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

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.

Oxolane Ammonium Salts (Muscarine-Like)—Synthesis and Microbiological Activity

“…As mentioned above, the highest antimicrobial activity was shown by compound 5d, which had the longest (decyl) hydrocarbon chain, while compound 5c (octyl) exhibited only residual antibacterial potential and no activity was observed for derivative 5b (hexyl). A similar correlation between the antimicrobial potential and the "size" of the hydrocarbon tail was also investigated in our previous study on Dxylopyranosides containing a quaternary ammonium aglycone [31]. Thus, it can be assumed that this compound (but also 5c in the case of staphylococci), similarly to other surfactants, disrupts the integrity of the bacterial/fungal cell membrane.…”

“…Due to the specificity of the amines used and to obtain the highest possible yields, individual salts were obtained under different conditions, as illustrated by the data in Table 1. Analysis of the data in Table 1 shows that, if possible, according to our previous experiences, the best yields in the quaternization reaction of derivative 4 were obtained using our previously developed [31] solvent-free method.…”