2018
DOI: 10.3390/md16110437
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6-Bromoindole Derivatives from the Icelandic Marine Sponge Geodia barretti: Isolation and Anti-Inflammatory Activity

Abstract: An UPLC-qTOF-MS-based dereplication study led to the targeted isolation of seven bromoindole alkaloids from the sub-Arctic sponge Geodia barretti. This includes three new metabolites, namely geobarrettin A–C (1–3) and four known compounds, barettin (4), 8,9-dihydrobarettin (5), 6-bromoconicamin (6), and l-6-bromohypaphorine (7). The chemical structures of compounds 1–7 were elucidated by extensive analysis of the NMR and HRESIMS data. The absolute stereochemistry of geobarrettin A (1) was assigned by ECD analy… Show more

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Cited by 32 publications
(29 citation statements)
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References 56 publications
(77 reference statements)
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“…In this study, we selected three species of Geodia because there was little intraspecific variation when cultured in M1 medium. In addition, G. barretti is the source of compounds with anti-inflammatory activity 29 . Cell density of G. barretti , Geodia sp., and G. neptuni was measured with a finer time resolution to understand the dynamics of cell division for each species (Fig.…”
Section: Resultsmentioning
confidence: 99%
“…In this study, we selected three species of Geodia because there was little intraspecific variation when cultured in M1 medium. In addition, G. barretti is the source of compounds with anti-inflammatory activity 29 . Cell density of G. barretti , Geodia sp., and G. neptuni was measured with a finer time resolution to understand the dynamics of cell division for each species (Fig.…”
Section: Resultsmentioning
confidence: 99%
“…The activity of these alkaloids as P2X7 receptor antagonists may therefore have broad therapeutic possibilities for inflammatory and immune-mediated diseases. The 6-bromoindole derivatives geobarettin B (18) and C (19), the 6-bromoindole alkaloids 6-bromoconicamin (20), and barettin (13), obtained from the sponge G. barretti, showed an anti-inflammatory effect on LPS-, TNF-α-, and IL-1β-stimulated dendritic cells, reducing IL-12p40 secretion [82]. Geobarettin C was also able to increase the levels of IL-10 secreted by these cells.…”
Section: Sponge-derived Alkaloidsmentioning
confidence: 99%
“…Natural compounds with antimicrobial, anti-inflammatory and anticancer activities have been isolated from marine invertebrates in the Arctic region [ 3 , 51 , 52 , 53 ] and in the marine Antarctic environment [ 54 , 55 , 56 , 57 ].…”
Section: Marine Compounds From Polar Regionsmentioning
confidence: 99%