New Discorhabdin B Dimers with Anticancer Activity from the Antarctic Deep-Sea Sponge Latrunculia biformis
Latrunculia sponges represent a rich source of discorhabdin-type pyrroloiminoquinone alkaloids, a few of which comprise a dimeric structure. The anticancer-activity-guided isolation of the n-hexane subextract of the Antarctic deep-sea sponge Latrunculia biformis yielded the known compound (-)-(1R,2R...
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ftunivkiel:oai:macau.uni-kiel.de:macau_mods_00000460 2024-06-23T07:47:08+00:00 New Discorhabdin B Dimers with Anticancer Activity from the Antarctic Deep-Sea Sponge Latrunculia biformis Li, Fengjie Janussen, Dorte Tasdemir, Deniz 2020 https://doi.org/10.3390/md18020107 https://nbn-resolving.org/urn:nbn:de:gbv:8-mods-2020-00178-0 https://macau.uni-kiel.de/receive/macau_mods_00000460 https://macau.uni-kiel.de/servlets/MCRFileNodeServlet/macau_derivate_00001448/marinedrugs-18-00107-v3.pdf eng eng Marine drugs -- 1660-3397 https://doi.org/10.3390/md18020107 https://nbn-resolving.org/urn:nbn:de:gbv:8-mods-2020-00178-0 https://macau.uni-kiel.de/receive/macau_mods_00000460 https://macau.uni-kiel.de/servlets/MCRFileNodeServlet/macau_derivate_00001448/marinedrugs-18-00107-v3.pdf https://creativecommons.org/licenses/by/4.0/ info:eu-repo/semantics/openAccess article ScholarlyArticle ddc:610 Published Version Antarctica Anticancer activity Ecd Spectroscopy Deep-sea Sponge Latrunculia Biformis Discorhabdin B Dimer article Text doc-type:Article 2020 ftunivkiel https://doi.org/10.3390/md18020107 2024-06-12T14:19:15Z Latrunculia sponges represent a rich source of discorhabdin-type pyrroloiminoquinone alkaloids, a few of which comprise a dimeric structure. The anticancer-activity-guided isolation of the n-hexane subextract of the Antarctic deep-sea sponge Latrunculia biformis yielded the known compound (-)-(1R,2R,6R,8S,6'S)-discorhabdin B dimer (1) and two new derivatives, (-)-(1S,2R,6R,8S,6'S)-discorhabdin B dimer (2) and (-)-(1R,2R,6R,8S,6'S)-16',17'-dehydrodiscorhabdin B dimer (3). The chemical structures of compounds 1-3 were elucidated by means of HR-ESIMS, NMR, [], ECD spectroscopy, and a comparison with the previously reported discorhabdin analogs. Compounds 1 and 2 showed significant in vitro anticancer activity against the human colon cancer cell line (HCT-116), with IC50 values of 0.16 and 2.01 µM, respectively. Compared to monomeric discorhabdins, dimeric discorhabdins are very rare in Nature. This study adds two new discorhabdin dimers (2 and 3) to this small pyrroloiminoquinone subfamily. This is also the first report of compound 1 as a natural product and the first assessment of its in vitro anticancer activity. Article in Journal/Newspaper Antarc* Antarctic Antarctica MACAU: Open Access Repository of Kiel University Antarctic The Antarctic Marine Drugs 18 2 107 |
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Open Polar |
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MACAU: Open Access Repository of Kiel University |
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ftunivkiel |
language |
English |
topic |
article ScholarlyArticle ddc:610 Published Version Antarctica Anticancer activity Ecd Spectroscopy Deep-sea Sponge Latrunculia Biformis Discorhabdin B Dimer |
spellingShingle |
article ScholarlyArticle ddc:610 Published Version Antarctica Anticancer activity Ecd Spectroscopy Deep-sea Sponge Latrunculia Biformis Discorhabdin B Dimer Li, Fengjie Janussen, Dorte Tasdemir, Deniz New Discorhabdin B Dimers with Anticancer Activity from the Antarctic Deep-Sea Sponge Latrunculia biformis |
topic_facet |
article ScholarlyArticle ddc:610 Published Version Antarctica Anticancer activity Ecd Spectroscopy Deep-sea Sponge Latrunculia Biformis Discorhabdin B Dimer |
description |
Latrunculia sponges represent a rich source of discorhabdin-type pyrroloiminoquinone alkaloids, a few of which comprise a dimeric structure. The anticancer-activity-guided isolation of the n-hexane subextract of the Antarctic deep-sea sponge Latrunculia biformis yielded the known compound (-)-(1R,2R,6R,8S,6'S)-discorhabdin B dimer (1) and two new derivatives, (-)-(1S,2R,6R,8S,6'S)-discorhabdin B dimer (2) and (-)-(1R,2R,6R,8S,6'S)-16',17'-dehydrodiscorhabdin B dimer (3). The chemical structures of compounds 1-3 were elucidated by means of HR-ESIMS, NMR, [], ECD spectroscopy, and a comparison with the previously reported discorhabdin analogs. Compounds 1 and 2 showed significant in vitro anticancer activity against the human colon cancer cell line (HCT-116), with IC50 values of 0.16 and 2.01 µM, respectively. Compared to monomeric discorhabdins, dimeric discorhabdins are very rare in Nature. This study adds two new discorhabdin dimers (2 and 3) to this small pyrroloiminoquinone subfamily. This is also the first report of compound 1 as a natural product and the first assessment of its in vitro anticancer activity. |
format |
Article in Journal/Newspaper |
author |
Li, Fengjie Janussen, Dorte Tasdemir, Deniz |
author_facet |
Li, Fengjie Janussen, Dorte Tasdemir, Deniz |
author_sort |
Li, Fengjie |
title |
New Discorhabdin B Dimers with Anticancer Activity from the Antarctic Deep-Sea Sponge Latrunculia biformis |
title_short |
New Discorhabdin B Dimers with Anticancer Activity from the Antarctic Deep-Sea Sponge Latrunculia biformis |
title_full |
New Discorhabdin B Dimers with Anticancer Activity from the Antarctic Deep-Sea Sponge Latrunculia biformis |
title_fullStr |
New Discorhabdin B Dimers with Anticancer Activity from the Antarctic Deep-Sea Sponge Latrunculia biformis |
title_full_unstemmed |
New Discorhabdin B Dimers with Anticancer Activity from the Antarctic Deep-Sea Sponge Latrunculia biformis |
title_sort |
new discorhabdin b dimers with anticancer activity from the antarctic deep-sea sponge latrunculia biformis |
publishDate |
2020 |
url |
https://doi.org/10.3390/md18020107 https://nbn-resolving.org/urn:nbn:de:gbv:8-mods-2020-00178-0 https://macau.uni-kiel.de/receive/macau_mods_00000460 https://macau.uni-kiel.de/servlets/MCRFileNodeServlet/macau_derivate_00001448/marinedrugs-18-00107-v3.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/md18020107 https://nbn-resolving.org/urn:nbn:de:gbv:8-mods-2020-00178-0 https://macau.uni-kiel.de/receive/macau_mods_00000460 https://macau.uni-kiel.de/servlets/MCRFileNodeServlet/macau_derivate_00001448/marinedrugs-18-00107-v3.pdf |
op_rights |
https://creativecommons.org/licenses/by/4.0/ info:eu-repo/semantics/openAccess |
op_doi |
https://doi.org/10.3390/md18020107 |
container_title |
Marine Drugs |
container_volume |
18 |
container_issue |
2 |
container_start_page |
107 |
_version_ |
1802651179540283392 |