scholarly journals Synthesis of 1-(5-Chloro-2-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylic Acid Derivatives and Their Antioxidant Activity

Molecules ◽  
2019 ◽  
Vol 24 (5) ◽  
pp. 971 ◽  
Author(s):  
Ingrida Tumosienė ◽  
Kristina Kantminienė ◽  
Ilona Jonuškienė ◽  
Artūras Peleckis ◽  
Sergey Belyakov ◽  
...  

A series of novel 1-(5-chloro-2-hydroxyphenyl)-5-oxopyrrolidine-3-carboxylic acid derivatives containing chloro, hydroxyl, isopropyl, nitro, nitroso, and amino substituents at benzene ring and 1-(5-chloro-2-hydroxyphenyl)-5-oxopyrrolidine-3-carbohydrazide derivatives bearing heterocyclic moieties were synthesized. Antioxidant activity of the synthesized compounds was screened by DPPH radical scavenging method and reducing power assay. A number of compounds were identified as potent antioxidants. Antioxidant activity of 1-(5-chloro-2-hydroxyphenyl)-4-(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)pyrrolidin-2-one has been tested to be 1.5 times higher than that of a well-known antioxidant ascorbic acid. 1-(5-Chloro-2-hydroxyphenyl)-4-(4-methyl-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)pyrrolidin-2-one has shown 1.35 times higher antioxidant activity than that of vitamin C by DPPH radical scavenging method and optical density value of 1.149 in reducing power assay. The structure of 1-(5-chloro-2-hydroxyphenyl)-N-(1,3-dioxoisoindolin-2-yl)-5-oxopyrrolidine-3-carboxamide was unambiguously assigned by means of X-ray diffraction analysis data.

2020 ◽  
Vol 2020 ◽  
pp. 1-16
Author(s):  
Nur Sumirah Mohd Dom ◽  
Nurshieren Yahaya ◽  
Zainah Adam ◽  
Nik Mohd Afizan Nik Abd. Rahman ◽  
Muhajir Hamid

The present study aimed to evaluate the potential of standardized methanolic extracts from seven Ficus deltoidea varieties in inhibiting the formation of AGEs, protein oxidation, and their antioxidant effects. The antiglycation activity was analyzed based on the inhibition of AGEs, fructosamine, and thiol groups level followed by the inhibition of protein carbonyl formation. The antioxidant activity (DPPH radical scavenging activity and reducing power assay) and total phenolic contents were evaluated. After 28 days of induction, all varieties of Ficus deltoidea extracts significantly restrained the formation of fluorescence AGEs by 4.55–5.14 fold. The extracts also reduced the fructosamine levels by 47.0–86.5%, increased the thiol group levels by 64.3–83.7%, and inhibited the formation of protein carbonyl by 1.36–1.76 fold. DPPH radical scavenging activity showed an IC50 value of 66.81–288.04 μg/ml and reducing power activity depicted at 0.02–0.24 μg/ml. The extent of phenolic compounds present in the extracts ranged from 70.90 to 299.78 mg·GAE/g. Apart from that, correlation studies between the activities were observed. This study revealed that seven varieties of Ficus deltoidea have the potential to inhibit AGEs formation and possess antioxidant activity that might be attributed to the presence of phenolic compounds.


2015 ◽  
Vol 34 (04) ◽  
pp. 399
Author(s):  
Paini Sri Widyawati ◽  
Anita Maya Suteja ◽  
Thomas Indarto Putut Suseno ◽  
Pricilia Monica ◽  
William Saputrajaya ◽  
...  

Organic Rices, such as Jasmine variety white organic rice, Saodah variety red organic rice, and Java variety black organic rice, are many cultivated by farmer in Indonesia, especially Sleman area, DI Yogyakarta. The potency of three varieties of organic rice as antioxidant source hasn’t been studied. Therefore this research was done to know the effect of pigment color difference in three varieties of organic rice on antioxidant activity, especially 1,1-diphenyl-2- pycrylhydrazyl (DPPH) radical scavenging activity and ion reducing power. The results showed that Saodah variety red organic rice had the highest antioxidant potency because it had the highest total phenol and total flavonoid, 37.93 mg GAE/g sample dry base and 0.85 mg CE/g sample dry base, respectively. However Saodah variety red organic rice had total anthocyanin lower than that of Java variety black organic rice, 0.0025 mg/g sample dry base and 0.024 mg/g sample dry base, respectively. Anthocyanin compounds identified in three varieties of organic rice were cyanidine-3-glucoside at 32 minute time retention and peonidine -3-glucoside at 37 minute time retention. 1,1-diphenyl-2-pycrylhydrazyl (DPPH) radical scavenging activity and ion reducing power of Saodah variety red organic rice were the highest, 0.90 mg equivalent vitamin E/g sample dry base and 278.28 mg equivalent vitamin E/g sample dry base, respectively.Keywords: Pigment, organic rice, antioxidant activity ABSTRAKBeras organik, meliputi beras putih varietas Jasmine, merah varietas Saodah, dan hitam varietas Jawa, banyak dibudidayakan oleh masyarakat di Indonesia, terutama daerah Sleman, D.I. Yogyakarta. Potensi ketiga jenis beras tersebut sebagai sumber antioksidan belum banyak dikaji. Oleh karena itu penelitian ini dilakukan untuk mengetahui pengaruh perbedaan pigmen pada ketiga jenis beras organik tersebut terhadap aktivitas antioksidan, khususnya kemampuan menangkap radikal bebas 2,2-difenil-1-pikrilhidrasil (DPPH) dan mereduksi ion besi. Hasil menunjukkan bahwa beras organik merah varietas Saodah paling berpotensi sebagai sumber antioksidan. Hal ini ditunjukkan dengan total fenol dan total flavonoid beras merah tertinggi dibandingkan kedua beras yang lain, masing-masing sebesar 37,93 mg GAE/g sampel db dan 0,85 mg CE/g sampel db. Meskipun beras organik merah mempunyai total antosianin (0,0025 mg/g sampel db) lebih rendah dari beras organik hitam (0,024 mg/g sampel db). Jenis senyawa antosianin yang terdeteksi pada ketiga jenis organik ini adalah sianidin-3-glukosida yang terdeteksi pada waktu retensi 32 menit dan peonidin-3-glukosida dengan waktu retensi 37 menit. Kemampuan menangkap radikal bebas DPPH dan kemampuan mereduksi ion besi beras organik merah tertinggi, masing-masing sebesar 0,90 mg ekuivalen vit E/g sampel db dan278,28 mg ekuivalen vit E/g sampel db.Kata kunci: Pigmen, beras organik, aktivitas antioksidan  


2011 ◽  
Vol 233-235 ◽  
pp. 2849-2854
Author(s):  
Jie Bi ◽  
Qing Li Yang ◽  
Li Na Yu ◽  
Jie Sun ◽  
Chu Shu Zhang

In this article, the antioxidant activity of the crude extract from peanut hulls was tested with phosphomolybdenum complex method, the reduction of K3Fe(CN)6 and DPPH assay. The IC50 value for DPPH radical scavenging lied 14.86μg ml-1, and 28 μg mL-1 of PHF exhibited total antioxidant activity and reducing power which were comparable to that of the ascorbic acid standard at 52.41 and 15.41 μg mL-1, respectively.


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.


Author(s):  
Amar Djemoui ◽  
Djamila Djemoui ◽  
Lahcene Souli ◽  
Ahmed Souadia ◽  
Messaoud Gouamid

Moringa oleifera Flowers extracts grown in Algerian Sahara were evaluated antidiabetic and antioxidant activity by means using divers established in vitro systems, such as α-Amylase inhibitory assay, DPPH radical scavenging assay, Phosphomolybdenum assay (PM) and Ferric reducing power assay (FRAP). Moreover, the total content of phenols, flavonoids and tannins from (MFCE) and various fractions was measured using colorimetric methods. Results demonstrated that TPC varied between 95,50  0,42 and 10, 49  0,053 mg GAE/g WE, while TFC was between 17,00  0, 011 and 2,47  0,014 mg GAE/g WE, In this study TTC ranged between 2,96 0,016 and 1,30 0, 014 mg GAE/g WE. All capacities of DPPH radical scavenging, Phosphomolybdenum (PM) and Ferric reducing power (FRAP) were found best in (MFEF) (IC50= 0,159± 0,004mg/ml, AEAC = 42.37 ± 0.28 mM and AEAC =104.05±0.41 mM respectively). Add to this (MFEF) showed the highest α-amylase inhibitory activity (I= 38,92 %).


2014 ◽  
Vol 703 ◽  
pp. 29-32
Author(s):  
Na Wang ◽  
Si Yu Liu ◽  
Xue Song Huang

Under the acidic condition, 6-gingerol (C17H26O4) reacted with hydroxylamine to generate 6-gingerol oxime (C17H27NO4). Single-crystal X-ray diffraction with CuKα radiation (λ = 1.54184 Å) revealed the crystal belongs to the orthorhombic system, the space ground is P212121 with a = 5.24240(10), b = 25.7792(4), c = 25.9824(5) Å, V = 3511.39(11) Å3, Z = 8, Mr = 309.40, Dc = 1.171mg/mm3, μ = 0.669mm-1, S = 1.035, F(000) = 1344.0, the final wR2 was 0.1132 (all data) and R1 was 0.0412 [I>2σ (I)]. Two molecules compose one monomeric unit in the crystal. And the hydrogen bonds construct the dimer and the integral crystal spacial structure. The antioxidant activity of the 6-gingerol oxime was tested by the scavenging effect on DPPH radical and potassium ferricyanide reducing power test while Vitamin C was regarded as the comparison. The IC50 of the oxime for the scavenging effect on DPPH was 0.0471 g/L which was less strong than Vitamin C. The reducing power of Vitamin C was about three times powerful than the 6-gingerol oxime.


2012 ◽  
Vol 209-211 ◽  
pp. 2009-2012 ◽  
Author(s):  
Ming Xiu Wei ◽  
Lin Tang ◽  
Qing Li Yang ◽  
Li Na Yu

High temperature peanut meal was fermented by double strains with solid-stated fermentation, using fermented product dissolved in water and via membrane separate, then obtained four molecular weight distribution(MWD), which were 10kDa. Using four MWD fermentation peptides do experimenting, separated, that is hydroxyl radical-scavenging, DPPH radical-scavenging, reducing power and ferrous ion-chelating, and compared with GSH, it shown that the peptides of 3kDa~10kDa MWD fermentation peptides have the max antioxidant activity, the second was the percolator of >10kDa MWD fermentation peptides, then was the peptides of 1kDa~3kDa MWD fermentation peptides and <1kDa MWD fermentation peptides had the least activity.


Marine Drugs ◽  
2018 ◽  
Vol 16 (9) ◽  
pp. 291 ◽  
Author(s):  
Weihua Jin ◽  
Langlang Ren ◽  
Bing Liu ◽  
Quanbin Zhang ◽  
Weihong Zhong

Glucuronomannan oligosaccharides (Gs) were derived from fucoidan, which was extracted from the brown alga Sargassum thunbergii. Sulfated glucuronomannan oligosaccharides (SGs) were obtained by the sulfation of Gs. NMR techniques were used to reveal that the order of sulfation was Man-C6 > Man-C4 > Man-C1R > GlcA-C3 > Man-C3 > GlcA-C2. Finally, the antioxidant activities (hydroxyl radical scavenging activity, superoxide radical scavenging activity, reducing power and DPPH radical scavenging activity) of Gs and SGs were determined. The findings showed that the higher the degree of polymerization, the better the activity, except for the hydroxyl radical scavenging activity. In addition, the higher the sulfate content, the lower the activities for the reducing power and DPPH radical scavenging activity. Opposite results were found for the superoxide radical scavenging activity. Finally, compared with fucoidan, most Gs and SGs had higher antioxidant activity, suggesting that they might be good candidates for antioxidants.


2020 ◽  
Vol 16 ◽  
Author(s):  
Sajjad Esmaeili ◽  
Nazanin Ghobadi ◽  
Donya Nazari ◽  
Alireza Pourhossein ◽  
Hassan Rasouli ◽  
...  

Background: Curcumin, as the substantial constituent of the turmeric plant (Curcuma longa), plays a significant role in the prevention of various diseases, including diabetes. It possesses ideal structure features as enzyme inhibitor, including a flexible backbone, hydrophobic nature, and several available hydrogen bond (H-bond) donors and acceptors. Objective: The present study aimed at synthesizing several novel curcumin derivatives and further evaluation of these compounds for possible antioxidant and anti-diabetic properties along with inhibitory effect against two carbohydrate-hydrolyzing enzymes, α-amylase and α-glucosidase, as these enzymes are therapeutic targets for attenuation of postprandial hyperglycemia. Methods: Therefore, curcumin-based pyrido[2,3-d]pyrimidine derivatives were synthesized and identified using an instrumental technique like NMR spectroscopy and then screened for antioxidant and enzyme inhibitory potential. Total antioxidant activity, reducing power assay and 1,1-diphenyl-2-picrylhydrazyl (DPPH• ) radical scavenging activity were done to appraisal the antioxidant potential of these compounds in vitro. Results: Compounds L6-L9 showed higher antioxidant activity while L4, L9, L12 and especially L8 exhibited the best selectivity index (lowest α-amylase/α-glucosidase inhibition ratio). Conclusion: These antioxidant inhibitors may be potential anti-diabetic drugs, not only to reduce glycemic index but also to limit the activity of the major reactive oxygen species (ROS) producing pathways.


2021 ◽  
Vol 11 (1) ◽  
Author(s):  
Song Yu ◽  
Xuetian Zhu ◽  
Helin Yang ◽  
Lihe Yu ◽  
Yifei Zhang

AbstractSeed deterioration, coupled with a decrease in nutrients, is unavoidable following long-term storage, and these seeds are therefore used as livestock fodder. Here, we developed a simple, rapid and efficient method of producing high amounts of antioxidants from deteriorated seeds via melatonin-induced germination. Legume seeds were subjected to high humidity at 55 °C for 12–36 h to obtain aged seeds with a 40% germination rate and severely reduced antioxidant nutrition (total phenolics content, ferric reducing power and 1,1-diphenyl-2-picryhydrazyl (DPPH) radical scavenging capacity). Aged seeds were then treated with 0.1 mM melatonin, resulting in the production of sprouts with a higher total phenolics content (fivefold), greater ferric reducing power (sevenfold) and greater DPPH radical scavenging capacity (twofold) compared to the aged seeds. These findings suggest that melatonin treatment efficiently converted aged seed reserve residues into antioxidant nutrients, providing an alternative use for deteriorated seeds in food production.


Sign in / Sign up

Export Citation Format

Share Document