- Alkamides from the fruits of Piper longum and Piper nigrum displaying potent cell adhesion inhibition.
Alkamides from the fruits of Piper longum and Piper nigrum displaying potent cell adhesion inhibition.
Bioorganic & medicinal chemistry letters (2008-08-02)
Seung Woong Lee, 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
PMID18672369
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.