Synthesis, Antimicrobial and Mutagenic Activity of a New Class of d-Xylopyranosides
Karol Sikora1,2, Piotr Szweda3, Karolina Słoczyńska4
1Faculty of Chemistry, University of Gdańsk, Wita Stwosza 63, 80-308 Gdańsk, Poland.
Abstract:
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 (1H, 13C, 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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