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.

Keywords: NMR; antimicrobial activity; d-xylosides; mutagenicity; quaternary ammonium salts.

Figure 1

Selected terpenoid xylosides isolated from (A) Actaea pachypoda [11], (B) Actaea asiatica [12], (C) Homonoia riparia [13] and (D) Actaea racemose [14]; (E) structure of quercetin-3-d-xylopyranoside; (F) structure of 4-O-(2′,3′,4′-tri-O-methyl-β-d-xylopyranosyl) diphyllin; (G) structure of p-nitrophenyl-β-d-xylopyranoside.

Figure 2

Ellipticine 1′,2′-trans-d-xylosides synthesized by Honda et al. [21].

Figure 3

Alkyl di-/tri-/tetraoxyethyl β-d-xylopyranosides prepared by Wu et al. [22].

Figure 4

Glucocationic class surfactants prepared by Quagliotto et al. [23].

Scheme 1

Synthesis of N-[2-(2′,3′,4′-tri-O-acetyl-α/β-d-xylopyranosyloxy)ethyl]ammonium bromides.