Identification of gymnodimine D and presence of gymnodimine variants in the dinoflagellate Alexandrium ostenfeldii from the Baltic Sea

Harju, Kirsi, Koskela, Harri, Kremp, Anke, Suikkanen, Sanna, de la Iglesia, Pablo, Miles, Christopher O, Krock, Bernd and Vanninen, Paula ;

Contact

Bernd.Krock [ at ] awi.de

Abstract

Gymnodimines are lipophilic toxins produced by the marine dinoflagellates Karenia selliformis and Alexandrium ostenfeldii. Currently four gymnodimine analogues are known and characterized. Here we describe a novel gymnodimine and a range of gymnodimine related compounds found in an A. ostenfeldii isolate from the northern Baltic Sea. Gymnodimine D (1) was extracted and purified from clonal cultures, and characterized by liquid chromatography-tandem mass spectrometry (LC-MS/MS), nuclear magnetic resonance (NMR) spectroscopy, and liquid chromatography-high resolution mass spectrometry (LC-HRMS) experiments. The structure of 1 is related to known gymnodimines (2-5) with a six-membered cyclic imine ring and several other fragments typical of gymnodimines. However, the carbon chain in the gymnodimine macrocyclic ring differs from the known gymnodimines in having two tetrahydrofuran rings in the macrocyclic ring.

Item Type

Article

Authors

Harju, Kirsi, Koskela, Harri, Kremp, Anke, Suikkanen, Sanna, de la Iglesia, Pablo, Miles, Christopher O, Krock, Bernd and Vanninen, Paula ;

Divisions

AWI Organizations > Biosciences > Ecological Chemistry

Primary Division

Organizations > AWI Organizations > Biosciences > Ecological Chemistry

Programs

Helmholtz Research Programs > PACES II (2014-2020) > TOPIC 2: Fragile coasts and shelf sea > WP 2.3: Evolution and adaptation to climate change and anthropogenic stress in coastal and shelf systems

Primary Topic

Helmholtz Programs > Helmholtz Research Programs > PACES II (2014-2020) > TOPIC 2: Fragile coasts and shelf sea > WP 2.3: Evolution and adaptation to climate change and anthropogenic stress in coastal and shelf systems

Publication Status

Published

Eprint ID

39723

DOI https://www.doi.org/10.1016/j.toxicon.2016.01.064

Cite as

Harju, K. , Koskela, H. , Kremp, A. , Suikkanen, S. , de la Iglesia, P. , Miles, C. O. , Krock, B. and Vanninen, P. (2016): Identification of gymnodimine D and presence of gymnodimine variants in the dinoflagellate Alexandrium ostenfeldii from the Baltic Sea , Toxicon, 112 , pp. 68-76 . doi: https://www.doi.org/10.1016/j.toxicon.2016.01.064