Norsesterterpene peroxide

Sigmosceptrellin A (114), a norsesterterpene peroxide, was isolated as a methyl ester from the Papua New Guinean Sigmosceptrella laevis. It consists of the ichthyotoxic fraction of this sponge along with its stereoisomers B and Mycaperoxide A (115) was related to sigmosceptrellins, in which 13-Me was... 

Sigmosceptrellin (6) and muqubilin (7) are norsesterterpene peroxides which we reisolated from the Red Sea sponges Sigmosceptrella and Prianos sp., and previously described by Kashman and Rotem in 1979, and by Albericci and co-workers 3 years later. The structural similarity to the artemisinins, which peroxide moieties contribute to their antimalarial activity, suggests that the antimalarial activities of these compounds may be... 

Albericci, M., J.C. Braekman, D. Daloze, and B. Tursch Chemical Studies of Marine Invertebrates. XLV. The Chemistry of Three Norsesterterpene Peroxides from the Sponge Sigmosceptrella laevis. Tetrahedron 38, 1881-1890 (1982). 

Albericd, M., Breakman, J.C., Daloze, D., and Tursch, B. (1982) Marine Invertebrates. XLV. The chemistry of three norsesterterpene peroxides from the sponge SigmosceptreUa laevis. Tetrahedron, 38, 1881-1890. 

Dai, J., Liu, Y, Zhou, Y.-D., and Nagle, D.G. (2007a) Hypoxia-selective antitumor agents norsesterterpene peroxides from the marine sponge Diacamus levii preferentially suppress the growth of tumor cells under hypoxic conditions. J, Nat, Prod, 70, 130-133. 

El Sayed, K.A., Hamann, M.T., Hashish, N.E., Shier, W.T., Kelly, M., and Khan, A.A. (2001a) Anthnalarial, antiviral and antitoxoplasmosis norsesterterpenes peroxides acids from the Red Sea sponge Diacamus erythraeanus. J. Nat. Prod., 64, 522-524. 

Phuwapraisirisan, P., Matsrmaga, S., Fusetani, N., Chaitanawisuti, N., Kritsanapuntu, S., and Menasveta, P. (2003) Mycaperoxide H, a new cytotoxic norsesterterpene peroxide from a Thai marine sponge Mycale sp./. Nat. Prod., 66, 289-291. 

Youssef D.T.A. (2004) Tasnemoxides A-C, new cytotoxic cyclic norsesterterpene peroxides from the Red Sea sponge Diacarnus erythraenus. J. Nat. Prod., 67,112-114,... 

There are three classes of cyclic peroxides that were found in marine sponges steroidal peroxides, norsesterterpene and norditerpene peroxides, and polykide peroxides many of them were isolated and their relative and absolute stereochemistry was determined. Most of them (even as crude extracts) show exceptional antimicrobial and antifungal propoperties (cf. Section 8.10.3). For example, the norsesterterpene 1,2-dioxides mycaperoxides A and B 222 and 223 (Scheme 63) showed significant cytotoxicity and in vitro antiviral activity. 

Ovenden, S.P.B. and Capon, R.J. (1998) Truncuhns G—I new norsesterterpenes cyclic peroxides from a Southern Australian... 

Capon, R.J., MacLeod, J.K., and Willis, A.C. (1987) Trunculins A and B norsesterterpenes cyclic peroxides from a marine sponge, LatruncuUa brevis. J. Org. Chem., 52, 339-342. 

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