Alkamides from the fruits of Piper longum and Piper nigrum displaying potent cell adhesion inhibition

Bioorg Med Chem Lett. 2008 Aug 15;18(16):4544-6. doi: 10.1016/j.bmcl.2008.07.045. Epub 2008 Jul 15.

Abstract

Eight alkamides 1-8 were isolated by bioassay-guided isolation of EtOH extracts of the fruits of Piper longum and Piper nigum (Piperaceae). Their structures were elucidated by spectroscopic analysis ((1)H, (13)C NMR, and ESI-MS) as follows: guineensine (1), retrofracamide C (2), (2E,4Z,8E)-N-[9-(3,4-methylenedioxyphenyl)-2,4,8-nonatrienoyl]piperidine (3), pipernonaline (4), piperrolein B (5), piperchabamide D (6), pellitorin (7), and dehydropipernonaline (8). Their compounds 3-5, 7, and 8 inhibited potently the direct binding between sICAM-1 and LFA-1 of THP-1 cells in a dose-dependent manner, with IC(50) values of 10.7, 8.8, 13.4, 13.5, and 6.0 microg/mL, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biological Assay
  • Cell Adhesion / drug effects*
  • Cell Line
  • Chemistry, Pharmaceutical / methods
  • Drug Design
  • Ethanol / pharmacology
  • Humans
  • Inhibitory Concentration 50
  • Magnetic Resonance Spectroscopy
  • Models, Chemical
  • Piper / chemistry
  • Piper / metabolism*
  • Piper nigrum / chemistry
  • Piper nigrum / metabolism*
  • Plant Extracts / pharmacology*
  • Spectrometry, Mass, Electrospray Ionization
  • Spectrophotometry / methods

Substances

  • Plant Extracts
  • Ethanol