Pyrroloiminoquinone pigments from Didymium iridis

Secondary metabolites of slime molds (myxomycetes)

“…16), were isolated from the fruiting bodies of D. bahiense (Ishibashi et al, 2001) and from the marine sponge Zyzzya , respectively. A green pigment, makaluvamine I (68), and also damirone C (69) were produced by slime mold Didymium iridis (Nakatani et al, 2005b). Isolation of makaluvamine I (68) and damirone C (69) has previously been reported from a marine sponge Zyzzya fuliginosa or Histodermella sp.…”

Current Perspectives on Pyrroloiminoquinones: Distribution, Biosynthesis and Drug Discovery Potential

“…Makaluvamines have also been isolated from latrunculid sponge species collected off South Africa [22,48,49], the Korean peninsula [16], New Zealand [50] and Australia [21]. Interestingly, simple makaluvamines bearing either no substituents or only exhibiting N-methylation have been purified from cultured myxomycetes, Didymium iridis and Didymium bahiense, isolated from Japanese forest litter samples [25,26]. Makaluvamines are thought to be the biosynthetic precursors to more complex pyrroloiminoquinones and the sulfur-containing makaluvamine F may represent a precursor to sulfur-containing discorhabdins [50].…”

“…Pyrroloiminoquinones have been mostly isolated from marine sponges of the order Poecilosclerida, with Latrunculiidae species from temperate and cold-water environments such as New Zealand, South Africa, the Arctic, and Antarctic as well as warm-water Acarnidae species from the Indo-Pacific proving particularly productive sources [2][3][4]. Nevertheless, members of this class of alkaloids have been reported from ascidians [23,24] and simple representatives have also been isolated from cultured myxomycetes [25,26]. Moreover, closely related alkaloids have been reported in hydroids [27,28], terrestrial fungi [29][30][31][32] and marine actinobacteria [33,34].…”

Formation of Trideuteromethylated Artifacts of Pyrrole-Containing Natural Products

“…5 Other examples of bioactive natural products containing the motif include the lamellarins, 7 prodiginines, 8 lukianols, 9 polycitones, 10 marinopyrroles, 11 pseudilins, 12 halitulin, 13 and the discorhabdins. 14 The pyrroloiminoquinones are cytotoxic alkaloids most commonly isolated from marine sponges, 15 hydroids, 16 cultured myxomycetes, 17 and the fruiting bodies of terrestrial fungi. 18 Structurally, they are based on a tricyclic pyrrolo[4,3,2de]quinoline core common to marine natural products such as makaluvamines (and related compounds damirones, batzellines, and macrophilones), bispyrroloiminoquinones (tsitsikammamines, zyzzyanones, and wakayins), and the disco-rhabdins (and related compounds prianosins and epinardins).…”

“…The pyrroloiminoquinones are cytotoxic alkaloids most commonly isolated from marine sponges, hydroids, cultured myxomycetes, and the fruiting bodies of terrestrial fungi . Structurally, they are based on a tricyclic pyrrolo­[4,3,2- de ]­quinoline core common to marine natural products such as makaluvamines (and related compounds damirones, batzellines, and macrophilones), bispyrroloiminoquinones (tsitsikammamines, zyzzyanones, and wakayins), and the discorhabdins (and related compounds prianosins and epinardins). , Over 110 members of the pyrroloiminoquinone class have been reported to date, and more than 50 of those are discorhabdins .…”