Abstract
Terpene content of two distinct collections of the nudibranch Phyllidia coelestis from the South China Sea has been chemically analyzed. A series of amphilectene diterpenes, most likely of dietary origin, with isocyano and formamido functionalities have been isolated from both collections and spectroscopically characterized by an exhaustive nuclear magnetic resonance (NMR) analysis. Interestingly, the structural architecture of compounds 5–7 and 9 with both 8,13-cis and 12,13-cis ring junctions is unprecedented in the amphilectene skeleton. Metabolite 3, which was the most abundant in the nudibranch’s mantle, has been shown to deter feeding by a generalist predator, supporting its involvement in chemical defense.
Highlights
Nudibranchs are a group of gastropod mollusks lacking shells [1] that are widely distributed in all seas through the world
Two populations of Phyllidia coelestis of 10 and 9 individuals were collected at Hainan Island
Terpene isonitriles often co-occurring with oxidized derivatives with formamido, isocyanate, isonitriles often co-occurring with oxidized derivatives formamido, and Terpene isothiocyanate functionalities are secondary metabolites of a with restricted group isocyanate, of marine and isothiocyanate functionalities are secondary metabolites of a restricted group of marine sponges sponges [8,9,14]
Summary
Nudibranchs are a group of gastropod mollusks lacking shells [1] that are widely distributed in all seas through the world. Phyllidia and Phyllidiella have been chemically investigated resulting in the isolation of numerous bioactive sesquiterpenes with different structural architectures all exhibiting nitrogenous functional groups, such as cyano, isocyano, isothiocyano, and formamido functionalities [8,9]. These compounds display pronounced antimalarial [10,11], antifouling [12] and other biological properties [9,13,14]. The unprecedented 12,13-cis ring junctions are presented here
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