Characterization of polar brevetoxin derivatives isolated from Karenia brevis cultures and natural blooms.

Toxicon

Gulf Coast Seafood Laboratory, US Food and Drug Administration, P.O. Box 158, 1 Iberville Drive, Dauphin Island, AL 36528-0158, USA.

Published: July 2006

AI Article Synopsis

  • Several new types of brevetoxin derivatives were identified in cultures and natural blooms of Karenia brevis using advanced extraction and mass spectrometry techniques.
  • These new derivatives are more polar than previously known brevetoxins and were not easily extracted using traditional non-polar solvents.
  • The newly identified compounds include hydrolyzed forms of various brevetoxins and were found to be more abundant in bloom water than in cell-rich samples, posing cytotoxic effects in neuroblastoma cell assays and contributing to toxin levels in Eastern oysters exposed to blooms.

Article Abstract

Several novel brevetoxin derivatives were isolated and identified in Karenia brevis cultures and natural blooms by using solid phase extraction (SPE) and LC/MS(MS) techniques. These analogs were more polar compared with previously described brevetoxins, and were poorly extractable by conventional non-polar solvent (chloroform) partitioning. Brevetoxin analogs were structurally confirmed as hydrolyzed (open A-ring) forms of brevetoxins PbTx-1, PbTx-7, PbTx-2, and PbTx-3, and of oxidized PbTx-1 and PbTx-2. Some of these open A-ring derivatives were in greater abundance than their non-hydrolyzed counterparts. All were in much greater abundance in bloom water filtrate compared with cell-rich fractions. Open A-ring compounds were cytotoxic in mouse neuroblastoma (N2a) cell assay. In the K. brevis bloom-exposed Eastern oyster, brevetoxin metabolites with opened A rings were identified (e.g., open-ring cysteine-PbTx conjugates), contributing to their overall toxin burden.

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http://dx.doi.org/10.1016/j.toxicon.2006.04.015DOI Listing

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