6-Bromoindole Derivatives from the Icelandic Marine Sponge Geodia barretti: Isolation and Anti-Inflammatory Activity
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),...
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ftpubmed:oai:pubmedcentral.nih.gov:6266195 2023-05-15T15:08:17+02:00 6-Bromoindole Derivatives from the Icelandic Marine Sponge Geodia barretti: Isolation and Anti-Inflammatory Activity Di, Xiaxia Rouger, Caroline Hardardottir, Ingibjorg Freysdottir, Jona Molinski, Tadeusz F. Tasdemir, Deniz Omarsdottir, Sesselja 2018-11-08 http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6266195/ http://www.ncbi.nlm.nih.gov/pubmed/30413031 https://doi.org/10.3390/md16110437 en eng MDPI http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6266195/ http://www.ncbi.nlm.nih.gov/pubmed/30413031 http://dx.doi.org/10.3390/md16110437 © 2018 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). CC-BY Article Text 2018 ftpubmed https://doi.org/10.3390/md16110437 2018-12-09T01:25:47Z 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 analysis and Marfey’s method employing the new reagent l-Nα-(1-fluoro-2,4-dinitrophenyl)tryptophanamide (l-FDTA). The isolated compounds were screened for anti-inflammatory activity using human dendritic cells (DCs). Both 2 and 3 reduced DC secretion of IL-12p40, but 3 concomitantly increased IL-10 production. Maturing DCs treated with 2 or 3 before co-culturing with allogeneic CD4+ T cells decreased T cell secretion of IFN-γ, indicating a reduction in Th1 differentiation. Although barettin (4) reduced DC secretion of IL-12p40 and IL-10 (IC50 values 11.8 and 21.0 μM for IL-10 and IL-12p40, respectively), maturing DCs in the presence of 4 did not affect the ability of T cells to secrete IFN-γ or IL-17, but reduced their secretion of IL-10. These results indicate that 2 and 3 may be useful for the treatment of inflammation, mainly of the Th1 type. Text Arctic PubMed Central (PMC) Arctic Marine Drugs 16 11 437 |
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Article Di, Xiaxia Rouger, Caroline Hardardottir, Ingibjorg Freysdottir, Jona Molinski, Tadeusz F. Tasdemir, Deniz Omarsdottir, Sesselja 6-Bromoindole Derivatives from the Icelandic Marine Sponge Geodia barretti: Isolation and Anti-Inflammatory Activity |
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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 analysis and Marfey’s method employing the new reagent l-Nα-(1-fluoro-2,4-dinitrophenyl)tryptophanamide (l-FDTA). The isolated compounds were screened for anti-inflammatory activity using human dendritic cells (DCs). Both 2 and 3 reduced DC secretion of IL-12p40, but 3 concomitantly increased IL-10 production. Maturing DCs treated with 2 or 3 before co-culturing with allogeneic CD4+ T cells decreased T cell secretion of IFN-γ, indicating a reduction in Th1 differentiation. Although barettin (4) reduced DC secretion of IL-12p40 and IL-10 (IC50 values 11.8 and 21.0 μM for IL-10 and IL-12p40, respectively), maturing DCs in the presence of 4 did not affect the ability of T cells to secrete IFN-γ or IL-17, but reduced their secretion of IL-10. These results indicate that 2 and 3 may be useful for the treatment of inflammation, mainly of the Th1 type. |
format |
Text |
author |
Di, Xiaxia Rouger, Caroline Hardardottir, Ingibjorg Freysdottir, Jona Molinski, Tadeusz F. Tasdemir, Deniz Omarsdottir, Sesselja |
author_facet |
Di, Xiaxia Rouger, Caroline Hardardottir, Ingibjorg Freysdottir, Jona Molinski, Tadeusz F. Tasdemir, Deniz Omarsdottir, Sesselja |
author_sort |
Di, Xiaxia |
title |
6-Bromoindole Derivatives from the Icelandic Marine Sponge Geodia barretti: Isolation and Anti-Inflammatory Activity |
title_short |
6-Bromoindole Derivatives from the Icelandic Marine Sponge Geodia barretti: Isolation and Anti-Inflammatory Activity |
title_full |
6-Bromoindole Derivatives from the Icelandic Marine Sponge Geodia barretti: Isolation and Anti-Inflammatory Activity |
title_fullStr |
6-Bromoindole Derivatives from the Icelandic Marine Sponge Geodia barretti: Isolation and Anti-Inflammatory Activity |
title_full_unstemmed |
6-Bromoindole Derivatives from the Icelandic Marine Sponge Geodia barretti: Isolation and Anti-Inflammatory Activity |
title_sort |
6-bromoindole derivatives from the icelandic marine sponge geodia barretti: isolation and anti-inflammatory activity |
publisher |
MDPI |
publishDate |
2018 |
url |
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6266195/ http://www.ncbi.nlm.nih.gov/pubmed/30413031 https://doi.org/10.3390/md16110437 |
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Arctic |
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Arctic |
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Arctic |
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Arctic |
op_relation |
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6266195/ http://www.ncbi.nlm.nih.gov/pubmed/30413031 http://dx.doi.org/10.3390/md16110437 |
op_rights |
© 2018 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). |
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CC-BY |
op_doi |
https://doi.org/10.3390/md16110437 |
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Marine Drugs |
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16 |
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11 |
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437 |
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1766339666353586176 |