Clathrina clathrus

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. C. exists in the brilliant yellow Mediterranean sponge Clathrina clathrus (Calcispongiae) as a 2 1 Zn complex C,6H,5N504, Mr 341.33, cryst., mp. 260-262 °C (decomp.), it has antimycotic activity against Candida albicans and Saccharomyces cerevi-siae. Leucetta microrhaphis contains the related (9E)-clathridine-9-(2-sulfoethylimine), yellow needles, CigHjoNjOsS, Mr 449.12, mp. 115-211 °C (decomp.). 

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. 

Clathridine and its putative precursor, dathridimine, were fotmd in 2010 in a Mediterranean Clathrina clathrus collected near Marseille, France. After separation of bacteria cells from sponge cells it was shown that both compounds are genuine sponge metabolites (Roue et al., 2010). Me... 

Aiello, A., Ciminiello, P., Fattomsso, E., and Magno, S. (1988) Three new 7-keto sterols from the Mediterranean sponge Clathrina clathrus. Steroids, 52, 533-542. 

Ciminiello, P., Fattorusso, E Magno, S and Mangoni, A, (1989) Clathridine and its zinc complex, novel metabolites from the marine sponge Clathrina clathrus. Tetrahedron, 45, 3873-3878,... 

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