Bromotryptamine and Imidazole Alkaloids with Anti-inflammatory Activity from the Bryozoan Flustra foliacea
Chemical investigation of the marine bryozoan Flustra foliacea collected in Iceland resulted in isolation of 13 new bromotryptamine alkaloids, flustramines Q-W (1-7) and flustraminols C-H (8-13), and two new imidazole alkaloids, flustrimidazoles A and B (14 and 15), together with 12 previously descr...
Published in: | Journal of Natural Products |
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ACS (American Chemical Society)
2020
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Online Access: | https://oceanrep.geomar.de/id/eprint/50985/ https://oceanrep.geomar.de/id/eprint/50985/1/acs.jnatprod.0c00126.pdf https://doi.org/10.1021/acs.jnatprod.0c00126 |
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ftoceanrep:oai:oceanrep.geomar.de:50985 2023-05-15T16:48:11+02:00 Bromotryptamine and Imidazole Alkaloids with Anti-inflammatory Activity from the Bryozoan Flustra foliacea Di, Xiaxia Wang, Shuqi Oskarsson, Jon T. Rouger, Caroline Tasdemir, Deniz Hardardottir, Ingibjorg Freysdottir, Jona Wang, Xiao Molinski, Tadeusz F. Omarsdottir, Sesselja 2020-10-05 text https://oceanrep.geomar.de/id/eprint/50985/ https://oceanrep.geomar.de/id/eprint/50985/1/acs.jnatprod.0c00126.pdf https://doi.org/10.1021/acs.jnatprod.0c00126 en eng ACS (American Chemical Society) https://oceanrep.geomar.de/id/eprint/50985/1/acs.jnatprod.0c00126.pdf Di, X. , Wang, S., Oskarsson, J. T., Rouger, C., Tasdemir, D. , Hardardottir, I., Freysdottir, J., Wang, X. , Molinski, T. F. and Omarsdottir, S. (2020) Bromotryptamine and Imidazole Alkaloids with Anti-inflammatory Activity from the Bryozoan Flustra foliacea. Journal of Natural Products, 83 (10). pp. 2854-2866. DOI 10.1021/acs.jnatprod.0c00126 <https://doi.org/10.1021/acs.jnatprod.0c00126>. doi:10.1021/acs.jnatprod.0c00126 info:eu-repo/semantics/restrictedAccess Article PeerReviewed 2020 ftoceanrep https://doi.org/10.1021/acs.jnatprod.0c00126 2023-04-07T15:52:52Z Chemical investigation of the marine bryozoan Flustra foliacea collected in Iceland resulted in isolation of 13 new bromotryptamine alkaloids, flustramines Q-W (1-7) and flustraminols C-H (8-13), and two new imidazole alkaloids, flustrimidazoles A and B (14 and 15), together with 12 previously described compounds (16-27). Their structures were established by detailed spectroscopic analysis using 1D and 2D NMR and HRESIMS. Structure 2 was verified by calculations of the 13C and 1H NMR chemical shifts using density functional theory. The relative and absolute configurations of the new compounds were elucidated on the basis of coupling constant analysis, NOESY, [α]D, and ECD spectroscopic data, in addition to chemical derivatization. The compounds were tested for in vitro anti-inflammatory activity using a dendritic cell model. Eight compounds (1, 3, 5, 13, 16, 18, 26, and 27) decreased dendritic cell secretion of the pro-inflammatory cytokine IL-12p40, and two compounds (4 and 14) increased secretion of the anti-inflammatory cytokine IL-10. Deformylflustrabromine B (27) showed the most potent anti-inflammatory effect (IC50 2.9 μM). These results demonstrate that F. foliacea from Iceland expresses a broad range of brominated alkaloids, many without structural precedents. The potent anti-inflammatory activity in vitro of metabolite 27 warrants further investigations into its potential as a lead for inflammation-related diseases. Article in Journal/Newspaper Iceland OceanRep (GEOMAR Helmholtz Centre für Ocean Research Kiel) Journal of Natural Products 83 10 2854 2866 |
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Open Polar |
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OceanRep (GEOMAR Helmholtz Centre für Ocean Research Kiel) |
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ftoceanrep |
language |
English |
description |
Chemical investigation of the marine bryozoan Flustra foliacea collected in Iceland resulted in isolation of 13 new bromotryptamine alkaloids, flustramines Q-W (1-7) and flustraminols C-H (8-13), and two new imidazole alkaloids, flustrimidazoles A and B (14 and 15), together with 12 previously described compounds (16-27). Their structures were established by detailed spectroscopic analysis using 1D and 2D NMR and HRESIMS. Structure 2 was verified by calculations of the 13C and 1H NMR chemical shifts using density functional theory. The relative and absolute configurations of the new compounds were elucidated on the basis of coupling constant analysis, NOESY, [α]D, and ECD spectroscopic data, in addition to chemical derivatization. The compounds were tested for in vitro anti-inflammatory activity using a dendritic cell model. Eight compounds (1, 3, 5, 13, 16, 18, 26, and 27) decreased dendritic cell secretion of the pro-inflammatory cytokine IL-12p40, and two compounds (4 and 14) increased secretion of the anti-inflammatory cytokine IL-10. Deformylflustrabromine B (27) showed the most potent anti-inflammatory effect (IC50 2.9 μM). These results demonstrate that F. foliacea from Iceland expresses a broad range of brominated alkaloids, many without structural precedents. The potent anti-inflammatory activity in vitro of metabolite 27 warrants further investigations into its potential as a lead for inflammation-related diseases. |
format |
Article in Journal/Newspaper |
author |
Di, Xiaxia Wang, Shuqi Oskarsson, Jon T. Rouger, Caroline Tasdemir, Deniz Hardardottir, Ingibjorg Freysdottir, Jona Wang, Xiao Molinski, Tadeusz F. Omarsdottir, Sesselja |
spellingShingle |
Di, Xiaxia Wang, Shuqi Oskarsson, Jon T. Rouger, Caroline Tasdemir, Deniz Hardardottir, Ingibjorg Freysdottir, Jona Wang, Xiao Molinski, Tadeusz F. Omarsdottir, Sesselja Bromotryptamine and Imidazole Alkaloids with Anti-inflammatory Activity from the Bryozoan Flustra foliacea |
author_facet |
Di, Xiaxia Wang, Shuqi Oskarsson, Jon T. Rouger, Caroline Tasdemir, Deniz Hardardottir, Ingibjorg Freysdottir, Jona Wang, Xiao Molinski, Tadeusz F. Omarsdottir, Sesselja |
author_sort |
Di, Xiaxia |
title |
Bromotryptamine and Imidazole Alkaloids with Anti-inflammatory Activity from the Bryozoan Flustra foliacea |
title_short |
Bromotryptamine and Imidazole Alkaloids with Anti-inflammatory Activity from the Bryozoan Flustra foliacea |
title_full |
Bromotryptamine and Imidazole Alkaloids with Anti-inflammatory Activity from the Bryozoan Flustra foliacea |
title_fullStr |
Bromotryptamine and Imidazole Alkaloids with Anti-inflammatory Activity from the Bryozoan Flustra foliacea |
title_full_unstemmed |
Bromotryptamine and Imidazole Alkaloids with Anti-inflammatory Activity from the Bryozoan Flustra foliacea |
title_sort |
bromotryptamine and imidazole alkaloids with anti-inflammatory activity from the bryozoan flustra foliacea |
publisher |
ACS (American Chemical Society) |
publishDate |
2020 |
url |
https://oceanrep.geomar.de/id/eprint/50985/ https://oceanrep.geomar.de/id/eprint/50985/1/acs.jnatprod.0c00126.pdf https://doi.org/10.1021/acs.jnatprod.0c00126 |
genre |
Iceland |
genre_facet |
Iceland |
op_relation |
https://oceanrep.geomar.de/id/eprint/50985/1/acs.jnatprod.0c00126.pdf Di, X. , Wang, S., Oskarsson, J. T., Rouger, C., Tasdemir, D. , Hardardottir, I., Freysdottir, J., Wang, X. , Molinski, T. F. and Omarsdottir, S. (2020) Bromotryptamine and Imidazole Alkaloids with Anti-inflammatory Activity from the Bryozoan Flustra foliacea. Journal of Natural Products, 83 (10). pp. 2854-2866. DOI 10.1021/acs.jnatprod.0c00126 <https://doi.org/10.1021/acs.jnatprod.0c00126>. doi:10.1021/acs.jnatprod.0c00126 |
op_rights |
info:eu-repo/semantics/restrictedAccess |
op_doi |
https://doi.org/10.1021/acs.jnatprod.0c00126 |
container_title |
Journal of Natural Products |
container_volume |
83 |
container_issue |
10 |
container_start_page |
2854 |
op_container_end_page |
2866 |
_version_ |
1766038287094382592 |