Populusene A, an Anti-inflammatory Diterpenoid with a Bicyclo[8,4,1]pentadecane Scaffold from Populus euphratica Resins

Populusene A (1), an unprecedented carbon skeleton featuring a bicyclo[8.4.1]­pentadecane nucleus and a bridgehead double bond (anti-Bredt system), and populusin A (2), a cembrane-type diterpenoid possessing an uncommon dioxatricyclo­[6.6.1.1^2,5]­hexadecane scaffold, were isolated from the exudates of Populus euphratica. Their structures were elucidated by spectroscopic, computational, and crystallographic methods. A plausible biosynthetic route for 1 and 2 was proposed. Compounds 1 and 2 were found to significantly inhibit the production of TNF-α and IL-6 and the expression of iNOS, COX-2, and p-NF-κB at 125 nM in RAW264.7 cells.