target compounds were obtained and characterized by NMR and HRMS. The antioxidant activities of those compounds were evaluated in three different assays. Except 3e and 3y, all other compounds demonstrated significant 2,2and#39;-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) (ABTS) free radical cation scavenging activity ranging from IC50 3.4 to 24.4 μM, which were more potent than L-ascorbic acid (IC50=24.8 μM). Compounds 3b-3d, 3f-3k, 3m-3x were better than Trolox (18.3 M). Moreover, the ferric reducing antioxidant power (FRAP) of all compounds were discovered to be more potent than L-ascorbic acid (40.7 mmol/g), except 3e, all other compounds (141.5-202.1 mmol/g) were better than Trolox (94.7 mmol/g). Compounds 3a-3d, 3f-3j, 3l-3m, 3o, 3q, 3t, 3v-3y exhibited more potent hydroxyl radical scavenging activity (IC50=245.1-475.1 M) than L-ascorbic acid (554.4 M) and Trolox (500.4 M). Compounds 3q, 3t and 3y exhibited more potent -Glucosidase inhibition activity (39.1-52.4 M) than Acarbose (60.9 M). Compounds 3a, 3d, 3f-3m, 3s-3t, 3v-3y showed some acetylcholinesterase inhibition activities, compounds 3a, 3d, 3f-3j, 3l-3m, 3o-3p, 3s-3t, 3w showed some butyrylcholinesterase inhibition activities.

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The Antioxidant and Antiproliferative Activities of 1,2,3-Triazolyl-L-Ascorbic Acid Derivatives

International Journal of Molecular Sciences ◽

10.3390/ijms20194735 ◽

2019 ◽

Vol 20 (19) ◽

pp. 4735 ◽

Cited By ~ 1

Author(s):

Anja Harej ◽

Andrijana Meščić Macan ◽

Višnja Stepanić ◽

Marko Klobučar ◽

Krešimir Pavelić ◽

...

Keyword(s):

Antioxidant Activity ◽

Ascorbic Acid ◽

Radical Scavenging Activity ◽

Radical Scavenging ◽

Hydrogen Atom Transfer ◽

Breast Adenocarcinoma ◽

Scavenging Activity ◽

Activity Data ◽

Oh Groups ◽

Mcf 7

The novel 4-substituted 1,2,3-triazole L-ascorbic acid (L-ASA) conjugates with hydroxyethylene spacer as well as their conformationally restricted 4,5-unsaturated analogues were synthesized as potential antioxidant and antiproliferative agents. An evaluation of the antioxidant activity of novel compounds showed that the majority of the 4,5-unsaturated L-ASA derivatives showed a better antioxidant activity compared to their saturated counterparts. m-Hydroxyphenyl (7j), p-pentylphenyl (7k) and 2-hydroxyethyl (7q) substituted 4,5-unsaturated 1,2,3-triazole L-ASA derivatives exhibited very efficient and rapid (within 5 min) 2,2-diphenyl-1-picrylhydrazyl (DPPH•) radical scavenging activity (7j, 7k: IC50 = 0.06 mM; 7q: IC50 = 0.07 mM). In vitro scavenging activity data were supported by in silico quantum-chemical modelling. Thermodynamic parameters for hydrogen-atom transfer and electron-transfer radical scavenging pathways of anions deprotonated at C2-OH or C3-OH groups of L-ASA fragments were calculated. The structure activity analysis (SAR) through principal component analysis indicated radical scavenging activity by the participation of OH group with favorable reaction parameters: the C3-OH group of saturated C4-C5(OH) derivatives and the C2-OH group of their unsaturated C4=C5 analogues. The antiproliferative evaluation showed that p-bromophenyl (4e: IC50 = 6.72 μM) and p-pentylphenyl-substituted 1,2,3-triazole L-ASA conjugate (4k: IC50 = 26.91 μM) had a selective cytotoxic effect on breast adenocarcinoma MCF-7 cells. Moreover, compound 4e did not inhibit the growth of foreskin fibroblasts (IC50 > 100 μM). In MCF-7 cells treated with 4e, a significant increase of hydroxylated hypoxia-inducible transcription factor 1 alpha (HIF-1α) expression and decreased expression of nitric oxide synthase 2 (NOS2) were observed, suggesting the involvement of 4e in the HIF-1α signaling pathway for its strong growth-inhibition effect on MCF-7 cells.

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Inhibition of LDL oxidation by melatonin requires supraphysiologic concentrations

Clinical Chemistry ◽

10.1093/clinchem/44.9.1931 ◽

1998 ◽

Vol 44 (9) ◽

pp. 1931-1936 ◽

Cited By ~ 32

Author(s):

P Barton Duell ◽

David L Wheaton ◽

Amy Shultz ◽

Hien Nguyen

Keyword(s):

Antioxidant Activity ◽

Ascorbic Acid ◽

Metal Ion ◽

Radical Scavenging Activity ◽

Radical Scavenging ◽

Ldl Oxidation ◽

Human Macrophage ◽

Published Data ◽

Scavenging Activity ◽

Mediated Oxidation

Abstract Melatonin has been suggested as a potent antioxidant that may protect against development of atherosclerosis and cancer; however, these effects are unproven and controversial. The antioxidant capacity of melatonin was tested in comparison with α-tocopherol, ascorbic acid, and the melatonin precursors tryptophan and serotonin, by measuring inhibition of metal ion-mediated and human macrophage-mediated oxidation of LDL. Melatonin had weak antioxidant activity that was detectable only at concentrations 10 000- to 100 000-fold higher than physiologic concentrations. These results were comparable with published data showing that the radical scavenging activity of melatonin requires markedly supraphysiologic concentrations. In contrast, α-tocopherol was 50- to 100-fold more potent and was efficacious at physiologic concentrations. Ascorbic acid and tryptophan also were active at physiologic concentrations and were significantly more potent than melatonin. In summary, extremely supraphysiologic concentrations of melatonin had only weak antioxidant activity, which was surpassed by α-tocopherol, ascorbic acid, and tryptophan.

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Antioxidant Activity and Acteoside Analysis of Abeliophyllum distichum

Antioxidants ◽

10.3390/antiox9111148 ◽

2020 ◽

Vol 9 (11) ◽

pp. 1148 ◽

Cited By ~ 1

Author(s):

Hak-Dong Lee ◽

Ji Hyun Kim ◽

Qi Qi Pang ◽

Pil-Mun Jung ◽

Eun Ju Cho ◽

...

Keyword(s):

Antioxidant Activity ◽

Antioxidative Activity ◽

Radical Scavenging Activity ◽

Radical Scavenging ◽

Nutritional Supplements ◽

Scavenging Activity ◽

Antioxidant Agent ◽

Abeliophyllum Distichum ◽

Potential Use

This study determined acteoside and its content in Abeliophyllum distichum via HPLC/UV and LC/ESI-MS to obtain insights into the potential use of this plant as an antioxidant agent. Moreover, 1,1-diphenyl-2-picrylhydrazyl (DPPH), hydroxyl (•OH), and O2− radical scavenging activity assays were performed to assess in vitro antioxidative activity. The DPPH, •OH, and O2− radical scavenging activities of A. distichum leaf EtOH extracts at a 250 μg/mL concentration were 88.32%, 94.48%, and 14.36%, respectively, whereas those of stem extracts at the same concentration were 88.15%, 88.99%, and 15.36%, respectively. The contents of acteoside in A. distichum leaves and stems were 162.11 and 29.68 mg/g, respectively. Acteoside was identified as the main antioxidant compound in A. distichum leaves, which resulted in DPPH, •OH, and O2− radical scavenging activities of 82.84%, 89.46%, and 30.31%, respectively, at a 25 μg/mL concentration. These results indicate that A. distichum leaves and stems containing the antioxidant acteoside can be used as natural ingredients for functional and nutritional supplements.

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In Vitro Free Radical Scavenging Activity and Total Flavonoid of Abelmoschus manihot (L.) Medic Extracts

Applied Mechanics and Materials ◽

10.4028/www.scientific.net/amm.140.355 ◽

2011 ◽

Vol 140 ◽

pp. 355-359 ◽

Cited By ~ 1

Author(s):

Yan Qiu ◽

Jian Jun Song

Keyword(s):

Ascorbic Acid ◽

Radical Scavenging Activity ◽

Radical Scavenging ◽

Reducing Power ◽

Total Flavonoid ◽

Scavenging Activity ◽

Ic50 Values ◽

Hydrogen Radicals ◽

Dpph Radical Scavenging

The Ablmoschus manihot (L.) Medic, an edible hibiscus of the Malvaceae family, is abundant with total flavonoid. The content of total flavonoid from A. manihot flowers (TFA) was extracted by 70% ethanol (ethanol:water, 70:30). The scavenging effects of TFA on superoxide anions and hydrogen radicals were related to the total flavonoid concentrations with the IC50 values of 63.90 ±2.21 μg/mL and 266.88±28.32 μg/mL, respectively. However, the IC50 values of standard ascorbic acid were 436.52 ±14.36 μg/mL and 439.58±21.41 μg/mL, respectively. The DPPH radical scavenging activity increased with increasing of TFA concentrations and the highest inhibition was 94.63 ±3.01% at 50 μg/mL, as compared to ascorbic acid 34.94 ±1.50%. The extract also showed good reducing power. The data from this study suggest A. manihot flower extract has significant potential to use as health supplements and nutraceuticals.

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Protective effects of fungal β-(1→3)-D-glucan against oxidative stress cytotoxicity induced by depleted uranium in isolated rat hepatocytes

Human & Experimental Toxicology ◽

10.1177/0960327110372643 ◽

2010 ◽

Vol 30 (3) ◽

pp. 173-181 ◽

Cited By ~ 37

Author(s):

Jalal Pourahmad ◽

Fatemeh Shaki ◽

Farahnaz Tanbakosazan ◽

Ruhollah Ghalandari ◽

Hossein Ali Ettehadi ◽

...

Keyword(s):

Oxidative Stress ◽

Radical Scavenging Activity ◽

Radical Scavenging ◽

Rat Hepatocytes ◽

Depleted Uranium ◽

Glutathione Depletion ◽

Scavenging Activity ◽

Isolated Rat Hepatocytes ◽

Membrane Rupture ◽

Isolated Rat

Previous reports suggested that certain carbohydrate polymers, such as β-(1→3)-D-glucan, may possess free radical scavenging activity. The present study examined the free radical scavenging activity of a carbohydrate polymer, β-(1→3)-D-glucan against oxidative stress induced by depleted uranium in isolated rat hepatocytes. Addition of U (VI) (uranyl acetate) to isolated rat hepatocytes results in reactive oxygen species (ROS) formation, rapid glutathione depletion, mitochondrial membrane potential collapse and lysosomal membrane rupture before hepatocyte lysis occurred. Our results showed that quite similar to silymarin, which is a known antioxidant and radical scavenger, tiny concentration of β-glucan (138 nM) very successfully protected the hepatocytes against cell lysis and all oxidative stress cytotoxicity endpoints caused by depleted uranium including ROS formation, glutathione depletion, decreased mitochondrial membrane potential, lysosomal membrane rupture and caspase 3 activity increase. In conclusion, our results confirmed the antioxidant and radical scavenging activity of β-(1→3)-D-glucan and suggested this compound and silymarin as possible drug candidates for prophylaxis and treatment against depleted uranium toxic effects.

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