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1.
Pharm Biol ; 62(1): 713-766, 2024 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-39392281

RESUMEN

CONTEXT: The emergence of pan-resistant bacteria requires the development of new antibiotics and antibiotic potentiators. OBJECTIVE: This review identifies antibacterial phenolic compounds that have been identified in Asian and Pacific Angiosperms from 1945 to 2023 and analyzes their strengths and spectra of activity, distributions, molecular masses, solubilities, modes of action, structures-activities, as well as their synergistic effects with antibiotics, toxicities, and clinical potential. METHODS: All data in this review was compiled from Google Scholar, PubMed, Science Direct, Web of Science, and library search; other sources were excluded. We used the following combination of keywords: 'Phenolic compound', 'Plants', and 'Antibacterial'. This produced 736 results. Each result was examined and articles that did not contain information relevant to the topic or coming from non-peer-reviewed journals were excluded. Each of the remaining 467 selected articles was read critically for the information that it contained. RESULTS: Out of ∼350 antibacterial phenolic compounds identified, 44 were very strongly active, mainly targeting the cytoplasmic membrane of Gram-positive bacteria, and with a molecular mass between 200 and 400 g/mol. 2-Methoxy-7-methyljuglone, [6]-gingerol, anacardic acid, baicalin, vitexin, and malabaricone A and B have the potential to be developed as antibacterial leads. CONCLUSIONS: Angiosperms from Asia and the Pacific provide a rich source of natural products with the potential to be developed as leads for treating bacterial infections.


Asunto(s)
Antibacterianos , Fenoles , Antibacterianos/farmacología , Antibacterianos/aislamiento & purificación , Fenoles/farmacología , Fenoles/aislamiento & purificación , Asia , Humanos , Extractos Vegetales/farmacología , Extractos Vegetales/aislamiento & purificación , Bacterias Grampositivas/efectos de los fármacos , Animales , Magnoliopsida/química , Relación Estructura-Actividad
2.
Sci Rep ; 14(1): 23200, 2024 10 05.
Artículo en Inglés | MEDLINE | ID: mdl-39368983

RESUMEN

Turbinaria ornata, Polycladia myrica, and Padina pavonica is a perennial Mediterranean-native seaweed that is commonly used for mass display. The principal aims of this reconnaissance were the isolation of various compounds from methanolic seaweeds extraction and screening the potential effect as antibacterial, and antioxidant. The micro-dilution method was used to measure antibacterial activity. Gas chromatography-mass spectrophotometry (GC. Mass) abused to analyze the chemical components of the methanolic seaweed extract. The existence of 19 secondary metabolites was discovered using GC-MS analysis: 8 different compounds for each seaweed's species. Among these bioactive compounds, 4 compounds from P. pavonica extract showed the binding affinity and ability to react with Beta-ketoacyl synthase (PDB ID 1EK4) of Escherichia coli. The phytocompounds' drug-like and poisonous characteristics were predicted. Auto Dock was used to examine the ligand receptor complexes' binding strength. T. ornate and P. pavonica had the highest activity against K. pneumonia, with 22.50 mm (0.78 µg/ml) and 22.23 mm (5.10 µg/ml) obtained, respectively. In a concentration-dependent manner, the extract components demonstrated substantial antioxidant activity. P. pavonica had the highest scavenging activity (78.00%, IC50 = 6.35 µg/ml), while ascorbic acid had a 96.45% scavenging impact. Because the chemicals bind to the Lipinski Ro5, they have drug-like characteristics. The compounds had no hepatotoxic effects. P. pavonica extract has the prospect of being used as a source of medicinal drug-like chemicals. The docking investigation found a strong correlation between the experimental results and the docking results. Finally, brown seaweed extract, particularly P. pavonica extract, demonstrated strong antibacterial, antioxidant, and free radical scavenging properties.


Asunto(s)
Antibacterianos , Antioxidantes , Fitoquímicos , Algas Marinas , Algas Marinas/química , Antioxidantes/farmacología , Antioxidantes/química , Antioxidantes/aislamiento & purificación , Fitoquímicos/farmacología , Fitoquímicos/química , Fitoquímicos/aislamiento & purificación , Antibacterianos/farmacología , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Extractos Vegetales/farmacología , Extractos Vegetales/química , Simulación de Dinámica Molecular , Pruebas de Sensibilidad Microbiana , Simulación del Acoplamiento Molecular , Escherichia coli/efectos de los fármacos , Cromatografía de Gases y Espectrometría de Masas
3.
Molecules ; 29(18)2024 Sep 19.
Artículo en Inglés | MEDLINE | ID: mdl-39339441

RESUMEN

Four new alkaloids, vibripyrrolidine A (1), vibripiperazine A (2), and vibridiazinane A, B (3, 4), comprising one pyrrolidine, one piperazine, and two diazinane alkaloids, along with two known analogs (5, 6), were isolated from the marine bacterium Vibrio ruber ZXR-93 cultured in ISP2 medium. Their chemical structures were elucidated by analysis of their 1D and 2D NMR, mass spectra, and electronic circular dichroism (ECD) calculations. Compounds 1 and 3-6 showed vigorous antibacterial activity against Staphylococcus aureus, with MIC values ranging from 0.96 to 7.81 µg/mL. Moreover, compound 1 exhibited robust anti-inflammatory activity in vitro using the LPS-induced RAW264.7 macrophage model. All compounds also showed moderate antineoplastic activity against cervical cancer cells (HeLa) and gastric cancer cells (SGC-7901).


Asunto(s)
Alcaloides , Antibacterianos , Pruebas de Sensibilidad Microbiana , Pirrolidinas , Staphylococcus aureus , Vibrio , Humanos , Alcaloides/farmacología , Alcaloides/química , Alcaloides/aislamiento & purificación , Ratones , Animales , Antibacterianos/farmacología , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Pirrolidinas/química , Pirrolidinas/farmacología , Células RAW 264.7 , Staphylococcus aureus/efectos de los fármacos , Vibrio/efectos de los fármacos , Antineoplásicos/farmacología , Antineoplásicos/química , Estructura Molecular , Piperazina/química , Piperazina/farmacología , Línea Celular Tumoral , Piperazinas/farmacología , Piperazinas/química , Piperazinas/aislamiento & purificación , Células HeLa
4.
Mar Drugs ; 22(9)2024 Aug 24.
Artículo en Inglés | MEDLINE | ID: mdl-39330261

RESUMEN

Antimicrobial resistance is a critical global health issue, with rising resistance among bacteria and fungi. Marine organisms have emerged as promising, but underexplored, sources of new antimicrobial agents. Among them, marine polychaetes, such as Halla parthenopeia, which possess chemical defenses, could attract significant research interest. This study explores the antimicrobial properties of hallachrome, a unique anthraquinone found in the purple mucus of H. parthenopeia, against Gram-negative bacteria (Escherichia coli ATCC 25922, Pseudomonas aeruginosa ATCC 9027), Gram-positive bacteria (Enterococcus faecalis ATCC 29212, Staphylococcus aureus ATCC 6538, Staphylococcus epidermidis ATCC 12228), and the most common human fungal pathogen Candida albicans ATCC 10231. Antibacterial susceptibility testing revealed that Gram-negative bacteria were not inhibited by hallachrome at concentrations ≤2 mM. However, Gram-positive bacteria showed significant growth inhibition at 0.12-0.25 mM, while C. albicans was inhibited at 0.06 mM. Time-kill studies demonstrated dose-dependent growth inhibition of susceptible strains by hallachrome, which exerted its effect by altering the membrane permeability of C. albicans, E. faecalis, and S. epidermidis after 6 h and S. aureus after 24 h. Additionally, hallachrome significantly reduced biofilm formation and mature biofilm in S. aureus, E. faecalis, and C. albicans. Additionally, it inhibited hyphal growth in C. albicans. These findings highlight hallachrome's potential as a novel antimicrobial agent, deserving further exploration for clinical experimentation.


Asunto(s)
Antraquinonas , Candida albicans , Pruebas de Sensibilidad Microbiana , Poliquetos , Candida albicans/efectos de los fármacos , Animales , Antraquinonas/farmacología , Antraquinonas/química , Antraquinonas/aislamiento & purificación , Bacterias Grampositivas/efectos de los fármacos , Antiinfecciosos/farmacología , Antiinfecciosos/química , Antibacterianos/farmacología , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Bacterias Gramnegativas/efectos de los fármacos , Organismos Acuáticos , Biopelículas/efectos de los fármacos
5.
Mar Drugs ; 22(9)2024 Aug 30.
Artículo en Inglés | MEDLINE | ID: mdl-39330273

RESUMEN

A chemical investigation of the extracts from the soft coral Litophyton brassicum led to the isolation and identification of four new meroterpenes, brassihydroxybenzoquinone A and B (1 and 2) and brassinaphthoquinone A and B (3 and 4), along with two known related meroterpenes (5 and 6). Their structures were elucidated using high-resolution electrospray ionization mass spectrometry (HRESIMS), nuclear magnetic resonance (NMR) spectroscopy, and a comparison with the literature data. All compounds were evaluated for antibacterial activity against six pathogenic bacterial strains and for cytotoxic activity against three cancer cell lines. In the cytotoxic assay, all compounds were inactive at 10 µM against the A549, HeLa, and MDA-MB-231 cell lines. In the antibacterial assay, compounds 1 and 2 exhibited moderate inhibitory activity with minimum inhibitory concentrations (MIC) ranging from 8 to 64 µg/mL.


Asunto(s)
Antozoos , Antibacterianos , Pruebas de Sensibilidad Microbiana , Terpenos , Antozoos/química , Animales , Humanos , Línea Celular Tumoral , Terpenos/farmacología , Terpenos/química , Terpenos/aislamiento & purificación , Antibacterianos/farmacología , Antibacterianos/química , Antibacterianos/aislamiento & purificación , China , Antineoplásicos/farmacología , Antineoplásicos/química , Antineoplásicos/aislamiento & purificación , Espectroscopía de Resonancia Magnética , Células HeLa , Espectrometría de Masa por Ionización de Electrospray , Estructura Molecular
6.
Mar Drugs ; 22(9)2024 Aug 30.
Artículo en Inglés | MEDLINE | ID: mdl-39330277

RESUMEN

Stonikacidin A (1), the first representative of a new class of 4-bromopyrrole alkaloids containing an aldonic acid core, was isolated from the marine sponge Lissodendoryx papillosa. The compound is named in honor of Prof. Valentin A. Stonik, who is one of the outstanding investigators in the field of marine natural chemistry. The structure of 1 was determined using NMR, MS analysis, and chemical correlations. The L-idonic acid core was established by the comparison of GC, NMR, MS, and optical rotation data of methyl-pentaacetyl-aldonates obtained from the hydrolysis products of 1 and standard hexoses. The L-form of the idonic acid residue in 1 was confirmed by GC analysis of pentaacetate of (S)-2-butyl ester of the hydrolysis product from 1 and compared with corresponding derivatives of L- and D-idonic acids. The biosynthetic pathway for stonikacidin A (1) was proposed. The alkaloid 1 inhibited the growth of Staphylococcus aureus and Escherichia coli test strains, as well as affected the formation of S. aureus and E. coli biofilms. Compound 1 inhibited the activity of sortase A. Molecular docking data showed that stonikacidin A (1) can bind with sortase A due to the interactions between its bromine atoms and some amino acid residues of the enzyme.


Asunto(s)
Alcaloides , Escherichia coli , Poríferos , Staphylococcus aureus , Animales , Poríferos/química , Staphylococcus aureus/efectos de los fármacos , Alcaloides/farmacología , Alcaloides/química , Alcaloides/aislamiento & purificación , Escherichia coli/efectos de los fármacos , Simulación del Acoplamiento Molecular , Antibacterianos/farmacología , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Pirroles/farmacología , Pirroles/química , Pirroles/aislamiento & purificación , Biopelículas/efectos de los fármacos , Pruebas de Sensibilidad Microbiana , Proteínas Bacterianas , Océano Pacífico , Cisteína Endopeptidasas , Aminoaciltransferasas
7.
Mar Drugs ; 22(9)2024 Sep 05.
Artículo en Inglés | MEDLINE | ID: mdl-39330288

RESUMEN

Twelve compounds, including four undescribed cytochalasins, xylariachalasins A-D (1-4), four undescribed polyketides (5-8), and four known cytochalasins (9-12), were isolated from the mangrove endophytic fungus Xylaria arbuscula QYF. Their structures and absolute configurations were established by extensive spectroscopic analyses (1D and 2D NMR, HRESIMS), electronic circular dichroism (ECD) calculations, 13C NMR calculation and DP4+ analysis, single-crystal X-ray diffraction, and the modified Mosher ester method. Compounds 1 and 2 are rare cytochalasin hydroperoxides. In bioactivity assays, Compound 2 exhibited moderate antimicrobial activities against Staphylococcus aureus and Candida albicans with MIC values of 12.5 µM for both Compound 10 exhibited significant cytotoxic activity against MDA-MB-435 with an IC50 value of 3.61 ± 1.60 µM.


Asunto(s)
Candida albicans , Citocalasinas , Pruebas de Sensibilidad Microbiana , Policétidos , Staphylococcus aureus , Xylariales , Policétidos/farmacología , Policétidos/química , Policétidos/aislamiento & purificación , Citocalasinas/farmacología , Citocalasinas/química , Citocalasinas/aislamiento & purificación , Xylariales/química , Staphylococcus aureus/efectos de los fármacos , Candida albicans/efectos de los fármacos , Línea Celular Tumoral , Humanos , Antineoplásicos/farmacología , Antineoplásicos/química , Antineoplásicos/aislamiento & purificación , Antibacterianos/farmacología , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Estructura Molecular , Endófitos/química , Cristalografía por Rayos X
8.
PeerJ ; 12: e18053, 2024.
Artículo en Inglés | MEDLINE | ID: mdl-39346038

RESUMEN

Antibiotic resistance in shrimp farms has emerged as an extremely serious situation worldwide. The main aim of this study was to optimize the cultural conditions for producing new antibiotic agents from marine Streptomyces species. Streptomyces SK3 was isolated from marine sediment and was identified by its 16S rDNA as well as biochemical characteristics. This microbe produced the highest concentration of bioactive secondary metabolites (BSMs) when cultured in YM medium (YM/2). It produced the maximum total protein (41.8 ± 6.36 mg/ml) during the late lag phase period. The optimum incubation temperature was recorded at 30 °C; BSMs were not produced at ≤10 °C within an incubation period of 3-4 days. The suitable agitation speed was found to be 200 rpm with pH 7.00. The proper carbon, nitrogen, and trace elements supplementation consisted of starch, malt extract, calcium carbonate (CaCO3), and magnesium sulfate (MgSO4). The ethyl acetate extract was found to act strongly against three vibriosis pathogens, Vibrio harveyi, Vibrio parahaemolyticus, and Vibrio vunificus, as indicated by the inhibition zones at 34.5, 35.4, and 34.3 mm, respectively. The extract showed the strongest anti-V. harveyi activity, as indicated by minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) values of 0.101 ± 0.02 and 0.610 ± 0.04 mg/ml, respectively. Basic chemical investigation of the crude extract using thin layer chromatography (TLC), bioautography, liquid chromatography tandem mass spectrometry (LC‒MS/MS), Fourier transform infrared spectroscopy (FTIR), and proton nuclear magnetic resonance (1H-NMR) revealed that the active components were the terpenoid and steroid groups of compounds. They showed carboxylic acid and ester functions in their molecules.


Asunto(s)
Antibacterianos , Penaeidae , Streptomyces , Vibrio , Streptomyces/metabolismo , Streptomyces/aislamiento & purificación , Streptomyces/genética , Animales , Penaeidae/microbiología , Antibacterianos/farmacología , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Vibrio/efectos de los fármacos , Medios de Cultivo/química , Sedimentos Geológicos/microbiología , Pruebas de Sensibilidad Microbiana , Acuicultura/métodos
9.
Lett Appl Microbiol ; 77(9)2024 Sep 02.
Artículo en Inglés | MEDLINE | ID: mdl-39264087

RESUMEN

This study reports the isolation and characterization of a Streptomyces sp. from soil, capable of producing bioactive secondary metabolites active against a variety of bacterial human pathogens. We targeted the antimicrobial activity against Escherichia coli ATCC-BAA 2469, a clinically relevant strain of bacteria harbouring resistance genes for carbapenems, extended spectrum beta-lactams, tetracyclines, fluoroquinones, etc. Preliminary screening using the spot inoculation technique identified Streptomyces sp. NP73 as the potent strain among the 74 isolated Actinomycetia strain. 16S rRNA gene and whole genome sequencing (WGS) confirmed its taxonomical identity and helped in the construction of the phylogenetic tree. WGS revealed the predicted pathways and biosynthetic gene clusters responsible for producing various types of antibiotics including the isolated compound. Bioactivity guided fractionation and chemical characterization of the active fraction, carried out using liquid chromatography, gas chromatography-mass spectrometry, infra-red spectroscopy, and nuclear magnetic resonance spectroscopy, led to the tentative identification of the active compound as Pyrrolo[1,2-a] pyrazine-1,4-dione, hexahydro-, a diketopiperazine molecule. This compound exhibited excellent antimicrobial and anti-biofilm properties against E. coli ATCC-BAA 2469 with an MIC value of 15.64 µg ml-1, and the low cytotoxicity of the compound identified in this study provides hope for future drug development.


Asunto(s)
Antibacterianos , Farmacorresistencia Bacteriana Múltiple , Escherichia coli , Pruebas de Sensibilidad Microbiana , Filogenia , ARN Ribosómico 16S , Microbiología del Suelo , Streptomyces , Streptomyces/química , Streptomyces/aislamiento & purificación , Streptomyces/genética , Streptomyces/clasificación , Streptomyces/metabolismo , Escherichia coli/efectos de los fármacos , Escherichia coli/genética , India , Antibacterianos/farmacología , Antibacterianos/química , Antibacterianos/aislamiento & purificación , ARN Ribosómico 16S/genética , Bosques , Biopelículas/efectos de los fármacos , Secuenciación Completa del Genoma , Humanos , Familia de Multigenes
10.
Sci Rep ; 14(1): 21573, 2024 09 16.
Artículo en Inglés | MEDLINE | ID: mdl-39284874

RESUMEN

Herbal medicines are important for ensuring sustainable development goals (SDGs) in healthcare, particularly in developing countries with high rates of antimicrobial resistance (AMR) and little access to medical facilities. Thymus vulgaris is a widely used herbal medicinal plant known for its secondary metabolites and antimicrobial properties. The present study involved a comprehensive examination of the isolation, characterization, and antibacterial activity of Thymus vulgaris obtained from Ethiopia. The aerial part of the plant Thymus vulgaris was successively extracted with hexane, chloroform, and methanol based on differences in polarity. Phytochemical screening tests conducted against hexane, chloroform and MeOH crude extracts indicated the presence of some secondary metabolites. Based on the thin-layer chromatography tests, the chloroform extract was subjected to column chromatography, yielding Tv-2 compounds, namely 5-isopropyl-2-methylphenol. The structures of the compounds were elucidated via spectroscopic methods (UV-Vis, FT-IR and NMR). We investigated the antibacterial properties of hexane crude extract, chloroform crude extract, MeOH crude extract, and isolated fractions derived from T. vulgaris against various bacterial strains. This study contributes to a better understanding of the bioactive components present in Thymus vulgaris crude extracts and their potential role in tackling microbial infections.


Asunto(s)
Antibacterianos , Pruebas de Sensibilidad Microbiana , Extractos Vegetales , Thymus (Planta) , Thymus (Planta)/química , Extractos Vegetales/farmacología , Extractos Vegetales/química , Antibacterianos/farmacología , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Etiopía , Bacterias/efectos de los fármacos , Fitoquímicos/farmacología , Fitoquímicos/química , Fitoquímicos/aislamiento & purificación
11.
Pak J Pharm Sci ; 37(3): 651-662, 2024 May.
Artículo en Inglés | MEDLINE | ID: mdl-39340856

RESUMEN

Sesbania grandiflora also known as Agasthya has potent antibiofilm activity and its bioactive compounds obtained from the leaves are medicarpin, isoniazid and 4-methyl oxazole. Extra cellular polymeric substances (EPS) created by the bacterium involve the formation of biofilm and this causes the infections such as nosocomial infections, and urinary tract infections. Pseudomonas aeruginosa has been linked with high levels of intracellular Cyclic-di-Guanosine Monophosphate (c-di-GMP; PA4781) in biofilm formation. In this study, Human BLAST analysis of c-di-GMP Phosphodiesterase has been carried out and it shows an insignificant result and it is believed to be a possible drug target for UTI infection caused by P. aeruginosa. Its protein structure was retrieved from PDB database which was subjected to molecular docking against S. grandiflora bioactive compounds and control drug ciprofloxacin. Compounds taken for the study were screened for ADMET properties and drug-likeliness properties. Molecular interaction analysis of c-di-GMP with medicarpin compound shows -6.75 Kcal/mol binding energy with two hydrogen bonds when compared to the control drug with -6.86 kcal/mol binding energy and two hydrogen bonds respectively. Hence, our findings in the current study suggest that medicarpin could be an inhibitor of c-di-GMP and possess anti-biofilm activity, which could be validated experimentally.


Asunto(s)
Simulación del Acoplamiento Molecular , Pseudomonas aeruginosa , Sesbania , Pseudomonas aeruginosa/efectos de los fármacos , Pseudomonas aeruginosa/enzimología , Sesbania/química , Antibacterianos/farmacología , Antibacterianos/aislamiento & purificación , Extractos Vegetales/farmacología , Extractos Vegetales/química , Biopelículas/efectos de los fármacos , 3',5'-GMP Cíclico Fosfodiesterasas/antagonistas & inhibidores , 3',5'-GMP Cíclico Fosfodiesterasas/metabolismo , Inhibidores de Fosfodiesterasa/farmacología , Inhibidores de Fosfodiesterasa/aislamiento & purificación , Inhibidores de Fosfodiesterasa/química , Humanos
12.
Arch Microbiol ; 206(10): 396, 2024 Sep 09.
Artículo en Inglés | MEDLINE | ID: mdl-39249533

RESUMEN

Bacteria threaten human and animal health, and standard antibiotics no longer effective. Antibiotic-resistant microorganisms can make infection treatment challenging and perhaps fail. Investigating the attributes of cyclotide, a peptide with promising antibacterial properties that holds great potential in the field of antibiotic research. The structure of these cyclic peptides involves six conserved cysteine residues that form three disulfide bonds, resulting in a cyclic cystine knot (CCK). This feature guarantees their durability when exposed to changes in temperature, chemicals, and enzymatic degradation. The two cyclotides, cycloviolacin O17 and mra30, were obtained from Viola dalatensis Gadnep through a series of techniques including the use of a 50% acetonitrile/49% miliQ water/1% formic acid solution for extraction, ammonium salt precipitation, RP-HPLC purification and sequence identification by LC-MS/MS. These cyclotides exhibit antibacterial effects on specific strains of bacteria like Staphylococcus aureus, Bacillus subtilis, and Pseudomonas aeruginosa at a concentration of 0.2 mg/mL, leading to inhibition zones ranging from 10 to 14 mm. In addition, the disulfide bonds play a crucial role in the antibacterial function of cyclotides. Disrupting the disulfide bonds through ankylation reaction results in the loss of antibacterial properties in the cyclotides (cyO17 and mra30). The minimum inhibitory concentration (MIC) values of mra30 and cyO17 are significantly low, ranging from 0.1 to 0.6 µM. These values are approximately three times lower than the MIC values observed in salt precipitation samples.


Asunto(s)
Antibacterianos , Ciclotidas , Pruebas de Sensibilidad Microbiana , Viola , Antibacterianos/farmacología , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Ciclotidas/química , Ciclotidas/farmacología , Ciclotidas/aislamiento & purificación , Viola/química , Staphylococcus aureus/efectos de los fármacos , Pseudomonas aeruginosa/efectos de los fármacos , Espectrometría de Masas en Tándem , Bacillus subtilis/efectos de los fármacos , Secuencia de Aminoácidos , Bacterias/efectos de los fármacos
13.
J Nat Prod ; 87(9): 2263-2271, 2024 Sep 27.
Artículo en Inglés | MEDLINE | ID: mdl-39255387

RESUMEN

Three new dihydroflavonols, gloverinols A-C (1-3), a new flavon-3-ol, gloverinol D (4), two new isoflavans, gloveriflavan A (5) and B (6), and seven known compounds were isolated from the root bark of Dalbergia gloveri. The structures of the isolates were elucidated by using NMR, ECD, and HRESIMS data analyses. Among the isolated compounds, gloverinol B (2), gloveriflavan B (6), and 1-(2,4-dihydroxyphenyl)-3-hydroxy-3-(4-hydroxyphenyl)-1-propanone (10) were the most active against Staphylococcus aureus, with MIC values of 9.2, 18.4, and 14.2 µM, respectively.


Asunto(s)
Dalbergia , Pruebas de Sensibilidad Microbiana , Corteza de la Planta , Raíces de Plantas , Staphylococcus aureus , Corteza de la Planta/química , Raíces de Plantas/química , Estructura Molecular , Staphylococcus aureus/efectos de los fármacos , Dalbergia/química , Antibacterianos/farmacología , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Flavonoides/farmacología , Flavonoides/química , Flavonoides/aislamiento & purificación , Isoflavonas/farmacología , Isoflavonas/química , Isoflavonas/aislamiento & purificación
14.
J Appl Microbiol ; 135(9)2024 Sep 02.
Artículo en Inglés | MEDLINE | ID: mdl-39138062

RESUMEN

AIM: The aim of this study was to purify proanthocyanidins from areca nut seeds (P-AN) and to investigate the bactericidal activity and mechanism of the purified products against Streptococcus mutans. METHODS AND RESULTS: Ultra-performance liquid chromatography tandem quadrupole time-of-flight mass spectrometry, Fourier transform infrared, Matrix-assisted laser desorption/ ionization time of flight mass spectrometry (MADLI-TOF-MS), and thiolysis experiment were used for P-AN chemical analysis. Time-kill analysis and glycolytic pH drop were used to evaluate the activity of S. mutans in vitro. Meanwhile, the investigation of the bacteriostatic mechanism included membrane protein, fluidity, permeability, and integrity tests. The results showed that P-AN was a kind of proanthocyanidin mainly composed of B-type proanthocyanidins and their polymers. Moreover, MADLI-TOF-MS and thiolysis experiments demonstrated that the degree of polymerization of P-AN was 13. The time-kill analysis showed that P-AN had strong bactericidal activity against S. mutans. P-AN at minimum inhibitory concentration (MIC) concentrations was able to induce S. mutans death, while complete lethality occurred at 2 MIC. Glycolysis test showed that P-AN significantly inhibited S. mutans acid production (P < .01). The morphological changes of S. mutans were observed by scanning electron microscopy and transmission electron microscopy experiments, which indicated that P-AN destroyed the cellular structure of S. mutans. At the same time, significant changes were observed in membrane proteins, fluidity, permeability, and integrity. CONCLUSION: P-AN can effectively inhibit the activity of S. mutans. P-AN can reduce the erosion of the tooth surface by the acid of S. mutans. P-AN could break the structure of the cell membrane protein of S. mutans. P-AN could destroy the integrity of membrane, resulting in the death of S. mutans.


Asunto(s)
Antibacterianos , Pruebas de Sensibilidad Microbiana , Proantocianidinas , Semillas , Streptococcus mutans , Proantocianidinas/farmacología , Proantocianidinas/aislamiento & purificación , Proantocianidinas/química , Streptococcus mutans/efectos de los fármacos , Semillas/química , Antibacterianos/farmacología , Antibacterianos/aislamiento & purificación , Nueces/química , Extractos Vegetales/farmacología , Extractos Vegetales/química , Extractos Vegetales/aislamiento & purificación
15.
Arch Microbiol ; 206(9): 372, 2024 Aug 10.
Artículo en Inglés | MEDLINE | ID: mdl-39126528

RESUMEN

Endophytic bacteria found in marine macroalgae have been studied for their potential antimicrobial activity, consequently, they could serve as a valuable source of bioactive compounds to control pathogenic bacteria, yeasts, and fungi. Algae endophytic bacteria were isolated from Caulerpa sp., Ulva sp., Ahnfeltiopsis sp., and Chondracantus chamissoi from Yacila and Cangrejo Beaches (Piura, Peru). Antimicrobial assays against pathogenic bacteria were evaluated using cross-culture, over-plate, and volatile organic compound tests. Afterward, the minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) of selected crude extracts were determined, also ITS molecular analysis, antifungal activity, and PCR of iturin, fengycin, and surfactin genes were performed for bacteria strains exhibiting better activity. Forty-six algae endophytic bacteria were isolated from algae. Ten strains inhibited gram-positive pathogenic bacteria (Enterococcus faecalis, Staphylococcus epidermidis, S. aureus, and Listeria monocytogenes), and 12 inhibited gram-negative bacteria (Escherichia coli and Salmonella enteric sv typhimurium). Bacteria with better activity belong to Bacillus sp., Kluyvera ascorbata, Pantoea agglomerans, Leclercia adecarboxylata, and Enterobacter sp., which only four showed antifungal activities against Candida albicans, C. tropicalis, Colletotrichium sp., Fusarium sp., Fusarium oxysporum, and Alternaria sp. Furthermore, K. ascorbata YAFE21 and Bacillus sp. YCFE4 exhibited iturin and fengycin genes. The results indicate that the algae endophytic bacteria found in this study, particularly K. ascorbata YAFE21, Bacillus sp. YCFR6, L. adecarboxylata CUFE2, Bacillus sp. YUFE8, Enterobacter sp. YAFL1, and P. agglomerans YAFL6, could be investigated as potential producers of antimicrobial compounds due to their broad activity against various microorganisms.


Asunto(s)
Endófitos , Pruebas de Sensibilidad Microbiana , Algas Marinas , Endófitos/aislamiento & purificación , Endófitos/genética , Endófitos/metabolismo , Endófitos/química , Endófitos/clasificación , Algas Marinas/microbiología , Bacterias/efectos de los fármacos , Bacterias/aislamiento & purificación , Bacterias/clasificación , Antiinfecciosos/farmacología , Antiinfecciosos/aislamiento & purificación , Antibacterianos/farmacología , Antibacterianos/aislamiento & purificación , Antifúngicos/farmacología , Antifúngicos/aislamiento & purificación , Hongos/efectos de los fármacos , Hongos/aislamiento & purificación , Hongos/clasificación , Bacterias Gramnegativas/efectos de los fármacos , Ulva/microbiología , Caulerpa/microbiología , Bacterias Grampositivas/efectos de los fármacos
16.
J Nat Med ; 78(4): 919-928, 2024 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-39127865

RESUMEN

Basidiomycetes with a wide variety of skeletons of secondary metabolites can be expected to be the source of new interesting biological compounds. During our research on basidiomycetes, two new C-29 oxygenated oleanane-type triterpenes (1 and 2) and torulosacid (3), a muurolene type sesquiterpenoid with a five-membered ether ring along with nine known compounds (4-12), were isolated from the MeOH extract of the fruiting bodies of Fuscoporia torulosa. The structures of 1-3 were determined by NMR and HREIMS analysis. Further studies on the stereochemistry of 3 were conducted using X-ray crystallographic analysis and comparison of experimental and calculated ECD spectra. In the antimicrobial assay of isolates, 1, 7, and 9 showed growth inhibitory activity against methicillin-resistant Staphylococcus aureus and other gram-positive strains. Isolation of oleanane type triterpenes from fungi including basidiomycetes, is a unique report that could lead to further isolation of new compounds and the discovery of unique biosynthetic enzymes.


Asunto(s)
Cuerpos Fructíferos de los Hongos , Pruebas de Sensibilidad Microbiana , Sesquiterpenos , Cuerpos Fructíferos de los Hongos/química , Sesquiterpenos/química , Sesquiterpenos/farmacología , Sesquiterpenos/aislamiento & purificación , Estructura Molecular , Basidiomycota/química , Ácido Oleanólico/química , Ácido Oleanólico/análogos & derivados , Ácido Oleanólico/aislamiento & purificación , Ácido Oleanólico/farmacología , Triterpenos/química , Triterpenos/aislamiento & purificación , Triterpenos/farmacología , Antibacterianos/farmacología , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Cristalografía por Rayos X , Staphylococcus aureus Resistente a Meticilina/efectos de los fármacos
17.
Mar Drugs ; 22(8)2024 Jul 30.
Artículo en Inglés | MEDLINE | ID: mdl-39195470

RESUMEN

Atopic dermatitis (AD) is a chronic skin condition that is characterized by dysregulated immune responses and a heightened risk of Staphylococcus aureus infections, necessitating the advancement of innovative therapeutic methods. This study explored the potential of (6Z,9Z,12Z,15Z)-(2R,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexyl octadeca-6,9,12,15-tetraenoate (HSN-S1), a compound derived from the marine alga Hizikia fusiformis, which shows anti-inflammatory, antimicrobial, and immunomodulatory properties. HSN-S1 was isolated and characterized using advanced chromatographic and spectroscopic methods. Its efficacy was evaluated via in vitro assays with keratinocytes, macrophages, and T cells to assess cytokine suppression and its immunomodulatory effects; its antibacterial activity against S. aureus was quantified. The in vivo effectiveness was validated using a 2,4-dinitrochlorobenzene-induced AD mouse model that focused on skin pathology and cytokine modulation. HSN-S1 significantly reduced pro-inflammatory cytokine secretion, altered T-helper cell cytokine profiles, and showed strong antibacterial activity against S. aureus. In vivo, HSN-S1 alleviated AD-like symptoms in mice and reduced skin inflammation, transepidermal water loss, serum immunoglobulin-E levels, and Th2/Th17 cytokine outputs. These findings suggest HSN-S1 to be a promising marine-derived candidate for AD treatment, as it offers a dual-target approach that could overcome the limitations of existing therapies, hence warranting further clinical investigation.


Asunto(s)
Antibacterianos , Citocinas , Dermatitis Atópica , Inmunosupresores , Phaeophyceae , Staphylococcus aureus , Dermatitis Atópica/tratamiento farmacológico , Animales , Ratones , Phaeophyceae/química , Antibacterianos/farmacología , Antibacterianos/aislamiento & purificación , Staphylococcus aureus/efectos de los fármacos , Citocinas/metabolismo , Humanos , Inmunosupresores/farmacología , Inmunosupresores/aislamiento & purificación , Inmunosupresores/química , Modelos Animales de Enfermedad , Ésteres/farmacología , Ésteres/química , Femenino , Ratones Endogámicos BALB C , Organismos Acuáticos , Queratinocitos/efectos de los fármacos
18.
Talanta ; 280: 126746, 2024 Dec 01.
Artículo en Inglés | MEDLINE | ID: mdl-39182415

RESUMEN

Magnetic solid-phase extraction (MSPE) technology for tetracycline (TCC) was developed by employing the novel and pre-designed Fe3O4-COOH@hydrogen-bonded organic frameworks (HOFs) adsorbents in complex food samples. The HOF shell was grown onto the Fe3O4-COOH core by in-situ self-assembled method. The excellent MSPE performances with less solvent, less adsorbent and time consumption were derived from the hydrogen bonding, π-π and hydrophobic interactions between HOF shell and TCC. Combined with HPLC analysis, Fe3O4@ HOFs adsorbent reduced matrix effects and the established MSPE-HPLC method for TCC gave the linearity of 0.001-6 µg mL-1 with the limit of detection 0.0003 µg mL-1. The recoveries in pure milk, canned yellow peach and carrot were 82.4-103.7 %. The method provided a simple, efficient and dependable alternative to monitor trace TCC antibiotics in food or environmental samples.


Asunto(s)
Contaminación de Alimentos , Estructuras Metalorgánicas , Extracción en Fase Sólida , Tetraciclina , Extracción en Fase Sólida/métodos , Cromatografía Líquida de Alta Presión/métodos , Tetraciclina/análisis , Tetraciclina/aislamiento & purificación , Tetraciclina/química , Estructuras Metalorgánicas/química , Contaminación de Alimentos/análisis , Enlace de Hidrógeno , Leche/química , Adsorción , Límite de Detección , Antibacterianos/análisis , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Análisis de los Alimentos/métodos , Fenómenos Magnéticos , Animales , Óxido Ferrosoférrico/química , Daucus carota/química
19.
Phytochemistry ; 228: 114253, 2024 Dec.
Artículo en Inglés | MEDLINE | ID: mdl-39168425

RESUMEN

Cultivation and extraction of the fungus Stereum hirsutum (Willd.) Pers. yielded 12 isopentenyl benzene derivatives, including six previously undescribed derivatives, named stereuins A-F. Their structures were established based on NMR and mass spectroscopy analyses, supplemented by comparison with previously reported data. Stereuins A-C are unique benzoate derivatives containing fatty acid subunits. Stereuins D and E feature a valylene group and a 6/6/6 ring system. In vitro, stereuin A significantly promoted neurite outgrowth. Several compounds exhibited antibacterial activity against Staphylococcus aureus. Stereuin F has an IC50 value of 5.2 µg/mL against S. aureus, comparable to the positive control, penicillin G sodium (1.4 µg/mL).


Asunto(s)
Antibacterianos , Pruebas de Sensibilidad Microbiana , Staphylococcus aureus , Antibacterianos/farmacología , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Staphylococcus aureus/efectos de los fármacos , Estructura Molecular , Basidiomycota/química , Relación Estructura-Actividad , Animales , Derivados del Benceno/farmacología , Derivados del Benceno/química , Derivados del Benceno/aislamiento & purificación , Proyección Neuronal/efectos de los fármacos , Relación Dosis-Respuesta a Droga , Ratas
20.
Phytochemistry ; 227: 114232, 2024 Nov.
Artículo en Inglés | MEDLINE | ID: mdl-39097216

RESUMEN

A bioassay-guided isolation from Atractylodes lancea (Thunb.) DC. obtained 22 compounds, including eight previously undescribed sesquiterpenoids and polyacetylenes (1, 3 and 12-17), as well as fourteen known analogues, and their structures were confirmed by extensive spectroscopic methods. This study evaluated their antibacterial activity against methicillin resistant Staphylococcus aureus (MRSA) for the first time, as well as anti-inflammatory activity. Most of them, including new compounds, showed varying degrees of antibacterial activity against S. aureus and MRSA. Notably, compound 21 exhibited significant antibacterial activity against four different bacteria (MIC 6.25-20.00 µg/mL). This suggested that 21 may have the potential to be developed into a broad-spectrum antibacterial agent. Moreover, except for 9 and 11, most compounds exhibited great anti-inflammatory activity (IC50 1.92-37.91 µM), and iNOS might be a potential target of these compounds according to the molecular docking analysis.


Asunto(s)
Antibacterianos , Antiinflamatorios , Atractylodes , Staphylococcus aureus Resistente a Meticilina , Pruebas de Sensibilidad Microbiana , Atractylodes/química , Antibacterianos/farmacología , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Staphylococcus aureus Resistente a Meticilina/efectos de los fármacos , Antiinflamatorios/farmacología , Antiinflamatorios/química , Antiinflamatorios/aislamiento & purificación , Estructura Molecular , Simulación del Acoplamiento Molecular , Animales , Relación Estructura-Actividad , Ratones , Relación Dosis-Respuesta a Droga , Antiinflamatorios no Esteroideos/farmacología , Antiinflamatorios no Esteroideos/química , Antiinflamatorios no Esteroideos/aislamiento & purificación , Óxido Nítrico Sintasa de Tipo II/antagonistas & inhibidores , Óxido Nítrico Sintasa de Tipo II/metabolismo , Bioensayo , Células RAW 264.7 , Staphylococcus aureus/efectos de los fármacos
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