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

Fengjie Li; Pankaj Pandey; Dorte Janussen; Amar G Chittiboyina; Daneel Ferreira; Deniz Tasdemir

doi:10.1021/acs.jnatprod.0c00023

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. 2020 Mar 27;83(3):706-713. doi: 10.1021/acs.jnatprod.0c00023. Epub 2020 Feb 27.

Authors

Fengjie Li¹, Pankaj Pandey², Dorte Janussen³, Amar G Chittiboyina², Daneel Ferreira², Deniz Tasdemir^{1

4}

Affiliations

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 National Center for Natural Products Research and Department of Biomolecular Sciences, Division of Pharmacognosy, School of Pharmacy, University of Mississippi, University, Mississippi 38677, United States.
³ Senckenberg Research Institute and Natural History Museum, Senckenberganlage 25, 60325 Frankfurt, Germany.
⁴ Faculty of Mathematics and Natural Sciences, Kiel University, Christian-Albrechts-Platz 4, 24118 Kiel, Germany.

PMID: 32105471
DOI: 10.1021/acs.jnatprod.0c00023

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).

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Alkaloids / isolation & purification
Alkaloids / pharmacology*
Animals
Antarctic Regions
Antineoplastic Agents / isolation & purification
Antineoplastic Agents / pharmacology*
Biological Products / isolation & purification
Biological Products / pharmacology
Cell Line, Tumor
Humans
Molecular Structure
Porifera / chemistry*

Substances

Alkaloids
Antineoplastic Agents
Biological Products