title: Identification of gymnodimine D and presence of gymnodimine variants in the dinoflagellate Alexandrium ostenfeldii from the Baltic Sea.
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.
authors.affiliation: 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.
authors.forename: Kirsi
authors.initials: K
authors.lastname: Harju
authors.affiliation: VERIFIN, Department of Chemistry, P.O. Box 55, A. I. Virtasen aukio 1, FI-00014, University of Helsinki, Finland.
authors.forename: Harri
authors.initials: H
authors.lastname: Koskela
authors.affiliation: Finnish Environment Institute, Marine Research Centre, Erik Palménin aukio 1, FI-00560, Helsinki, Finland.
authors.forename: Anke
authors.initials: A
authors.lastname: Kremp
authors.affiliation: Finnish Environment Institute, Marine Research Centre, Erik Palménin aukio 1, FI-00560, Helsinki, Finland.
authors.forename: Sanna
authors.initials: S
authors.lastname: Suikkanen
authors.affiliation: IRTA, Carretera de Poble Nou, km 5.5, 43540, Sant Carles de la Rápita, Spain.
authors.forename: Pablo
authors.initials: P
authors.lastname: de la Iglesia
authors.affiliation: 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.
authors.forename: Christopher O
authors.initials: CO
authors.lastname: Miles
authors.affiliation: Alfred Wegener Institute, Am Handelshafen 12, D-27570, Bremerhaven, Germany.
authors.forename: Bernd
authors.initials: B
authors.lastname: Krock
authors.affiliation: VERIFIN, Department of Chemistry, P.O. Box 55, A. I. Virtasen aukio 1, FI-00014, University of Helsinki, Finland.
authors.forename: Paula
authors.initials: P
authors.lastname: Vanninen
mesh_terms: D001267:Atlantic Ocean; D002478:Cells, Cultured; D002851:Chromatography, High Pressure Liquid; D002999:Clone Cells; D004141:Dinoflagellida / Q000737:chemistry / Q000166:cytology / Q000254:growth & development / Q000378:metabolism*; D057097:Harmful Algal Bloom; D006575:Heterocyclic Compounds, 3-Ring / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism; D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism*; D006844:Hydrocarbons, Cyclic / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism*; D007097:Imines / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism; D008387:Marine Toxins / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism*; D008745:Methylation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D021241:Spectrometry, Mass, Electrospray Ionization; D013237:Stereoisomerism; D013548:Sweden; D053719:Tandem Mass Spectrometry
chemical_list: D006575:Heterocyclic Compounds, 3-Ring; D006576:Heterocyclic Compounds, 4 or More Rings; D006844:Hydrocarbons, Cyclic; D007097:Imines; D008387:Marine Toxins; C569130:gymnodimine A; C409490:gymnodimine B; C000612207:gymnodimine C; C000612206:gymnodimine D
keywords: Alexandrium ostenfeldii; Dinoflagellate; Gymnodimine; High resolution mass spectrometry; Liquid chromatography–mass spectrometry; Nuclear magnetic resonance