Terpene isonitriles

Wright AD, Wang H, Gurrath M, Kdnig GM, Kocak G, Neumann G, Loria P, Foley M, Tilley L (2001) Inhibition of Heme Detoxification Processes Underlies the Antimalarial Activity of Terpene Isonitrile Compounds from Marine Sponges. J Med Chem 44 873... 

Nitrogen-Containing Terpenes Isonitriles and Reiated Derivatives... 

Wright, A.D., Wang, H., Gurrath, M., Kdnig, G.M., Kocak, G., Neumann, G., Loria, P., Foley, M., and Tilley, L. (2001) Inhibition of heme detoxification processes underlies the antimalarial activity of terpene isonitrile compounds from marine sponges. I. Med. Chem., 44, 873-885. 

These derivatives are interesting insofar as this category of nitrogen terpenes, which possess functional isothiocyanate and N-formylamino groups, is common in sponges of the family Axinellidae (Hahchondrida). The only notable difference is that Axinellidae almost always contain the corresponding isonitrile derivative, whereas this does not seem to have been identified so far in any member of the Lithistida. 

One point about isonitriles and isothiocyano and N-formylamino derivatives concerns the fact that they have always been observed on terpenic skeletons, to the exclusion of any other supporting structure. In addition, nearly 150 molecules are now known and ah are either sesquiterpenes or diterpenes. The carbon skeletons are numerous and often original, such as axane, spiroaxane, pupukeanane, amphilectane and cycloamphilectane. Most of these skeletons are presented in Figure 19.54. 

Figure 19.54 Terpenic carbon skeletons bearing isonitrile and related groups.

The biosynthesis of sesquiterpenes containing isonitrile and isothiocyanate groups was also investigated by incorporation of cyanide and potassium thiocyanate labeled with carbon 14 in the sponge Acanthdla cavernosa, which is consumed by the nudibranch Phyllidiella =Phyllidia) pustulosa. The results show that the mollusk does not synthesize de novo any nitrogen-containing terpene and consequently it acquires the sesquiterpenes substituted... 

---