Quinolone alkaloids from Evodiae fructus inhibit LFA-1/ICAM-1-mediated cell adhesion

Abstract

Four quinolone alkaloids were isolated by bioactivity-guided fractionation from the methanol extracts of Evodiae fructus fruits. Structures of compounds were elucidated by spectroscopic analysis (1H-, 13C-NMR and MS), as follows: 1-methyl-2-undecyl-4(1H)-quinolone (1), evocarpine (2), dihydroevocarpine (3) and mixture of [1-methyl-2-[(Z)-10- pentadecenyl]-4(1H)- quinolone and 1-methyl-2-[(Z)-6-pentadecenyl]-4(1H)-quinolone] (4). They inhibited the interaction of sICAM-1 and LFA-1 in THP-1 cells at IC50 values of >150 (1), 109.8 (2), >150 (3) and 40.9 μM (4), respectively.