Aplysina cauliformis

Ciminiello P, Dell Aversano C, Fattorusso E, Magno S, Pansini M (1999) Chemistry of Verongida Sponges. 9. Secondary Metabolite Composition of the Caribbean Sponge Aplysina cauliformis. J Nat Prod 62 590... 

Rodriguez, A.D. and Pina, I.C. (1993) The structures of aplysinamisines I, II, and III new bromotyrosine-derived alkaloids from the Caribbean sponge Aplysina cauliformis. J. Nat. Prod., 56, 907-914. 

The enantiomer of purealidin J, pseudoceratinine A (119), was reported one year later from Pseudoceratina verrucosa 89). Pseudoceratinine A showed a negative optical rotation and Cotton effects near 250 and 290 nm, which is opposite to that of aerothionin (68), whose absolute stereochemistry was determined by X-ray and CD spectra 60). Aplysinamisine I (120), which can be considered as a 11,12-dehydro product of aerophobin-2 (114), was isolated from the Caribbean sponge Aplysina cauliformis 83). 

In a continuing report, several enantiopure spiroisoxazohne amides were prepared using the above method and tested on an isoxazoline-splitting enzyme, which is involved in an injury-induced defense reaction of the sponge Aplysina cauliformis (227). The results indicated that the bromoatoms in the cyclohexenone moiety are important for enzyme binding, while the presence of the N-H bond of a monoalkylamide turned out to be mandatory for ring fission. 

---