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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ftoceanrep:oai:oceanrep.geomar.de:48995 2023-05-15T14:03:29+02:00 New Discorhabdin B Dimers with Anticancer Activity from the Antarctic Deep-Sea Sponge Latrunculia biformis Li, Fengjie Janussen, Dorte Tasdemir, Deniz 2020-02-11 text https://oceanrep.geomar.de/id/eprint/48995/ https://oceanrep.geomar.de/id/eprint/48995/1/marinedrugs-18-00107-v2.pdf https://oceanrep.geomar.de/id/eprint/48995/2/marinedrugs-18-00107-s001.pdf https://doi.org/10.3390/md18020107 en eng MDPI https://oceanrep.geomar.de/id/eprint/48995/1/marinedrugs-18-00107-v2.pdf https://oceanrep.geomar.de/id/eprint/48995/2/marinedrugs-18-00107-s001.pdf Li, F., Janussen, D. and Tasdemir, D. (2020) New Discorhabdin B Dimers with Anticancer Activity from the Antarctic Deep-Sea Sponge Latrunculia biformis. Open Access Marine Drugs, 18 (2). p. 107. DOI 10.3390/md18020107 <https://doi.org/10.3390/md18020107>. doi:10.3390/md18020107 cc_by_4.0 info:eu-repo/semantics/openAccess Article PeerReviewed 2020 ftoceanrep https://doi.org/10.3390/md18020107 2023-04-07T15:49:25Z 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 OceanRep (GEOMAR Helmholtz Centre für Ocean Research Kiel) Antarctic The Antarctic Marine Drugs 18 2 107 |
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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 |
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 |
spellingShingle |
Li, Fengjie Janussen, Dorte Tasdemir, Deniz New Discorhabdin B Dimers with Anticancer Activity from the Antarctic Deep-Sea Sponge Latrunculia biformis |
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 |
publisher |
MDPI |
publishDate |
2020 |
url |
https://oceanrep.geomar.de/id/eprint/48995/ https://oceanrep.geomar.de/id/eprint/48995/1/marinedrugs-18-00107-v2.pdf https://oceanrep.geomar.de/id/eprint/48995/2/marinedrugs-18-00107-s001.pdf https://doi.org/10.3390/md18020107 |
geographic |
Antarctic The Antarctic |
geographic_facet |
Antarctic The Antarctic |
genre |
Antarc* Antarctic |
genre_facet |
Antarc* Antarctic |
op_relation |
https://oceanrep.geomar.de/id/eprint/48995/1/marinedrugs-18-00107-v2.pdf https://oceanrep.geomar.de/id/eprint/48995/2/marinedrugs-18-00107-s001.pdf Li, F., Janussen, D. and Tasdemir, D. (2020) New Discorhabdin B Dimers with Anticancer Activity from the Antarctic Deep-Sea Sponge Latrunculia biformis. Open Access Marine Drugs, 18 (2). p. 107. DOI 10.3390/md18020107 <https://doi.org/10.3390/md18020107>. doi:10.3390/md18020107 |
op_rights |
cc_by_4.0 info:eu-repo/semantics/openAccess |
op_doi |
https://doi.org/10.3390/md18020107 |
container_title |
Marine Drugs |
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18 |
container_issue |
2 |
container_start_page |
107 |
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1766274165551136768 |