Next Article in Journal
Production of β-methylamino-L-alanine (BMAA) and Its Isomers by Freshwater Diatoms
Next Article in Special Issue
Alkaloid Lindoldhamine Inhibits Acid-Sensing Ion Channel 1a and Reveals Anti-Inflammatory Properties
Previous Article in Journal
Botulinum Neurotoxin A Intravesical Injections in Interstitial Cystitis/Bladder Painful Syndrome: A Systematic Review with Meta-Analysis
Previous Article in Special Issue
Cytotoxic and Proapoptotic Activity of Sanguinarine, Berberine, and Extracts of Chelidonium majus L. and Berberis thunbergii DC. toward Hematopoietic Cancer Cell Lines
Open AccessArticle

Nigritanine as a New Potential Antimicrobial Alkaloid for the Treatment of Staphylococcus aureus-Induced Infections

1
Center For Life Nano [email protected], Istituto Italiano di Tecnologia, Viale Regina Elena 291, 00161 Rome, Italy
2
Department of Chemistry and Technology of Drugs, “Department of Excellence 2018−2022”, Sapienza University of Rome, P.le Aldo Moro 5, 00185 Rome, Italy
3
Laboratory affiliated to Pasteur Italia-Fondazione Cenci Bolognetti, Department of Biochemical Sciences, Sapienza University of Rome, P.le Aldo Moro 5, 00185 Rome, Italy
4
Department of Biotechnology, Chemistry and Pharmacy, “Department of Excellence 2018−2022”, University of Siena, via Aldo Moro 2, 53100 Siena, Italy
*
Authors to whom correspondence should be addressed.
Toxins 2019, 11(9), 511; https://doi.org/10.3390/toxins11090511
Received: 24 July 2019 / Revised: 26 August 2019 / Accepted: 30 August 2019 / Published: 1 September 2019
(This article belongs to the Special Issue Biological Activities of Alkaloids: From Toxicology to Pharmacology)
Staphylococcus aureus is a major human pathogen causing a wide range of nosocomial infections including pulmonary, urinary, and skin infections. Notably, the emergence of bacterial strains resistant to conventional antibiotics has prompted researchers to find new compounds capable of killing these pathogens. Nature is undoubtedly an invaluable source of bioactive molecules characterized by an ample chemical diversity. They can act as unique platform providing new scaffolds for further chemical modifications in order to obtain compounds with optimized biological activity. A class of natural compounds with a variety of biological activities is represented by alkaloids, important secondary metabolites produced by a large number of organisms including bacteria, fungi, plants, and animals. In this work, starting from the screening of 39 alkaloids retrieved from a unique in-house library, we identified a heterodimer β-carboline alkaloid, nigritanine, with a potent anti-Staphylococcus action. Nigritanine, isolated from Strychnos nigritana, was characterized for its antimicrobial activity against a reference and three clinical isolates of S. aureus. Its potential cytotoxicity was also evaluated at short and long term against mammalian red blood cells and human keratinocytes, respectively. Nigritanine showed a remarkable antimicrobial activity (minimum inhibitory concentration of 128 µM) without being toxic in vitro to both tested cells. The analysis of the antibacterial activity related to the nigritanine scaffold furnished new insights in the structure–activity relationships (SARs) of β-carboline, confirming that dimerization improves its antibacterial activity. Taking into account these interesting results, nigritanine can be considered as a promising candidate for the development of new antimicrobial molecules for the treatment of S. aureus-induced infections. View Full-Text
Keywords: natural products; alkaloids; plant secondary metabolites; β-carboline; Staphylococcus aureus; antimicrobial activity; cytotoxicity natural products; alkaloids; plant secondary metabolites; β-carboline; Staphylococcus aureus; antimicrobial activity; cytotoxicity
Show Figures

Graphical abstract

MDPI and ACS Style

Casciaro, B.; Calcaterra, A.; Cappiello, F.; Mori, M.; Loffredo, M.R.; Ghirga, F.; Mangoni, M.L.; Botta, B.; Quaglio, D. Nigritanine as a New Potential Antimicrobial Alkaloid for the Treatment of Staphylococcus aureus-Induced Infections. Toxins 2019, 11, 511.

Show more citation formats Show less citations formats
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map

1
Back to TopTop