Metabolites from the Sea Hare Aplysia fasciata

Examination of the digestive and hermaphroditic glands' organic extract of the sea hare Aplysia fasciata yielded 16 metabolites, including eight sesquiterpenes, three diterpenes, and five C(15)-acetogenins. Among them, three sesquiterpenes, 6-hydroxy-1-brasilene (1), epibrasilenol acetate (2), and 6-epi-beta-snyderol (3), one acetogenin, (3Z,9Z)-7-chloro-6-hydroxy-12-oxo-pentadeca-3,9-dien-1-yne (4), and one diterpene, 16-acetoxy-15-bromo-7-hydroxy-9(11)-parguerene (5), are new natural products. The structure elucidation and the assignment of the relative configurations of the isolated natural products were established on the basis of extensive analyses of their spectroscopic data (NMR, MS, IR).