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),...
Published in: | Marine Drugs |
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MDPI
2018
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Online Access: | https://oceanrep.geomar.de/id/eprint/44712/ https://oceanrep.geomar.de/id/eprint/44712/1/marinedrugs-16-00437-v3.pdf https://oceanrep.geomar.de/id/eprint/44712/2/marinedrugs-16-00437-s001.pdf https://doi.org/10.3390/md16110437 |
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ftoceanrep:oai:oceanrep.geomar.de:44712 2023-05-15T15:08:28+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 Tasdemir, Deniz Omarsdottir, Sesselja 2018-11-08 text https://oceanrep.geomar.de/id/eprint/44712/ https://oceanrep.geomar.de/id/eprint/44712/1/marinedrugs-16-00437-v3.pdf https://oceanrep.geomar.de/id/eprint/44712/2/marinedrugs-16-00437-s001.pdf https://doi.org/10.3390/md16110437 en eng MDPI https://oceanrep.geomar.de/id/eprint/44712/1/marinedrugs-16-00437-v3.pdf https://oceanrep.geomar.de/id/eprint/44712/2/marinedrugs-16-00437-s001.pdf Di, X., Rouger, C., Hardardottir, I., Freysdottir, J. , Molinski, T., Tasdemir, D. and Omarsdottir, S. (2018) 6-Bromoindole Derivatives from the Icelandic Marine Sponge Geodia barretti: Isolation and Anti-Inflammatory Activity. Open Access Marine Drugs, 16 (11). p. 437. DOI 10.3390/md16110437 <https://doi.org/10.3390/md16110437>. doi:10.3390/md16110437 cc_by_4.0 info:eu-repo/semantics/openAccess Article PeerReviewed 2018 ftoceanrep https://doi.org/10.3390/md16110437 2023-04-07T15:42:02Z 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. Article in Journal/Newspaper Arctic OceanRep (GEOMAR Helmholtz Centre für Ocean Research Kiel) Arctic Marine Drugs 16 11 437 |
institution |
Open Polar |
collection |
OceanRep (GEOMAR Helmholtz Centre für Ocean Research Kiel) |
op_collection_id |
ftoceanrep |
language |
English |
description |
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 |
Article in Journal/Newspaper |
author |
Di, Xiaxia Rouger, Caroline Hardardottir, Ingibjorg Freysdottir, Jona Molinski, Tadeusz Tasdemir, Deniz Omarsdottir, Sesselja |
spellingShingle |
Di, Xiaxia Rouger, Caroline Hardardottir, Ingibjorg Freysdottir, Jona Molinski, Tadeusz Tasdemir, Deniz Omarsdottir, Sesselja 6-Bromoindole Derivatives from the Icelandic Marine Sponge Geodia barretti: Isolation and Anti-Inflammatory Activity |
author_facet |
Di, Xiaxia Rouger, Caroline Hardardottir, Ingibjorg Freysdottir, Jona Molinski, Tadeusz 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 |
https://oceanrep.geomar.de/id/eprint/44712/ https://oceanrep.geomar.de/id/eprint/44712/1/marinedrugs-16-00437-v3.pdf https://oceanrep.geomar.de/id/eprint/44712/2/marinedrugs-16-00437-s001.pdf https://doi.org/10.3390/md16110437 |
geographic |
Arctic |
geographic_facet |
Arctic |
genre |
Arctic |
genre_facet |
Arctic |
op_relation |
https://oceanrep.geomar.de/id/eprint/44712/1/marinedrugs-16-00437-v3.pdf https://oceanrep.geomar.de/id/eprint/44712/2/marinedrugs-16-00437-s001.pdf Di, X., Rouger, C., Hardardottir, I., Freysdottir, J. , Molinski, T., Tasdemir, D. and Omarsdottir, S. (2018) 6-Bromoindole Derivatives from the Icelandic Marine Sponge Geodia barretti: Isolation and Anti-Inflammatory Activity. Open Access Marine Drugs, 16 (11). p. 437. DOI 10.3390/md16110437 <https://doi.org/10.3390/md16110437>. doi:10.3390/md16110437 |
op_rights |
cc_by_4.0 info:eu-repo/semantics/openAccess |
op_doi |
https://doi.org/10.3390/md16110437 |
container_title |
Marine Drugs |
container_volume |
16 |
container_issue |
11 |
container_start_page |
437 |
_version_ |
1766339828892303360 |