Tridiscorhabdin and Didiscorhabdin, the First Discorhabdin Oligomers Linked with a Direct C–N Bridge from the Sponge Latrunculia biformis Collected from the Deep Sea in Antarctica

Guided by LC-MS/MS molecular networking-based metabolomics and cytotoxic activity, two new discorhabdin-type alkaloids, tridiscorhabdin (1) and didiscorhabdin (2), were isolated from the sponge Latrunculia biformis, collected from the Weddell Sea (Antarctica) at -291 m depth. Their structures were e...

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Bibliographic Details
Published in:Journal of Natural Products
Main Authors: Li, Fengjie, Pandey, Pankaj, Janussen, Dorte, Chittiboyina, Amar G., Ferreira, Daneel, Tasdemir, Deniz
Format: Article in Journal/Newspaper
Language:English
Published: ACS (American Chemical Society) 2020
Subjects:
Weddell
Weddell Sea
Antarc*
Antarctica
Antarctica Journal
Online Access:https://oceanrep.geomar.de/id/eprint/49482/
https://oceanrep.geomar.de/id/eprint/49482/1/acs.jnatprod.0c00023.pdf
https://oceanrep.geomar.de/id/eprint/49482/2/np0c00023_si_001.pdf
https://doi.org/10.1021/acs.jnatprod.0c00023
Description
Summary:Guided by LC-MS/MS molecular networking-based metabolomics and cytotoxic activity, two new discorhabdin-type alkaloids, tridiscorhabdin (1) and didiscorhabdin (2), were isolated from the sponge Latrunculia biformis, collected from the Weddell Sea (Antarctica) at -291 m depth. Their structures were established by HRESIMS, NMR, [α]D, and ECD data coupled with DFT calculations. Both compounds bear a novel C-N bridge (C-1/N-13) between discorhabdin monomers, and 1 represents the first trimeric discorhabdin molecule isolated from Nature. Tridiscorhabdin (1) exhibited strong cytotoxic activity against the human colon cancer cell line HCT-116 (IC50 value 0.31 μM).

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