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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ftunivfrankfurt:oai:publikationen.ub.uni-frankfurt.de:53318 2024-04-21T07:52:06+00:00 New discorhabdin alkaloids from the antarctic deep-sea sponge Latrunculia biformis Li, Fengjie Peifer, Christian Janussen, Dorte Tasdemir, Deniz 2019-07-25 application/octet-stream http://publikationen.ub.uni-frankfurt.de/frontdoor/index/index/docId/53318 https://nbn-resolving.org/urn:nbn:de:hebis:30:3-533182 https://doi.org/10.3390/md17080439 http://publikationen.ub.uni-frankfurt.de/files/53318/container.zip eng eng http://publikationen.ub.uni-frankfurt.de/frontdoor/index/index/docId/53318 urn:nbn:de:hebis:30:3-533182 https://nbn-resolving.org/urn:nbn:de:hebis:30:3-533182 https://doi.org/10.3390/md17080439 http://publikationen.ub.uni-frankfurt.de/files/53318/container.zip http://creativecommons.org/licenses/by/4.0/ info:eu-repo/semantics/restrictedAccess ddc:590 article doc-type:article 2019 ftunivfrankfurt https://doi.org/10.3390/md17080439 2024-03-28T00:30:57Z 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 Publication Server of Goethe University Frankfurt am Main Marine Drugs 17 8 439 |
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Open Polar |
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Publication Server of Goethe University Frankfurt am Main |
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ftunivfrankfurt |
language |
English |
topic |
ddc:590 |
spellingShingle |
ddc:590 Li, Fengjie Peifer, Christian Janussen, Dorte Tasdemir, Deniz New discorhabdin alkaloids from the antarctic deep-sea sponge Latrunculia biformis |
topic_facet |
ddc:590 |
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 |
http://publikationen.ub.uni-frankfurt.de/frontdoor/index/index/docId/53318 https://nbn-resolving.org/urn:nbn:de:hebis:30:3-533182 https://doi.org/10.3390/md17080439 http://publikationen.ub.uni-frankfurt.de/files/53318/container.zip |
genre |
Antarc* Antarctic |
genre_facet |
Antarc* Antarctic |
op_relation |
http://publikationen.ub.uni-frankfurt.de/frontdoor/index/index/docId/53318 urn:nbn:de:hebis:30:3-533182 https://nbn-resolving.org/urn:nbn:de:hebis:30:3-533182 https://doi.org/10.3390/md17080439 http://publikationen.ub.uni-frankfurt.de/files/53318/container.zip |
op_rights |
http://creativecommons.org/licenses/by/4.0/ info:eu-repo/semantics/restrictedAccess |
op_doi |
https://doi.org/10.3390/md17080439 |
container_title |
Marine Drugs |
container_volume |
17 |
container_issue |
8 |
container_start_page |
439 |
_version_ |
1796935362284617728 |