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ID: ALA1156593

Journal: Bioorg Med Chem Lett

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

Authors: Lee SW, Kim YK, Kim K, Lee HS, Choi JH, Lee WS, Jun CD, Park JH, Lee JM, Rho MC.

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.

CiteXplore: 18672369

DOI: 10.1016/j.bmcl.2008.07.045