Paralytic Shellfish Poisoning (PSP) toxins are potent neurotoxins responsible for a number of seafood poisonings occurring worldwide. Within the PSP toxins class, the great variety of closely related structures and varying toxicities present significant challenges to both analytical and natural products chemists. The chemical investigation of highly toxic mussels collected in June 2000 along eastern-Canada coasts is presented. The research led to the isolation of three new derivatives of saxitoxin, 11a- and 11b-hydroxy-N-sulfocarbamoyl saxitoxin (M1a, M1b) and 11,11-dihydroxy-N-sulfocarbamoyl saxitoxin (M2). Their structures were established by hydrophilic interaction liquid chromatography-mass spectrometry (HILIC-MS) and 1H and 13C NMR spectroscopy. The M2 structure contains a very unusual vicinal gem-diols moiety, which is unique in marine natural products chemistry. Besides the novelty of the M1a, M1b and M2 structures, which represent significant additions to the PSP toxins class, the finding of the new toxins unequivocally demonstrates the power of HILIC-MS to detect the presence in shellfish tissues of new saxitoxin analogues together with known derivatives. This method represents a valuable tool for scientists involved in both regulatory and research field. The new toxins are not produced by plankton but appear to be metabolites formed in shellfish, which sheds new light on the fate of PSP toxins as they enter the food web.

Isolation and Structure Elucidation of New and Unusual Saxitoxin Analogues from Mussels

DELL'AVERSANO, CARMELA;FATTORUSSO, ERNESTO;
2002

Abstract

Paralytic Shellfish Poisoning (PSP) toxins are potent neurotoxins responsible for a number of seafood poisonings occurring worldwide. Within the PSP toxins class, the great variety of closely related structures and varying toxicities present significant challenges to both analytical and natural products chemists. The chemical investigation of highly toxic mussels collected in June 2000 along eastern-Canada coasts is presented. The research led to the isolation of three new derivatives of saxitoxin, 11a- and 11b-hydroxy-N-sulfocarbamoyl saxitoxin (M1a, M1b) and 11,11-dihydroxy-N-sulfocarbamoyl saxitoxin (M2). Their structures were established by hydrophilic interaction liquid chromatography-mass spectrometry (HILIC-MS) and 1H and 13C NMR spectroscopy. The M2 structure contains a very unusual vicinal gem-diols moiety, which is unique in marine natural products chemistry. Besides the novelty of the M1a, M1b and M2 structures, which represent significant additions to the PSP toxins class, the finding of the new toxins unequivocally demonstrates the power of HILIC-MS to detect the presence in shellfish tissues of new saxitoxin analogues together with known derivatives. This method represents a valuable tool for scientists involved in both regulatory and research field. The new toxins are not produced by plankton but appear to be metabolites formed in shellfish, which sheds new light on the fate of PSP toxins as they enter the food web.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11588/505858
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