Chemistry of Sponges, VII. 11,19-Dideoxyfistularin 3 and 11-Hydroxyaerothionin, Bromotyrosine Derivatives from Pseudoceratina durissima

The Marine Bromotyrosine Derivatives

“…Both compounds exhibited antiviral activity against feline leukemia virus with ED 50 values of 42 μM and 22 μM, respectively. 11,19-Dideoxyfistularin-3 (83) was reported as an antibiotic from the sponge Pseudoceratina durissima, which is more active than aerothionin (68) and homoaerothionin (69) (63). 19-Deoxyfistularin 3 (84) and 19-deoxy-11-oxofistularin 3 (85) were isolated from an undescribed Italian sponge Verongia sp.…”

“…3,5-Dibromo-4-(3′-N,N-dimethylaminopropyloxy)cinnamic acid (63) and its ethyl ester (64) were identified from the Caribbean sponge Pseudoceratina crassa by spectroscopic methods and total synthesis (53). LL-PPA216 (65) was first isolated as dextrorota-tory ([α] D + 8.9°) from the sponge Verongia lacunosa collected off the coast of Puerto Rico by Borders et al in 1977 (54), and appeared to be the first bromine compound containing 2-oxazolidone rings isolated from a sponge.…”

Further dibromotyrosine-derived metabolites from the marine sponge Aplysina caissara

“…Specific rotations were measured on a Perkin Elmer 241 polarimeter in MeOH. NMR spectra were recorded either on a Bruker ARX 9.4 T instrument, operating at 400 MHz for 1 H and 100 MHz for 13 C channels, respectively, or on a Bruker DRX300 7.05 T, operating at 300 MHz for 1 H and 75 MHz for 13 C, respectively. All NMR spectra were obtained at 25 o C using TMS as internal reference.…”

“…10 Nevertheless, similar experiments carried out with extracts of the sponges A. insularis and A. archeri did not presented similar results, since the dibromotyrosine metabolites of these sponges did not suffer degradation when stored in alcohol. 11 A second recollection of A. caissara, followed by immediate animal freezing at -20 o C, rapid transportation to laboratory, freeze-drying and extraction, yielded, after several chromatographic separations, no trace of caissarines A (1) and B (2), 9 but gave fistularin-3 (3), 12 11-hydroxyaerothionin (4), 13 and five unprecedented dibromotyrosine derivatives, named agelocaissarines A1 (5), A2 (6), B1 (7), B2 (8) and caissarine C (9). Herein we report the isolation and structure determination of the new dibromotyrosine derivatives 5-9 as well as the absolute configuration of the spiroxazolidine moiety of compounds 3, 4 and 9 isolated from A. caissara.…”

Synthesis and Absolute Configuration of Acanthodendrilline, a New Cytotoxic Bromotyrosine Alkaloid from the Thai Marine Sponge <i>Acanthodendrilla</i> sp.

“…1) The remarkable diversities of their chemical structures, together with the wide range of bioactivities, including antimicrobial, [2][3][4][5][6] antiviral, 7) antiprotozoal, 8) cytotoxic, 3,4,[9][10][11][12] anti-inflammatory, 13) and enzyme inhibitory activities, [14][15][16] make them highly attractive to both natural product chemists and molecular biologists. In the course of our search for bioactive secondary metabolites from Thai marine organisms, we recently reported the isolation of a series of bromotyrosine alkaloids from the Thai marine sponge Acanthodendrilla sp.…”