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Abstract
Two new briarane metabolites—fragilides K (1) and L (2)—along with five known analogues—gemmacolide X, praelolide, juncins P and ZI, and gemmacolide V (3–7)—were extracted and purified from Junceella fragilis, a gorgonian coral. Based on data obtained via spectroscopic techniques, the structures of new briaranes 1 and 2 were determined and the cyclohexane rings in 1 and 2 were found to exist in chair and twist boat conformation, respectively. Additionally, anti-inflammatory analysis showed that briaranes 2, 3, and 6 inhibited pro-inflammatory inducible nitric oxide synthase protein expression and briaranes 3 and 7 suppressed the cyclooxygenase-2 level, in LPS-stimulated murine macrophage-like RAW264.7 cells.
Highlights
Junceella fragilis (Ridley, 1884) [1,2,3], a gorgonian coral, has been reported to contain high levels of diterpenoids with a briarane carbon skeleton
The in vitro anti-inflammatory activities of compounds 1–7 were assessed by investigating their inhibition effects on LPS-induced pro-inflammatory inducible nitric oxide synthase (iNOS) and COX-2 protein expressions in the macrophage cell line using western blot analysis [24,25,26]
Gorgonian corals belonging to the family Ellisellidae have proven to be a rich source of interesting polyoxygenated and chlorinated briarane-related natural products with complex structures and extensive bioactivities
Summary
Junceella fragilis (Ridley, 1884) (family Ellisellidae) [1,2,3], a gorgonian coral, has been reported to contain high levels of diterpenoids with a briarane carbon skeleton. These diterpenoids often have complex structures and possess varied bioactivities [4,5,6,7,8,9]. We isolated and determined the structures of these briaranes, and performed anti-inflammatory assays to determine their anti-inflammatory activities in terms of targeting inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) in a macrophage in vitro system. Praelolide (4), juncins P (5) and ZI (6), gemmacolide V (7), and junceellonoid B (8)
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