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 11-hydroxysaxitoxin (M2), while the other three were found to be new saxitoxin analogues, namely, 11-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.
Isolation and Structure Elucidation of New and Unusual Saxitoxin Analogues from Mussels / Dell'Aversano, Carmela; J. A., Walter; I. A., Burton; D. J., Stirling; Fattorusso, Ernesto; M. A., Quilliam. - In: JOURNAL OF NATURAL PRODUCTS. - ISSN 0163-3864. - STAMPA. - 71:(2008), pp. 1518-1523. [10.1021/np800066r]
Isolation and Structure Elucidation of New and Unusual Saxitoxin Analogues from Mussels
DELL'AVERSANO, CARMELA;FATTORUSSO, ERNESTO;
2008
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 11-hydroxysaxitoxin (M2), while the other three were found to be new saxitoxin analogues, namely, 11-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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
