Antioxidant and intestinal anti-inflammatory effects of plant-derived coumarin derivatives

Phytomedicine ◽  
2014 ◽  
Vol 21 (3) ◽  
pp. 240-246 ◽  
Author(s):  
Aline Witaicenis ◽  
Leonardo Noboru Seito ◽  
Alexandre da Silveira Chagas ◽  
Luiz Domingues de Almeida ◽  
Ana Carolina Luchini ◽  
...  
Keyword(s):  
Coumarin Derivatives ◽  
Anti Inflammatory

Pharmacologically potentials of different substituted coumarin derivatives

2019 ◽  
Author(s):  
Chem Int
Keyword(s):  
Benzene Ring ◽  
Bioactive Compounds ◽  
Biological Activities ◽  
Pharmacological Properties ◽  
Coumarin Derivatives ◽  
Wide Range ◽  
Anti Oxidant ◽  
Anti Inflammatory ◽  
Coumarin Compounds

Coumarin and its derivatives are widely spread in nature. Coumarin goes to agroup as benzopyrones, which consists of a benzene ring connected to a pyronemoiety. Coumarins displayed a broad range of pharmacologically useful profile.Coumarins are considered as a promising group of bioactive compounds thatexhibited a wide range of biological activities like anti-microbial, anti-viral,antiparasitic, anti-helmintic, analgesic, anti-inflammatory, anti-diabetic, anticancer,anti-oxidant, anti-proliferative, anti-convulsant, and antihypertensiveactivities etc. The coumarin compounds have immense interest due to theirdiverse pharmacological properties. In particular, these biological activities makecoumarin compounds more attractive and testing as novel therapeuticcompounds.

ROS Inhibitory Activity and Cytotoxicity Evaluation of Benzoyl, Acetyl, Alkyl Ester, and Sulfonate Ester Substituted Coumarin Derivatives

2020 ◽  
Vol 16 (8) ◽  
pp. 1099-1111
Author(s):  
Uzma Salar ◽  
Khalid M. Khan ◽  
Almas Jabeen ◽  
Aisha Faheem ◽  
Farwa Naqvi ◽  
...  
Keyword(s):  
Inhibitory Activity ◽  
Antiinflammatory Drug ◽  
Vital Role ◽  
Alkyl Ester ◽  
Flufenamic Acid ◽  
Coumarin Derivatives ◽  
Inflammatory Disorders ◽  
Enhanced Chemiluminescence ◽  
Anti Inflammatory ◽  
Sulfonate Ester

Background: A number of non-steroidal anti-inflammatory drugs (NSAIDs) including aspirin, indomethacin, ibuprofen, flufenamic acid, and phenylbutazone are being clinically used to treat inflammatory disorders. These NSAIDs are associated with serious side effects such as gastric ulceration, nephrotoxicity, and bleeding. Therefore, the identification of potent and safe therapy for inflammatory disorders is still of great interest to the medicinal chemist. Methods: A series of varyingly substituted benzoyl, acetyl, alkyl ester, and sulfonate ester substituted coumarins 1-64 were screened for the inhibition of ROS, generated from zymosan activated whole blood phagocytes, using luminol-enhanced chemiluminescence technique. Results: Among all tested compounds, 8 (IC50 = 65.0 ± 3.1 μM), 24 (IC50 = 41.8 ± 1.5 μM), 26 (IC50 = 10.6 ± 2.8 μM), 28 (IC50 = 20.9 ± 1.5 μM), and 41 (IC50 = 4.6 ± 0.3 μM) showed good anti- inflammatory potential as compared to standard antiinflammatory drug ibuprofen (IC50 = 54.3 ± 1.9 μM). Specifically, compounds 24, 26, 28, and 41 showed superior activity than standard antiinflammatory drug. Furthermore, compounds 12 (IC50 = 219.0 ± 1.4 μM), 14 (IC50 = 216.5 ± 6.2 μM), 16 (IC50 = 187.4 ± 2.2 μM), and 20 (IC50 = 196.2 ± 2.0 μM) showed moderate ROS inhibitory activity. Limited SAR study revealed that the hydroxy-substituted compound showed better ROS inhibition potential in case of 3-benzoyl and 3-ethylester coumarin derivatives. Whereas, chloro substitution was found to be important in case of 3-acetyl coumarin derivatives. Similarly, in case of sulfonate ester, chloro, and nitro groups especially at positions -4 and -3 of ring “R” played vital role in ROS inhibition. Furthermore, cytotoxicity of all active compounds was also checked on NIH-3T3 cell line. Compounds 12, 14, and 20 were found to be non-cytotoxic. Whereas, 8, 16, 24, 26, 28, and 41 were found to be very weak cytotoxic as compared to standard cycloheximide (IC50 = 0.13 ± 0.02 μM). Conclusion: Identified ROS inhibitors offer the possibility of additional modifications that could give rise to lead structures for further research in order to obtain more potent, and safer antiinflammatory agent.

scholarly journals Studies on the antiplatelet and antithrombotic profile of anti-inflammatory coumarin derivatives

2015 ◽  
Vol 30 (6) ◽  
pp. 925-933 ◽  
Author(s):  
Christos Kontogiorgis ◽  
Orazio Nicolotti ◽  
Giuseppe Felice Mangiatordi ◽  
Massimiliano Tognolini ◽  
Foteini Karalaki ◽  
...  
Keyword(s):  
Coumarin Derivatives ◽  
Anti Inflammatory

scholarly journals Synthesis and Evaluation of New Coumarin Derivatives as Antioxidant, Antimicrobial, and Anti-Inflammatory Agents

Molecules ◽  
2020 ◽  
Vol 25 (14) ◽  
pp. 3251 ◽  
Author(s):  
Hanan M. Alshibl ◽  
Ebtehal S. Al-Abdullah ◽  
Mogedda E. Haiba ◽  
Hamad M. Alkahtani ◽  
Ghada E.A. Awad ◽  
...  
Keyword(s):  
Significant Inhibition ◽  
Coumarin Derivatives ◽  
Paw Oedema ◽  
Cox 2 ◽  
Anti Inflammatory ◽  
Rat Paw ◽  
Orally Active ◽  
Rat Paw Oedema ◽  
Sulfonamide Compound

New pyranocoumarin and coumarin-sulfonamide derivatives were prepared and evaluated for their antioxidant, antimicrobial, and/or anti-inflammatory activities. Coumarin-sulfonamide compounds 8a–d demonstrated significant antioxidant activity, while 7c,d, 8c,d, and 9c,d exhibited antimicrobial activity equal to or higher than the standard antimicrobials against at least one tested microorganism. Regarding the anti-inflammatory testing, pyranocoumarins 2b, 3a,b and 5c and coumarin-sulfonamide compound 9a showed more potent antiproteinase activity than aspirin in vitro; however, five compounds were as potent as aspirin. The anti-inflammatory activity of the promising compounds was further assessed pharmacologically on formaldehyde-induced rat paw oedema and showed significant inhibition of oedema. For in vitro COX-inhibitory activity of coumarin derivatives, pyranocoumarin derivative 5a was the most selective (SI = 152) and coumarin-sulfonamide derivative 8d was most active toward COX-2 isozyme. The most active derivatives met the in silico criteria for orally active drugs; thus, they may serve as promising candidates to develop more potent and highly efficient antioxidant, antimicrobial, and/or anti-inflammatory agents.

Synthesis, anti-inflammatory, analgesic, 5-lipoxygenase (5-LOX) inhibition activities, and molecular docking study of 7-substituted coumarin derivatives

2016 ◽  
Vol 67 ◽  
pp. 130-138 ◽  
Author(s):  
Pavan Srivastava ◽  
Vivek K. Vyas ◽  
Bhavesh Variya ◽  
Palak Patel ◽  
Gulamnizami Qureshi ◽  
...  
Keyword(s):  
Molecular Docking ◽  
Docking Study ◽  
Coumarin Derivatives ◽  
Molecular Docking Study ◽  
Anti Inflammatory

New Coumarin Derivatives as Potent Selective COX-2 Inhibitors: Synthesis, Anti-Inflammatory, QSAR, and Molecular Modeling Studies

2015 ◽  
Vol 348 (12) ◽  
pp. 875-888 ◽  
Author(s):  
Dina H. Dawood ◽  
Rasha Z. Batran ◽  
Thoraya A. Farghaly ◽  
Mohammed A. Khedr ◽  
Mohamed M. Abdulla
Keyword(s):  
Molecular Modeling ◽  
Coumarin Derivatives ◽  
Modeling Studies ◽  
Molecular Modeling Studies ◽  
Cox 2 ◽  
Anti Inflammatory ◽  
Cox 2 Inhibitors

Synthesis of Bioactives Coumarin Derivatives, Phthalocyanines and Terminal Conjugated Dienes via a Ruthenium Catalyzed Cross-Metathesis: Application to Renewable Resources

2016 ◽  
Vol 842 ◽  
pp. 1-45
Author(s):  
Hallouma Bilel ◽  
Rawdha Medyouni ◽  
A.S. Al-Ayed ◽  
Naceur Hamdi ◽  
Cédric Fischmeister ◽  
...  
Keyword(s):  
Antibacterial Activity ◽  
Antioxidant Activities ◽  
Radical Scavenging ◽  
Nucleophilic Aromatic Substitution ◽  
Coumarin Derivatives ◽  
E Coli ◽  
Cross Metathesis ◽  
Anti Oxidant ◽  
Hydroxy Coumarin ◽  
Anti Inflammatory

This study aimed for the synthesis of 4-Aryl-2-amino-6-(4-hydroxy coumarin-3-yl) pyridine-3-carbonitriles derivatives 4, suitable for use as antibacterial, anti-oxidant and anti-inflammatory activities via a versatile, readily accessible 3-((2E)-3(aryl)prop-2-enoyl)-2H-chromen-2-one, 3, which was prepared by refluxing 3-acetyl-4-hydroxycoumarin with aromatic aldehydes in chloroform in the presence of a catalytic amount of piperidine. Then the direct reaction of the obtained chalcones 3 with malonitrile in the presence of ammonium acetate in one step gave products 4. Most of the new compound 4 exhibit moderate antibacterial activity against Gram Negative bacterial strains (E. coli, K. pneumonia, S. typhi and S. flexneri). In addition, the compounds 4 were investigated for anti-oxidant activities by super oxide radical, DPPH (2,2-Diphenyl-1-picrylhydrazyl), and hydroxyl radical scavenging assays, where most of the compounds displayed significant antioxidant activities. Furthermore, these 4-Aryl-2-amino-6-(4-hydroxy coumarin-3-yl) pyridine-3-carbonitriles 4 were evaluated for anti-inflammatory activity by indirect haemolytic and lipoxygenase inhibition assays where compounds revealed good activity. The preparation of novel metal-free phthalocyanines and metallophthalocyanine complexes 11 and 12 (MPcs, M = Co, Zn, Cu and Mn), with four peripheral 6-hydroxy-4-methylcoumarin and 6-hydroxycoumarin substituents, were also prepared by cyclotetramerization of compounds 7 and 10 with the corresponding metal salts (Zn(OAc)2.2H2O, Co(OAc)2.4H2O, CuCl, Mn(OAc)2.4H2O) as a template for macrocycle formation in 2-(N,N-dimethylamino)ethanol.The electronic spectra of these compounds exhibit a band of coumarin identity together with characteristic bands of the phthalocyanine core. The new compounds were screened for antibacterial activity. Most of them are active against E. coli and S. aureus. In addition, some novel 3-acetylcoumarin derivatives 17 were prepared in good yields. Their invitro antioxidant activities were assayed by the quantitative 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity method. In this way, novel coumarin phtalonitriles derivatives 42-44 were synthesized.The synthesis of these coumarin phtalonitriles was resulting from a nucleophilic aromatic substitution reaction between 4-nitrophtalonitrile and coumarins derivatives. The complexing properties of the coumarin derivatives toward alkali metal, alkaline earth metal, some transition metals and some heavy metal cations have been investigated in acetonitrile by means of UV spectrophotometry absorption and conductivity methods. Thus, the stoichiometry of the complexes formed and their stability constants were determined. We report also in this book chapter a sequence of two ruthenium-catalyzed transformations, namely olefin cross metathesis with allylic chloride followed by elimination, which gives a straightforward access to terminal 1,3-dienes from natural products. The structures of all the new obtained compounds were confirmed by elemental analysis, IR, and multinuclear/multidimensional NMR spectroscopy (1H, 13C-NMR, NOESY, HMBC) which allowed assignment of the complete network of proton and carbon atoms).

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