Neolignans and polyoxygenated seco-cyclohexenes from the stems and leaves of Piper suipigua Buch.-Ham. ex D. Don

Nat Prod Res. 2023 May;37(9):1429-1438. doi: 10.1080/14786419.2021.2011274. Epub 2021 Dec 5.

Abstract

Five new compounds including, a neolignan, eupomatenoid-19 (1) and four polyoxygenated seco-cyclohexenes, artahongkongenes G-J (2-5), together with fifteen known compounds (6-20) were isolated from the stems and leaves of Piper suipigua Buch.-Ham. ex D. Don. Their structures were determined by spectroscopic evidence (IR, UV, 1H NMR, 13C NMR and 2 D NMR) as well as MS. The absolute configurations of polyoxygenated seco-cyclohexenes 2-8 were identified by NOESY data and by comparison of their experimental and calculated ECD spectral data. Neolignans, eupomatenoid-19 (1) and eupomatenoid-7 (10), displayed cytotoxicity against several cancer cell lines. In addition, eupomatenoid-7 (10) showed antibacterial activity against Bacillus cereus, Bacillus subtilis and Staphylococcus aureus.

Keywords: Piper suipigua Buch.-Ham. ex D. Don; Piperaceae; antibacterial activity; cytotoxicity; neolignan; polyoxygenated seco-cyclohexene.

MeSH terms

  • Cyclohexenes / analysis
  • Lignans* / analysis
  • Lignans* / pharmacology
  • Molecular Structure
  • Piper* / chemistry
  • Plant Extracts / chemistry
  • Plant Leaves / chemistry

Substances

  • Lignans
  • Cyclohexenes
  • Plant Extracts