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.
Seung Woong Lee  1 ,  Young Kook Kim ,  Koanhoi Kim ,  Hyun Sun Lee ,  Jung Ho Choi ,  Woo Song Lee ,  Chang-Duk Jun ,  Jee Hun Park ,  Jeong Min Lee ,  Mun-Chual Rho
Affiliations
  • 1. Natural Medicine Research Center, Korea Research Institute of Bioscience and Biotechnology, Daejeon 305-806, Republic of Korea.
PMID: 18672369 DOI: 10.1016/j.bmcl.2008.07.045
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.