Fragilides K and L, New Briaranes from the Gorgonian Coral .

Two new briarane metabolites—fragilides K () and L ()—along with five known analogues—gemmacolide X, praelolide, juncins P and ZI, and gemmacolide V (⁻)—were extracted and purified from , a gorgonian coral. Based on data obtained via spectroscopic techniques, the structures of new briaranes and were determined and the cyclohexane rings in and were found to exist in chair and twist boat conformation, respectively. Additionally, anti-inflammatory analysis showed that briaranes , , and inhibited pro-inflammatory inducible nitric oxide synthase protein expression and briaranes and suppressed the cyclooxygenase-2 level, in LPS-stimulated murine macrophage-like RAW264.7 cells.