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.