Chemical constituents from seeds of Aplinia katsumadai, inhibition on NF-κB activation and anti-tumor effect

Abstract

To study the chemical constituents from the seeds of A. katsumadai, and their inhibition on NF-kappaB activation and antitumor effect. Tweleve compounds were isolated from the seeds of Aplinia katsumadai on repeated column chromatography on silica gel, and Sephadex LH-20, and their structures were determined mainly by means of MS and NMR techniques; and their inhibition on NF-kappaB activation and antitumor effect were also tested by High-Content Screening (image-based) with immunofluorescent probe and MTT method, respectively. From the EtOAC fraction of the seeds of A. katsumadai 12 compounds were isolated and identified as follows: (3S,5S)-trans-3,5-dihydroxy-1 ,7-diphenyl-hept-1-ene (1), (3R,5S)-trans-3,5-dihydroxy-1,7-diphenyl-hept-1-ene (2), 5-hydroxy-1,7-diphenyl-hepta-6-en-3-one (3), cardamonin (4), alpinetin(5), pinocembrin(6), pinostrobin(7), naringenin (8), (+)-catechin(9), chrysin(10), rutin(11) and 2,4- dihydroxy-6-phenethl-benzinic acid methyl ester (12). Compound 14 showed inhibitory effect on NF-kappaB activation with the IC50 values as 14.8, 16.5, 23.2 and 7. 5 micromol x L(-1), respectively. Compound 4 displayed cytotoxicity against leukemia K562 cells and human hepatoma cell line SMMC-7721 with IC50 values as 3.2 and 3.5 mg x L(-1), and compound 6 showed moderate cytotoxicity against SMMC-7721 with the IC50 value as 18.3 mg x L(-1). Compounds 7-12 were isolated from A. katsumadai for the first time and Compound 12 were isolated from the genus Aplinia for the first time; compound 4 has the activity of anti-tumor and NF-kappaB activation inhibition, compounds 1-3 have the activity NF-KB activation inhibition.