New nor-chamigrane and bisabolane sesquiterpenoids from the sea hare Aplysia dactylomela

A Survey of Recently Discovered Naturally Occurring Organohalogen Compounds

“…Neither metabolite exhibits appreciable cytotoxicity toward A549, MCF-7, and HepG2 cancer cell lines. 128 The sea hare A. kurodai, collected in Japan, contains the novel labdane-type diterpenes azuriaplysins A (279) and B (280), the structures of which are confirmed by total syntheses of both enantiomers of 279 and 280. Only azuriaplysin B (280) is cytotoxic to HeLa cells (IC 50 8.1 μM).…”

“…Another specimen of A. dactylomela from a different part of Vietnam affords the new 277 and 278 . Neither metabolite exhibits appreciable cytotoxicity toward A549, MCF-7, and HepG2 cancer cell lines . The sea hare A. kurodai , collected in Japan, contains the novel labdane-type diterpenes azuriaplysins A ( 279 ) and B ( 280 ), the structures of which are confirmed by total syntheses of both enantiomers of 279 and 280 .…”

Diversity of Halogenated Secondary Metabolites in Okinawan Aplysia argus Including 12‐Hydroxypinnaterpene C and Their Feeding Targets

“…[1,2] Many of these metabolites exhibit potent cytotoxic, neurotoxic, antifungal, antimicrobial, and antibiofouling activities. [3,4] Despite containing chemicals with strong protective properties, A. argus selectively preys on Laurencia species and can store secondary metabolites from red seaweeds in specialised digestive glands. Although the first investigation of the chemical composition of Aplysia species was reported more than half a century ago, it continues to be an attractive subject for medical and pharmaceutical research because of its ability to concentrate natural products from different algal species that grow in distinct locations.…”