New Discorhabdin Alkaloids from the Antarctic Deep-Sea Sponge Latrunculia biformis
The sponge genus Latrunculia is a prolific source of discorhabdin type pyrroloiminoquinone alkaloids. In the continuation of our research interest into this genus, we studied the Antarctic deep-sea sponge Latrunculia biformis that showed potent in vitro anticancer activity. A targeted isolation proc...
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Online Access: | https://doi.org/10.3390/md17080439 https://nbn-resolving.org/urn:nbn:de:gbv:8-mods-2020-00105-1 https://macau.uni-kiel.de/receive/macau_mods_00000282 https://macau.uni-kiel.de/servlets/MCRFileNodeServlet/macau_derivate_00001259/marinedrugs-17-00439-v2(1).pdf |
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ftunivkiel:oai:macau.uni-kiel.de:macau_mods_00000282 2024-06-23T07:45:58+00:00 New Discorhabdin Alkaloids from the Antarctic Deep-Sea Sponge Latrunculia biformis Li, Fengjie Peifer, Christian Janussen, Dorte Tasdemir, Deniz 2019 https://doi.org/10.3390/md17080439 https://nbn-resolving.org/urn:nbn:de:gbv:8-mods-2020-00105-1 https://macau.uni-kiel.de/receive/macau_mods_00000282 https://macau.uni-kiel.de/servlets/MCRFileNodeServlet/macau_derivate_00001259/marinedrugs-17-00439-v2(1).pdf eng eng Marine drugs -- 1660-3397 https://doi.org/10.3390/md17080439 https://nbn-resolving.org/urn:nbn:de:gbv:8-mods-2020-00105-1 https://macau.uni-kiel.de/receive/macau_mods_00000282 https://macau.uni-kiel.de/servlets/MCRFileNodeServlet/macau_derivate_00001259/marinedrugs-17-00439-v2(1).pdf https://creativecommons.org/licenses/by/4.0/ info:eu-repo/semantics/openAccess article ScholarlyArticle ddc:580 Published Version Antarctica Molecular docking Deep-sea Sponge Molecular Networking Latrunculia Discorhabdin article Text doc-type:Article 2019 ftunivkiel https://doi.org/10.3390/md17080439 2024-06-12T14:19:15Z The sponge genus Latrunculia is a prolific source of discorhabdin type pyrroloiminoquinone alkaloids. In the continuation of our research interest into this genus, we studied the Antarctic deep-sea sponge Latrunculia biformis that showed potent in vitro anticancer activity. A targeted isolation process guided by bioactivity and molecular networking-based metabolomics yielded three known discorhabdins, (-)-discorhabdin L (1), (+)-discorhabdin A (2), (+)-discorhabdin Q (3), and three new discorhabdin analogs (-)-2-bromo-discorhabdin D (4), (-)-1-acetyl-discorhabdin L (5), and (+)-1-octacosatrienoyl-discorhabdin L (6) from the MeOH-soluble portion of the organic extract. The chemical structures of 1-6 were elucidated by extensive NMR, HR-ESIMS, FT-IR, [α]D, and ECD (Electronic Circular Dichroism) spectroscopy analyses. Compounds 1, 5, and 6 showed promising anticancer activity with IC50 values of 0.94, 2.71, and 34.0 µM, respectively. Compounds 1-6 and the enantiomer of 1 ((+)-discorhabdin L, 1e) were docked to the active sites of two anticancer targets, topoisomerase I-II and indoleamine 2,3-dioxygenase (IDO1), to reveal, for the first time, the binding potential of discorhabdins to these proteins. Compounds 5 and 6 are the first discorhabdin analogs with an ester function at C-1 and 6 is the first discorhabdin bearing a long-chain fatty acid at this position. This study confirms Latrunculia sponges to be excellent sources of chemically diverse discorhabdin alkaloids. Article in Journal/Newspaper Antarc* Antarctic Antarctica MACAU: Open Access Repository of Kiel University Antarctic The Antarctic Marine Drugs 17 8 439 |
institution |
Open Polar |
collection |
MACAU: Open Access Repository of Kiel University |
op_collection_id |
ftunivkiel |
language |
English |
topic |
article ScholarlyArticle ddc:580 Published Version Antarctica Molecular docking Deep-sea Sponge Molecular Networking Latrunculia Discorhabdin |
spellingShingle |
article ScholarlyArticle ddc:580 Published Version Antarctica Molecular docking Deep-sea Sponge Molecular Networking Latrunculia Discorhabdin Li, Fengjie Peifer, Christian Janussen, Dorte Tasdemir, Deniz New Discorhabdin Alkaloids from the Antarctic Deep-Sea Sponge Latrunculia biformis |
topic_facet |
article ScholarlyArticle ddc:580 Published Version Antarctica Molecular docking Deep-sea Sponge Molecular Networking Latrunculia Discorhabdin |
description |
The sponge genus Latrunculia is a prolific source of discorhabdin type pyrroloiminoquinone alkaloids. In the continuation of our research interest into this genus, we studied the Antarctic deep-sea sponge Latrunculia biformis that showed potent in vitro anticancer activity. A targeted isolation process guided by bioactivity and molecular networking-based metabolomics yielded three known discorhabdins, (-)-discorhabdin L (1), (+)-discorhabdin A (2), (+)-discorhabdin Q (3), and three new discorhabdin analogs (-)-2-bromo-discorhabdin D (4), (-)-1-acetyl-discorhabdin L (5), and (+)-1-octacosatrienoyl-discorhabdin L (6) from the MeOH-soluble portion of the organic extract. The chemical structures of 1-6 were elucidated by extensive NMR, HR-ESIMS, FT-IR, [α]D, and ECD (Electronic Circular Dichroism) spectroscopy analyses. Compounds 1, 5, and 6 showed promising anticancer activity with IC50 values of 0.94, 2.71, and 34.0 µM, respectively. Compounds 1-6 and the enantiomer of 1 ((+)-discorhabdin L, 1e) were docked to the active sites of two anticancer targets, topoisomerase I-II and indoleamine 2,3-dioxygenase (IDO1), to reveal, for the first time, the binding potential of discorhabdins to these proteins. Compounds 5 and 6 are the first discorhabdin analogs with an ester function at C-1 and 6 is the first discorhabdin bearing a long-chain fatty acid at this position. This study confirms Latrunculia sponges to be excellent sources of chemically diverse discorhabdin alkaloids. |
format |
Article in Journal/Newspaper |
author |
Li, Fengjie Peifer, Christian Janussen, Dorte Tasdemir, Deniz |
author_facet |
Li, Fengjie Peifer, Christian Janussen, Dorte Tasdemir, Deniz |
author_sort |
Li, Fengjie |
title |
New Discorhabdin Alkaloids from the Antarctic Deep-Sea Sponge Latrunculia biformis |
title_short |
New Discorhabdin Alkaloids from the Antarctic Deep-Sea Sponge Latrunculia biformis |
title_full |
New Discorhabdin Alkaloids from the Antarctic Deep-Sea Sponge Latrunculia biformis |
title_fullStr |
New Discorhabdin Alkaloids from the Antarctic Deep-Sea Sponge Latrunculia biformis |
title_full_unstemmed |
New Discorhabdin Alkaloids from the Antarctic Deep-Sea Sponge Latrunculia biformis |
title_sort |
new discorhabdin alkaloids from the antarctic deep-sea sponge latrunculia biformis |
publishDate |
2019 |
url |
https://doi.org/10.3390/md17080439 https://nbn-resolving.org/urn:nbn:de:gbv:8-mods-2020-00105-1 https://macau.uni-kiel.de/receive/macau_mods_00000282 https://macau.uni-kiel.de/servlets/MCRFileNodeServlet/macau_derivate_00001259/marinedrugs-17-00439-v2(1).pdf |
geographic |
Antarctic The Antarctic |
geographic_facet |
Antarctic The Antarctic |
genre |
Antarc* Antarctic Antarctica |
genre_facet |
Antarc* Antarctic Antarctica |
op_relation |
Marine drugs -- 1660-3397 https://doi.org/10.3390/md17080439 https://nbn-resolving.org/urn:nbn:de:gbv:8-mods-2020-00105-1 https://macau.uni-kiel.de/receive/macau_mods_00000282 https://macau.uni-kiel.de/servlets/MCRFileNodeServlet/macau_derivate_00001259/marinedrugs-17-00439-v2(1).pdf |
op_rights |
https://creativecommons.org/licenses/by/4.0/ info:eu-repo/semantics/openAccess |
op_doi |
https://doi.org/10.3390/md17080439 |
container_title |
Marine Drugs |
container_volume |
17 |
container_issue |
8 |
container_start_page |
439 |
_version_ |
1802643314187436032 |