Date of Award

12-2004

Degree Type

Thesis

Degree Name

M.S.

Degree Program

Chemistry

Department

Chemistry

Major Professor

Cole, Richard

Second Advisor

Wang, Guangdi

Third Advisor

Tarr, Matthew

Fourth Advisor

Rosenzweig, Zeev

Abstract

Brevetoxins are natural neurotoxins that are produced by "red tide" algae. In this study, brevetoxin-1 and brevetoxin-2 were incubated with rat liver hepatocytes and rat liver microsomes, respectively. After clean-up steps, samples were analyzed by liquid chromatography (LC) coupled with electrospray mass spectrometry (LC-MS). For the incubation sample of brevetoxin- 1, two metabolites were found: brevetoxin-1-M1 and brevetoxin- 1-M2. The tandem mass spectrometry study of the [brevetoxin-1- M1+H]+ led to the conclusion that it was formed by converting one double bond in the E or F ring of brevetoxin-1 into a diol. The second metabolite (brevetoxin-1-M2) is proposed to be a hydrolysis product of brevetoxin-1 involving opening of the lactone ring with the addition of a water molecule. The study of incubation of brevetoxin-2 found two metabolites: brevetoxin-2- M1 gave a large [M-H]- peak, and its product ion mass spectrum allowed the deduction that this metabolite was the hydrolysis product of brevetoxin-2; the second metabolite (brevetoxin-2-M2) was deduced to have the same structure as that of brevetoxin-3.

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The University of New Orleans and its agents retain the non-exclusive license to archive and make accessible this dissertation or thesis in whole or in part in all forms of media, now or hereafter known. The author retains all other ownership rights to the copyright of the thesis or dissertation.

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