Structure and Synthesis of Bromoindoles from the Marine Sponge Pseudosuberites hyalinus

Purification and characterization of antibacterial compounds of Pseudoalteromonas flavipulchra JG1

“…The growth of V. anguillarum was inhibited more by the mixture of compounds than by each of the five compounds individually (results not shown), suggesting that the compounds may act synergistically. Although the structures of the five compounds described here have been reported previously (Niu et al, 2003;Yang et al, 2000;Rasmussen et al, 1993;Kuberski & Gebicki, 1992;Shi et al, 2009), they were first discovered to exhibit antibacterial activities in this work.…”

“…3. They were identified as phydroxybenzoic acid (1) (Niu et al, 2003), trans-cinnamic acid (2) (Yang et al, 2000), 6-bromoindolyl-3-acetic acid (3) (Rasmussen et al, 1993), N-hydroxybenzoisoxazolone (4) (Kuberski & Gebicki, 1992) and 29-deoxyadenosine (5) (Shi et al, 2009), by detailed spectroscopic analysis and comparison with the literature.…”

Chemical and Biological Aspects of Marine Sponges from the Family Mycalidae

“…Brominated indoles have been reported widely in the sponge class Demospongiae [10] in the orders Dictyoceratida, Poecilosclerida, Tetractinellida, and Suberitida. In particular from the genera Dysidea [11], Iotrochota [12,13], Tedania (Tedania) [14], Corallistes [15], Pleroma [16], Hymeniacidon [17], Pseudosuberites [18], and Spongosorites [19]. Brominated indoles have also been reported in other non-sponge marine taxa, for example, 12 from the ascidian Leptoclinides durus [20] and 14 from bacteria isolated from marine sediment [21].…”

“…Mycaleoxime (47) differs from the other pyrrole derivatives by the presence of a carbonyl group adjacent to the pyrrole nucleus and a terminal aldoxime group. The new compounds mycalazals 3-13 (49-59) and mycalenitriles 1-3 (60-62) (distinguished by a terminal nitrile group) were found in M. (Carmia) cecilia from Mexico [27], with the eight known pyrrole derivatives 16,18,35,36,41,43,63, and 64 [23,25]. In 2009, 16 and 46 were reisolated from an Indonesian M. (Carmia) phyllophila [28].…”

“…The nitrile 43 was an active inhibitor of the proliferation of the parasite Leishmania mexicana with an LD 50 value of 12 µg/mL [25]. A library of 22 pyrrole-2-carboxaldehydes including the mycalazals 3-13 (49)(50)(51)(52)(53)(54)(55)(56)(57)(58)(59), the mycalenitriles 1-3 (60)(61)(62), and the known pyrrole-2-carboxaldehydes 16,18,35,36,41,43,63, and 64 were screened against a panel of cell lines (LN-caP, IGROV, SK-BR3, SK-MEL-28, A-549, K-562, PANCI, LOVO, and HeLa cell lines), which resulted in some interesting structure activity observations (see [27] for specific GI 50 values). The authors compared the LN-caP cell line inhibition with the structures of the compounds and found that activity was associated with the presence of a single double bond, activity decreased with three double bonds, and was lost completely with two double bonds or saturated alkyl chains [27].…”