Stylotella aurantium

Ecological studies indicate that the Australian sponge Stylotella aurantium inhibits the settlement of ascidian larvae. A dichloroimine metabolite, stylotellane B (132), was isolated which displayed weak P-388 activity [105],... 

Styloguanidins, e.g. 135, chitinase inhibitors from the marine sponge Stylotella aurantium, inhibit the moulting of cyprid larvae of barnacles at a concentration of 10 ppm [108]. They are closely related to palauamine (67). 

The new red algal species Laurencia mariannensis from the Great Barrier Reef provides the novel sesquiterpene 297, along with the known pacifenol and deoxy-prepacifenol, which are now fully characterized by NMR for the first time (539). The Philippine Laurencia majuscula has furnished 13 novel halogenated sesquiterpenes 298-310, of which the major components are the majapolenes A (298, 299) (two diastereomers), which are also found in Laurencia caraibica (540). Most of these compounds occur as inseparable diastereomers. A collection of Laurencia majuscula from the South China Sea has yielded the cedrene-type sesquiterpene majusin (311) (541). A new sesquiterpene dichloroimine, stylotellane A (312), was isolated from the sponge Stylotella aurantium (Fig. 3.3) (542). 

Fig. 3.3 Stylotella aurantium, a sponge that produces the dichloroimine stylotellane A (312) (Photo A. Flowers)...

Simpson JS, Raniga P, Garson MJ (1997) Biosynthesis of Dichloroimines in the Tropical Marine Sponge Stylotella aurantium. Tetrahedron Lett 38 7947... 

Musman M, Tanaka J, Higa T (2001) New Sesquiterpene Carbonimidic Dichlorides and Related Compounds from the Sponge Stylotella aurantium. J Nat Prod 64 111... 

Brust A, Garson MJ (2004) Dereplication of Complex Natural Product Mixtures by 2D NMR Isolation of a New Carbonimidic Dichloride of Biosynthetic Interest from the Tropical Marine Sponge Stylotella aurantium. ACGC Chem Res Commun 17 33... 

Patil AD, Freyer AJ, Killmer L, Hofmann G, Johnson RK (1997) Z-Axinohydantoin and Debromo-Z-axinohydantoin from the Sponge Stylotella aurantium Inhibitors of Protein Kinase C. Nat Prod Lett 9 201... 

Kinnel RB, Gehrken H-P, Swali R, Skoropowski G, Scheuer PJ (1998) Palau amine and Its Congeners A Family of Bioactive Bisguanidines from the Marine Sponge Stylotella aurantium. J Org Chem 63 3281... 

Kato T, Shizuri Y, Izumida H, Yokoyama A, Endo M (1995) Styloguanidines, New Chitinase Inhibitors from the Marine Sponge Stylotella aurantium. Tetrahedron Lett 36 2133... 

Simpson, J. S., Raniga, P., and Garson, M. J., Biosynthesis of dichloroimines in the tropical marine sponge Stylotella aurantium, Tetrahedron Lett., 38, 7947, 1997. 

This class of cyclic oroidin derivatives also parallels the above N-7/C-11 + N-1/ C-12 class in the presence of complex derivatives in which the isophakellin skeleton appears to be conjugated with an aminoimidazolyl propene unit. These isomers of palau amines are called styloguanidines (58-60) they have been isolated from the same sponge that contains palau amines, Stylotella aurantium [90]. 

Kinnel, R.B., Gehrken, H.-P, SwaU, R. etal. (1998) Palau amine and its congeners A family of bioactive bisguanidines from the marine sponge Stylotella aurantium. The Journal of Organic Chemistry, 63, 3281-3286. 

Patil, A. D., Freyer, A. J., Killmer, L., Holinann, G., Johnson, R. K., (1997). Z-axinohydantoin and debromo-Z-axinohydantoin from the sponge Stylotella aurantium. Inhibitors of protein kinase C. Nat. Prod. Lett. 9,201-207. 

Kato, T., Shizuri, Y., Izumida, H., Yokoyama, A., Endo, M., (1995). Styloguanidines, new ehitinase inhibitors from the marine sponge Stylotella aurantium. Tetrahedron Lett. 36,2133-2136. 

Cyclic peptide antibiotic. Constit. of the sponges Phakellia costata and Stylotella aurantium. Cytotoxic. Amorph. solid. Mp 247-249°. [a] -50.5 (c, 0.33 in CHCI3). 

Alkaloid from the marine sponge Stylotella aurantium. Potent chitinase inhibitor. 

Their significant bioactivities and daunting structural complexity are good enough reasons for captivating organic chemists who have exerted intensive effort to access those alkaloids. For instance, palau amine 247, a polycyclic alkaloid isolated from Stylotella aurantium, exhibits immunosuppressive activity and moderate cytotoxicity. Indeed,... 

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