Identification of acrolein from the ozone oxidation of unsaturated fatty acids.
By-products of lipoperoxidation reactions may be associated with the genesis or the progression of several diseases as arteriosclerosis, diabetes and cancer, among many others. Acrolein, at first a widely distributed environmental pollutant, is currently known as a compound capable of being generated as a result of metabolic reactions within biological systems, highly toxic and the most electrophilic of the alpha, beta-unsaturated aldehydes formed during lipoperoxidation. In the present study: 1. The separation of acrolein and malondialdehyde was achieved at alkaline pH with the use of high voltage capillary electrophoresis in uncoated fused-silica capillaries. 2. It was demonstrated how the oxidation of fatty acids (arachidonic/linoleic) with ozone generates, in dose-dependent form, acrolein as one of the by-products of the lipoperoxidation process. The oxidation of open human erythrocyte membranes with ozone also generated acrolein. 3. After aldolic condensation, aldol-acrolein derivative has a positive reaction with 2-thiobarbituric acid (TBA) and shows a maximum absorption at 498 nm. This novel characteristic is used in its identification after the separation of the by-products. 4. It is possible to suggest that in the classic reaction of the denominated thiobarbituric acid reactive substances (TBARS), when used as an indicator of the degree of peroxidation in biological systems, a portion of acrolein could be present but dwarfed by the TBA-MDA adduct.
Medina-Navarro
R
R
Specialties Hospital, Medical Research Unit in Biochemistry, Mexican Institute of Social Security, Mexico.
Mercado-Pichardo
E
E
Hernández-Pérez
O
O
Hicks
J J
JJ
D000171:Acrolein / Q000302:isolation & purification / Q000378:metabolism*; D004305:Dose-Response Relationship, Drug; D005231:Fatty Acids, Unsaturated / Q000378:metabolism*; D006801:Humans; D015227:Lipid Peroxidation / Q000187:drug effects; D010083:Oxidants, Photochemical / Q000494:pharmacology*; D010084:Oxidation-Reduction; D010126:Ozone / Q000494:pharmacology*; D013858:Thiobarbiturates / Q000378:metabolism; D017392:Thiobarbituric Acid Reactive Substances / Q000378:metabolism
D005231:Fatty Acids, Unsaturated; D010083:Oxidants, Photochemical; D013858:Thiobarbiturates; D017392:Thiobarbituric Acid Reactive Substances; D010126:Ozone; D000171:Acrolein; C029684:thiobarbituric acid