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Article ; Online: In vitro and in silico studies of chalcones derived from natural acetophenone inhibitors of NorA and MepA multidrug efflux pumps in Staphylococcus aureus.

Freitas, Thiago S / Xavier, Jayze C / Pereira, Raimundo L S / Rocha, Janaína E / Campina, Fábia F / de Araújo Neto, José B / Silva, Maria M C / Barbosa, Cristina R S / Marinho, Emmanuel S / Nogueira, Carlos E S / Dos Santos, Hélcio S / Coutinho, Henrique D M / Teixeira, Alexandre M R

Microbial pathogenesis

2021 Volume 161, Issue Pt B, Page(s) 105286

Abstract: Bacterial resistance induced by efflux pumps is a frequent concern in clinical treatments involving multi-resistant bacteria. Staphylococcus aureus is a microorganism responsible for several types of infections and has several strains carrying efflux ... ...

Abstract	Bacterial resistance induced by efflux pumps is a frequent concern in clinical treatments involving multi-resistant bacteria. Staphylococcus aureus is a microorganism responsible for several types of infections and has several strains carrying efflux pumps, among them are the strain 1199B (NorA overexpresser), and the strain K2068 (MepA overexpresser). In this work, four chalcones derived from Croton anisodontus with modifications in the B ring in their structures were tested regarding their ability to inhibit NorA and MepA efflux pumps. The efflux pump inhibition mechanism was tested with the ethidium bromide substrate in the presence and absence of standard efflux pump inhibitors. The minimum inhibitory concentration values were also compared to those of strains that do not overexpress these efflux pumps. In order to gain some insights about the efflux pump mechanisms of these chalcones, two homology models were created (NorA and MepA) for a docking procedure. In addition, the ADME properties (absorption, distribution, metabolism and excretion) were also evaluated. The tested chalcones promoted synergism of the norfloxacin antibiotic by inhibiting associated efflux pumps. All four tested chalcones appear to bind to the binding sites of the efflux pump models in the same fashion as other chalcones with efflux pump inhibition capabilities. It was also verified that the chalcones 1-4 are well absorbed in the intestine, but with a decrease in their bioavailability, resulting in a low volume of distribution in the blood plasma, in addition to having a mild CNS activity. However, the chalcone 3 and 4 were not toxic due to metabolic activation. Whereas the chalcones 1 and 2 present a mutagenic risk, depending on the oral dose administered. The tested chalcones have not antibacterial activity; however, they are capable of inhibiting efflux pumps for the 1199B and K2068 strains. They promoted synergism of the norfloxacin antibiotic by inhibiting associated efflux pumps, as well as other associated mechanisms.
MeSH term(s)	Acetophenones/pharmacology ; Anti-Bacterial Agents/pharmacology ; Bacterial Proteins/metabolism ; Chalcone ; Chalcones/pharmacology ; Microbial Sensitivity Tests ; Multidrug Resistance-Associated Proteins ; Staphylococcus aureus/metabolism
Chemical Substances	Acetophenones ; Anti-Bacterial Agents ; Bacterial Proteins ; Chalcones ; Multidrug Resistance-Associated Proteins ; Chalcone (5S5A2Q39HX)
Language	English
Publishing date	2021-11-16
Publishing country	England
Document type	Journal Article
ZDB-ID	632772-2
ISSN	1096-1208 ; 0882-4010
ISSN (online)	1096-1208
ISSN	0882-4010
DOI	10.1016/j.micpath.2021.105286
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Article ; Online: ADMET study, spectroscopic characterization and effect of synthetic nitro chalcone in combination with norfloxacin, ciprofloxacin, and ethidium bromide against Staphylococcus aureus efflux pumps.

Rocha, Janaína E / de Freitas, Thiago S / Xavier, Jayze C / Pereira, Raimundo L S / Pereira Junior, Francisco N / Nogueira, Carlos E S / Marinho, Márcia M / Bandeira, Paulo N / Rodrigues, Leilane G / Marinho, Emmanuel S / de Lacerda, Bruna C G V / de Andrade, Edlane Martins / Teixeira, Alexandre M R / Dos Santos, Hélcio S / Coutinho, Henrique D M

Fundamental & clinical pharmacology

2022 Volume 37, Issue 1, Page(s) 163–173

Abstract: Chalcones are present in a wide variety of plants, having in their structure two aromatic rings that are linked together by a chain composed of three carbon atoms with α, β-unsaturated to carbonyl system. Bacteria have several drug resistance mechanisms, ...

Abstract	Chalcones are present in a wide variety of plants, having in their structure two aromatic rings that are linked together by a chain composed of three carbon atoms with α, β-unsaturated to carbonyl system. Bacteria have several drug resistance mechanisms, among them the efflux pump; this mechanism, when active, is able to expel different compounds from inside bacterial cells. Several efflux pumps have already been identified for Staphylococcus aureus bacteria, including MepA and NorA. Many chalcones have been isolated and identified with various activities, such as antimicrobial. In view of this, this article aimed to evaluate the antibiotic modifying effect of chalcone (E)-1-(2-hydroxyphenyl)-3-(3-nitrophenyl)prop-2-en-1-one against S. aureus carrier of NorA and MepA efflux pump. Regarding the antibiotic, there was a synergism when associated with ciprofloxacin in SA-K2068 strain, showing this chalcone as an alternative to reverse the resistance to this medicine. The physicochemical properties calculated were fundamental in the description of the predicted pharmacokinetic properties. Despite the mutagenic risk caused by the metabolic activation of nitrochalcone, it is possible to notice a pharmacological principle in a longer half-life for the performance of biological activities. The compound has a good bioavailability, as it is highly absorbed in the intestine and easily transported by plasma proteins, in addition to not presenting neurotoxic, hepatotoxic, and cardiotoxic damage.
MeSH term(s)	Humans ; Norfloxacin/pharmacology ; Ciprofloxacin/pharmacology ; Staphylococcus aureus ; Ethidium/metabolism ; Ethidium/pharmacology ; Chalcone/pharmacology ; Chalcone/metabolism ; Chalcones/pharmacology ; Multidrug Resistance-Associated Proteins ; Microbial Sensitivity Tests ; Anti-Bacterial Agents/pharmacology ; Staphylococcal Infections
Chemical Substances	Norfloxacin (N0F8P22L1P) ; Ciprofloxacin (5E8K9I0O4U) ; Ethidium (EN464416SI) ; Chalcone (5S5A2Q39HX) ; Chalcones ; Multidrug Resistance-Associated Proteins ; Anti-Bacterial Agents
Language	English
Publishing date	2022-09-16
Publishing country	England
Document type	Journal Article
ZDB-ID	639134-5
ISSN	1472-8206 ; 0767-3981
ISSN (online)	1472-8206
ISSN	0767-3981
DOI	10.1111/fcp.12830
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Article: Anti-inflammatory effect, antibiotic potentiating activity against multidrug-resistant strains of Escherichia coli and Staphylococcus aureus, and evaluation of antibiotic resistance mechanisms by the ibuprofen derivative methyl 2-(-4-isobutylphenyl)propanoate

Microbial pathogenesis. 2022 Sept., v. 170

2022

Abstract: The prevalence of multidrug-resistant (MDR) bacteria and the limited efficacy of current available antibiotics cause every year approximately 700 000 deaths per year. This study aimed to evaluate the anti-inflammatory effect and antibacterial potential ... ...

Abstract	The prevalence of multidrug-resistant (MDR) bacteria and the limited efficacy of current available antibiotics cause every year approximately 700 000 deaths per year. This study aimed to evaluate the anti-inflammatory effect and antibacterial potential of the ibuprofen derivative Methyl 2-(-4-isobutylphenyl)propanoate (MET-IBU). The molecular structure of MET-IBU was confirmed by Nuclear Magnetic Resonance (NMR) and, Attenuated Total Reflectance Fourier Transform Infrared spectroscopy (ATR-FTIR) spectroscopy. Our in vivo study using adult zebrafish model demonstrated that the ibuprofen derivative MET-IBU also possesses anti-inflammatory effect, and in vitro antibacterial activity assays showed that in the association of ampicillin, norfloxacin, and gentamicin with MET-IBU occurred reduction in the minimum inhibitory concentration (MIC) for MDR bacterial strains of Escherichia coli 06 and Staphylococcus aureus 10, indicating a potentiating in the growth inhibition of these pathogenic bacteria. Regarding the strain of Staphylococcus aureus K2068 (overexpressing mepA gene), a potentiation of ethidium bromide was found in the association with MET-IBU, indicating the action of this compound on the efflux pump mechanism present in this strains. This result corroborates the molecular docking study that indicated a high affinity of the MET-IBU with the MepA efflux pump. It was also noticed an antibiotic potentiating activity in the association MET-IBU with norfloxacin against strains of Staphylococcus aureus 1199B (overexpressing norA gene) when compared to the norfloxacin control. This enhanced antibiotic effect of MET-IBU is associated with a second resistance mechanism, which is due to the modification in the topoisomerase enzyme. These results bring attention to the ibuprofen derivative MET-IBU as possible candidate for the development of new options for the treatment of bacterial infections with protective anti-inflammatory action.
Keywords	Danio rerio ; Escherichia coli ; Fourier transform infrared spectroscopy ; adults ; ampicillin ; anti-inflammatory activity ; antibacterial properties ; antibiotic resistance ; chemical structure ; enzymes ; ethidium ; genes ; gentamicin ; growth retardation ; ibuprofen ; minimum inhibitory concentration ; models ; multiple drug resistance ; norfloxacin ; nuclear magnetic resonance spectroscopy ; pathogenesis ; transporters
Language	English
Dates of publication	2022-09
Publishing place	Elsevier Ltd
Document type	Article
ZDB-ID	632772-2
ISSN	1096-1208 ; 0882-4010
ISSN (online)	1096-1208
ISSN	0882-4010
DOI	10.1016/j.micpath.2022.105697
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Article: Effect of hybrid combinations of Erythroxylum revolutum Mart. leaf ethanolic extract or alkaloid-enriched fraction with antibiotic drugs against multidrug-resistant bacteria strains

Barbosa, Maísa F.S. / Miranda, Paulo H.O. / Souza, Carlos A. / Ramos, Clécio S. / Melo, André L. / Rocha, Janaína E. / Bezerra, Camila F. / Costa, Maria S. / Veras, Helenicy N.H. / Coutinho, Henrique D.M. / Menezes, Irwin R.A. / Saraiva, Rogério A.

Phytomedicine plus. 2021 Nov., v. 1, no. 4

2021

Abstract: Background The combination between antibiotic drugs and extracts derived from medicinal plants is one of the promising strategies against multidrug-resistant (MDR) bacterial strains to overwhelm the antimicrobial resistance. Hypothesis/Purpose We aimed ... ...

Abstract	Background The combination between antibiotic drugs and extracts derived from medicinal plants is one of the promising strategies against multidrug-resistant (MDR) bacterial strains to overwhelm the antimicrobial resistance. Hypothesis/Purpose We aimed to evaluate the antibacterial effect of hybrid combinations of ethanolic extract (EREE) or alkaloid-enriched fraction (ERAF) obtained from Erythroxylum revolutum leaves and conventional antibiotic drugs. Methods We tested the antimicrobial activity of EREE and ERAF in vitro against gram-positive (Staphyloccocus aureus) and Gram-negative (Escherichia coli and Pseudomonas aeruginosa) standard and MDR strains. Additionally, we performed phytochemical studies using GC/MS, ¹H, ¹³C NMR spectra, and two-dimensional techniques. Results Although the minimum inhibitory concentration (MIC) values of EREE or ERAF alone against bacterial growth were ≥ 1024 µg/ml, we denoted a total synergism effect in the hybrid combinations ERAF + gentamicin, ERAF + norfloxacin, and ERAF + erythromycin against MDR S. aureus strain, with a significant MIC reduction of 84.7%, 75.0%, and 89.85%, respectively. Although EREE demonstrated a total synergism effect in the hybrid combination gentamicin + EREE (with a significant decrease of MIC of 68.8%), on the contrary, EREE also elicited a strong antagonist effect in some hybrid combinations against the MDR bacteria strains tested. Phytochemical studies revealed in ERAF the presence of two tropane alkaloids described for the first time in the family Erythroxylaceae: 6-(2’-methylbutyryloxy)-3-hydroxytropane (87.07%) and 6-butyryloxy-3-hydroxytropane (12.93%). Conclusion Together, these data can highlight the first evidence of enriched-alkaloid fractions of E. revolutum in hybrid combinations with antibiotics, and propose tropane alkaloids from E. revolutum as new potential candidates in drug combinations for the treatment of infections caused by MDR S. aureus, which is one of the main agents causing infections with death worldwide.
Keywords	Erythroxylum ; Escherichia coli ; Pseudomonas aeruginosa ; Staphylococcus aureus ; antagonists ; antibacterial properties ; antibiotic resistance ; bacterial growth ; death ; erythromycin ; gentamicin ; hybrids ; leaves ; minimum inhibitory concentration ; multiple drug resistance ; norfloxacin ; phytochemicals ; synergism
Language	English
Dates of publication	2021-11
Publishing place	Elsevier B.V.
Document type	Article
ISSN	2667-0313
DOI	10.1016/j.phyplu.2021.100105
Database	NAL-Catalogue (AGRICOLA)

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Article: FTIR analysis of pyrogallol and phytotoxicity-reductive effect against mercury chloride

Rocha, Janaina E / Guedes, Tássia T. A. M / Bezerra, Camila F / Costa, Maria do S / Campina, Fabia F / de Freitas, Thiago S / Sousa, Amanda K / Sobral Souza, Celestina E / Silva, Maria K. N / Lobo, Yedda M / Pereira-Junior, Francisco N / da Silva, João H / Menezes, Irwin R. A / Teixeira, Raimundo N. P / Colares, Aracélio V / Coutinho, Henrique D. M

Environmental geochemistry and health. 2021 June, v. 43, no. 6

2021

Abstract: Human activities, especially in industry, have contributed to soil contamination with heavy or toxic metals. The objective of this study was to determine the chelating effect and antioxidant activity of pyrogallol, as well as to evaluate its ... ...

Abstract	Human activities, especially in industry, have contributed to soil contamination with heavy or toxic metals. The objective of this study was to determine the chelating effect and antioxidant activity of pyrogallol, as well as to evaluate its cytoprotective activity in prokaryotic and eukaryotic models, animal and plant, respectively, against toxic mercury chloride action. Antioxidant activity was determined by DPPH where pyrogallol showed considerable action, chelating even iron ions. For the microbiologic activity assays, microdilution was performed to obtain the minimal inhibitory concentration, minimum bactericidal and minimum fungicide concentration, from which the sub-inhibitory concentrations were determined. The product did not conferred cytoprotection to the tested bacteria and fungi. To evaluate plant cytoprotection, Lactuta sativa seeds were used together with the product at a sub-allelopathic concentration with different HgCl₂ concentrations. In this case, the tannin conferred cytoprotection to the plant model, allowing the best growth and development of caulicles and radicles, thus preserving tissues necessary for plant survival. From the results, it is observable that pyrogallol possesses cytoprotective action in the eukaryotic plant model, this action being useful as an alternative which favors the growth of plants in contaminated areas, as the recovering of crop fields or reforestation projects.
Keywords	Lactuca sativa ; antioxidant activity ; geochemistry ; growth and development ; humans ; industry ; mercuric chloride ; minimum inhibitory concentration ; models ; pyrogallol ; reforestation ; soil pollution ; toxicity
Language	English
Dates of publication	2021-06
Size	p. 2433-2442.
Publishing place	Springer Netherlands
Document type	Article
Note	NAL-AP-2-clean
ZDB-ID	52039-1
ISSN	1573-2983 ; 0142-7245 ; 0269-4042
ISSN (online)	1573-2983
ISSN	0142-7245 ; 0269-4042
DOI	10.1007/s10653-020-00607-1
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Article: Gas chromatography coupled to mass spectrometry (GC-MS) characterization and evaluation of antibacterial bioactivities of the essential oils from Piper arboreum Aubl., Piper aduncum L. e Piper gaudichaudianum Kunth

da Silva, Ana Cristina A / Matias, Edinardo F. F / Rocha, Janaína E / Araújo, Ana Carolina Justino de / de Freitas, Thiago S / Campina, Fábia F / Costa, Maria do S / Silva, Luiz E / Amaral, Wanderlei do / Maia, Beatriz Helena L. N. S / Ferriani, Aurea P / Bezerra, Camila F / Iriti, Marcello / Coutinho, Henrique D. M

Zeitschrift für Naturforschung. 2021 Jan. 27, v. 76, no. 1-2

2021

Abstract: The objective of this study was to determine the chemical profile and to evaluate the antibacterial activity of the essential oils of Piper species and modulation of the antibiotic activity, using the microdilution method to determine the minimum ... ...

Abstract	The objective of this study was to determine the chemical profile and to evaluate the antibacterial activity of the essential oils of Piper species and modulation of the antibiotic activity, using the microdilution method to determine the minimum inhibitory concentration. The chemical components were characterized by gas chromatography coupled to mass spectrometry, which revealed β-copaen-4-α-ol (31.38%), spathulenol (25.92%), and germacrene B (21.53%) as major constituents of the essential oils of Piper arboreum, Piper aduncum, and Piper gaudichaudianum, respectively. The essential oils analyzed in this study did not present a clinically relevant activity against standard and multiresistant Escherichia coli. However, in the case of multiresistant Staphylococcus aureus, there was a significant activity, corroborating with reports in the literature, where Gram-positive bacteria are more susceptible to antimicrobial activity. The essential oils modulated the effect of the antibiotics norfloxacin and gentamicin, having on the latter greater modulating effect; however, for erythromycin, no statistically significant effect was observed. In conclusion, the results obtained in this study demonstrated that the essential oils of the analyzed Piper species present an inhibitory effect against S. aureus and modulate antibiotic activity, most of which presents synergistic activity.
Keywords	Escherichia coli ; Piper aduncum ; Staphylococcus aureus ; antibacterial properties ; erythromycin ; gentamicin ; germacrene ; minimum inhibitory concentration ; norfloxacin ; spathulenol ; synergism
Language	English
Dates of publication	2021-0127
Size	p. 35-42.
Publishing place	De Gruyter
Document type	Article
Note	NAL-AP-2-clean
ZDB-ID	124636-7
ISSN	1865-7125 ; 0341-0382 ; 0341-0471 ; 0939-5075
ISSN (online)	1865-7125
ISSN	0341-0382 ; 0341-0471 ; 0939-5075
DOI	10.1515/znc-2020-0045
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Article ; Online: In vitro and in silico studies of chalcones derived from natural acetophenone inhibitors of NorA and MepA multidrug efflux pumps in Staphylococcus aureus

Freitas, Thiago S. / Xavier, Jayze C. / Pereira, Raimundo L.S. / Rocha, Janaína E. / Campina, Fábia F. / de Araújo Neto, José B. / Silva, Maria M.C. / Barbosa, Cristina R.S. / Marinho, Emmanuel S. / Nogueira, Carlos E.S. / dos Santos, Hélcio S. / Coutinho, Henrique D.M. / Teixeira, Alexandre M.R.

Microbial Pathogenesis. 2021 Dec., v. 161 p.105286-

2021

Abstract	Bacterial resistance induced by efflux pumps is a frequent concern in clinical treatments involving multi-resistant bacteria. Staphylococcus aureus is a microorganism responsible for several types of infections and has several strains carrying efflux pumps, among them are the strain 1199B (NorA overexpresser), and the strain K2068 (MepA overexpresser). In this work, four chalcones derived from Croton anisodontus with modifications in the B ring in their structures were tested regarding their ability to inhibit NorA and MepA efflux pumps. The efflux pump inhibition mechanism was tested with the ethidium bromide substrate in the presence and absence of standard efflux pump inhibitors. The minimum inhibitory concentration values were also compared to those of strains that do not overexpress these efflux pumps. In order to gain some insights about the efflux pump mechanisms of these chalcones, two homology models were created (NorA and MepA) for a docking procedure. In addition, the ADME properties (absorption, distribution, metabolism and excretion) were also evaluated. The tested chalcones promoted synergism of the norfloxacin antibiotic by inhibiting associated efflux pumps. All four tested chalcones appear to bind to the binding sites of the efflux pump models in the same fashion as other chalcones with efflux pump inhibition capabilities. It was also verified that the chalcones 1–4 are well absorbed in the intestine, but with a decrease in their bioavailability, resulting in a low volume of distribution in the blood plasma, in addition to having a mild CNS activity. However, the chalcone 3 and 4 were not toxic due to metabolic activation. Whereas the chalcones 1 and 2 present a mutagenic risk, depending on the oral dose administered. The tested chalcones have not antibacterial activity; however, they are capable of inhibiting efflux pumps for the 1199B and K2068 strains. They promoted synergism of the norfloxacin antibiotic by inhibiting associated efflux pumps, as well as other associated mechanisms.
Keywords	Croton ; Staphylococcus aureus ; absorption ; acetophenones ; antibacterial properties ; antibiotics ; bioavailability ; blood plasma ; chalcone ; computer simulation ; ethidium ; excretion ; intestines ; metabolism ; minimum inhibitory concentration ; mutagens ; norfloxacin ; oral administration ; pathogenesis ; risk ; synergism ; toxicity ; transporters ; NorA ; MepA ; Efflux pumps ; ADMET ; Molecular docking
Language	English
Dates of publication	2021-12
Publishing place	Elsevier Ltd
Document type	Article ; Online
ZDB-ID	632772-2
ISSN	1096-1208 ; 0882-4010
ISSN (online)	1096-1208
ISSN	0882-4010
DOI	10.1016/j.micpath.2021.105286
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Article ; Online: Evaluation of chelating and cytoprotective activity of vanillin against the toxic action of mercuric chloride as an alternative for phytoremediation.

da Silva, Joelma P / do S Costa, Maria / Campina, Fabia F / Bezerra, Camila F / de Freitas, Thiago S / Sousa, Amanda K / Sobral Souza, Celestina E / de Matos, Yedda M L S / Pereira-Junior, Francisco N / Menezes, Irwim R A / Coutinho, Henrique D M / Rocha, Janaína E

Environmental geochemistry and health

2020 Volume 43, Issue 4, Page(s) 1609–1616

Abstract: Mercury is widely found in nature, however, in low concentrations, but anthropological activities have increased its concentration considerably. This causes various environmental hazards and human health. Many substances are capable of reversing the ... ...

Abstract	Mercury is widely found in nature, however, in low concentrations, but anthropological activities have increased its concentration considerably. This causes various environmental hazards and human health. Many substances are capable of reversing the toxicity of mercuric chloride in the environment. The aim of the present study was to determine the chelating effect of vanillin, as well as to evaluate its capacity for cytoprotection in prokaryotic and eukaryotic plant models. Chelating activity was determined from vanillin's ability to reduce iron III ions. To evaluate cytoprotection in a unicellular prokaryotic and eukaryotic model, Escherichia coli and Candida albicans, respectively, were used. And to evaluate the cytoprotective activity in vegetables, lettuce seeds were submitted to different concentrations of mercuric chloride and its association with the sub-allelopathic concentration of vanillin (32 µg/mL). Vanillin has been found to have antioxidant activity as it can reduce iron III ions. The use of vanillin also allows for better growth and development of Lactuca sativa seed root and stem, also allowing better preservation of its biochemical structures. These results are quite important, as environmental contamination by heavy metals has increased dramatically and finding a viable alternative to grow vegetables in contaminated areas is very valid.
MeSH term(s)	Antioxidants/chemistry ; Benzaldehydes/chemistry ; Biodegradation, Environmental ; Chelating Agents/chemistry ; Ferric Compounds/chemistry ; Humans ; Lactuca ; Mercuric Chloride/toxicity ; Mercury ; Metals, Heavy/analysis ; Seeds/chemistry ; Vegetables
Chemical Substances	Antioxidants ; Benzaldehydes ; Chelating Agents ; Ferric Compounds ; Metals, Heavy ; Mercuric Chloride (53GH7MZT1R) ; vanillin (CHI530446X) ; Mercury (FXS1BY2PGL)
Language	English
Publishing date	2020-03-04
Publishing country	Netherlands
Document type	Journal Article
ZDB-ID	52039-1
ISSN	1573-2983 ; 0142-7245 ; 0269-4042
ISSN (online)	1573-2983
ISSN	0142-7245 ; 0269-4042
DOI	10.1007/s10653-020-00538-x
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Article ; Online: Gas chromatography coupled to mass spectrometry (GC-MS) characterization and evaluation of antibacterial bioactivities of the essential oils from

da Silva, Ana Cristina A / Matias, Edinardo F F / Rocha, Janaína E / Araújo, Ana Carolina Justino de / de Freitas, Thiago S / Campina, Fábia F / Costa, Maria do S / Silva, Luiz E / Amaral, Wanderlei do / Maia, Beatriz Helena L N S / Ferriani, Aurea P / Bezerra, Camila F / Iriti, Marcello / Coutinho, Henrique D M

Zeitschrift fur Naturforschung. C, Journal of biosciences

2020 Volume 76, Issue 1-2, Page(s) 35–42

Abstract: The objective of this study was to determine the chemical profile and to evaluate the antibacterial activity of the essential oils ... ...

Abstract	The objective of this study was to determine the chemical profile and to evaluate the antibacterial activity of the essential oils of
MeSH term(s)	Anti-Bacterial Agents/chemistry ; Anti-Bacterial Agents/pharmacology ; Escherichia coli/drug effects ; Oils, Volatile/chemistry ; Oils, Volatile/pharmacology ; Piper/chemistry ; Plant Oils/chemistry ; Plant Oils/pharmacology ; Sesquiterpenes/analysis ; Sesquiterpenes, Germacrane/analysis ; Staphylococcus aureus/drug effects
Chemical Substances	Anti-Bacterial Agents ; Oils, Volatile ; Plant Oils ; Sesquiterpenes ; Sesquiterpenes, Germacrane ; beta copaene ; spathulenol (7XV9L96SJJ)
Language	English
Publishing date	2020-07-16
Publishing country	Germany
Document type	Journal Article
ZDB-ID	124636-7
ISSN	1865-7125 ; 0341-0382 ; 0341-0471 ; 0939-5075
ISSN (online)	1865-7125
ISSN	0341-0382 ; 0341-0471 ; 0939-5075
DOI	10.1515/znc-2020-0045
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Article ; Online: Direct antibacterial and antibiotic resistance modulatory activity of chalcones synthesized from the natural product 2-hydroxy-3,4,6-trimethoxyacetophenone.

Freitas, Thiago Sampaio de / Xavier, Jayze da Cunha / Pereira, Raimundo L S / Rocha, Janaina E / Muniz, Dédora F / da Silva, Priscila T / da Hora, João P / Dos Santos, Hélcio S / Bandeira, Paulo N / Nogueira, Carlos E S / Teixeira, Alexandre M R / Coutinho, Henrique D M

FEMS microbiology letters

2020 Volume 367, Issue 15

Abstract: Antibiotic for clinical use lose its effectiveness over time due to bacterial resistance. In this work, four chalcones with modifications in their ligands were synthesized from the natural product 2-hydroxy-3,4,6-trimethoxyacetophenone, characterized by ... ...

Abstract	Antibiotic for clinical use lose its effectiveness over time due to bacterial resistance. In this work, four chalcones with modifications in their ligands were synthesized from the natural product 2-hydroxy-3,4,6-trimethoxyacetophenone, characterized by nuclear magnetic resonance (NMR) and infrared spectroscopy, and tested in bacterial models to investigate the direct and modifiers effects of the antibiotic activity of these four novel chalcones. The tests followed the broth microdilution methodology to obtain the Minimum Inhibitory Concentration (MIC). The MIC/8 of the products were used in the resistance reversion test. The chalcone 2 showed the best result in terms of direct activity, with MIC 645 μg/mL for Staphylococcus aureus and 812 μg/mL for Escherichia coli. While, for the bacterial resistance reversal test, the chalcones presented several synergistic interactions, being that chalcone 4 had the best interaction with the tested antibiotics. It was found that the type of ligand, as well as its position in the ring, interferes in the modulation of the antibiotic activity. Our results show that chalcones are strong candidates to be used as antibacterial drug or in combination with antibiotics for the treatment of infections caused by multidrug-resistant (MDR) strains.
MeSH term(s)	Acetophenones/chemistry ; Anti-Bacterial Agents/chemical synthesis ; Anti-Bacterial Agents/pharmacology ; Chalcones/chemical synthesis ; Chalcones/pharmacology ; Drug Resistance, Bacterial/drug effects ; Escherichia coli/drug effects ; Staphylococcus aureus/drug effects
Chemical Substances	2-hydroxy-3,4,6-trimethoxyacetophenone ; Acetophenones ; Anti-Bacterial Agents ; Chalcones
Language	English
Publishing date	2020-08-04
Publishing country	England
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	752343-9
ISSN	1574-6968 ; 0378-1097
ISSN (online)	1574-6968
ISSN	0378-1097
DOI	10.1093/femsle/fnaa124
Database	MEDical Literature Analysis and Retrieval System OnLINE

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