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 | Zendy

Fengjie Li | Zendy; Pankaj Pandey | Zendy; Dorte Janussen | Zendy; Amar G. Chittiboyina | Zendy; Daneel Ferreira | Zendy; Deniz Taşdemir | Zendy

Open Access

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

Author(s) -

Fengjie Li,

Pankaj Pandey,

Dorte Janussen,

Amar G. Chittiboyina,

Daneel Ferreira,

Deniz Taşdemir

Publication year - 2020

Publication title -

journal of natural products

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.976

H-Index - 139

eISSN - 1520-6025

pISSN - 0163-3864

DOI - 10.1021/acs.jnatprod.0c00023

Subject(s) - sponge , stereochemistry , monomer , cancer cell lines , bridge (graph theory) , chemistry , biology , cancer cell , cancer , botany , genetics , organic chemistry , polymer , anatomy

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 (IC 50 value 0.31 μM).

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