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

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Title
Alkamides from the fruits of Piper longum and Piper nigrum displaying potent cell adhesion inhibition
Author(s)
Seung Woong Lee; Young Kook Kim; K Kim; Hyun Sun Lee; Jung Ho Choi; Woo Song Lee; C D Jun; J H Park; J M Lee; Mun Chual Rho
Bibliographic Citation
Bioorganic & Medicinal Chemistry Letters, vol. 18, no. 16, pp. 4544-4546
Publication Year
2008
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 (1H, 13C 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 IC50 values of 10.7, 8.8, 13.4, 13.5, and 6.0 μg/mL, respectively.
Keyword
AlkamidesCell adhesion moleculesPiper longum L.Piper nigum L.PiperaceaeTHP-1 cells
ISSN
0960-894X
Publisher
Elsevier
DOI
http://dx.doi.org/10.1016/j.bmcl.2008.07.045
Type
Article
Appears in Collections:
Jeonbuk Branch Institute > Functional Biomaterial Research Center > 1. Journal Articles
Ochang Branch Institute > Natural Product Research Center > 1. Journal Articles
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