title: Characterization of polar brevetoxin derivatives isolated from Karenia brevis cultures and natural blooms.
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.
authors.affiliation: Gulf Coast Seafood Laboratory, US Food and Drug Administration, P.O. Box 158, 1 Iberville Drive, Dauphin Island, AL 36528-0158, USA. ann.abraham@fda.hhs.gov
authors.forename: Ann
authors.initials: A
authors.lastname: Abraham
authors.forename: Steven M
authors.initials: SM
authors.lastname: Plakas
authors.forename: Zhihong
authors.initials: Z
authors.lastname: Wang
authors.forename: Edward L E
authors.initials: EL
authors.lastname: Jester
authors.forename: Kathleen R
authors.initials: KR
authors.lastname: El Said
authors.forename: Hudson R
authors.initials: HR
authors.lastname: Granade
authors.forename: Michael S
authors.initials: MS
authors.lastname: Henry
authors.forename: Patricia C
authors.initials: PC
authors.lastname: Blum
authors.forename: Richard H
authors.initials: RH
authors.lastname: Pierce
authors.forename: Robert W
authors.initials: RW
authors.lastname: Dickey
mesh_terms: D000818:Animals; D045744:Cell Line, Tumor; D002853:Chromatography, Liquid; D049896:Crassostrea / Q000378:metabolism; D004141:Dinoflagellida / Q000472:pathogenicity*; D008387:Marine Toxins / Q000737:chemistry / Q000302:isolation & purification / Q000633:toxicity*; D013058:Mass Spectrometry; D051379:Mice; D009447:Neuroblastoma / Q000473:pathology; D035964:Oxocins / Q000737:chemistry / Q000302:isolation & purification / Q000633:toxicity*; D000095702:Polyether Toxins
chemical_list: D008387:Marine Toxins; D035964:Oxocins; C053342:brevetoxin; D000095702:Polyether Toxins