Sponge diterpenes

Koenig GM, Wright AD, Angerhofer CK. (1996) Novel potent antimalarial diterpene isocyanates, isothiocyanates, and isonitrile from tropical marine sponge Cymbastela hooperi. J Org Chem 61 3259-3267. 

Kohmoto, S. McConnell, O.J. Wright, A. Cross, S. (1987) Isospongiadiol, a cytotoxic and antiviral diterpene from a Caribbean deep water marine sponge, Spongia sp. Chem. Lett., 1687-90. 

Umeyama, A. Machida, M. Nozaki, M. Arihara, S. (1998) Peroxypolasol and mugipolasol two novel diterpenes from the marine sponge Epipolasis sp. J. Nat. Prod., 61, 1435-6. 

Vuong, D. Capon, R.J. (2000) Phorbasin A a novel skeleton diterpene from a southern Australian marine sponge, Phorbas species. J. Nat. Prod., 63, 1684-5. 

A Japanese sponge of the Adociidae family contained 10-isothiocyanatobiflora-4,15-diene (290), which was identified by spectral analysis [283], A. cavernosa from Fiji yielded a diterpene isothiocyanate (291) [284]. 

The marine isothiocyanates, with more than 80 compounds isolated so far, form the largest group of naturally occurring isothiocyanates. This well-established group of marine natural products is constituted mainly by terpene metabolites present as sesquiterpene and diterpene derivatives. The non-terpene isothiocyanate compounds include two cylindricine alkaloids and a series of long-chain aliphatic metabolites. Marine sponges constitute the main source of these compounds, although they are also found in nudibranches and tunicates. 

Two acyclic diterpene tetraene isothiocyanates have been isolated from sponges so far. Famesyl isothiocyanate (220) was obtained from Pseudaxinyssa pitys [184] while compound (+)-221 was isolated from Halichondria sp. [185]. Their structures were elucidated by interpretation of their spectral data. 

Compounds 237 and 238 are the only isothiocyanate diterpenes with a biflorane carbon skeleton that do not belong to the kalihinol family. They are diastereosiomers of 10-isothiocyanatobiflora-4,15-diene. A planar structure was reported for compound 237, which was obtained from an unidentified sponge of the Family Adocidae [191]. A... 

Wolf D, Schmitz FJ (1998) New Diterpene Isonitriles from the Sponge Phakellia pulcher-rima. J Nat Prod 61 1524... 

Garson, M. J., Biosynthesis of the novel diterpene isonitrile diisocyanoadociane by a marine sponge of the Amphimedon genus incorporation studies with [14C]cyanide and sodium [2-14C]acetate, J. Chem. Soc. Chem. Commun., 35, 1986. 

Fookes, C. J. R., Garson, M. J., MacLeod, J. K., Skelton, B. W., and White, A. H., Biosynthesis of diisocyanoadociane, a novel diterpene from the marine sponge Amphimedon sp. Crystal structure of a monoamide derivative, J. Chem. Soc. Perkin Trans. I, 1003, 1988. 

Thompson, J. E., Murphy, P. T., Bergquist, P. R., and Evans, E. A., Environmentally induced variation in diterpene composition of the marine sponge Rhopaloeides odorabile, Biochem. Syst. Ecol., 15, 595, 1987. 

Mayol, L., Piccialli, V., and Sica, D., Gracilin A, a unique nor-diterpene metabolite from the marine sponge Spongionella gracilis, Tetrahedron, 26, 1357, 1985. 

Manriquez, V., San-Martin, A., Rovirosa, J., Darias, J., and Peters, K., Structure of membranolide, a diterpene from the antarctic sponge Dendrilla membranosa, Acta Cryst. Sect. C, 46, 2486, 1990. 

---