Baccaramiones A-D, Four Highly Oxygenated and Rearranged Trinorditerpenoids from Baccaurea ramiflora .

Baccaramiones A-D ( 1 - 4 ), four highly oxygenated and rearranged trinorditerpenoids, were isolated from Baccaurea ramiflora . Compound 1 is a 1(10 → 5)- abeo -15,16,17-trinor- ent -abietane featuring a unique 5/6/6 spirocyclic scaffold, and 2 - 4 are the first example of a novel 20(10 → 5)- abeo -15,16,17-trinor- ent -abietane skeleton. Their structures were established by spectroscopic analysis, X-ray crystallography, and electronic circular dichroism calculations. A plausible biosynthetic pathway for 1-4 was proposed. Interestingly, compounds 3 and 4 exhibited significant immunosuppressive activities against concanavalin A-induced T cell proliferation and lipopolysaccharide-induced B cell proliferation in vitro.