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Toxicon. 2016 Mar 15;112:68-76. doi: 10.1016/j.toxicon.2016.01.064. Epub 2016 Jan 29.

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

Author information

1
VERIFIN, Department of Chemistry, P.O. Box 55, A. I. Virtasen aukio 1, FI-00014, University of Helsinki, Finland. Electronic address: kirsi.harju@helsinki.fi.
2
VERIFIN, Department of Chemistry, P.O. Box 55, A. I. Virtasen aukio 1, FI-00014, University of Helsinki, Finland.
3
Finnish Environment Institute, Marine Research Centre, Erik Palménin aukio 1, FI-00560, Helsinki, Finland.
4
IRTA, Carretera de Poble Nou, km 5.5, 43540, Sant Carles de la Rápita, Spain.
5
Norwegian Veterinary Institute, P.O. Box 750 Sentrum, N-0106, Oslo, Norway; Department of Pharmaceutical Chemistry, School of Pharmacy, University of Oslo, P.O. Box 1068 Blindern, N-0316, Oslo, Norway.
6
Alfred Wegener Institute, Am Handelshafen 12, D-27570, Bremerhaven, Germany.

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.

KEYWORDS:

Alexandrium ostenfeldii; Dinoflagellate; Gymnodimine; High resolution mass spectrometry; Liquid chromatography–mass spectrometry; Nuclear magnetic resonance

PMID:
26829651
DOI:
10.1016/j.toxicon.2016.01.064
[Indexed for MEDLINE]

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