Phytochemical study: molecular docking of eugenol derivatives as antioxidant and antimicrobial agents

2022 ◽  
Vol 19 ◽  
Author(s):  
Achraf Abdou ◽  
Sabrine Idouaarame ◽  
Mohammed Salah ◽  
Nabil Nor ◽  
Soukaina Zahm, ◽  
...  

Abstract: Eugenol (4-allyl-2-methoxyphenol) is a natural phenolic compound present in certain aromatic plants; however, it is generally extracted from essential oil of Eugenia caryophyllata (Syzygiumaromaticum) (L.) Merr. and L.M. Perry. This bioactive natural compound has generated considerable biological interest with well-known antimicrobial and antioxidant actions. The authors have aimed to the evaluations of eugenol derivatives and their as antimicrobial and antioxidant agent with the aid of molecular dynamic simulation. The starting material was extracted from cloves using hydrodistillation. Two eugenol derivatives, acetyleugenol (4-allyl-2-methoxyphenylacetate) and epoxyeugenol (4-allyl-2-methoxyphenol) were prepared and tested against two strains Escherichia coli (E. Coli) and Staphylococcus aureus (S. Aureus). The results have revealed that the three compounds (Eugenol, acetyleugenol and epoxyeugenol) possess important potentials of inhibition against E. coli and S. Aureus. The antioxidant activity of eugenol derivatives was evaluated by the reaction with DPPH (1,1-diphenyl-2-picrylhydrazyl), showed that the epoxyeugenol was the most active compound. The molecular docking scores of three compounds and the amino acids in the active site pockets of the selected proteins of the two bacteria have approved and explain the biological experimental outcomes.

2019 ◽  
Vol 15 ◽  
Author(s):  
Thais Batista Fernandes ◽  
Natanael Dante Segretti ◽  
Felipe Rebello Lourenço ◽  
Thalita Marcílio Cândido ◽  
André Rolim Baby ◽  
...  

Background: Antimicrobial resistance is a persistent problem about infections treatment and carries needing for develop new antimicrobial agents. Inhibiting of bacterial β-ketoacyl acyl carrier protein synthase III (FabH), which catalyzes the condensation reaction between a CoA-attached acetyl group and an ACP-attached malonyl group in bacteria is an interesting strategy to find new antibacterial agents. Objective: The aim of this work was to design and synthesize arylsulfonylhydrazones potentially FabH inhibitors and evaluate their antimicrobial activity. Methods: MIC50 of sulfonylhydrazones against E. coli and S. aureus was determined. Antioxidant activity was evaluated by DPPH (1-1’-diphenyl-2-picrylhydrazyl) assay and cytotoxicity against LL24 lung fibroblast cells was verified by MTT method. Principal component analysis (PCA) was performed in order to suggest a structure-activity relationship. Molecular docking allowed to propose sulfonylhydrazones interactions with FabH. Results: The most active compound showed activity against S. aureus and E. coli, with MIC50 = 0.21 and 0.44 µM, respectively. PCA studies correlated better activity to lipophilicity and molecular docking indicated that sulfonylhydrazone moiety is important to hydrogen-bond with FabH while methylcatechol ring performs π-π stacking interaction. The DPPH assay revealed that some sulfonylhydrazones derived from the methylcatechol series had antioxidant activity. None of the evaluated compounds was cytotoxic to human lung fibroblast cells, suggesting that the compounds might be considered safe at the tested concentration. Conclusion: Arylsufonylhydrazones is a promising scaffold to be explored for design of new antimicrobial agents.


Molecules ◽  
2020 ◽  
Vol 25 (12) ◽  
pp. 2766 ◽  
Author(s):  
Heba E. Hashem ◽  
Abd El-Galil E. Amr ◽  
Eman S. Nossier ◽  
Elsayed A. Elsayed ◽  
Eman M. Azmy

To develop new antimicrobial agents, a series of novel thiourea derivatives incorporated with different moieties 2–13 was designed and synthesized and their biological activities were evaluated. Compounds 7a, 7b and 8 exhibited excellent antimicrobial activity against all Gram-positive and Gram-negative bacteria, and the fungal Aspergillus flavus with minimum inhibitory concentration (MIC) values ranged from 0.95 ± 0.22 to 3.25 ± 1.00 μg/mL. Furthermore, cytotoxicity studies against MCF-7 cells revealed that compounds 7a and 7b were the most potent with IC50 values of 10.17 ± 0.65 and 11.59 ± 0.59 μM, respectively. On the other hand, the tested compounds were less toxic against normal kidney epithelial cell lines (Vero cells). The in vitro enzyme inhibition assay of 8 displayed excellent inhibitory activity against Escherichia coli DNA B gyrase and moderate one against E. coli Topoisomerase IV (IC50 = 0.33 ± 1.25 and 19.72 ± 1.00 µM, respectively) in comparison with novobiocin (IC50 values 0.28 ± 1.45 and 10.65 ± 1.02 µM, respectively). Finally, the molecular docking was done to position compound 8 into the E. coli DNA B and Topoisomerase IV active pockets to explore the probable binding conformation. In summary, compound 8 may serve as a potential dual E. coli DNA B and Topoisomerase IV inhibitor.


2009 ◽  
Vol 3 (1) ◽  
pp. 103-107 ◽  
Author(s):  
Hend A. Hamedo

Technological application of essential oils, as natural antimicrobial agents, to reduce the effect of pathogenic microorganisms, requires new methods of detection. The present work evaluated the parameters of antimicrobial activity of the essential oils of rosemary (Rosmarinus officinalis) on two pathogenic strains Escherichia coli and Staphylococcus aureus. The MBC and MIC values were of 2.5, 25 μl ml-1, and values of 1.25 and 5 μl ml-1 for the two strains respectively. In this study, an attempt has been made to evaluate randomly amplified polymorphic DNA (RAPD) analysis for its potential to establish antimicrobial effect of rosemary essential oil. For the preliminary assessment, this study compared the effects occurring at molecular levels in E. coli and Staph. aureus exposed to rosemary essential oil at the MIC concentrations for the two organisms. The qualitative modifications arising in random amplified polymorphic DNA (RAPD) profiles as a measure of DNA effects were compared with control which showed many differences. In conclusion, the measurement of parameters at molecular levels is valuable for investigating the specific effects of agents interacting with DNA.


2021 ◽  
Vol 17 ◽  
Author(s):  
Shaik Adamshafi ◽  
Venkatarao Veera ◽  
Mohan Rao SVM ◽  
Kishore Pilli VVN

Introduction: Progress in the development of triazolyl-oxadiazoles is a bisphosphonate-700 inhibitor is still continuing with an outcome of the good scaffold as oxadiazole as well as triazoles individually for antibacterial activity. Hence, we proposed a suitable approach for the synthesis of dual heterocyclic analogues consisting of the therapeutically used non steroidal anti-inflammatory drugs in a combined form and evaluated for their antibacterial, antifungal activities, docking studies. Methods: The chemical structures were confirmed by various spectroscopic methods like IR, 1H NMR, 13C NMR, mass, and elemental analysis. The antibacterial, antifungal activity of these compounds was screened against Gram-positive, Gram-negative bacteria and fungal stains by agar well diffusion method. The crystal structure of S. aureus complexed with active site of bisphosphonate BPH-700 (2ZCS) was obtained from the Protein Database (PDB, http://www.rcsb.org). Molecular properties, drug likeness score, lipophilicity and solubility parameters by Molinspiration and Molsoft software. 7f (2-NO2, 5-Ome), 7g (3-Cl, 4-Cl), 7a (2-NO2) Results: Among the synthesised NSAID-triazolyl-oxadiazole containing 2-nitro-5-methoxy (7f), 3,4-dichloro (7g) derivatives were found to be high active antibacterial agents against S. aureus, E. coli with MICs 16, 19 μg/mL respectively. 2-nitro-5-methoxy (7f), 4-bromo (7h) and 2-nitro (7a) derivatives displayed superior antifungal activity against A. niger and MICs 56, 76, 130 μg/mL respectively. From molecular docking NSAID linked to 3,4-dichloro analogue (7g) revealed stronger binding interaction (ΔG =7.90 Kcal/Mol) with amino acids Asp49 (1.19 A˚), Arg45 (2.17 A˚), Lys17, Lys46 in the active site of S. aureus complexed with bisphosphonate Bph-700 (2ZCS). The compounds followed the Lipinski ‘Rule of five’ were synthesized for antimicrobial screening as oral bioavailable drugs/leads. Maximum drug likeness model score 0.49, 0.41 was found for compounds 7h, 7b. Conclusion: The present work, through simple synthetic approaches, led to the development of novel hybrids of triazole-oxadiazole pharmacophores that exhibited remarkable biological activities against different microorganisms. The compounds showed suitable drug like properties and are expected to present good bioavailability profile. Discussion: An efficient combination of molecular modeling and biological activity provided an insight into QSAR guide lines that could aid in further development of these derivatives.


Author(s):  
Patil Tejaswini D. ◽  
Amrutkar Sunil V.

Background: DNA gyrase subunit B (1KZN) is an attractive target for antibacterial drug development because of its role in DNA replication. The fast development of antimicrobial medication resistance necessitates the quick discovery of new antimicrobial medicines. Objective: The goal of this research is to design, synthesize, and discover benzo-fused five-membered nitrogen-containing heterocycles that bind to DNA gyrase subunit B via molecular docking (1KZN). Methods: Based on literature research, 2-(1H-1,2,3-Benzotriazol-1-yl)-N-substituted acetamide was synthesized using an efficient method. All synthesized compounds were evaluated for antibacterial activity against three distinct organisms: E. coli, Pseudomonas aeruginosa, Staphylococcus aureus. In a docking investigation, the chemical interacts with the active site of DNA gyrase subunit B (1KZN), indicating that it might have antibacterial action. Conclusion: According to the findings of this research, the compounds 3d and 3f show antibacterial properties. For Staphylococcus aureus, 3c has the potential to be an antibacterial agent.


2002 ◽  
Vol 46 (4) ◽  
pp. 943-946 ◽  
Author(s):  
Maria D. F. S. Barbosa ◽  
Gaoyun Yang ◽  
Jie Fang ◽  
Michael G. Kurilla ◽  
David L. Pompliano

ABSTRACT Osmotically stabilized Escherichia coli cells subjected to freezing and thawing were utilized as the source of enzymes for a peptidoglycan pathway assay that can be used to simultaneously test all targets of the committed steps of cell wall biosynthesis. The use of 14C-labeled UDP-N-acetylglucosamine (UDP-GlcNAc) as a substrate allows the direct detection of cross-linked peptidoglycan formed. The assay was validated with known antibiotics. Fosfomycin was the strongest inhibitor of the pathway assay, with a 50% inhibitory concentration of 1 μM. Flavomycin, bacitracin, vancomycin, d-cycloserine, penicillin G, and ampicillin also inhibited formation of radiolabeled peptidoglycan by the E. coli cells. Screening of compounds identified two inhibitors of the pathway, Cpd1 and Cpd2. Subsequent tests with a biochemical assay utilizing purified enzyme implicated UDP-GlcNAc enolpyruvyl transferase (MurA) as the target of Cpd1. This compound inhibits the first enzyme of the pathway in a time-dependent manner. Moreover, enzyme inactivation is dependent on preincubation in the presence of UDP-GlcNAc, which forms a complex with MurA, exposing its active site. Cpd1 also displayed antimicrobial activity against a panel of microorganisms. The pathway assay used in conjunction with assays for individual enzymes provides an efficient means of detecting and characterizing novel antimicrobial agents.


Author(s):  
Sourav Das ◽  
Sharat Sarmah ◽  
Sona Lyndem ◽  
Atanu Singha Roy

A new strain of a novel infectious disease affecting millions of people, caused by severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) has recently been declared as a pandemic by the World Health Organization (WHO). Currently, several clinical trials are underway to identify specific drugs for the treatment of this novel virus. The inhibition of the SARS-CoV-2 main protease is necessary for the blockage of the viral replication. Here, in this study, we have utilized a blind molecular docking approach to identify the possible inhibitors of the SARS-CoV-2 main protease, by screening a total of 33 molecules which includes natural products, anti-virals, anti-fungals, anti-nematodes and anti-protozoals. All the studied molecules could bind to the active site of the SARS-CoV-2 protease (PDB: 6Y84), out of which rutin (a natural compound) has the highest inhibitor efficiency among the 33 molecules studied, followed by ritonavir (control drug), emetine (anti-protozoal), hesperidin (a natural compound), lopinavir (control drug) and indinavir (anti-viral drug). All the molecules, studied out here could bind near the crucial catalytic residues, HIS41 and CYS145 of the main protease, and the molecules were surrounded by other active site residues like MET49, GLY143, HIS163, HIS164, GLU166, PRO168, and GLN189. As this study is based on molecular docking, hence being particular about the results obtained, requires extensive wet-lab experimentation and clinical trials under <i>in vitro</i> as well as <i>in vivo </i>conditions.


2020 ◽  
Author(s):  
Sourav Das ◽  
Sharat Sarmah ◽  
Sona Lyndem ◽  
Atanu Singha Roy

A new strain of a novel infectious disease affecting millions of people, caused by severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) has recently been declared as a pandemic by the World Health Organization (WHO). Currently, several clinical trials are underway to identify specific drugs for the treatment of this novel virus. The inhibition of the SARS-CoV-2 main protease is necessary for the blockage of the viral replication. Here, in this study, we have utilized a blind molecular docking approach to identify the possible inhibitors of the SARS-CoV-2 main protease, by screening a total of 33 molecules which includes natural products, anti-virals, anti-fungals, anti-nematodes and anti-protozoals. All the studied molecules could bind to the active site of the SARS-CoV-2 protease (PDB: 6Y84), out of which rutin (a natural compound) has the highest inhibitor efficiency among the 33 molecules studied, followed by ritonavir (control drug), emetine (anti-protozoal), hesperidin (a natural compound), lopinavir (control drug) and indinavir (anti-viral drug). All the molecules, studied out here could bind near the crucial catalytic residues, HIS41 and CYS145 of the main protease, and the molecules were surrounded by other active site residues like MET49, GLY143, HIS163, HIS164, GLU166, PRO168, and GLN189. As this study is based on molecular docking, hence being particular about the results obtained, requires extensive wet-lab experimentation and clinical trials under <i>in vitro</i> as well as <i>in vivo </i>conditions.


2017 ◽  
Vol 5 (2) ◽  
pp. 256-260 ◽  
Author(s):  
Shiv Nandan Sah ◽  
Sunil Regmi ◽  
Man Kumar Tamang

Various medicinal plants are common in use in Nepal for the treatment of different diseases. Nowadays, drug resistance has emerged as a major problem for various infections, in such case plants can be used as alternative for the production of new antimicrobial agents. Thuja (in Nepali: dhupi) is a small evergreen genus of the Cupressaceae family. This species is widely cultivated as a common ornamental plant in Nepal and India. This study examined the antibacterial activity of Thuja leaves extract on gram positive (Staphylococcus aureus and Streptococcus spp.) and gram-negative bacteria (E. coli and Pseudomonas aeruginosa). Thuja leaves were collected from different localities of Dharan, and dried under shade for 10 days. They were then grinded using mechanical grinder. Leaf extract (oleoresin) was obtained by soxhlet extraction technique using mixture of Ethyl acetate, Ethanol and chloroform in the ratio 40:30:30 as the solvent. The antibacterial activity of Thuja oleoresin was tested using both Agar well diffusion as well as disc diffusion technique. Minimum Inhibitory Concentration(MIC) was  determined by agar well diffusion on MHA plates. Thuja oleoresin showed distinct antibacterial activity towards all four isolates on both agar well and disc diffusion methods. MIC for Pseudomonas aeruginosa and Streptococcus spp. was found to be 12.5 µl whereas for E. coli and Staphylococcus aureus, MIC was 25 µl. Thus from our results, it is concluded that Thuja leaves have antibacterial effects and can be a potential source for production of antibacterial drugs.Int. J. Appl. Sci. Biotechnol. Vol 5(2): 256-260


2021 ◽  
Vol 2021 ◽  
pp. 1-9
Author(s):  
Azumah Ayamah ◽  
Augustina Angelina Sylverken ◽  
Linda Aurelia Ofori

The demand for ready-to-eat (RTE) foods is handy to busy urban dwellers. Handling, processing, and selling are known to contaminate these foods and cause foodborne outbreaks. This study assessed a load of S. aureus and E. coli in khebabs (beef, chevon, and gizzard) sold on the KNUST campus and its environs and how resistant they are to clinically relevant antimicrobial agents. Thirty-six (36) khebab samples were purchased from vendors at Kotei, Ayeduase, Kentinkrono, Boadi, KNUST campus, and Ayigya. They were analyzed for S. aureus and E. coli and their resistance to clinically relevant antimicrobial agents checked using standard methods. S. aureus and E. coli load ranged from 4.09 to 5.96 CFU/g and 1.79 to 6.12 MPN/g in beef, 4.02 to 6.01 CFU/g and 1.99 to 4.44 MPN/g in chevon, and 5.37 to 6.18 CFU/g and 1.79 to 6.10 MPN/g in gizzard khebabs in the different locations. E. coli (n = 27) were multiresistant to ampicillin, tetracycline, gentamicin, cefuroxime, ceftriaxone, cefotaxime, and cotrimoxazole (51.85%) and susceptible to chloramphenicol (100%). S. aureus (n = 36) isolates were multiresistant to penicillin, tetracycline, flucloxacillin, cefuroxime, ampicillin (97.22%), erythromycin (75%), cotrimoxazole (86.11%), and gentamicin (69.44%). It can therefore be concluded that the majority of khebabs from the KNUST campus and its environs were contaminated with S. aureus and E. coli above the acceptable standard limits (≤4 log10 CFU/g and ˂2 log10MPN/g, respectively). Also, the S. aureus and E. coli isolated were multiresistant to the antibiotics tested and could be a medium for the transmission of antibiotic-resistant bacteria and therefore expose consumers to a high risk of contracting foodborne infections with drug-resistant strains.


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