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

Haber, Markus; Carbone, Marianna; Ilan, Micha; Gavagnin, Margherita

doi:10.3998/ark.5550190.0011.218

Cited by 12 publications

(6 citation statements)

References 24 publications

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“…The production of P-2-AI in Cymbastela cantharella [ 123 ] and Prosuberites laughlini [ 124 ] is subsequently reflected by their molecular phylogenetic position in this clade, e.g., [ 63 , 64 , 65 ]. This Agelasida sensu Morrow et al [ 65 ] clade is further corroborated by additional recent biochemical reports of P-2-AIs, e.g., [ 125 , 126 , 127 , 128 ], as well as molecular phylogenetic studies [ 67 ].…”

Section: Specificity and Phylogenetic Relevance Of Sponge Compoundssupporting

confidence: 74%

A Soft Spot for Chemistry–Current Taxonomic and Evolutionary Implications of Sponge Secondary Metabolite Distribution

et al. 2021

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Marine sponges are the most prolific marine sources for discovery of novel bioactive compounds. Sponge secondary metabolites are sought-after for their potential in pharmaceutical applications, and in the past, they were also used as taxonomic markers alongside the difficult and homoplasy-prone sponge morphology for species delineation (chemotaxonomy). The understanding of phylogenetic distribution and distinctiveness of metabolites to sponge lineages is pivotal to reveal pathways and evolution of compound production in sponges. This benefits the discovery rate and yield of bioprospecting for novel marine natural products by identifying lineages with high potential of being new sources of valuable sponge compounds. In this review, we summarize the current biochemical data on sponges and compare the metabolite distribution against a sponge phylogeny. We assess compound specificity to lineages, potential convergences, and suitability as diagnostic phylogenetic markers. Our study finds compound distribution corroborating current (molecular) phylogenetic hypotheses, which include yet unaccepted polyphyly of several demosponge orders and families. Likewise, several compounds and compound groups display a high degree of lineage specificity, which suggests homologous biosynthetic pathways among their taxa, which identifies yet unstudied species of this lineage as promising bioprospecting targets.

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Section: Specificity and Phylogenetic Relevance Of Sponge Compoundssupporting

confidence: 74%

A Soft Spot for Chemistry–Current Taxonomic and Evolutionary Implications of Sponge Secondary Metabolite Distribution

et al. 2021

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“…44 Bioassay-guided fractionation led to the isolation of a novel alkaloid debromocarteramine 41, along with the known compounds hymenidin and carteramine A 40. 45 Three unprecedented alkaloids, named stylissazoles A-C 42-44, were isolated from the marine sponges Stylissa carteri, collected off the coast of the Solomon Islands. 46 An updated universal biosynthetic pathway was proposed to interpret the generation of these unique skeletons.…”

Section: Introductionmentioning

confidence: 99%

Muscarine, imidazole, oxazole, and thiazole alkaloids

2011

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“…GU059941) yielded a novel antibacterial alkaloid debromo-carteramine A 63 as well as the known compound hymenidin 64. 117 Secondary metabolites may have multiple defensive roles for the producer. A study of co-occurring Mediterranean sponges, Axinella polypoides and A. verrucosa, collected from the Gulf of Naples, Italy investigated two solvent partitions and pyrroleimidazole compounds, hymenidin 64 and debromo-carteramine A 63, for microbial antifouling activity, antibacterial activity and feeding deterrence activity against the generalist shrimp Palaemon elegans.…”

Section: Spongesmentioning

confidence: 99%