scholarly journals Chemical Analysis and Antioxidant and Antimicrobial Activity of Essential oils from Artemisia negrei L. against Drug-Resistant Microbes

2021 ◽  
Vol 2021 ◽  
pp. 1-9
Author(s):  
Khalid Chebbac ◽  
Abdelfattah EL Moussaoui ◽  
Mohammed Bourhia ◽  
Ahmad Mohammad Salamatullah ◽  
Abdulhakeem Alzahrani ◽  
...  

Background. Artemisia negrei L. (A. negrei) is a medicinal and aromatic plant belonging to the family Asteraceae that is more widespread in the folded Middle Atlas Mountains, Morocco. Materials and Methods. This study was run to investigate the phytochemical composition and antioxidant, antibacterial, and antifungal activities of Artemisia negrei L. essential oil. This oil was extracted from the fresh plant material by using the Clevenger apparatus. The phytochemical composition was characterized by GC-MS. The antioxidant activity was evaluated using different methods including DPPH, β-carotene bleaching, and total antioxidant capacity. The antibacterial activity was tested vs. multidrug-resistant bacteria including both Gram-negative and Gram-positive using inhibition zones in agar media and minimum inhibitory concentration (MIC) bioassays. The antifungal activity was conducted on Candida albicans, Aspergillus niger, Aspergillus flavus, and Fusarium oxysporum using a solid medium assay. Results. The chromatographic characterization of essential oils of A. negrei revealed the presence of 34 compounds constituting 99.91% of the total essential oil. The latter was found to have promising antioxidant activity by all bioassays used such as DPPH, β-carotene bleaching, and total antioxidant capacity. The results obtained showed that our plant oils had potent antibacterial activity towards Gram-negative (E. coli 57, E. coli 97, K. pneumonia, and P. aeruginosa) and Gram-positive (S. aureus), so that the maximum inhibition zones and MIC values were around 18–37 mm and 3.25 to 12.5 mg/mL, respectively. The oil also showed antifungal activity towards Candida albicans, Fusarium oxysporum, and Aspergillus Niger except for flavus species. Conclusion. The findings obtained in the work showed that A. negrei can serve as a valuable source of natural compounds that can be used as a new weapon to fight radical damage and resistant microbes.

Author(s):  
V.N. Bhadani ◽  
H.D. Purohit ◽  
Dipak M. Purohit

Isoxazoline derivatives shows various types of therapeutic activities like antimicrobial[1], anti-inflammatory[2], anticonvulsant[3], Hypoglycemic[4] etc. getting to synthesized in view of 3-Aryl-5-[(4′-difluoromethoxy)(3′-hydroxy)phenyl]-4,5-dihydro isoxazole (4a-4i) have been synthesized. All the newly synthesized compounds were screened for their antibacterial activity against S. aureus, M. luteus (Gram-positive bacteria), E. coli, S. thyphi (Gram-negative bacteria) and antifungal activity against Candida albicans (Fungi). The biological activities (MIC) of the synthesized compounds were compared with known standard drugs.


2020 ◽  
Vol 15 (6) ◽  
pp. 665-679
Author(s):  
Alok K. Srivastava ◽  
Lokesh K. Pandey

Background: [1, 3, 4]oxadiazolenone core containing chalcones and nucleosides were synthesized by Claisen-Schmidt condensation of a variety of benzaldehyde derivatives, obtained from oxidation of substituted 5-(3/6 substituted-4-Methylphenyl)-1, 3, 4-oxadiazole-2(3H)-one and various substituted acetophenone. The resultant chalcones were coupled with penta-O-acetylglucopyranose followed by deacetylation to get [1, 3, 4] oxadiazolenone core containing chalcones and nucleosides. Various analytical techniques viz IR, NMR, LC-MS and elemental analysis were used to confirm the structure of the synthesised compounds.The compounds were targeted against Bacillus subtilis, Staphylococcus aureus and Escherichia coli for antibacterial activity and Aspergillus flavus, Aspergillus niger and Fusarium oxysporum for antifungal activity. Methods: A mixture of Acid hydrazides (3.0 mmol) and N, Nʹ- carbonyl diimidazole (3.3 mmol) in 15 mL of dioxane was refluxed to afford substituted [1, 3, 4]-oxadiazole-2(3H)-one. The resulted [1, 3, 4]- oxadiazole-2(3H)-one (1.42 mmol) was oxidized with Chromyl chloride (1.5 mL) in 20 mL of carbon tetra chloride and condensed with acetophenones (1.42 mmol) to get chalcones 4. The equimolar ratio of obtained chalcones 4 and β -D-1,2,3,4,6- penta-O-acetylglucopyranose in presence of iodine was refluxed to get nucleosides 5. The [1, 3, 4] oxadiazolenone core containing chalcones 4 and nucleosides 5 were tested to determined minimum inhibitory concentration (MIC) value with the experimental procedure of Benson using disc-diffusion method. All compounds were tested at concentration of 5 mg/mL, 2.5 mg/mL, 1.25 mg/mL, 0.62 mg/mL, 0.31 mg/mL and 0.15 mg/mL for antifungal activity against three strains of pathogenic fungi Aspergillus flavus (A. flavus), Aspergillus niger (A. niger) and Fusarium oxysporum (F. oxysporum) and for antibacterial activity against Gram-negative bacterium: Escherichia coli (E. coli), and two Gram-positive bacteria: Staphylococcus aureus (S. aureus) and Bacillus subtilis(B. subtilis). Result: The chalcones 4 and nucleosides 5 were screened for antibacterial activity against E. coli, S. aureus and B. subtilis whereas antifungal activity against A. flavus, A. niger and F. oxysporum. Compounds 4a-t showed good antibacterial activity whereas compounds 5a-t containing glucose moiety showed better activity against fungi. The glucose moiety of compounds 5 helps to enter into the cell wall of fungi and control the cell growth. Conclusion: Chalcones 4 and nucleosides 5 incorporating [1, 3, 4] oxadiazolenone core were synthesized and characterized by various spectral techniques and elemental analysis. These compounds were evaluated for their antifungal activity against three fungi; viz. A. flavus, A. niger and F. oxysporum. In addition to this, synthesized compounds were evaluated for their antibacterial activity against gram negative bacteria E. Coli and gram positive bacteria S. aureus, B. subtilis. Compounds 4a-t showed good antibacterial activity whereas 5a-t showed better activity against fungi.


2010 ◽  
Vol 7 (s1) ◽  
pp. S400-S404 ◽  
Author(s):  
B. Lakshminarayanan ◽  
V. Rajamanickam ◽  
T. Subburaju ◽  
L. A. Pradeep Rajkumar ◽  
H. Revathi

Some new 3-(substituted)-chromen-2-one have been synthesized by condensation of 3-acetylchromen-2-one with various aromatic aldehyde in presence of ethanol and alkali. The synthesized compounds were identified by spectral data and screened for their antibacterial activity againstB. pumilis, B. substilisandE. coliand antifungal activity againstA. nigerandCandida albicans. Among the synthesized compounds, some compounds of aryl chromen, which are having electron releasing substituent such as methoxy and hydroxyl at various positions, showed moderate to considerable antibacterial and antifungal activities.


2020 ◽  
Vol 20 (3) ◽  
pp. 722
Author(s):  
Erwin Abdul Rahim ◽  
Nur Istiqomah ◽  
Gilang Almilda ◽  
Ahmad Ridhay ◽  
Ni Ketut Sumarni ◽  
...  

This study was aimed to prepare polyeugenol with high molecular weight and to evaluate its antibacterial and antioxidant activities. First, polyeugenol was synthesized from eugenol in the presence of H2SO4-CH3COOH (4:1) as catalyst. The synthesized polyeugenol was weighed by using viscometer, revealing its high molecular weight of (7.76–21.9) × 105 g/mol. Furthermore, the antibacterial activity of the polyeugenol was conducted against Staphylococcus aureus and Escherichia coli bacteria. It was conducted by applying well diffusion method at 1, 2, 3, 4 and 5% concentrations to observe inhibition zones, in which the tests showed that the antibacterial activity of the polyeugenol against S. aureus were 17.42, 17.76, 18.79, 21.42 and 22.55 mm, while those against E. coli were 15.87, 17.23, 17.56, 18.24 and 19.21 mm, respectively. In short, these results indicated a strong antibacterial activity. Then, tests on antioxidant activity against free radical DPPH (2,2-diphenyl-1-pycrylhydrazyl) gave the IC50 value of 80.47 µg/mL, indicating a strong antioxidant activity. Therefore, the polymer synthesized in this work has a high potential to be applied in various biomedical applications.


2018 ◽  
Vol 2018 ◽  
pp. 1-5 ◽  
Author(s):  
Ali Yetgin ◽  
Kerem Canlı ◽  
Ergin Murat Altuner

In this study, antimicrobial activities of two different samples ofAllium sativumL. from Turkey (TR) (Taşköprü, Kastamonu, Turkey) and China (CN) were determined. A broad spectrum of Gram-negative and Gram-positive bacteria (17 bacteria) including species ofBacillus,Enterobacter,Enterococcus,Escherichia,Klebsiella,Listeria,Pseudomonas,Salmonella, andStaphylococcuswere used for testing antibacterial activity. In addition, antifungal activity againstCandida albicanswas also investigated. Antimicrobial activity was tested by using 3 different processes (chopping, freezing, and slicing by the disk diffusion method). The results showed that TR garlic presented more antimicrobial activity than CN garlic. Mechanism of activity of CN garlic could be proposed to be different from that of TR garlic.


2019 ◽  
Vol 70 (10) ◽  
pp. 3603-3610
Author(s):  
Madalina Mihalache ◽  
Cornelia Guran ◽  
Aurelia Meghea ◽  
Vasile Bercu ◽  
Ludmila Motelica ◽  
...  

The three copper complexes having a-ketoglutaric acid (H2A) and 1- (o-tolyl) biguanide (TB) ligands have been synthesized and characterized. The proposed formulas for these complexes are: [Cu(TB)(HA)]Cl (C1), [Cu(TB)(HA)CH3COO]�H2O (C2) and [Cu(TB)(HA)](NO3) (C3) where HA represents deprotonated H2A. The complexes obtained were tested for antibacterial activity against Staphylococcus aureus ATCC 25923 and Pseudomonas aeruginosa ATCC 27853, antifungal activity on Candida albicans ATCC 10231 and antitumor activity on HeLa tumor cells. Due to the antitumor, antifungal, antimicrobial activity and inhibition of inert substrate adhesion, complexes synthesized could be used for potential therapeutic applications.


2019 ◽  
Vol 15 (4) ◽  
pp. 341-351 ◽  
Author(s):  
Ana P. Bettencourt ◽  
Marián Castro ◽  
João P. Silva ◽  
Francisco Fernandes ◽  
Olga P. Coutinho ◽  
...  

Background: Previous publications show that the addition of a phenolic antioxidant to an antifungal agent, considerably enhances the antifungal activity. Objective: Synthesis of novel compounds combining phenolic units with linear or cyclic nitrogencontaining organic molecules with antioxidant/antifungal activity using methodologies previously developed in the group. Methods: Several N- [1,2-dicyano-2- (arylidenamino) vinyl]-O-alkylformamidoximes 3 were synthesized and cyclized to 4,5-dicyano-N- (N´-alcoxyformimidoyl)-2-arylimidazoles 4 upon reflux in DMF, in the presence of manganese dioxide or to 6-cyano-8-arylpurines 5 when the reagent was refluxed in acetonitrile with an excess of triethylamine. These compounds were tested for their antioxidant activity by cyclic voltammetry, DPPH radical (DPPH•) assay and deoxyribose degradation assay. The minimum inhibitory concentration (MIC) of all compounds was evaluated against two yeast species, Saccharomyces cerevisiae and Candida albicans, and against bacteria Bacillus subtilis (Gram-positive) and Escherichia coli (Gram negative). Their cytotoxicity was evaluated in fibroblasts. Results: Among the synthetised compounds, five presented higher antioxidant activity than reference antioxidant Trolox and from these compounds, four presented antifungal activity without toxic effects in fibroblasts and bacteria. Conclusion: Four novel compounds presented dual antioxidant/antifungal activity at concentrations that are not toxic to bacteria and fibroblasts. The active molecules can be used as an inspiration for further studies in this area.


2020 ◽  
Vol 16 (4) ◽  
pp. 481-488
Author(s):  
Heli Sanghvi ◽  
Satyendra Mishra

Background: Curcumin, one of the most important pharmacologically significant natural products, has gained significant consideration among scientists for decades since its multipharmacological activities. 1, 3-Dicarbonyl moiety of curcumin was found to be accountable for the rapid degradation of curcumin molecule. The aim of present work is to replace 1, 3-dicarbonyl moiety of curcumin by pyrazole and phenylpyrazole derivatives with a view to improving its stability and to investigate the role of substitution in N-phenylpyrazole curcumin on its antibacterial activity against both Gram-positive as well as Gram-negative bacteria. Methods: Pyrazole derivatives of curcumin were prepared by heating curcumin with phenyhydrazine/ substituted phenyhydrazine derivatives in AcOH. The residue was purified by silica gel column chromatography. Structures of purified compounds were confirmed by 1H NMR and Mass spectroscopy. The synthesized compounds were evaluated for their antibacterial activity by the microdilution broth susceptibility test method against gram positive (S. aureus) and gram negative (E. coli). Results: Effects of substitution in N-phenylpyrazole curcumin derivatives against S. aureus and E. coli were studied. The most active N-(3-Nitrophenylpyrazole) curcumin (12) exhibits twenty-fold more potency against S. aureus (MIC: 10μg/mL)) and N-(2-Fluoroophenylpyrazole) curcumin (5) fivefold more potency against E. coli (MIC; 50 μg/mL) than N-phenylpyrazole curcumin (4). Whereas, a remarkable decline in anti-bacterial activity against S. aureus and E. coli was observed when electron donating groups were incorporated in N-phenylpyrazole curcumin (4). Comparative studies of synthesized compounds suggest the effects of electron withdrawing and electron donating groups on unsubstituted phenylpyrazole curcumin (4). Conclusion: The structure-activity relationship (SAR) results indicated that the electron withdrawing and electron donating at N-phenylpyrazole curcumin played key roles for their bacterial inhibitory effects. The results of the antibacterial evaluation showed that the synthesized pyrazole derivatives of curcumin displayed moderate to very high activity in S. aureus. In conclusion, the series of novel curcumin derivatives were designed, synthesized and tested for their antibacterial activities against S. aureus and E. coli. Among them, N-(3-Nitrophenylpyrazole curcumin; 12) was most active against S. aureus (Gram-positive) and N-(2-Fluoroophenylpyrazole) curcumin (5) against E. coli (Gram-negative) bacteria.


2021 ◽  
Vol 21 (1) ◽  
Author(s):  
Tessa B. Moyer ◽  
Ashleigh L. Purvis ◽  
Andrew J. Wommack ◽  
Leslie M. Hicks

Abstract Background Plant defensins are a broadly distributed family of antimicrobial peptides which have been primarily studied for agriculturally relevant antifungal activity. Recent studies have probed defensins against Gram-negative bacteria revealing evidence for multiple mechanisms of action including membrane lysis and ribosomal inhibition. Herein, a truncated synthetic analog containing the γ-core motif of Amaranthus tricolor DEF2 (Atr-DEF2) reveals Gram-negative antibacterial activity and its mechanism of action is probed via proteomics, outer membrane permeability studies, and iron reduction/chelation assays. Results Atr-DEF2(G39-C54) demonstrated activity against two Gram-negative human bacterial pathogens, Escherichia coli and Klebsiella pneumoniae. Quantitative proteomics revealed changes in the E. coli proteome in response to treatment of sub-lethal concentrations of the truncated defensin, including bacterial outer membrane (OM) and iron acquisition/processing related proteins. Modification of OM charge is a common response of Gram-negative bacteria to membrane lytic antimicrobial peptides (AMPs) to reduce electrostatic interactions, and this mechanism of action was confirmed for Atr-DEF2(G39-C54) via an N-phenylnaphthalen-1-amine uptake assay. Additionally, in vitro assays confirmed the capacity of Atr-DEF2(G39-C54) to reduce Fe3+ and chelate Fe2+ at cell culture relevant concentrations, thus limiting the availability of essential enzymatic cofactors. Conclusions This study highlights the utility of plant defensin γ-core motif synthetic analogs for characterization of novel defensin activity. Proteomic changes in E. coli after treatment with Atr-DEF2(G39-C54) supported the hypothesis that membrane lysis is an important component of γ-core motif mediated antibacterial activity but also emphasized that other properties, such as metal sequestration, may contribute to a multifaceted mechanism of action.


Molecules ◽  
2021 ◽  
Vol 26 (10) ◽  
pp. 2888
Author(s):  
Carmen M. S. Ambrosio ◽  
Gloria L. Diaz-Arenas ◽  
Leidy P. A. Agudelo ◽  
Elena Stashenko ◽  
Carmen J. Contreras-Castillo ◽  
...  

Essential oils (EOs) from Citrus are the main by-product of Citrus-processing industries. In addition to food/beverage and cosmetic applications, citrus EOs could also potentially be used as an alternative to antibiotics in food-producing animals. A commercial citrus EO—Brazilian Orange Terpenes (BOT)—was fractionated by vacuum fractional distillation to separate BOT into various fractions: F1, F2, F3, and F4. Next, the chemical composition and biological activities of BOT and its fractions were characterized. Results showed the three first fractions had a high relative amount of limonene (≥10.86), even higher than the whole BOT. Conversely, F4 presented a larger relative amount of BOT’s minor compounds (carvone, cis-carveol, trans-carveol, cis-p-Mentha-2,8-dien-1-ol, and trans-p-Mentha-2,8-dien-1-ol) and a very low relative amount of limonene (0.08–0.13). Antibacterial activity results showed F4 was the only fraction exhibiting this activity, which was selective and higher activity on a pathogenic bacterium (E. coli) than on a beneficial bacterium (Lactobacillus sp.). However, F4 activity was lower than BOT. Similarly, F4 displayed the highest antioxidant activity among fractions (equivalent to BOT). These results indicated that probably those minor compounds that detected in F4 would be more involved in conferring the biological activities for this fraction and consequently for the whole BOT, instead of the major compound, limonene, playing this role exclusively.


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