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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ftpubmed:oai:pubmedcentral.nih.gov:6722921 2023-05-15T13:53:41+02:00 New Discorhabdin Alkaloids from the Antarctic Deep-Sea Sponge Latrunculia biformis Li, Fengjie Peifer, Christian Janussen, Dorte Tasdemir, Deniz 2019-07-25 http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6722921/ http://www.ncbi.nlm.nih.gov/pubmed/31349703 https://doi.org/10.3390/md17080439 en eng MDPI http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6722921/ http://www.ncbi.nlm.nih.gov/pubmed/31349703 http://dx.doi.org/10.3390/md17080439 © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). CC-BY Article Text 2019 ftpubmed https://doi.org/10.3390/md17080439 2019-09-15T00:21:47Z 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 IC(50) 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. Text Antarc* Antarctic PubMed Central (PMC) Antarctic The Antarctic Marine Drugs 17 8 439 |
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Article Li, Fengjie Peifer, Christian Janussen, Dorte Tasdemir, Deniz New Discorhabdin Alkaloids from the Antarctic Deep-Sea Sponge Latrunculia biformis |
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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 IC(50) 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 |
Text |
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 |
publisher |
MDPI |
publishDate |
2019 |
url |
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6722921/ http://www.ncbi.nlm.nih.gov/pubmed/31349703 https://doi.org/10.3390/md17080439 |
geographic |
Antarctic The Antarctic |
geographic_facet |
Antarctic The Antarctic |
genre |
Antarc* Antarctic |
genre_facet |
Antarc* Antarctic |
op_relation |
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6722921/ http://www.ncbi.nlm.nih.gov/pubmed/31349703 http://dx.doi.org/10.3390/md17080439 |
op_rights |
© 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). |
op_rightsnorm |
CC-BY |
op_doi |
https://doi.org/10.3390/md17080439 |
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Marine Drugs |
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17 |
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