Aplysina thiona

Thompson JE, Barrow KD, Faulkner DJ (1983) Localization of Two Brominated Metabolites, Aerothionin and Homoaerothionin, in Spherulous Cells of the Marine Sponge Aplysina fistularis (= Verongia thiona). Acta Zool 64 199... 

Thompson, J. E., Barrows, K. D., and Faulkner, D. J., Localization of two brominated metabolites, aerothionin and homoaerothionin, in spherulous cells of the marine sponge Aplysina fistularis (= Verongia thiona), Acta Zool., 64, 199, 1983. 

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... 

SPECTRAL data UV, IR, PMR, Mass Spec organism Verongia thiona and Aplysina (or Verongia) aerophoba (Porifera) reference 135, 305... 

Walkup, R.D., G.C. Jamieson, M.R. Ratcliff, and C. Djerassi Phospholipid Studies of Marine Organisms 2. Phospholipids, Phospholipid-Bound Fatty Acids and Free Sterols of the Sponge Aplysina fistularis (Pallas) Forma fulva (Pallas) (= Ve-rongia thiona). Isolation and Structure Elucidation of Unprecedented Branched Fatty Acids. Lipids 16, 631 (1981). 

Verongia aeropboba, Verongia thiona Moody et al, 1972 11-Oxoaefothionin (R = O, n = 1) Aplysina lacunosa Acosta and Rodriguez, 1992... 

Cruz, F., Quijano, L., Gomez-Garbay, F., and Rios, T. (1990) Bromina-ted metabolites from the sponge Aplysina [Verongia) thiona. J. Nat. Prod., 53, 543-548. 

Walkup, R.D., Jamieson, G.C., Ratcliff, M.R., and Djerassi, C. (1981) Phospholipid studies of marine organisms 2. Phospholipids, phospholipid-bound fatty acids and free sterols of the sponge Aplysina fistularis (Pallas) forma fidva (Pallas) (= Verongia thiona). Isolation and stmcture elucidation of unprecedented branched fatty acids. Lipids, 16, 631-646. 

Two additional mixed ketals, aplysinketal A (5) and aplysinketal B (6), along with 7 and 8, were obtained from the Mexican sponge Aplysina (Verongia) thiona (7). Unlike 2 and 3, the structure of aplysinketal A (5) was shown to be only one of the two diastereoisomers by X-ray and NMR data. Furthermore, the mixed ketals 5 and 6 would not be expected to be formed without simultaneous formation of the dimethoxy ketal 2, which was never detected. According to these results, aplysinketal A (5) and aplysinketal B (6) are very likely to be natural products. The diethyl ketal 9 was obtained from a Turkish sponge V. aerophoba (8). 

Fattorusso, E., L. Minale, K. Moody, G. Sodano, and R. H. Thomson Homo-aerothionin, a second tetrabromo-compound from Aplysina aerophoba and Verongia thiona. Gazz. Chim. it. 101, 61 (1971). 

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