Selective phytotoxic activity of 2,3,11β,13-tetrahydroaromaticin and ilicic acid isolated from Inula graveolens.

Inula graveolens is a poisonous annual plant of Mediterranean origin. The invasive nature of the plant suggests that it may possess phytotoxic activity. The aim of this study was to assess the ability of I. graveolens to inhibit the growth of different plants in Petri dish and to identify the main bioactive compounds. Bio-guided fractionation of the plant extracts led to the isolation of 2,3,11β,13-tetrahydroaromaticin (THA) and ilicic acid. Both compounds showed selective and significant phytotoxic activity at 25 ppm. Root length of barley, oat, millet, tuberous canary grass and lentils were significantly reduced by 25 ppm of THA, while the root of cauliflower, cress and radish were similarly reduced by ilicic acid at 25 ppm. The structure of each compound was elucidated by using NMR and HR-MS. X-ray crystallography of THA is reported for the first time to confirm the relative stereochemistry of the compound.