Four new N-phenethylbenzamide derivatives from the stems of piper betle and their antimicrobial activity

Nat Prod Res. 2023 Jun;37(12):1969-1977. doi: 10.1080/14786419.2022.2114473. Epub 2022 Aug 22.

Abstract

Four new N-phenethylbenzamide derivatives, named piperbetamides A-D (1-4), and six allylbenzene derivatives (5-10) were isolated from the stems of Piper betle L. Their structures were determined by HR-ESI-MS and NMR spectroscopic methods. Compounds 1-10 were evaluated for their inhibitory effects on the growth of nine microorganisms including five Gram-negative (Escherichia coli, Salmonella enterica serovar Typhimurium, Shigella flexneri, Pseudomonas aeruginosa, and Extended-spectrum beta-lactam resistant Klebsiella pneumoniae), three Gram-positive (Listeria monocytogenes, Methicilin-resistant Staphylococcus aureus, Vancomycin-resistant Enterococcus faecalis), and one yeast (Candida albicans) strains. Compounds 1, 3, 4, 6 and 10 exhibited potential antimicrobial activity against S. flexneri, L. monocytogenes, methicillin-resistant S. aureus and vancomycin-resistant E. faecalis with minimum inhibitory concentration (MIC) values in the range of 16-32 µg/mL.

Keywords: Piper betle; Piperaceae; allylbenzene derivative; antimicrobial activity; phenethylbenzamide derivative.

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Methicillin-Resistant Staphylococcus aureus*
  • Piper betle*
  • Vancomycin / pharmacology

Substances

  • Anti-Bacterial Agents
  • Vancomycin
  • N-phenethylbenzamide