scholarly journals Synthesis and Structure-Activity Relationship of Daphnetin Derivatives as Potent Antioxidant Agents

Molecules ◽  
2018 ◽  
Vol 23 (10) ◽  
pp. 2476 ◽  
Author(s):  
Yangliu Xia ◽  
Chen Chen ◽  
Yong Liu ◽  
Guangbo Ge ◽  
Tongyi Dou ◽  
...  

In this study, daphnetin 1 was chosen as the lead compound, and C-3 or C-4-substituted daphnetins were designed and synthesized to explore the potential relationship between the antioxidant activities and the chemical structures of daphnetin derivatives. The antioxidant activities of the generated compounds were evaluated utilizing the free radical scavenging effect on 2,2′-diphenyl-1-picrylhydrazyl, 2,2′-azinobis-(3-ethylbenzthiazoline-6-sulfonate) cation, and the ferric reducing power assays, and were then compared with those of the standard antioxidant Trolox. The results showed that the catechol group was the key pharmacophore for the antioxidant activity of the daphnetins. The introduction of an electron-withdrawing hydrophilic group at the C-4 position of daphnetin enhanced the antioxidative capacity, but this trend was not observed for C-3 substitution. In addition, introduction of a a hydrophobic phenyl group exerted negative effects on the antioxidant activity in both the C-3 and C-4 substitutions. Among all of the derivatives tested, the most powerful antioxidant was 4-carboxymethyl daphnetin (compound 9), for which the strongest antioxidant activity was observed in all of the assays. In addition, compound 9 also displayed strong pharmaceutical properties in the form of metabolic stability. To summarize, compound 9 holds great potential to be developed as an antioxidant agent with excellent antioxidant activity and proper pharmacokinetic behavior.

2019 ◽  
Vol 17 (1) ◽  
pp. 823-830 ◽  
Author(s):  
Hatem A. Abuelizz ◽  
Hanan A.A. Taie ◽  
Mohamed Marzouk ◽  
Rashad Al-Salahi

AbstractA series of 2-methylthio-pyrido-triazolopyrimidines (1-17) were prepared by the reaction of dimethyl-N-cyanoimidodithiocarbonate with hydrazinopyridine carboxylic acid as starting reactants. Their chemical structures were affirmed with HREI-MS, IR and NMR analyses. The target compounds (1-17) were evaluated for their antioxidant activity using 1,1-diphenyl-2-picryl hydrazyl (DPPH) radical scavenging, ferric reduction antioxidant power (FRAP) and reducing power capability (RPC). The results revealed that some pyrido-triazolopyrimidines showed good activity as antioxidant agents, in particular, compounds 12 and 15 were found to possess good antioxidant activity. Butylated hydroxyl toluene (BHT) was used as reference drug.


2009 ◽  
Vol 2009 ◽  
pp. 1-6 ◽  
Author(s):  
K. Nagendra Prasad ◽  
Jing Hao ◽  
Chun Yi ◽  
Dandan Zhang ◽  
Shengxiang Qiu ◽  
...  

Antioxidant activities of wampee peel extracts using five different solvents (ethanol, hexane, ethyl acetate, butanol and water) were determined by using in-vitro antioxidant models including total antioxidant capability, 1,1-diphenyl-2-picryl hydrazyl (DPPH) radical scavenging activity, reducing power, and superoxide scavenging activity. Ethyl acetate fraction (EAF) exhibited the highest antioxidant activity compared to other fractions, even higher than synthetic antioxidant butylated hydroxyl toluene (BHT). In addition, the EAF exhibited strong anticancer activities against human gastric carcinoma (SGC-7901), human hepatocellular liver carcinoma (HepG-2) and human lung adenocarcinoma (A-549) cancer cell lines, higher than cisplatin, a conventional anticancer drug. The total phenolic content of wampee fraction was positively correlated with the antioxidant activity. This is the first report on the antioxidant and anticancer activities of the wampee peel extract. Thus, wampee peel can be used potentially as a readily accessible source of natural antioxidants and a possible pharmaceutical supplement.


INDIAN DRUGS ◽  
2021 ◽  
Vol 58 (10) ◽  
pp. 34-41
Author(s):  
Kanthlal S. K. ◽  
Jipnomon Joseph ◽  
Bindhu P. Paul ◽  
Vijayakumar M ◽  
Rema Shree A. B. ◽  
...  

Amomum subulatum, commonly known as large or black cardamom, is a commonly used spice in Indian kitchens and is traditionally used to treat various ailments. To add more knowledge about the medicinal values of the fruit, this study was conducted to evaluate the in vitro antioxidant activities of aqueous, methanol, ethanol, hydro alcohol, ethyl acetate, acetone and chloroform extracts of the fruit. Preliminary assessment was done to detect the presence of phytoconstituents using identification tests. The antioxidant activity was measured by employing methods such as diphenylpicrylhydrazyl (DPPH) radical scavenging assay, total antioxidant activity equivalent to ascorbic acid, reducing power assay and superoxide anion scavenging assay. The antioxidant activities were compared with their respective phenol and flavonoid contents. Preliminary assessment revealed that large cardamom fruit is a good source of all the bioactive constituents as well as phenol and flavonoid essential for medicinal values. The extract obtained by polar solvents showed the highest antioxidant efficacy in relation to its phenol content. Also, all the solvent-soluble fractions showed a concentration-dependent antioxidant effect. Results from our study prove that large cardamom can alleviate oxidative stress, suggesting the potential of large cardamom as a functional food


2019 ◽  
Vol 2019 ◽  
pp. 1-7 ◽  
Author(s):  
Terence Nguema Ongone ◽  
Redouane Achour ◽  
Mostafa El Ghoul ◽  
Latyfa El Ouasif ◽  
Meryem El Jemli ◽  
...  

The aim of this work is to deepen the pharmacological effect of 4-phenyl-1,5-benzodiazepin-2-one derivatives which have a similar structure to nonionic surfactants: 4-phenyl-1,5-benzodiazepin-2-one is the hydrophilic head, and the carbon chain is hydrophobic tail. The antinociceptive activity of 4-phenyl-1,5-benzodiazepin-2-one derivatives was determined using acetic acid-induced writhing and tail immersion tests. In addition, the in vitro antioxidant activities of the tested derivatives were determined by using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging method and ferric reducing power assay. A single oral administration of these compounds at the doses of 50 and 100 mg/kg significantly reduced the number of abdominal writhes induced by acetic acid injection. Acute pretreatment with 4-phenyl-1,5-benzodiazepin-2-one derivatives at the dose of 100 mg/kg caused a significant increase in the tail withdrawal latency in the tail immersion test. Additionally, a significant scavenging activity in DPPH and reducing power was observed in testing antioxidant assays. Finally, we carried out a study of the antioxidant activity of these derivatives. The results of this study reveal that these compounds have a low antioxidant activity compared to the BHT. It decreases with the polarity of the molecule. The present study suggests that 4-phenyl-1,5-benzodiazepin-2-one derivatives possess potent antinociceptive and antioxidant effects, which suggest that the tested compounds may be useful in the treatment of pain and oxidation disorders.


Metabolites ◽  
2020 ◽  
Vol 10 (3) ◽  
pp. 114 ◽  
Author(s):  
Vuanghao Lim ◽  
Sara Ghorbani Gorji ◽  
Venea Dara Daygon ◽  
Melissa Fitzgerald

Selected Australian native fruits such as Davidson’s plum, finger lime and native pepperberry have been reported to demonstrate potent antioxidant activity. However, comprehensive metabolite profiling of these fruits is limited, therefore the compounds responsible are unknown, and further, the compounds of nutritional value in these native fruits are yet to be described. In this study, untargeted and targeted metabolomics were conducted using the three fruits, together with assays to determine their antioxidant activities. The results demonstrate that targeted free and hydrolysed protein amino acids exhibited high amounts of essential amino acids. Similarly, important minerals like potassium were detected in the fruit samples. In antioxidant activity, Davidson’s plum reported the highest activity in ferric reducing power (FRAP), finger lime in antioxidant capacity (ABTS), and native pepperberry in free radical scavenging (DPPH) and phosphomolybdenum assay. The compounds responsible for the antioxidant activity were tentatively identified using untargeted GC×GC-TOFMS and UHPLC-QqQ-TOF-MS/MS metabolomics. A clear discrimination into three clusters of fruits was observed using principal component analysis (PCA) and partial least squares (PLS) analysis. The correlation study identified a number of compounds that provide the antioxidant activities. GC×GC-TOFMS detected potent aroma compounds of limonene, furfural, and 1-R-α-pinene. Based on the untargeted and targeted metabolomics, and antioxidant assays, the nutritional potential of these Australian bush fruits is considerable and supports these indigenous fruits in the nutraceutical industry as well as functional ingredients for the food industry, with such outcomes benefiting Indigenous Australian communities.


2020 ◽  
Vol 15 (5) ◽  
pp. 1934578X2092488
Author(s):  
Qiushan Zhang ◽  
Jin Shao ◽  
Tong Zhao ◽  
Lei He ◽  
Huiping Ma ◽  
...  

In the present study, the antioxidant property of 4 flavones (moslosooflavone, wogonin, isowogonin, and norwogonin) was evaluated using 6 different assays: 1,1-diphenyl-2-picrylhydrazyl (DPPH·), superoxide (O2 •−), and nitric oxide (NO) radical scavenging assays, ferrous iron chelation, reducing power, and total antioxidant capacity. The 4 flavones exhibited antioxidant activities with decreasing order as norwogonin > isowogonin >> wogonin> moslosooflavone. The present results demonstrated that norwogonin and isowogonin exhibited excellent antioxidant activity, which was mainly based on the presence of C-8 hydroxyl group.


Molecules ◽  
2019 ◽  
Vol 24 (15) ◽  
pp. 2817 ◽  
Author(s):  
Ding-Tao Wu ◽  
Wen Liu ◽  
Qiao-Hong Han ◽  
Ping Wang ◽  
Xian-Rong Xiang ◽  
...  

In order to explore Cassia seed polysaccharides (CSPs) as natural antioxidants for application in the functional-food industry, microwave-assisted extraction (MAE) was optimized for the extraction of CSPs by using a response surface methodology. Furthermore, the chemical structures and antioxidant activities of CSPs extracted by MAE and hot water extraction were investigated and compared. The maximum extraction yield of CSPs extracted by MAE (8.02 ± 0.19%) was obtained at the optimized extraction parameters as follows: microwave power (415 W), extraction time (7.0 min), and ratio of water to raw material (51 mL/g). Additionally, the contents of the uronic acids, molecular weight, ratio of constituent monosaccharides, intrinsic viscosities, and degrees of esterification of CSPs were significantly affected by the MAE method. Moreover, CSPs exhibited remarkable 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) ABTS, 2,2-diphenyl-1-(2,4,6-trinitrophenyl) hydrazyl DPPH, nitric oxide, and hydroxyl radical scavenging activities as well as reducing power. The high antioxidant activities observed in CSPs extracted by MAE could be partially attributed to its low molecular weights and high content of unmethylated galacturonic acid. Results indicate that the MAE method could be an efficient technique for the extraction of CSPs with high antioxidant activity, and CSPs could be further explored as functional food ingredients.


2014 ◽  
Vol 2014 ◽  
pp. 1-7 ◽  
Author(s):  
Junghyun Roh ◽  
Seungwon Shin

Purpose. The purpose of this study is to determine the antifungal and antioxidant activities of the essential oil fromAngelica koreana.Methods. Essential oil was obtained from the dried roots ofA. koreanaby steam distillation, and its composition was identified by gas chromatography and mass spectrometry (GC-MS). The minimal inhibitory concentrations (MICs) of the oil fraction and its main components were determined by broth dilution assay using common pathogenicAspergillusandTrichophytonspecies. The combined effects of the oils with itraconazole were evaluated using a checkerboard titer test. In addition, 1,1-diphenyl-2-picryl-hydrazil (DPPH) free radical scavenging, nitrite inhibition, and reducing power were determined to assess the antioxidant activity of this oil.Results. The essential oil fraction and its main components showed inhibitory activity against all of the tested fungi, with minimal inhibitory concentrations (MICs) of 250–1000 μg/mL. Furthermore, this oil exhibited synergism when combined with itraconazole.Conclusion. In the treatment of infections caused byAspergillusandTrichophytonspecies, combining itraconazole with eitherA. koreanaessential oil or its main components may reduce the minimum effective dose of itraconazole required and, thus, minimize its side effects. In addition, this oil is a promising source of natural antioxidant agents.


2009 ◽  
Vol 64 (3-4) ◽  
pp. 197-200 ◽  
Author(s):  
Hari Datta Bhattarai ◽  
Babita Paudel ◽  
Hong Kum Lee ◽  
Hyuncheol Oh ◽  
Joung Han Yim

Antioxidant agents against reactive oxygen species can be used for several cosmetic and medicinal applications. This study’s objective was to evaluate the antioxidant activities of Polytrichastrum alpinum (Hedw.) G. L. Sm. (Polytrichaceae), an Antarctic moss species collected from King George Island (Antarctica). The identifi cation of the moss species was performed on the basis of morphological characteristics and molecular sequencing of the 18S rRNA gene. Two benzonaphthoxanthenones: ohioensins F and G, were isolated from the extract after several chromatographic procedures. The various in vitro antioxidant capacities of a methanolic extract of P. alpinum and the isolated compounds were evaluated by analyzing the scavenging capacities of free radicals of 2,2-azino-bis(3-ethylbenzthiazoline- 6-sulfonic acid) (ABTS) and 2,2-diphenyl-1-picrylhydrazyl (DPPH), the total phenol assay with Folin-Ciocalteu reagent, the ferric ion (Fe3+) reducing power and the nitric oxide (NO) scavenging activity and compared to those of commercial standards for each assay. The experimental data showed that even the crude extract of P. alpinum exhibited potent antioxidant activity. The antioxidant activity was increased two- to seven-fold for the purified compounds. The antioxidant activities of both purified compounds were found to be more or less the same in all experiments. However, the obtained data showed that the Fe3+ reducing power of the purified compounds and crude methanolic extract was almost the same suggesting the presence of other stronger reducing agents in the methanolic extract which could not be isolated in the present experiment. Therefore, further work on the isolation of these stronger antioxidant agents from this moss specimen of the extreme environment is warranted. Developments of laboratory mass culture techniques are anticipated to achieve bulk production of the active constituents for commercial application.


2010 ◽  
Vol 5 (3) ◽  
pp. 338-345 ◽  
Author(s):  
Mohammad Ebrahimzadeh ◽  
Seyed Nabavi ◽  
Seyed Nabavi ◽  
Bahman Eslami

AbstractAntioxidant activity of the aerial part and bulbs of Allium paradoxum was investigated by eight in vitro assay systems. Extracts showed good antioxidant activity. IC50 for 1,1-diphenyl-2-picryl hydrazyl radical-scavenging activity was 890.9±43.2 and 984.9±33.5 µg/ml for the aerial part and bulbs, respectively. The aerial parts have better reducing power than bulb extracts but not comparable with Vitamin C (P>0.001). Extracts showed weak Fe2+ chelating ability, the IC50 being 959±47 and 530±24 µg/ml for bulbs and aerial parts, respectively. Both tested extracts exhibited good hydrogen peroxide scavenging in a concentration dependent manner. They exhibited good antioxidant activity against the hemoglobin-induced linoleic acid system that was comparable with vitamin C (P>0.01). They showed good activity against cumene hydro peroxide induced hemolysis in RBCs. In addition, they possessed antihemolytic activity. The extract from aerial parts had significantly higher total phenol and flavonoid content than did bulbs. Amounts of eight elements (Cu, Mn, Zn, Fe, Ni, Pb, Cd and Cr) were also determined in the bulb and aerial part using atomic absorption spectroscopy. They contained higher Fe and Mn contents than other elements.


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