Modulation of the antibiotic activity against multidrug resistant strains of coumarins isolated from Rutaceae species

Madeiro, Sara A. L.; Borges, Nathalie H. P. B.; Souto, Augusto Lopes; Figueiredo, Pedro Thiago Ramalho de; Siqueira-Júnior, José P.; Tavares, Josean Fechine

doi:10.1016/j.micpath.2017.01.028

Cited by 22 publications

(12 citation statements)

References 19 publications

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“…6′,7′-Dihydroxybergamottin was the most active against all the bacteria strains tested, probably because of the aliphatic chain in C5 position; similar activity was noticed for peucedanin and officinalin isobutyrate. In 2017, Madeiro and co-workers focalized their interest towards the antibiotic activity of coumarins isolated from Rutacea species ( Figure 19) [85]. Bergapten, xantoxin, isopimpinellin and imperatorin did not exhibit any antibacterial activity, even at the highest concentration, against S. aureus strains resistant to tetracycline, erythromycin and norfloxacin.…”

Section: ) Andmentioning

confidence: 99%

“…In 2017, Madeiro and co-workers focalized their interest towards the antibiotic activity of coumarins isolated from Rutacea species ( Figure 19 ) [ 85 ]. Bergapten, xantoxin, isopimpinellin and imperatorin did not exhibit any antibacterial activity, even at the highest concentration, against S. aureus strains resistant to tetracycline, erythromycin and norfloxacin.…”

Section: Biological Activitiesmentioning

confidence: 99%

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An Overview of Coumarin as a Versatile and Readily Accessible Scaffold with Broad-Ranging Biological Activities

Annunziata

Pinna

Dallavalle

et al. 2020

IJMS

223

156

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Privileged structures have been widely used as an effective template for the research and discovery of high value chemicals. Coumarin is a simple scaffold widespread in Nature and it can be found in a considerable number of plants as well as in some fungi and bacteria. In the last years, these natural compounds have been gaining an increasing attention from the scientific community for their wide range of biological activities, mainly due to their ability to interact with diverse enzymes and receptors in living organisms. In addition, coumarin nucleus has proved to be easily synthetized and decorated, giving the possibility of designing new coumarin-based compounds and investigating their potential in the treatment of various diseases. The versatility of coumarin scaffold finds applications not only in medicinal chemistry but also in the agrochemical field as well as in the cosmetic and fragrances industry. This review is intended to be a critical overview on coumarins, comprehensive of natural sources, metabolites, biological evaluations and synthetic approaches.

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Section: ) Andmentioning

confidence: 99%

Section: Biological Activitiesmentioning

confidence: 99%

An Overview of Coumarin as a Versatile and Readily Accessible Scaffold with Broad-Ranging Biological Activities

Annunziata

Pinna

Dallavalle

et al. 2020

IJMS

223

156

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“…Compounds 4 and 5 have been previously identified from many plant taxa, including P. triradiatus (Hochst ex Boiss.) (Halim et al, 1995), Metrodorea mollis and Pilocarpus spicatus (Rutaceae) (Madeiro et al, 2017).…”

Section: Isopimpinellin (5)mentioning

confidence: 99%

Deverra tortuosa (Desf.) DC from Saudi Arabia as a new source of marmin and furanocoumarins derivatives with α-glucosidase, antibacterial and cytotoxic activities

Oueslati

Guetat

Bouajila

et al. 2021

Heliyon

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Deverra tortuosa (Desf.) DC (Syn. Pituranthos tortusus (Desf.) Benth. & Hook.f.) is a species belonging to the Apiaceae family that is common in the Northern Region of Saudi Arabia. The plant is well known in traditional medicine along the Arabian ecoregion. In the framework of the present study, the crude extract of n-hexane and ethyl acetate of the seeds were fractionated to purify major bioactive secondary metabolites. Five compounds were identified for the first time from the seeds of D. tortuosa : Marmin 1 , Pituranthoside 2 , Isoimperatorin 3 , Bergapten 4 and Isopimpinellin 5 . Their structures were elucidated using 1D and 2D NMR, (ESI)-MS and IR spectroscopic analyses. The cytotoxic, α-glucosidase and antibacterial activities of the pure phytochemicals were also evaluated.

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“…In an ongoing project to evaluate coumarins as modulators of antibiotic resistance, the modulatory activity of semisynthetic and commercial coumarins [ 36 ], as well as of furanocoumarins isolated from Rutaceae species [ 37 ] has been demonstrated. Still regarding the furanocoumarins, bergapten, and isopimpinellin do not modulate the resistance to norfloxacin and to ethidium bromide in an effluxing Staphylococcus aureus strain.…”

Section: Introductionmentioning

confidence: 99%

Modulation of Drug Resistance by Furanochromones in NorA Overexpressing Staphylococcus Aureus

Rodrigues

Borges

Nogueira

et al. 2022

Evidence-Based Complementary and Alternative Medicine

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Khellin and visnagin are natural furanochromones that photoreact with DNA. Khellin has been used in the treatment of vitiligo and psoriasis, as well as in the treatment of angina pectoris and asthma due to its potent action as a coronary vasodilator and antispasmodic agent. The present study aimed to investigate whether the compounds khellin and visnagin act as inhibitors of NorA protein, an efflux pump overproduced by the strain of Staphylococcus aureus SA-1199B that confers resistance to the fluoroquinolones, such as norfloxacin and ciprofloxacin. These substances alone did not show antibacterial activity against the strain tested. On the other hand, when these compounds were added to the culture medium at subinhibitory concentration, they were able to reduce the minimum inhibitory concentration (MIC) of norfloxacin, ethidium bromide, as well as berberine, suggesting that these compounds are modulating agents of norfloxacin resistance, possibly due to NorA inhibition. Molecular docking analysis showed that both khellin and visnagin form hydrogen bonds with Arg310, an important residue in the interaction between NorA and its substrates, supporting the hypothesis that these compounds are NorA inhibitors. These results suggest a possible application of khellin and visnagin as adjuvants to norfloxacin in the treatment of infections caused by strains of S. aureus that overproduce NorA.

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Modulation of the antibiotic activity against multidrug resistant strains of coumarins isolated from Rutaceae species

Cited by 22 publications

References 19 publications

An Overview of Coumarin as a Versatile and Readily Accessible Scaffold with Broad-Ranging Biological Activities

An Overview of Coumarin as a Versatile and Readily Accessible Scaffold with Broad-Ranging Biological Activities

Deverra tortuosa (Desf.) DC from Saudi Arabia as a new source of marmin and furanocoumarins derivatives with α-glucosidase, antibacterial and cytotoxic activities

Modulation of Drug Resistance by Furanochromones in NorA Overexpressing Staphylococcus Aureus

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