Lignans and coumarins from the roots of Anthriscus sylvestris and their increase of caspase-3 activity in HL-60 cells

Abstract

A new lignan, sylvestrin (1), was isolated from the MeOH-soluble fraction of the roots of Anthriscus sylvestris HOFFM. (Umbelliferae), along with six lignans (2-7), three coumarins (8-10), and a polyacetylene (11). The structure of sylvestrin was determined to be 2-(3′,4′,5′- trimethoxybenzylidene)-3-(3″,4″-methylendioxybenzyl) -γ-butyrolactone (1) by spectroscopic means, including 2D-NMR. The eleven compounds were assessed for their abilities to activate a caspase-3 in human promyeloid leukemic HL-60 cells. The intracellular caspase-3 activity of (-)-deoxypodophyllotoxin (3), angeloyl podophyllotoxin (5), deoxypicropodophyllin (6), picropodophyllotoxin (7), and falcarindiol (11) increased approximately 4.6, 3.6, 3.7, 3.9, and 3.9-fold, at 0.001, 1, 1, 1, and 20 μM, respectively, over that of the untreated control. In addition, compounds 3, 5, 6, and 7 showed apoptosis-inducing activities that were measured by DNA fragmentation in HL-60 cells. © 2007 Pharmaceutical Society of Japan.