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

Li, Pandey, Janussen, Chittiboyina, Ferreira, Tasdemir (2020) 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 J Nat Prod (IF: 5.1) 83(3) 706-713

Abstract

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).

Links

http://www.ncbi.nlm.nih.gov/pubmed/32105471
http://dx.doi.org/10.1021/acs.jnatprod.0c00023

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