Reinvestigation into the structure of oroidin, a bromopyrrole derivative from marine sponge

Chemical defenses of the Caribbean sponges Agelas wiedenmayeri and Agelas conifera

“…Isolation of brominated alkaloids from a specimen of Agelas wiedenmayeri, which had been collected in May 1998 at North Dry Rocks, Key Largo, was performed using a previously described procedure (Assmann et al 1999). The isolated bromopyrrole alkaloids of both A. conifera and A. wiedenmayeri were identified by comparison of mass spectrometry and NMR data with those previously reported (Forenza et al 1971, Garcia et al 1973, Walker et al 1981, Kobayashi et al 1990, Keifer et al 1991 as well as on the basis of 2D NMR data (COSY, HSQC, HMBC).…”

Structure of debromo-carteramine A, a novel bromopyrrole alkaloid from the Mediterranean sponge Axinella verrucosa

“…[1][2][3][4][5][6][7] Historically, these compounds, which have been found only in the marine environment to date, have attracted the attention of natural product chemists because of their structural complexity. Today, the interest is sparked not only by the wide structural diversity, ranging from simple molecules like oroidin 8,9 to complex structures like palau'amine 10,11 and stylissadine A and B, 12 but also by their organic synthesis, 13 bio-synthesis, 14 and pharmacological activities. 6,7,15 Furthermore, these compounds have a chemo-ecological interest due to their role in chemically mediated interactions such as in the chemical defense against predators 16,17 and fouling organisms.…”

Bromopyrrole Alkaloids from Okinawan Marine Sponges <i>Agelas</i> spp.

“…4). Nagelamide W (9) (6) and Nagelamides U-W (7)(8)(9) might be biogenetically generated by the addition of guanidine to oroidin.…”

“…15) As part of that research project, bromopyrrole alkaloids in sponges Agelas spp. (SS-162, SS-307) were investigated, resulting in the isolation of 18 unique alkaloids including five dimeric bromopyrrole alkaloids (1-5), ten monomeric bromopyrrole alkaloids (6)(7)(8)(9)(10)(11)(12)(13)(14)(15), and three conjugates of monomeric bromopyrrole alkaloid and hydroxykynurenine (16)(17)(18). In this mini-review, we describe the isolation, structure elucidation, and antimicrobial activities of these alkaloids.…”

“…Representative bromopyrrole alkaloids, oroidin 8,9) and hymenidin, 10) are composed of an aminoimidazole moiety and a brominated pyrrole-amide moiety linked through a C 3 unit (Fig. 1).…”