Dibromotyrosine-derived metabolite

Hernandez-Guerrero, C. J., Zubra, E., Ortega, M. J., and Carballob, J. L. (2007). Cytotoxic dibromotyrosine-derived metabolites from the sponge Aplysina gerardogreeni. Bioorg. Med. Chem. 15, 5275-5282. 

A dibromotyrosin-derived metabolite present at 1.0% sponge dry weight, aerothionin (148), from Aplysina fistularis completely inhibits fish feeding when assayed in a 1.0% food pellet [115]. 

Venkateswarlu Y, Rama Rao M, Venkatesham U (1998) A New Dibromotyrosine-Derived Metabolite from the Sponge Psammaplysilla purpurea. J Nat Prod 61 1388... 

Okamoto Y, Ojika M, Kato S, Sakagami Y (2000) Ianthesines A-D, Four Novel Dibromotyrosine-Derived Metabolites from a Marine Sponge, Ianthella sp. Tetrahedron 56 5813... 

Copp, B. R., Ireland, C. M., Barrow, L. R. Psammaplysin C a new cytotoxic dibromotyrosine-derived metabolite from the marine sponge Druinella (= Psammaplysilla)purpurea. J. Nat. Prod. 1992, 55, 822-823. 

De Lira, TO., Berlinck, R.G.S., Nascimento, G.G.F., and Hajdu, E. (2006) Further dibromotyrosine-derived metabolites from the marine sponge Aplysina eaissara. J. Braz. Chem. Soc., 17, 1233-1240. 

Cytotoxic dibromotyrosine-derived metabolites from the sponge Aplysinagerardogreeni. Bioorg. Med. Chem., 15, 5275-5282. 

Okamoto, Y, Ojika, M., Kato, S., and Sakagami, Y. (2000) lanthesines A—D, four novel dibromotyrosine-derived metabolites from a marine sponge, lanthella sp. Tetrahedron, 56, 5813—5818. 

Verongia species,and it seems probable that 3,5-dibromotyrosine is a precursor of all the Verongia metabolites. The central C4N2 and C5N2chains of (81a) and (81b) are considered to be derived from ornithine and lysine, respectively. In view of the facile photochemical conversion of (79) into (80), it has been suggested that the natural amide (82) is derived biogenetically via lactone... 

All these Verongia metabolites seem fairly obviously biosynthetised from 3,5-dibromotyrosine or tyrosine via an epoxidation step and presumably the central C4N2 and C5N2 chains of aerothionin (7) and homoaerothionin (8) are derived from ornithine and lysine, respectively (143) [both dibromotyrosine and lysine have been found in sponge proteins (9,133)]. 

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