Zinc clathridine

Negatively charged alkaloids are rare. The isolation of the zinc salt Clathridin (6) (Scheme 2) from the marine sponge Clathrina clathrus was reported in 1990 (90T4387). Other examples are bis(isonaamidinato) A Zinc... 

Compound 325 is the taurine derivative of clathridine (a very stable zinc complex obtained from Clathrina clathrus) [240] and was isolated from the sponge Leucetta microrhaphis. Compound 325 is (9E)-clathridine 9-Ar-(2-sulfoethyl)imine and its structure was deduced by spectroscopic and chemical analysis, and confirmed by single crystal X-ray analysis. The taurine residue appears to sterically inhibit the formation of the zinc complex [241],... 

Clathridine A has shown antibacterial properties and exhibited anti-Candida albicans activity. The corresponding zinc complex has shown selective anti-Staphylococcus aureus activity [42]. 

Clathridine, an unusual alkaloid derived from imidazole and guanidine, was isolated in 1989, in the form of a 2 1 complex with a zinc atom, in the sponge Clathrina clathms. Since 1990, some other complexes of zinc have been isolated from calcareous sponges, such as the complex containing isonaamidine C (Alvi et al, 1993 Mancini et al, 1995 Fu et al, 1998). For additional information, see Chapter 19. 

In 1989, clathridine and its zinc complex were isolated from Clathrina clathrus, and the structure of the zinc complex in the solid state was obtained by X-ray diffraction (Ciminiello et al., 1989,1990a). Subsequently, other chiral zinc complexes were isolated with imidazole alkaloids from sponges of the genus Leucetta (Alvi et al., 1993 Mancini et al., 1995 Fu et al., 1998a). The roles of such complexes in sponges are still unknown. 

Ciminiello, P., Eattorusso, E., Magno, S., and Mangoni, A. (1989) Clathridine and its zinc complex, novel metabohtes from the marine sponge Ciathrina dadtrus. Tetrahedron, 45, 3873—3878. 

---