New natural product isolation and comparison of the secondary metabolite content of three distinct samples of the sea hare Aplysia dactylomela from Tenerife

Three distinct samples of the sea hare Aplysia dactylomela from two different locations around Tenerife (Spain) were investigated for their secondary metabolite content. The investigation resulted in the isolation of five new natural products (1, 2, 5-7), a number of compounds known from red algae of the genera Laurencia (4, 8-14) and Plocamium (17-19), and three known sea-hare metabolites (3, 15, 16). This is the first report of monoterpenes (17-19) from A. dactylomela. All structures were determined mainly by spectroscopic methods (1D and 2D NMR, MS, LR). Compounds 11, 14, 15, and 17 demonstrated significant cytotoxicity toward three cancer cell lines (HM02, HEP G2, and MCF 7; IC50 for 11, 7.0 to <1.0 mu g/mL; 14, <1.0 mu g/mL; 15, 17 to <1.0 mu g/mL; 17, 1.0 to 1.5 mu g/mL). Compounds 3, 8, 9, 11, 15, 18, and 19 exhibited activity in a brine shrimp bioassay in the range of 100% lethality within 24 h to 40% after 48 h. Metabolites 11, 14, 15, and 19 showed moderate antimicrobial activities (2-25 mm total/growth inhibition of several organisms), with 19 also being strongly algicidal (MIC 7-11 mu g/filter disk).