scholarly journals New Water-Soluble Condensed Heterocyclic Compounds with Antimicrobial Activity Based on Annulation Reactions of 8-Quinolinesulfenyl Halides with Natural Products and Alkenes

2021 ◽  
Vol 11 (18) ◽  
pp. 8532
Author(s):  
Vladimir A. Potapov ◽  
Roman S. Ishigeev ◽  
Lyudmila A. Belovezhets ◽  
Irina V. Shkurchenko ◽  
Svetlana V. Amosova
Keyword(s):  
Escherichia Coli ◽  
Antimicrobial Activity ◽  
Natural Products ◽  
Heterocyclic Compounds ◽  
Methyl Eugenol ◽  
Water Soluble ◽  
High Antimicrobial Activity ◽  
Enterococcus Durans ◽  
Terminal Alkenes ◽  
Styrene Derivatives

The annulation reactions of 8-quinolinesulfenyl halides with natural products and alkenes affording new water-soluble [1,4]thiazino[2,3,4-ij]quinolin-4-ium derivatives in high or quantitative yields are developed in this study. The reactions with styrene derivatives and terminal alkenes including allyl arenes proceed in a regioselective manner but with the opposite regiochemistry. The reactions with terminal alkenes including allyl arenes occur in an anti-Markovnikov fashion (regarding addition of the 8-quinolinesulfenyl electrophile to the double bond) to give 2-organyl-2Н,3Н-[1,4]thiazino[2,3,4-ij]quinolin-4-ium halides, while the reactions with styrene derivatives proceed in a Markovnikov fashion, leading to 3-substituted condensed heterocyclic compounds. In general, styrene derivatives demonstrate higher reactivity in the annulation reactions compared to the terminal alkenes. Antimicrobial activity of novel water-soluble compounds against Enterococcus durans, Bacillus subtilis and Escherichia coli are evaluated. The compounds with high antimicrobial activity are found. The annulation products of the reactions of 8-quinolinesulfenyl halides with 1H-indene, eugenol, methyl eugenol and 1-heptene, are superior in their activity compared to the antibiotic gentamicin.

scholarly journals A Novel Family of [1,4]Thiazino[2,3,4-ij]quinolin-4-ium Derivatives: Regioselective Synthesis Based on Unsaturated Heteroatom and Heterocyclic Compounds and Antibacterial Activity

Molecules ◽  
2021 ◽  
Vol 26 (18) ◽  
pp. 5579
Author(s):  
Vladimir A. Potapov ◽  
Roman S. Ishigeev ◽  
Lyudmila A. Belovezhets ◽  
Svetlana V. Amosova
Keyword(s):  
Escherichia Coli ◽  
Antibacterial Activity ◽  
Carbon Atom ◽  
Sulfur Atom ◽  
Heterocyclic Compounds ◽  
Allyl Chloride ◽  
Water Soluble ◽  
Enterococcus Durans ◽  
High Antibacterial Activity ◽  
Vinyl Group

A novel family of [1,4]thiazino[2,3,4-ij]quinolin-4-ium derivatives was synthesized by annulation reactions of 8-quinolinesulfenyl chloride with unsaturated heteroatom and heterocyclic compounds. It was found that the reactions with 4-pentenoic and 5-hexenoic acids, allyl chloride and bromide, allyl cyanate and vinyl heterocyclic compounds (N-vinyl pyrrolidin-2-one and 1-vinylimidazole) proceeded in a regioselective mode but with the opposite regiochemistry. The reactions with vinyl heterocyclic compounds included electrophilic addition of the sulfur atom of 8-quinolinesulfenyl chloride to the β-carbon atom of the vinyl group. In the case of other substrates, the annulation proceeded with the attachment of the sulfur atom to the α-carbon atom of the vinyl group. The antibacterial activity of novel water-soluble compounds against Enterococcus durans, Bacillus subtilis and Escherichia coli was evaluated. Compounds with high antibacterial activity were found.

scholarly journals Antimicrobial activity of enterocin obtained from Enterococcus durans on Shiga-like toxin-producing Escherichia coli

2019 ◽  
Vol 49 (9) ◽  
Author(s):  
Natara Favaro Tosoni ◽  
Hugo Felix Perini ◽  
Márcia Regina Terra ◽  
Marly Sayuri Katsuda ◽  
Márcia Cristina Furlaneto ◽  
...  
Keyword(s):  
Escherichia Coli ◽  
Antimicrobial Activity ◽  
Foodborne Pathogens ◽  
Food Contamination ◽  
Alternative Methods ◽  
Cell Integrity ◽  
Enterococcus Durans ◽  
Time Points ◽  
Food Processes ◽  
Potential Use

ABSTRACT: Shiga-like toxin-producing Escherichia coli (STEC) is an important source of food contamination that presents risks to human health. Several industrial food processes eliminate this microorganism; however, these processes can alter the characteristics of the product. Alternative methods of preservation have been identified as an option to control these foodborne pathogens. The purpose of this study was to evaluate the action of bacteriocins produced by Enterococcus durans MF5 in STEC cells. Cell-free supernatant (CFS) containing enterocins from the MF5 isolate was tested over different time points (6, 18, and 24 h). Enterocins present in the crude CFS showed inhibition against STEC at all time points. In the investigation of cell integrity, using propidium iodide and fluorescence microscopy, considerable cell death was observed within 6 h of the cells being in contact with the enterocins, which was also observed at the 18 and 24 h time points. These results showed that the enterocins produced by the MF5 isolate have potential use in the control of STEC.

Synthesis and antimicrobial evaluation of some heterocyclic compounds from 3-aryl-1-phenyl-1H-pyrazole-4-carbaldehydes

2018 ◽  
Vol 73 (6) ◽  
pp. 389-397 ◽  
Author(s):  
El Sayed Ramadan ◽  
Essam M. Sharshira ◽  
Ramadan I. El Sokkary ◽  
Noussa Morsy
Keyword(s):  
Escherichia Coli ◽  
Antimicrobial Activity ◽  
Heterocyclic Compounds ◽  
Knoevenagel Condensation ◽  
Green Solvent ◽  
Condensation Products ◽  
Diffusion Technique ◽  
Lactam Antibiotic ◽  
Antimicrobial Evaluation

AbstractA new series of chalcones, pyrazolinyl-pyrazoles, pyrazole-4-carbaldehyde oximes, pyrazole-4-carbonitriles, 5-pyrazolyl-1,2,4-triazolidine-3-thiones, and Knoevenagel condensation products was synthesized from 3-aryl-1-phenyl-1H-pyrazole-4-carbaldehydes. Most reactions were carried out either without solvent or in the presence of water as a green solvent. The structure of synthesized compounds was characterized by spectral and elemental analysis. The synthesized compounds were tested in vitro for their antimicrobial activity against Escherichia coli, Staphylococcus aureus, and Candida albicans in comparison with imipenem (intravenous β-lactam antibiotic) and clotrimazole (antifungal medication) as reference drugs by using the agar diffusion technique. 3-Aryl-1-phenyl-1H-pyrazole-4-carbonitriles 8b, 8c, and 8d showed significant antifungal activity against the fungus C. albicans.

scholarly journals The Antimicrobial Peptide Polyphemusin Localizes to the Cytoplasm of Escherichia coli following Treatment

2006 ◽  
Vol 50 (4) ◽  
pp. 1522-1524 ◽  
Author(s):  
Jon-Paul S. Powers ◽  
Morgan M. Martin ◽  
Danika L. Goosney ◽  
Robert E. W. Hancock
Keyword(s):  
Escherichia Coli ◽  
Antimicrobial Activity ◽  
Fluorescence Microscopy ◽  
Antimicrobial Peptide ◽  
Mechanism Of Action ◽  
Horseshoe Crab ◽  
Membrane Damage ◽  
Wild Type ◽  
High Antimicrobial Activity ◽  
Confocal Fluorescence

ABSTRACT The horseshoe crab peptide polyphemusin I possesses high antimicrobial activity, but its mechanism of action is as yet not well defined. Using a biotin-labeled polyphemusin I analogue and confocal fluorescence microscopy, we showed that the peptide accumulates in the cytoplasm of wild-type Escherichia coli within 30 min after addition without causing substantial membrane damage.

Surfactant-free synthesis of a water-soluble PEGylated nanographeneoxide/metal-oxide nanocomposite as engineered antimicrobial weaponry

2016 ◽  
Vol 4 (41) ◽  
pp. 6706-6715 ◽  
Author(s):  
Rahul Kumar Mishra ◽  
Yakov Shalom ◽  
Vijay Bhooshan Kumar ◽  
John H. T. Luong ◽  
Aharon Gedanken ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Metal Oxide ◽  
Water Soluble ◽  
High Antimicrobial Activity ◽  
Water Salt ◽  
Protein Rich

ZnCuO NPs deposited on NGO-PEG are non-toxic, exhibit high antimicrobial activity and show excellent dispersal in water, salt-rich and protein-rich solutions.

scholarly journals Antimicrobial Activity Jangjingki (Oxalis corniculata L.) Against The Growth Of Staphylococcus Aureus, Escherichia Coli, and Candida Albicans

2021 ◽  
Vol 4 (1) ◽  
pp. 1-11
Author(s):  
Misrahanum Misrahanum ◽  
Syarifah Dhea Almunawwarah ◽  
Hira Helwati ◽  
Hilda Maysarah ◽  
Sadli Sadli
Keyword(s):  
Escherichia Coli ◽  
Staphylococcus Aureus ◽  
Antimicrobial Activity ◽  
Methanol Extract ◽  
Water Soluble ◽  
Test Results ◽  
Soluble Extract ◽  
E Coli ◽  
Activity Test ◽  
Water Soluble Extract

Jangjingki (Oxalis corniculata L.) is a plant from Oxalidaceae that has potential as a natural antimicrobial agent. The purpose of this research is to see the antimicrobial activity of methanol extract of jangjingki against the growth of Staphylococcus aureus ATCC 25923, Escherichia coli ATCC 25922, and Candida albicans ATCC 10231. The thick extract of jangjingki was obtained by the maceration method with methanol solvent. At the same time, the antimicrobial activity test on S. aureus and E. Coli bacteria was carried out using the hole diffusion method. The simplicia characterization showed 7.17% water, 9.68% of total ash, 11.67% water-soluble extract, and 9.17% of the ethanol-soluble section. At the same time, the methanol extract of jangjingki characterization showed 22.5% of water, 10.16% of total ash, 55.83% water-soluble extract, and 62.91% of the ethanol-soluble section. Phytochemical test results showed that the methanol extract of jangjingki contains alkaloids, saponins, flavonoids, tannins, and steroids. The results of the antimicrobial activity test with variations in the concentration of jangjingki methanol extract 15, 20, 30, and 40% on S. aureus and E. Coli bacteria showed growth inhibition activity of these two bacteria, the largest diameter of the inhibition zone was formed when the extract was given a concentration of 40% with a diameter of the area. Resistance of 8,07 mm and 11 mm, respectively. Meanwhile, the test results of inhibition of growth of the fungus C. Albicans by presenting variations in the concentration of jangjingki methanol extract of 5, 10, 15, and 20% could not inhibit the growth fungus C. Albicans.

scholarly journals Enhancement of antimicrobial activity of antibiotics and antifungals by the use of natural products from Pityrogramma calomelanos (L.) link

2012 ◽  
Vol 64 (1) ◽  
pp. 43-48 ◽  
Author(s):  
Teógenes Souza ◽  
Maria Morais-Braga ◽  
José Costa ◽  
Antônio Saraiva ◽  
Henrique Coutinho
Keyword(s):  
Escherichia Coli ◽  
Antimicrobial Activity ◽  
Natural Products ◽  
Ethanol Extract ◽  
Good Activity ◽  
Mechanisms Of Resistance ◽  
Methanol Fraction ◽  
Microdilution Method ◽  
Bacteria And Fungi ◽  
Pityrogramma Calomelanos

The ethanol extract and methanol fraction of Pityrogramma calomelanos (L.) link were evaluated for antibacterial, antifungal and modulatory activities against strains of Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Candida albicans, C. krusei and C. tropicalis. The antimicrobial activity of the natural products was evaluated by the microdilution method associated or not with aminoglycosides and antifungals. The ethanol extract and methanol fraction of P. calomelanos showed good activity against S. aureus when associated with aminoglycosides and with benzoilmetronidazol against species of the genus Candida. These results indicate that P. calomelanos should be studied as a possible source of natural products to combat bacteria and fungi either directly or by modulating the mechanisms of resistance of these microorganisms, enhancing the antimicrobial activity of these drugs and combating microbial resistance.

Two Epimeric Flavalignans from Trichilia catigua (Meliaceae) with Antimicrobial Activity

2002 ◽  
Vol 57 (5-6) ◽  
pp. 483-488 ◽  
Author(s):  
Moacir G. Pizzolatti ◽  
Andreia F. Venson ◽  
Artur Smânia Júnior ◽  
Elza de F. A. Smânia ◽  
Raimundo Braz-Filho
Keyword(s):  
Escherichia Coli ◽  
Staphylococcus Aureus ◽  
Pseudomonas Aeruginosa ◽  
Antimicrobial Activity ◽  
Antibacterial Activity ◽  
Natural Products ◽  
Bacillus Cereus ◽  
Spectroscopic Data ◽  
2D Nmr ◽  
And Staphylococcus Aureus

A mixture of flavalignan cinchonains Ia and Ib was isolated from the bark of Trichilia catigua. The structures were established on the basis of spectroscopic data of the natural products and their methylated derivatives including 2D NMR experiments, and compared with data in the literature. These flavalignans exhibited antibacterial activity against Bacillus cereus, Escherichia coli, Pseudomonas aeruginosa and Staphylococcus aureus.

scholarly journals Antimicrobial Activity of Fomitopsis Officinalis (Vill.) Bondartsev & Singer in Pure Culture

2021 ◽  
Vol 5 (4) ◽  
pp. 220-227
Author(s):  
Oksana Mykchaylova ◽  
Nataliia Poyedіnok
Keyword(s):  
Escherichia Coli ◽  
Staphylococcus Aureus ◽  
Antimicrobial Activity ◽  
Bacillus Subtilis ◽  
Klebsiella Pneumoniae ◽  
Culture Fluid ◽  
High Antimicrobial Activity ◽  
Gram Negative ◽  
The World ◽  
Mycelial Mass

Background. According to the World Health Organization antibiotic resistance is among the top ten threats to human health, food safety and development. Today antibiotic resistance has reached alarmingly high levels all over the world. Meanwhile, the increase in the synthetic drugs' production has led to the pathogenic mycobiota's rapid adaptation to the created chemicals, which have a narrow focus of application. That is why in modern biotechnology and pharmacology much attention is paid to natural producers of biologically active compounds, in particular – to xylotrophic fungi. It has been experimentally proven that the xylotrophic macromycete Fomitopsis officinalis or tinder fungus can be considered to be a promising producer of pharmacological substances with a broad spectrum of action. Studies of active metabolites, contained in the mycelial mass, culture fluid of the medicinal xylotrophic macromycete F. officinalis, and determination of their biological action remain relevant. Objective. The objective was to determine the antimicrobial activity of culture fluid and mycelial mass of F. officinalis different strains from the mushrooms collection (IBK Mushroom Culture Collection of the M.G. Kholodny Institute of Botany, NAS of Ukraine) against gram-negative and gram-positive bacteria species. Methods. An in vitro study of the antimicrobial activity of ethyl acetate extracts of culture fluid and aqueous-ethyl extracts of mycelial mass for F. officinalis strains IBK-5004, IBK-2497, IBK-2498 against gram-positive Staphylococcus aureus (B-918), Bacillus subtilis (В-901) and gram-negative Escherichia coli (B-906), Bacillus subtilis (B-900), Klebsiella pneumoniae (M-123) bacteria by disc-diffusion method was conducted. Results. High antimicrobial activity of tinder fungus culture fluid and mycelial mass extracts against Staphylococcus aureus was established after the 21st day of cultivation, while on the 28th day the zone of growth retardation was maximal (15–25 mm). The highest indices were recorded in F. officinalis IBK-5004 (20–25 mm) and IBK-2498 (20–24 mm) strains. Antimicrobial activity against Klebsiella pneumoniae in culture fluid extracts was manifested on the 21st and 28th days of cultivation. The highest antimicrobial activity against Klebsiella pneumoniae was observed in the culture fluid of the strain F. officinalis IBK-5004, the diameter of the growth retardation zone was 18 mm on the 28th day of cultivation. Mycelial mass's extracts showed moderate activity on the 14th day of cultivation (7-8 mm); maximal activity was recorded on the 28th day (12–22 mm). The most active strain was Fomitopsis officinalis IBK-2498. No antimicrobial activity against test organisms was detected in the following studied strains: Escherichia coli, Pseudomonas aeruginosa, Bacillus subtilis. Conclusions. It has been established that the mycelial mass and culture fluid extracts of F. officinalis IBK-5004, IBK-2497, IBK-2498 strains have high antimicrobial activity against Staphylococcus aureus and moderate antimicrobial activity against Klebsiella pneumoniae on the 21st and 28th day of cultivation.

scholarly journals Antimicrobial activity of different substituted meso-porphyrin derivatives

2020 ◽  
Vol 28 (2) ◽  
pp. 205-216 ◽  
Author(s):  
Luminița Sălăgeanu ◽  
Delia Muntean ◽  
Horhat Florin George ◽  
Anca Lascu ◽  
Diana Anghel ◽  
...  
Keyword(s):  
Escherichia Coli ◽  
Staphylococcus Aureus ◽  
Antimicrobial Activity ◽  
Streptococcus Pyogenes ◽  
Antimicrobial Agents ◽  
Water Soluble ◽  
Diffusion Method ◽  
Dilution Method ◽  
Moderate Activity ◽  
Porphyrin Derivatives

AbstractThe increasing resistance against classical antibiotic treatment forces the researchers to develop novel non-toxic antimicrobial agents. The aim of this study was to determine the antimicrobial properties of seven different porphyrins having distinctive hydrophobicity/hydrophilicity: P1 meso-tetra(4-methoxy-phenyl)porphyrin, P2 Zn(II)-meso-5,10,15,20-tetrapyridylporphyrin, P3 meso-tetra(p-tolyl)porphyrin, P4 5,10,15,20-tetraphenylporphyrin; P5 (5,10,15,20-tetraphenylporphinato) dichlorophosphorus(V) chloride, P6 5,10,15,20-tetrakis-(N-methyl-4-pyridyl) porphyrin-Zn(II) tetrachloride, P7 Zn(II)-5,10,15,20-meso-tetrakis-(4-aminophenyl)porphyrin. The meso-porphyrin derivatives were screened for their antimicrobial activity against six reference strains: Streptococcus pyogenes ATCC 19615, Staphylococcus aureus ATCC 25923, Escherichia coli ATCC 25922, Klebsiella pneumoniae ATCC 700603, Pseudomonas aeruginosa ATCC27853 and Candida albicans ATCC 10231. The antimicrobial activity of these samples was evaluated by the agar disk diffusion method and dilution method, with the determination of the minimum inhibitory concentration (MIC), the minimum bactericidal concentration (MBC) and the minimum fungicidal concentration (MFC). The most significant result is provided by the water-soluble P5 manifesting an obvious antimicrobial activity against Streptococcus pyogenes. On the other hand, P6 is a moderately active derivative against Streptococcus pyogenes and Escherichia coli and P7 presents moderate activity against Streptococcus pyogenes and Staphylococcus aureus. All the tested porphyrin bases, presenting hydrophobic character, have no antimicrobial activity under the investigated conditions. The common characteristics of the porphyrins that act as promising antimicrobial agents in the non-irradiated methods are: the cationic nature, the increased hydrophilicity and the presence of both amino functional groups grafted on the porphyrin ring and the coordination with Zn or phosphorus in the inner core.

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