Aplysina aerophoba

The only known example of an activated defense in sponges arises from investigations of the defensive chemistry of Aplysina aerophoba. A wound-activated transformation of stored pro-toxins was found after disruption of compart-mentalization of this sponge [157,158]. 

Scheme 21 Wound-activated bioconversion of brominated isoxazoline alkaloids by the sponge Aplysina aerophoba...

Kloppel, A., Pfannkuchen, M., Putz, A., Proksch, P., and Brummer, F. (2008). Ex situ cultivation of Aplysina aerophoba close to in situ conditions Ecological, biochemical and histological aspects. Mar. Ecol. 29, 259-272. 

Fattorusso, E., Minale, L., Sodano, G., Moody, K., and Thomson, R. H. (1970). Aeroplysinin-I, a new bromo-compound from Aplysina aerophoba.. Chem. Soc. Chem. Commun. 751-752. 

Hentschel U, Schmid M, Wagner M, Fieseler L, Gemert C, Hacker J (2001) Isolation and Phylogenetic Analysis of Bacteria with Antimicrobial Activities from the Mediterranean Sponges Aplysina aerophoba and Aplysina cavernicola. FEMS Microbiol Ecol 35 305... 

Friedrich AB, Fischer I, Proksch P, Hacker J, Hentschel U (2001) Temporal Variation of the Microbial Community Associated with the Mediterranean Sponge Aplysina aerophoba. FEMS Microbiol Ecol 38 105... 

Ciminiello P, Fattorusso E, Forino M, Magno S, Pansini M (1997) Chemistry of Verongida Sponges VIII. Bromocompounds from the Mediterranean Sponges Aplysina aerophoba and Aplysina cavernicola. Tetrahedron 53 6565... 

Ebel R, Brenzinger M, Kunze A, Gross HJ, Proksch P (1997) Wound Activation of Protoxins in Marine Sponge Aplysina aerophoba. J Chem Ecol 23 1451... 

Ebel, R., Brenzinger, M., Kunze, A., Gross, H. J., and Proksch, P., Wound activation of protoxins in marine sponge Aplysina aerophoba, J. Chem. Ecol., 23, 1451, 1997. 

Among these keratose sponges, Aplysina aerophoba (Verongida) is said to be at least capable of biotransformation of the characteristic brominated tyrosine derivatives.46 They are held, evidently... 

Ciminiello, P., Fattorusso, E., Forino, M., Magno, S., and Pansini, M., Chemistry of Verongida sponges VIII — bromocompounds from the Mediterranean sponges Aplysina aerophoba and Aplysina caver-nicola, Tetrahedron, 53, 6565, 1997. 

Scheme 1 Wound-induced conversion of brominated isoxazoline alkaloids in Aplysina aerophoba.99,102...

Aerothionin, a tetrabromo derivative, has been isolated from sponges Aplysina aerophoba and Verongia thiona the proposed structure is 24 (46). The oxime 25 was formed by treatment of aerothionin with dilute alkali. The relative positions of the aromatic substituents in 25 were established by cleavage in hot 6 N HC1 to give 26 and a lactone subsequently converted by methylation to 27. The tetramethyl derivative of 25 was hydrolyzed to form... 

The above described rationale of SAR can be exemplified by the bioactivities of the bromotyrosine derivatives, aeroplysinin-1 and dienone, as well as their complicated molecular substrates aerophobin-1 and isofistularin-3, isolated from the Mediterranean sponge, Aplysina aerophoba. Aeroplysinin-1 and dienone exhibit pronounced biological activity whereas aerophobin-1 and isofistularin-3 were always inactive when tested in equimolar concentrations [23]. Aeroplysinin-1 and dienone are antibiotically active against a broad spectrum of marine bacteria such as Vibrio, Micrococcus, and Alteromonas species [24] and are also cytotoxic to Ehrlich ascites tumour cells and HeLa tumour cells in the microculture tetrazolium (MTT) and clonogenic assays [25]. In these assays, it has been demonstrated that the free radical transformation of aeroplysinin-1 and dienone to its semiquinone structures are responsible for the cytotoxicity [25], Aeroplysinin-1 and dienone are the pharmacophores of aerophobin-1 and isofistularin-3. 

Aeroplysinin-1, which shows antibacterial activity against Staphylococcus albus. Bacillus cereus, and B. subtilis, was isolated from the Mediterranean sponge Verongia ( s Aplysina) aerophoba. On the basis of spectral data, and degradation to the phenolic nitrile (77), structure (76) was assigned to... 

Brauers, G., Ebel, R., Edrada, R.-A, Wray, V., Berg, A., Grafe, U and Proksch, P. (2001) Hortein, a new natural product from the fungus Hortaea wemeckii associated with the sponge Aplysina aerophoba. J. Nat. Prod., 64, 651-652. 

---