Communiferulins, farnesylated coumarins from the roots of Ferula communis and their anti-neuroinflammatory activity

Three new farnesylated coumarins, communiferulins A–C (1–3), and a farnesylated chromone, ferchromone (4), were isolated from the roots of an Apiaceous plant Ferula communis. Their structures including the relative configurations were elucidated by a combination of spectroscopic analyses and calculations of the NMR data. Communiferulins A–C (1–3) had dihydrofuran rings fused to C-3 and C-4 of their coumarin moieties, while 3 possessed one additional furan ring. HPLC analyses using a chiral column showed 1–4 to be racemates, and the absolute configurations of (+)-1, (–)-1, (+)-2, and (–)-2 were deduced by comparison of their ECD spectra with TDDFT-calculated spectra. Communiferulins A (1) and B (2), and ferchromone (4) showed inhibitory activities on IL-1β production from LPS-stimulated microglial cells.