Hock cleavage of cholesterol 5alpha-hydroperoxide: an ozone-free pathway to the cholesterol ozonolysis products identified in arterial plaque and brain tissue.
Cholesterol 5alpha-hydroperoxide, the major product of 1O2-oxidation of cholesterol, readily undergoes acid-catalyzed (Hock) cleavage of the C5-C6 bond to yield the 5,6-secosterol ketoaldehyde and the product of its intramolecular aldolization. These cholesterol oxidation products have long been thought to arise solely from ozonolysis of cholesterol, prompting the recent suggestion that ozone is produced in humans following their identification in arterial and brain tissue extracts.
Brinkhorst
Johan
J
Department of Chemistry, Queen's University, 90 Bader Lane, Ontario, Canada K7L 3N6.
Nara
Susheel J
SJ
Pratt
Derek A
DA
D000447:Aldehydes / Q000737:chemistry / Q000378:metabolism; D050197:Atherosclerosis / Q000378:metabolism*; D001921:Brain / Q000378:metabolism*; D002784:Cholesterol / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D006801:Humans; D010084:Oxidation-Reduction; D010126:Ozone / Q000737:chemistry* / Q000378:metabolism*; D010777:Photochemistry; D026082:Singlet Oxygen / Q000737:chemistry / Q000378:metabolism
D000447:Aldehydes; D026082:Singlet Oxygen; D010126:Ozone; C002843:cholesterol hydroperoxide; D002784:Cholesterol