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United States Department of Agriculture

Agricultural Research Service

Title: Mass Spectrometric Evidence for the Anomalous Chemical Behavior of 11 Dehydrothromboxane B2

Authors
item Ferretti, Aldo
item Flanagan, Vincent

Submitted to: Chemistry and Physics of Lipids
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: April 13, 1995
Publication Date: N/A

Interpretive Summary: Heart attacks are caused by the formation of blood clots in the arteries of the heart. The process of clot formation is promoted by certain substances present in blood that interact with platelets. Some of these clot promoting substances belong to a family of hormones called eicosanoids. Current knowledge supports the theory that certain fatty substances in our diet can alter the quantity of those eicosanoids in blood. In order to study how eicosanoids form and break down, we developed a technique to measure these products in urine. During the development of the procedure we observed the formation of artifacts that adversely impact accuracy and sensitivity. We identified those artefacts and proposed ways to avoid their formation. This work will help in the development of dietary approaches to the control of risk for coronary heart disease and has potential importance to other scientists working in the field and to physicians as well.

Technical Abstract: When we subjected 11-dehydrothromboxane B2 (11-DTXB2), a metabolite of arachidonic acid, to standard chemical derivatization procedures we obtained a mixture of several products. Separation of the components was carried out by gas chromatography and their identification was accomplished through the study of their mass spectra which are presented here. Anomalous behaviors include methylation of allylic and alcoholic hydroxyl groups by diazomethane, unusually slow derivatization of one of the hydroxyl groups with N,O-bis(trimethylsilyl)-trifluoroacetamide (BSTFA) and etherification of another with ethanol. The underlying causes of these abnormal behaviors are not obvious but appear to be related, at least in part, to the opening/closure of a lactone ring in the molecule. These observations have some bearing on the development of procedures for GC-MS quantification of this important marker of thromboxane A2 synthesis in vivo and of similar compounds.

Last Modified: 4/20/2014
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