Anti-inflammatory Ursane- and Oleanane-Type Triterpenoids from Vitex negundo var. cannabifolia

Six new polyoxygenated triterpenoids, cannabifolins A–F (1–6), and eight known triterpenoids, 7–14, were isolated from the leaves of Vitex negundo var. cannabifolia. The absolute configuration of cannabifolin A (1) was determined by single-crystal X-ray crystallographic analysis. Compounds 1 and 2 represent a class of rare natural pentacyclic triterpenoids bearing cis-fused C/D rings and are the first examples of 12,19-epoxy ursane- and oleanane-type triterpenoids. Compounds 3, 7, 8, and 14 exhibited inhibition of nitric oxide production in lipopolysaccharide-induced RAW 264.7 macrophages with IC50 values in the range 24.9–40.5 μM.