| Title | Isolation and Structure Elucidation of New and Unusual Saxitoxin Analogues from Mussels. | | Author(s) | Dell'aversano C, Walter JA, Burton IW, Stirling DJ, Fattorusso E, Quilliam MA | | Institution | michael.quilliam@nrc-cnrc.gc.ca. | | Source | J Nat Prod 2008 Aug 13. | | Abstract | Chemical analyses of plankton and highly toxic mussel samples collected in eastern Canada during an intense bloom of the dinoflagellate Alexandrium tamarense established the presence of a complex mixture of paralytic shellfish poisoning (PSP) toxins. Application of a newly developed technique, hydrophilic interaction liquid chromatography-mass spectrometry, confirmed the identities of the known toxins and revealed the presence in the mussels of five saxitoxin analogues (M1-M5) that were not present in the plankton. Four of these compounds were isolated and their structures established by tandem mass spectrometry, 1D- and 2D-NMR spectroscopy, and chemical interconversion experiments. One of these was found to be 11beta-hydroxysaxitoxin (M2), while the other three were found to be new saxitoxin analogues, namely, 11beta-hydroxy- N-sulfocarbamoylsaxitoxin (M1), 11,11-dihydroxy- N-sulfocarbamoylsaxitoxin (M3), and 11,11-dihydroxysaxitoxin (M4). Compound M5 remains unidentified because of insufficient material for characterization. | | Language | ENG | | Pub Type(s) | JOURNAL ARTICLE
| | PubMed ID | 18698820 |
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