Axinella verrucosa

Aiello A, D Esposito M, Fattorusso E, Menna M, Miiller WEG, Perovic-Ottstadt S, Schroder HC (2006) Novel Bioactive Bromopyrrole Alkaloids from the Mediterranean Sponge Axinella verrucosa. Bioorg Med Chem 14 17... 

After the discovery of the C26-sterols in marine planktons, all the marine Cje-sterols were suggested to have originated from a phytoplankton. The occurrence of 19-nor-C26-sterol in A. polypoides, probably originating from C26-sterol in the diet, suggests that one of the processes involved in the biosynthesis of these 19-nor-sterols could be the removal of the Cjo-methyl group from the substrates [13]. The sterols in Axinella verrucosa were found to consist of a mixture of unique stanols containing a 3)8-hydroxymethyl-A-nor-5a-cholestane (22) nucleus with conventional side chains [14]. Cholest-4-en-3-one was found to be an intermediate in the bioconversion of cholesterol into 3)8-hydroxymethyl-A-nor-5a-cholestane [15]. 

Commune sin-related compounds are shown in Fig. (13). Jadulco and coworkers quite recently isolated communesins B (71), C (80), and D (72) from the fungus Penicillium sp. derived from the Mediterranean sponge Axinella verrucosa [51]. These three communesins have been shown to exhibit moderate antiproliferative activity in several bioassays performed on different leukemia cell lines. 

In has been hypothesized that this portion of the molecule could interact with hydrophobic groups in the receptor zone, so that the insertion of a polar group achieves the effect of making this interaction worse [15]. The 9-methoxy derivative of dispacamide B (8), isolated as a racemate from the Mediterranean sponge Axinella verrucosa [16], displayed neuroprotective activity against the agonist serotonin in vitro, with a potential to treat psychosis, different phobia and mood fluctuation disorders. 

Stevensine (= odiline) (23) has been isolated by Faulkner et al. from an unidentified marine sponge [26] and subsequently found in Pseudaxynissa cantharella [27], Axinella verrucosa [16], and in Stylissa carteri [28] along with 2-Debromostevensine (24). 

Ottstadt, S., Schroeder, H. C., (2006). Novel bioactive bromopyrrole alkaloids from the Mediterranean Axinella verrucosa. Bioorg. Med. Chem. 14, 17-24. 

MELTING point Acctatc, 64-65°C organism Axinella verrucosa (Porifera) reference 298... 

De Stefano, A., and G. Sodano Metabolism in Porifera. XII. Further Informations on the Biosynthesis of 3p-Hydroxymethyl-A- or-steranes in the Sponge Axinella verrucosa. Experientia 36, 630 (1980). 

De Rosa, M., Minale, L., and Sodano, G. (1975b) Metabolism in Porifera. IV. Biosynthesis of 3P-hydroxymethyl-A-nor-steranes in the sponge Axinella verrucosa. Experientia, 36, 630-632. 

De Stefano, A. and Sodano, G. (1980) Metabolism of Porifera. XII. The biosynthesis of 3p-hydroxymethyl-A-nor-5a-steranes from cholesterol by Axinella verrucosa. Experientia, 31, 408-409. 

The total sterol content of Axinella verrucosa is a mixture of unique stanols with a new 3 p-hydroxymethyl-A- or- 5a-cholestane nucleus carrying conventional Cs, Cg and Cio side chains 141). The major fraction... 

---