scholarly journals Synthesis of 4,4′-(arylmethylene)bis(3-methyl-1-phenyl-1H-pyrazol-5-ols) and evaluation of their antioxidant and anticancer activities

BMC Chemistry ◽  
2021 ◽  
Vol 15 (1) ◽  
Author(s):  
José Eduardo Cadena-Cruz ◽  
Luis M. Guamán-Ortiz ◽  
Juan Carlos Romero-Benavides ◽  
Natalia Bailon-Moscoso ◽  
Kevin E. Murillo-Sotomayor ◽  
...  
Keyword(s):  
Biological Activities ◽  
Radical Scavenging Activity ◽  
Radical Scavenging ◽  
Carcinoma Cells ◽  
Structural Motif ◽  
Scavenging Activity ◽  
Anticancer Activities ◽  
Different Types ◽  
Simple Filtration

Abstract Background Pyrazoles have attracted particular attention due to the diverse biological activities associated with this heterocyclic system, and some have been shown to be cytotoxic to several human cell lines. Several drugs currently on the market have this heterocycle as the key structural motif, and some have been approved for the treatment of different types of cancer. Results 4,4ʹ-(Arylmethylene)bis(1H-pyrazol-5-ols) derivatives 3a–q were synthetized by a three components reaction of 3-methyl-1-phenyl-5-pyrazolone (1) with various benzaldehydes 2 catalyzed by sodium acetate at room temperature. The structures of all synthesized compounds were characterized by physicochemical properties and spectral means (IR and NMR) and were evaluated for their radical scavenging activity by DPPH assay and tested in vitro on colorectal RKO carcinoma cells in order to determine their cytotoxic properties. All 4,4ʹ-(arylmethylene)bis(1H-pyrazol-5-ols) derivatives 3a–q were synthetized in high to excellent yield, and pure products were isolated by simple filtration. All compounds have good radical scavenging activity, and half of them are more active than ascorbic acid used as standard. Conclusion Several derivatives proved to be cytotoxic in the RKO cell line. In particular, compound 3i proved to be a very potent scavenger with an IC50 of 6.2 ± 0.6 µM and exhibited an IC50 of 9.9 ± 1.1 μM against RKO cell. Autophagy proteins were activated as a survival mechanism, whereas the predominant pathway of death was p53-mediated apoptosis.

scholarly journals Phytochemical, in-vitro biological and chemo-preventive profiling of Arisaema jacquemontii Blume tuber extracts

2019 ◽  
Vol 19 (1) ◽  
Author(s):  
Saira Tabassum ◽  
Muhammad Zia ◽  
Esperanza J. Carcahe de Blanco ◽  
Riffat Batool ◽  
Roohi Aslam ◽  
...  
Keyword(s):  
Cell Lines ◽  
Biological Activities ◽  
Radical Scavenging Activity ◽  
Radical Scavenging ◽  
Reducing Power ◽  
Scavenging Activity ◽  
Zone Of Inhibition ◽  
Meoh Extract ◽  
Etoac Extract

Abstract Background Arisaema jacquemontii is traditionally used in treatment of different diseases. In this study, phytochemical, in vitro biological and chemo-preventive screening of A. jacquemontii was carried out to explore its pharmacological potential. Methods The dried tuber of A. jacquemontii was extracted in 11 organic solvent mixture of different polarity. The extracts were screened for phytochemical assays (phenolics and flavonoids), antioxidants potential (free radical scavenging activity, total antioxidant activity, reducing power), biological activities (antibacterial, antifungal, cytotoxic, antileishmanial, protein kinase inhibition), and chemopreventive activities using different cell lines through standard protocols. Results Significant amount phenolic contents were determined in EtOH and MeOH extracts (210.3 ± 3.05 and 193.2 ± 3.15 μg GAE/mg, respectively). Maximum flavonoid content was determined in MeOH extract (22.4 ± 4.04 μg QE/mg). Noteworthy, DPPH scavenging activity was also recorded for MeOH extract (87.66%) followed by MeOH+EtOAc extract (85.11%). Considerable antioxidant capacity (7.8 ± 0.12 μg AAE/mg) and reducing power (3.1 ± 0.15 μg AAE/mg) was observed in extract of MeOH. The LC50 against brine shrimp and leishmanial parasite was found 9.01 and 12.87 μg/mL for n-Hex and CHCl3 extracts, respectively. The highest zone of inhibition against Streptomyces hyphae formation (12.5 ± 1.77 mm) by n-Hex extract. Growth zone of inhibition 13.8 ± 1.08 mm was recorded for EtOAc and MeOH extracts, respectively against Micrococcus luteus while 10.0 ± 0.11 mm for MeOH extract against Aspergillus flavus. In-vitro cytotoxic assay showed that n-Hex extract had higher cytotoxicity against DU-145 prostate cancer and HL-60 cancer cell lines. NF-kB and MTP potential showed 34.01 and 44.87 μg/mL for n-Hex and CHCl3 extracts, respectively in chemo-preventive potential. Conclusion The study concludes that Arisaema jacquemontii bears significant phytochemical activity and pharmacological activities, this plant can be further explored for isolation of active component against a number of aliments.

α-Glucosidase Inhibition, Antioxidant and Docking Studies of Hydroxycoumarins and their Mono and Bis O-alkylated/acetylated Analogs

2018 ◽  
Vol 15 (2) ◽  
pp. 127-135 ◽  
Author(s):  
Parvesh Singh ◽  
Nomandla Ngcoya ◽  
Ramgopal Mopuri ◽  
Nagaraju Kerru ◽  
Neha Manhas ◽  
...  
Keyword(s):  
In Silico ◽  
Biological Activities ◽  
Wide Spectrum ◽  
Radical Scavenging Activity ◽  
Radical Scavenging ◽  
Catalytic Site ◽  
Docking Simulations ◽  
In Silico Docking ◽  
Anti Oxidant

Background: Diabetes Mellitus (DM) is a complex metabolic disease illustrated by abnormally high levels of plasma glucose or hyperglycaemia. Accordingly, several α-glucosidase inhibitors have been developed for the treatment of diabetes and other degenerative disorders. While, a coumarin ring has the privilege to represent numerous natural and synthetic compounds with a wide spectrum of biological activities e.g. anti-cancer, anti-HIV, anti-viral, anti-malarial, anti-microbial, anti-convulsant, anti-hypertensive properties. Besides this, coumarins have also shown potential to inhibit α-glucosidase leading to a generation of new promising antidiabetic agents. However, the testing of O-substituted coumarins for α-glucosidase inhibition has evaded the attention of medicinal chemists. Methods: For O-alkylation/acetylation reactions, the hydroxyl coumarins (A-B) initially activated by K2CO3 in dry DMF were reacted with variedly substituted haloalkanes at room temperature under nitrogen. The synthesized compounds were tested for their α-glucosidase (from Saccharomyces cerevisiae) inhibitory activity and anti-oxidant activity using DPPH radical scavenging activity. In silico docking simulations were conducted using CDocker module in DS (Accelrys) to explore the binding modes of the representative compounds in the catalytic site of α-glucosidase. Results: All the coumarin analogues (A1, B1, A2-A10, B2-B8) including their precursors (A-B) were evaluated for their in vitro α-glucosidase inhibition using acarbose as a standard inhibitor. All the mono O-alkylated coumarins (except A1) showed significant (p <0.05) α-glucosidase inhibition relative to the hydroxyl coumarin (A) with IC50 values ranging between 11.084±0.117 to 145.24± 29.22 µg/mL. Compound 7-(benzyloxy)-4, 5-dimethyl-2H-chromen-2-one (A9) bearing a benzyl group (Ph-CH2-) at position 7 showed a remarkable (p <0.05) increase in the activity (IC50 = 11.084±0.117 µg/mL), almost four-fold more than acarbose (IC50 = 40.578±5.999 µg/mL). The introduction of –NO2 group dramatically improved the anti-oxidant activity of coumarin, while the O-alkylation/acetylation decreased the activity. Conclusion: The present study describes the synthesis of functionalized coumarins and their evaluation for α-glucosidase inhibition and antioxidant activity under in vitro conditions. Based on IC50 data, the mono O-alkylated coumarins were observed to be stronger inhibitors of α-glucosidase with respect to their bis O-alkylated analogues. Coumarin (A9) bearing O-benzyloxy group displayed the strongest α-glucosidase inhibition, even higher than the standard inhibitor acarbose. The coumarin (A10) bearing –NO2 group showed the highest anti-oxidant activity amongst the synthesized compounds, almost comparable to the ascorbic acid. Finally, in silico docking simulations revealed the role of hydrogen bonding and hydrophobic forces in locking the compounds in catalytic site of α-glucosidase.

scholarly journals Synthesis, Antiproliferative Activity and Radical Scavenging Ability of 5-O-Acyl Derivatives of Quercetin

Molecules ◽  
2021 ◽  
Vol 26 (6) ◽  
pp. 1608
Author(s):  
Stephen Lo ◽  
Euphemia Leung ◽  
Bruno Fedrizzi ◽  
David Barker
Keyword(s):  
Antiproliferative Activity ◽  
Biological Activities ◽  
Radical Scavenging Activity ◽  
Radical Scavenging ◽  
Breast Cancer Cell Lines ◽  
Scavenging Activity ◽  
Plant Materials ◽  
Wide Range ◽  
Derivatives Of ◽  
Acyl Derivatives

Quercetin is a flavonoid that is found in many plant materials, including commonly eaten fruits and vegetables. The compound is well known for its wide range of biological activities. In this study, 5-O-acyl derivatives of quercetin were synthesised and assessed for their antiproliferative activity against the HCT116 colon cancer and MDA-MB-231 breast cancer cell lines; and their radical scavenging activity against the 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical cation and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical species. Four derivatives were found to have improved the antiproliferative activity compared to quercetin whilst retaining radical scavenging activity.

scholarly journals Antioxidant and Anticancer Activities of Wampee (Clausena lansium(Lour.) Skeels) Peel

2009 ◽  
Vol 2009 ◽  
pp. 1-6 ◽  
Author(s):  
K. Nagendra Prasad ◽  
Jing Hao ◽  
Chun Yi ◽  
Dandan Zhang ◽  
Shengxiang Qiu ◽  
...  
Keyword(s):  
Antioxidant Activity ◽  
Ethyl Acetate ◽  
Antioxidant Activities ◽  
Radical Scavenging Activity ◽  
Radical Scavenging ◽  
Reducing Power ◽  
Total Phenolic ◽  
Liver Carcinoma ◽  
Scavenging Activity ◽  
Anticancer Activities

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.

Synthesis and Biological Activities of Hydroxytyrosol Ester Derivatives

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.

Synthesis and Evaluation of bis-Schiff Bases of Carbohydrazide as Antioxidant and Cytotoxic Agents

2021 ◽  
Vol 18 ◽  
Author(s):  
Sarosh Iqbal ◽  
Shumaila Kiran ◽  
Shahida Perveen ◽  
Rizwana Malik ◽  
Muhammad Taha ◽  
...  
Keyword(s):  
Schiff Bases ◽  
Radical Scavenging Activity ◽  
Radical Scavenging ◽  
Cytotoxic Agents ◽  
Scavenging Activity ◽  
Standard Drug ◽  
Age Related ◽  
Dpph Radical Scavenging ◽  
Better Than

Background & Introduction : Antioxidants are known to prevent oxidative stress-induced damage to the biomolecules and thus, delay the onset of cancers and many age-related diseases. Therefore, the development of novel and potent antioxidants is justified. Method: During this study, we synthesized symmetrical bis-Schiff bases of carbohydrazide 1-27, and evaluated their in vitro antioxidative activity and cytotoxic activity. Results: Among synthesized compounds, six compounds 20 (IC50 = 12.89 ± 0.02 µM), 16 (IC50 = 14.32 ± 0.43 µM), 17 (IC50 = 18.52 ± 0.83 µM), 19 (IC50 = 22.84 ± 0.62 µM), 24 (IC50 = 35.1 ± 0.82 µM) and 15 (IC50 = 40.03 ± 1.06 µM) showed an excellent 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity, better than the standard butylatedhydroxyanisole (BHA) (IC50 = 44.6 ± 0.6 µM). Likewise, two compounds 16 (IC50 = 4.3 ± 1.3 µM) and 20 (IC50 = 6.6 ± 1.6 µM) showed oxidative burst scavenging activity better than the standard drug ibuprofen (IC50 = 11.2 ± 1.9 µM). Some synthesized compounds showed good to moderate toxicity against prostate cancer (PC-3) cell lines. Conclusion: This study has identified potent antioxidants and good cytotoxic agents with the potential to further investigate.

scholarly journals GC-MS Assisted Phytoactive Chemical Compounds Identification and Profiling with Mineral Constituents from Biologically Active Extracts of Aerva javanica (Burm. f) Juss. ex Schult.

2018 ◽  
Vol 46 (2) ◽  
pp. 517-524
Author(s):  
Kandhan KARTHISHWARAN ◽  
Subban KAMALRAJ ◽  
Chelliah JAYABASKARAN ◽  
Shyam S. KURUP ◽  
Sabitha SAKKIR ◽  
...  
Keyword(s):  
Biological Activities ◽  
Radical Scavenging Activity ◽  
Antioxidant Properties ◽  
Radical Scavenging ◽  
Biologically Active ◽  
Scavenging Activity ◽  
Medicinal Uses ◽  
Chemical Structures ◽  
Aerial Parts ◽  
Mineral Constituents

Aerva javanica (Burm. f) Juss. ex Schult. (Family: Amaranthaceae) family is one of the traditional medicinal plant growing in the United Arab Emirates. Apart from studies related to some medicinal properties, phytochemical, GC MS compound characterization and biological activities still to be investigated. An experiment was conducted to determine the possible bioactive components with their chemical structures and elucidation of phytochemicals from the aerial parts of the plant. The macro and micro-mineral constituents and antioxidant activities were also evaluated. Aerial parts of A. javanica were extracted sequentially with hexane, chloroform, ethyl acetate, acetone, methanol by cold percolation method. Free radical scavenging and antioxidant properties of methanolic extract were evaluated by using in vitro antioxidant assays such as hydroxyl radical scavenging activity, 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals, superoxide radical scavenging activity and ABTS radical scavenging activity. Primary phytochemical and micro-macro element was tested using standard protocol. The chemical characterization was done with the help of Gas Chromatography-Mass Spectrometry (GC–MS), and the mass spectra of the total compounds in the extract were matched with the National Institute of Standard and Technology (NIST) library. Mineral constituents were identified and estimated by ICP-OES. Ninety-nine metabolites were obtained by GC-MS anslysis; indole was found to be major components followed by 2-Chlorallyl diethyldithiocarbamate (CDEC), Carbaril, Bis(2-ethylhexyl) phthalate, Quinoline, 4H-Cyclopenta[def]phenanthrene,2-[Bis(2-chloroethylamino)]-tetrahydro-2H-1,3,2-oxazaphosphorine-2-oxide, Phenobarbital, 1H-Indole, 2-methyl-, 2,3,7,8-Tetrachlorodibenzo-p-dioxin Disulfide, diphenyl. The presence of various bioactive compounds in the extract validates the traditional medicinal uses of this plant.

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