BIOMAT Database Logo BIOMAT Database Logo

Liquid chromatographic methods for the isolation and identification of new pectenotoxin-2 analogues from marine phytoplankton and shellfish. 1999

K J James, and A G Bishop, and R Draisci, and L Palleschi, and C Marchiafava, and E Ferretti, and M Satake, and T Yasumoto
Chemistry Department, Cork Institute of Technology, Bishopstown, Ireland. kjames@cit.ie

Two acidic analogues of the polyether marine toxin, pectenotoxin-2 (PTX-2), responsible for diarrhetic shellfish poisoning (DSP), have been isolated from the toxic marine phytoplankton (Dinophysis acuta), collected in Irish waters. Liquid chromatography with fluorimetric detection (LC-FLD) analyses of the extracts of bulk phytoplankton samples, following derivatisation with 9-anthryldiazomethane (ADAM) or 1-bromoacetylpyrene (BAP), showed a complex toxin profile with peaks corresponding to okadaic acid (OA) and its isomers, dinophysistoxin-2 (DTX-2) and DTX-2C, as well as other unidentified lipophilic acids. LC-UV analysis showed the presence of a diene moiety in these new compounds and two acids have been isolated. LC coupled with mass spectrometry (MS) and tandem mass spectrometry (LC-MS-MS) were used to gain structural information. Through flow injection analysis (FIA)-MS, both in positive and negative ion modes, the molecular weight of 876 for both compounds was determined. Collision Induced Dissociation (CID) from each parent ion, as performed both in positive and negative ion mode, produced mass spectra which were very similar to those obtained for authentic PTX-2 (mw 858). These new compounds have been confirmed to be pectenotoxin-2 seco acids (PTX-2SAs) and they are closely related to PTX-2 except that they contain an open chain carboxylic acid rather than a lactone ring. Toxic mussels also contained these pectenotoxin-2 analogues.

UI MeSH Term Description Entries
D008387 Marine Toxins Toxic or poisonous substances elaborated by marine flora or fauna. They include also specific, characterized poisons or toxins for which there is no more specific heading, like those from poisonous FISHES. Marine Biotoxins,Phycotoxins
D010839 Phytoplankton Free-floating minute organisms that are photosynthetic. The term is non-taxonomic and refers to a lifestyle (energy utilization and motility), rather than a particular type of organism. Most, but not all, are unicellular algae. Important groups include DIATOMS; DINOFLAGELLATES; CYANOBACTERIA; CHLOROPHYTA; HAPTOPHYTA; CRYPTOMONADS; and silicoflagellates.
D011714 Pyrans Pyran
D002853 Chromatography, Liquid Chromatographic techniques in which the mobile phase is a liquid. Liquid Chromatography
D005663 Furans Compounds with a 5-membered ring of four carbons and an oxygen. They are aromatic heterocycles. The reduced form is tetrahydrofuran. Tetrahydrofurans
D012758 Shellfish Aquatic invertebrates belonging to the phylum MOLLUSCA or the subphylum CRUSTACEA, and used as food.
D013058 Mass Spectrometry An analytical method used in determining the identity of a chemical based on its mass using mass analyzers/mass spectrometers. Mass Spectroscopy,Spectrometry, Mass,Spectroscopy, Mass,Spectrum Analysis, Mass,Analysis, Mass Spectrum,Mass Spectrum Analysis,Analyses, Mass Spectrum,Mass Spectrum Analyses,Spectrum Analyses, Mass
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D018942 Macrolides A group of often glycosylated macrocyclic compounds formed by chain extension of multiple PROPIONATES cyclized into a large (typically 12, 14, or 16)-membered lactone. Macrolides belong to the POLYKETIDES class of natural products, and many members exhibit ANTIBIOTIC properties. Macrolide

Related Publications

K J James, and A G Bishop, and R Draisci, and L Palleschi, and C Marchiafava, and E Ferretti, and M Satake, and T Yasumoto
Pectenotoxin-2 seco acid, 7-epi-pectenotoxin-2 seco acid and pectenotoxin-2 in shellfish and plankton from Portugal.
July 2002, Toxicon : official journal of the International Society on Toxinology,
K J James, and A G Bishop, and R Draisci, and L Palleschi, and C Marchiafava, and E Ferretti, and M Satake, and T Yasumoto
[Isolation of Salmonella from marine shellfish].
January 1979, Arquivos do Instituto Biologico,
K J James, and A G Bishop, and R Draisci, and L Palleschi, and C Marchiafava, and E Ferretti, and M Satake, and T Yasumoto
Identification of pectenotoxin-11 as 34S-hydroxypectenotoxin-2, a new pectenotoxin analogue in the toxic dinoflagellate Dinophysis acuta from New Zealand.
February 2006, Chemical research in toxicology,
K J James, and A G Bishop, and R Draisci, and L Palleschi, and C Marchiafava, and E Ferretti, and M Satake, and T Yasumoto
Isolation and structure determination of a new marine neurotoxin from the New Zealand shellfish, Austrovenus stutchburyi.
December 1994, Toxicon : official journal of the International Society on Toxinology,
K J James, and A G Bishop, and R Draisci, and L Palleschi, and C Marchiafava, and E Ferretti, and M Satake, and T Yasumoto
High-performance liquid chromatographic methods for determination of marine biotoxins.
November 1996, The Analyst,
K J James, and A G Bishop, and R Draisci, and L Palleschi, and C Marchiafava, and E Ferretti, and M Satake, and T Yasumoto
Comparison evaluation of liquid chromatographic and bioassay methods of analysis for determination of paralytic shellfish poisons in shellfish tissues.
January 1989, Journal - Association of Official Analytical Chemists,
K J James, and A G Bishop, and R Draisci, and L Palleschi, and C Marchiafava, and E Ferretti, and M Satake, and T Yasumoto
Liquid chromatographic mass spectrometric methods for the determination of marine polyether toxins.
January 1992, Bulletin de la Societe de pathologie exotique (1990),
K J James, and A G Bishop, and R Draisci, and L Palleschi, and C Marchiafava, and E Ferretti, and M Satake, and T Yasumoto
Quantification of diarrhetic shellfish toxins and identification of novel protein phosphatase inhibitors in marine phytoplankton and mussels.
January 1993, Toxicon : official journal of the International Society on Toxinology,
K J James, and A G Bishop, and R Draisci, and L Palleschi, and C Marchiafava, and E Ferretti, and M Satake, and T Yasumoto
Harmful marine phytoplankton and shellfish toxicity. Potential consequences of climate change.
December 1994, Annals of the New York Academy of Sciences,
K J James, and A G Bishop, and R Draisci, and L Palleschi, and C Marchiafava, and E Ferretti, and M Satake, and T Yasumoto
The detection and identification of 42,43,44,45,46,47,55-heptanor-41-oxoyessotoxin, a new marine toxin from adriatic shellfish, by liquid chromatography-mass spectrometry.
July 2002, Chemical research in toxicology,
Copied contents to your clipboard!