Synthesis, Antimicrobial and Mutagenic Activity of a New Class of d-Xylopyranosides

Eight N-[2-(2′,3′,4′-tri-O-acetyl-α/β-d-xylopyranosyloxy)ethyl]ammonium bromides, a new class of d-xylopyranosides containing a quaternary ammonium aglycone, were obtained. Their complete structure was confirmed using NMR spectroscopy ((1)H, (13)C, COSY and HSQC) and high-resolution mass spectrometr...

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Detalles Bibliográficos
Autores principales: Sikora, Karol, Szweda, Piotr, Słoczyńska, Karolina, Samaszko-Fiertek, Justyna, Madaj, Janusz, Liberek, Beata, Pękala, Elżbieta, Dmochowska, Barbara
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10215737/
https://www.ncbi.nlm.nih.gov/pubmed/37237791
http://dx.doi.org/10.3390/antibiotics12050888
Descripción
Sumario:Eight N-[2-(2′,3′,4′-tri-O-acetyl-α/β-d-xylopyranosyloxy)ethyl]ammonium bromides, a new class of d-xylopyranosides containing a quaternary ammonium aglycone, were obtained. Their complete structure was confirmed using NMR spectroscopy ((1)H, (13)C, COSY and HSQC) and high-resolution mass spectrometry (HRMS). An antimicrobial activity against fungi (Candida albicans, Candida glabrata) and bacteria (Staphylococcus aureus, Escherichia coli) and a mutagenic Ames test with Salmonella typhimurium TA 98 strain were performed for the obtained compounds. The greatest activity against the tested microorganisms was shown by glycosides with the longest (octyl) hydrocarbon chain in ammonium salt. None of the tested compounds exhibited mutagenic activity in the Ames test.

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