Secotrijugins A−D, four highly oxidized and rearranged limonoids from Trichilia sinensis and their anti-inflammatory activity

Four undescribed highly oxidized and rearranged limonoids, secotrijugins A-D, were purified from the leaves and twigs of Trichilia sinensis. Within them, secotrijugin A was characterized as a rare 30-nortrijugin-type limonoid with an unusual cleavage of 1,14-ether bond, secotrijugins B and C represented new examples with the cleavage of δ-lactone ring D, and secotrijugin D was a rare trijugin-type limonoid with an unusual 2,6-oxygen bridge. The structures of limonoids were characterized by means of spectroscopic analysis and ECD calculations. The cellular screening revealed that secotrijugin B was the most active against LPS-stimulated NO production in BV-2 cells, which played an anti-inflammatory role by downregulating COX-2 and iNOS protein expression. The further in vivo experiments confirmed that secotrijugin B had strong in vivo anti-inflammatory effect via suppressing NO and ROS generation.