The ozonation of unsaturated fatty acids: Aldehydes and hydrogen peroxide as products and possible mediators of ozone toxicity

Journal Article · Wed May 01 04:00:00 EDT 1991 · Chemical Research in Toxicology; (United States)

DOI:https://doi.org/10.1021/tx00021a014· OSTI ID:5996362

Pryor, W A; Das, B; Church, D F ^[1]

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1. Biodynamics Institute, Louisiana State University, Baton Rouge (United States)

The products of the reactions of ozone with aqueous emulsions of unsaturated fatty acids and with liposomes made from phosphatidylcholine esters were characterized. Ozonolysis of emulsions of methyl oleate yields approximately 1 mol of hydrogen peroxide and 2 mol of aldehydes per mole of ozone used and fatty acid reacted. That is, the net equation that occurs is RCH = CHR' + O3 + H2O----RCHO + R'CHO + H2O2 . Ozonolysis of emulsions of oleic, linoleic, linolenic, and arachidonic acids gives 1 mol of hydrogen peroxide per mole of ozone used. Only very low yields (less than 5%) of reducible materials other than hydrogen peroxide are observed, suggesting that the yields of organic peroxidic materials, including Criegee ozonides and lipid hydroperoxides, are small. Ozonolysis of rat erythrocyte ghost membranes and rat bronchoalveolar lavage also gives significant yields (about 50%) of hydrogen peroxide based on the moles of ozone consumed. Reactions of ozone with bovine serum albumin, glutathione, and glucose do not produce hydrogen peroxide, implying that the hydrogen peroxide formed during the ozonation of biological materials arises almost exclusively from ozone/olefin reactions. Hydrogen peroxide and aldehydes are suggested to be important mediators of the modifications observed in both the lung and extrapulmonary tissues when ozone is inhaled.

• OSTI ID: 5996362
• Journal Information: Chemical Research in Toxicology; (United States), Journal Name: Chemical Research in Toxicology; (United States) Vol. 4:3; ISSN 0893-228X; ISSN CRTOE
• Country of Publication: United States
• Language: English

Related Subjects

560300* -- Chemicals Metabolism & Toxicology
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
AIR POLLUTION
ALBUMINS
ALDEHYDES
ANIMALS
BIOLOGICAL MATERIALS
BIOSYNTHESIS
BLOOD
BLOOD CELLS
BODY FLUIDS
CARBOXYLIC ACIDS
CELL CONSTITUENTS
CELL MEMBRANES
CHEMICAL REACTIONS
DRUGS
EQUATIONS
ERYTHROCYTES
GLUTATHIONE
HYDROGEN COMPOUNDS
HYDROGEN PEROXIDE
LAVAGE
LIPOSOMES
MAMMALS
MATERIALS
MEMBRANES
ORGANIC ACIDS
ORGANIC COMPOUNDS
OXYGEN COMPOUNDS
OZONE
PEPTIDES
PEROXIDES
POLLUTION
POLYPEPTIDES
PROTEINS
RADIOPROTECTIVE SUBSTANCES
RATS
REDOX REACTIONS
RODENTS
SMOG
SYNTHESIS
TOXICITY
VERTEBRATES