Fragilisinins A–L, new briarane-type diterpenoids from gorgonian Junceella fragilis

Abstract

Our continuous study on the South China Sea gorgonian Junceella fragilis led to the isolation of twelve new briarane type diterpenoids, fragilisinins A-L (1-12), along with seven known analogues (13-19), including four naturally produced organoiodides (9-12), they are the first four iodine-containing briarane diterpenoids from this gorgonian species. Their structures were determined by MS, 1D and 2D NMR spectra analyses and by comparison with those reported in the literature. The configuration of 1 was confirmed by single-crystal X-ray diffraction data. The antifouling test showed that compounds 5, 6, 10, 13, and 15 had potent antifouling activities at nontoxic concentrations with EC50 values of 14.0, 12.6, 11.9, 5.6, and 10.0 μM, respectively. © 2014 The Royal Society of Chemistry.