Alkamides from the fruits of Piper longum and Piper nigrum displaying potent cell adhesion inhibition.
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.
Lee
Seung Woong
SW
Natural Medicine Research Center, Korea Research Institute of Bioscience and Biotechnology, Daejeon 305-806, Republic of Korea.
Kim
Young Kook
YK
Kim
Koanhoi
K
Lee
Hyun Sun
HS
Choi
Jung Ho
JH
Lee
Woo Song
WS
Jun
Chang-Duk
CD
Park
Jee Hun
JH
Lee
Jeong Min
JM
Rho
Mun-Chual
MC
D001681:Biological Assay; D002448:Cell Adhesion / Q000187:drug effects*; D002460:Cell Line; D002626:Chemistry, Pharmaceutical / Q000379:methods; D015195:Drug Design; D000431:Ethanol / Q000494:pharmacology; D006801:Humans; D020128:Inhibitory Concentration 50; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D031701:Piper / Q000737:chemistry / Q000378:metabolism*; D029222:Piper nigrum / Q000737:chemistry / Q000378:metabolism*; D010936:Plant Extracts / Q000494:pharmacology*; D021241:Spectrometry, Mass, Electrospray Ionization; D013053:Spectrophotometry / Q000379:methods
D010936:Plant Extracts; D000431:Ethanol