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Title 

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

Authors 

Seung Woong LeeYoung Kook KimK KimHyun Sun LeeJung Ho ChoiWoo Song LeeC D JunJ H ParkJ M LeeMun Chual Rho

Publisher 

Elsevier

Issue Date 

2008

Citation 

Bioorganic & Medicinal Chemistry Letters, vol. 18, no. 16, pp. 4544-4546

Keywords 

alkamidescell adhesion moleculespiper longum L.piper nigum L.piperaceaeTHP-1 cellsdehydropipernonalinefruitintercellular adhesion molecule 1pipernonaline

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.

ISSN 

0960-894X

Link 

http://dx.doi.org/10.1016/j.bmcl.2008.07.045

Appears in Collections

1. Journal Articles > Journal Articles

Registered Date

2019-05-02


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