Orthoquinone and Naphthalenone Derivatives from Berrya ammonilla and Their Anti-Inflammatory Activity

A new orthoquinone, berryammone A ( 1 ), and four new naphthalenone derivatives, berryammone B ( 2 ), berryammone C ( 3 ), 6- O -methylberryammone C ( 4 ), and 4- O -methylberryammone C ( 5 ), have been isolated from the stem of Berrya ammonilla , together with eleven known compounds ( 6 – 16 ). The structures of these new compounds were determined through spectroscopic and MS analyses. Among the isolates, compounds 1 – 3 , 5 , (+)-pinoresinol ( 6 ), and betulinic acid ( 12 ) exhibited inhibition (IC 50 ≤ 4.41 µM) of superoxide anion generation by human neutrophils in response to formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B (fMLP/CB). Compounds 1 , 2 , and 5 also inhibited fMLP/CB-induced elastase release with IC 50 values ≤ 3.95 µM.