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Open AccessArticle

New Discorhabdin Alkaloids from the Antarctic Deep-Sea Sponge Latrunculia biformis

1
GEOMAR Centre for Marine Biotechnology (GEOMAR-Biotech), Research Unit Marine Natural Products Chemistry, GEOMAR Helmholtz Centre for Ocean Research Kiel, Am Kiel-Kanal 44, 24106 Kiel, Germany
2
Pharmaceutical Chemistry, Kiel University, Gutenbergstraße 76, 24118 Kiel, Germany
3
Senckenberg Research Institute and Natural History Museum, Senckenberganlage 25, D-60325 Frankfurt, Germany
4
Faculty of Mathematics and Natural Sciences, Kiel University, Christian-Albrechts-Platz 4, 24118 Kiel, Germany
*
Author to whom correspondence should be addressed.
Mar. Drugs 2019, 17(8), 439; https://doi.org/10.3390/md17080439
Received: 14 June 2019 / Revised: 17 July 2019 / Accepted: 22 July 2019 / Published: 25 July 2019
(This article belongs to the Special Issue Bioactive Molecules from Extreme Environments)
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 16 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 16 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. View Full-Text
Keywords: Latrunculia; Antarctica; deep-sea sponge; molecular networking; molecular docking; discorhabdin Latrunculia; Antarctica; deep-sea sponge; molecular networking; molecular docking; discorhabdin
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MDPI and ACS Style

Li, F.; Peifer, C.; Janussen, D.; Tasdemir, D. New Discorhabdin Alkaloids from the Antarctic Deep-Sea Sponge Latrunculia biformis. Mar. Drugs 2019, 17, 439.

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