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Article

6-Bromoindole Derivatives from the Icelandic Marine Sponge Geodia barretti: Isolation and Anti-Inflammatory Activity

1
Faculty of Pharmaceutical Sciences, University of Iceland, Hagi, Hofsvallagata 53, IS-107 Reykjavik, Iceland
2
Department of Immunology and Centre for Rheumatology Research Landspitali-The National University Hospital of Iceland, Hringbraut, IS-101 Reykjavik, Iceland
3
GEOMAR Centre for Marine Biotechnology (GEOMAR-Biotech), Marine Natural Products Chemistry Research Unit, GEOMAR Helmholtz Centre for Ocean Research Kiel, Am Kiel-Kanal 44, 24106 Kiel, Germany
4
Faculty of Medicine, Biomedical Center, University of Iceland, Vatnsmyrarvegur 16, IS-101 Reykjavik, Iceland
5
Department of Chemistry and Biochemistry and Skaggs School of Pharmacy and Pharmaceutical Sciences, University of California, San Diego, La Jolla, CA 92093, USA
6
Faculty of Mathematics and Natural Sciences, Kiel University, Christian-Albrechts-Platz 4, 24118 Kiel, Germany
*
Author to whom correspondence should be addressed.
Current address: Univ. de Bordeaux, UFR des Sciences Pharmaceutiques, Unité de recherche Œnologie EA 4577, USC 1366 INRA, ISVV, 210 Chemin de Leysotte, CS 50008, 33882 Villenave d’Ornon, France.
Mar. Drugs 2018, 16(11), 437; https://doi.org/10.3390/md16110437
Received: 18 October 2018 / Revised: 5 November 2018 / Accepted: 6 November 2018 / Published: 8 November 2018
(This article belongs to the Special Issue Marine Anti-inflammatory Agents)
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 (13) and four known compounds, barettin (4), 8,9-dihydrobarettin (5), 6-bromoconicamin (6), and l-6-bromohypaphorine (7). The chemical structures of compounds 17 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. View Full-Text
Keywords: 6-bromoindole; Geodia barretti; anti-inflammatory activity; dendritic cells; T cell differentiation 6-bromoindole; Geodia barretti; anti-inflammatory activity; dendritic cells; T cell differentiation
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MDPI and ACS Style

Di, X.; Rouger, C.; Hardardottir, I.; Freysdottir, J.; Molinski, T.F.; Tasdemir, D.; Omarsdottir, S. 6-Bromoindole Derivatives from the Icelandic Marine Sponge Geodia barretti: Isolation and Anti-Inflammatory Activity. Mar. Drugs 2018, 16, 437. https://doi.org/10.3390/md16110437

AMA Style

Di X, Rouger C, Hardardottir I, Freysdottir J, Molinski TF, Tasdemir D, Omarsdottir S. 6-Bromoindole Derivatives from the Icelandic Marine Sponge Geodia barretti: Isolation and Anti-Inflammatory Activity. Marine Drugs. 2018; 16(11):437. https://doi.org/10.3390/md16110437

Chicago/Turabian Style

Di, Xiaxia, Caroline Rouger, Ingibjorg Hardardottir, Jona Freysdottir, Tadeusz F. Molinski, Deniz Tasdemir, and Sesselja Omarsdottir. 2018. "6-Bromoindole Derivatives from the Icelandic Marine Sponge Geodia barretti: Isolation and Anti-Inflammatory Activity" Marine Drugs 16, no. 11: 437. https://doi.org/10.3390/md16110437

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