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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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
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author Sikora, Karol
Szweda, Piotr
Słoczyńska, Karolina
Samaszko-Fiertek, Justyna
Madaj, Janusz
Liberek, Beata
Pękala, Elżbieta
Dmochowska, Barbara
author_facet Sikora, Karol
Szweda, Piotr
Słoczyńska, Karolina
Samaszko-Fiertek, Justyna
Madaj, Janusz
Liberek, Beata
Pękala, Elżbieta
Dmochowska, Barbara
author_sort Sikora, Karol
collection PubMed
description 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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spelling pubmed-102157372023-05-27 Synthesis, Antimicrobial and Mutagenic Activity of a New Class of d-Xylopyranosides Sikora, Karol Szweda, Piotr Słoczyńska, Karolina Samaszko-Fiertek, Justyna Madaj, Janusz Liberek, Beata Pękala, Elżbieta Dmochowska, Barbara Antibiotics (Basel) Article 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. MDPI 2023-05-10 /pmc/articles/PMC10215737/ /pubmed/37237791 http://dx.doi.org/10.3390/antibiotics12050888 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Sikora, Karol
Szweda, Piotr
Słoczyńska, Karolina
Samaszko-Fiertek, Justyna
Madaj, Janusz
Liberek, Beata
Pękala, Elżbieta
Dmochowska, Barbara
Synthesis, Antimicrobial and Mutagenic Activity of a New Class of d-Xylopyranosides
title Synthesis, Antimicrobial and Mutagenic Activity of a New Class of d-Xylopyranosides
title_full Synthesis, Antimicrobial and Mutagenic Activity of a New Class of d-Xylopyranosides
title_fullStr Synthesis, Antimicrobial and Mutagenic Activity of a New Class of d-Xylopyranosides
title_full_unstemmed Synthesis, Antimicrobial and Mutagenic Activity of a New Class of d-Xylopyranosides
title_short Synthesis, Antimicrobial and Mutagenic Activity of a New Class of d-Xylopyranosides
title_sort synthesis, antimicrobial and mutagenic activity of a new class of d-xylopyranosides
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10215737/
https://www.ncbi.nlm.nih.gov/pubmed/37237791
http://dx.doi.org/10.3390/antibiotics12050888
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