Hock cleavage of cholesterol 5alpha-hydroperoxide: an ozone-free pathway to the cholesterol ozonolysis products identified in arterial plaque and brain tissue

Journal of the American Chemical Society
Johan BrinkhorstDerek A Pratt

Abstract

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.

Citations

Aug 25, 2011·Chemical Reviews·Huiyong YinNed A Porter
Jul 3, 2013·Chemical Reviews·Janez Cerkovnik, Božo Plesničar
Sep 26, 2013·Chemical Research in Toxicology·Thiago C Genaro-MattosSayuri Miyamoto
Feb 8, 2011·Journal of Clinical Biochemistry and Nutrition·Junji TeraoNoriko Bando
Feb 22, 2014·Steroids·Jacek W Morzycki
Mar 9, 2013·Bioscience, Biotechnology, and Biochemistry·Susumu TomonoHiroshi Ohshima
Oct 15, 2014·Free Radical Research·Etsuo Niki
Feb 12, 2013·Free Radical Biology & Medicine·Noriyuki MiyoshiHiroshi Ohshima
Jun 10, 2009·Biochemical and Biophysical Research Communications·Achuthan C RaghavamenonRao M Uppu
May 24, 2016·Journal of the American Chemical Society·Zosia A M Zielinski, Derek A Pratt
Jun 9, 2009·Free Radical Biology & Medicine·Etsuo Niki
Mar 2, 2017·The Journal of Organic Chemistry·Zosia A M Zielinski, Derek A Pratt
Oct 26, 2018·Organic & Biomolecular Chemistry·Fenja L DueckerPhilipp Heretsch
Sep 5, 2015·Chemistry, an Asian Journal·Shū Kobayashi
May 16, 2015·Beilstein Journal of Organic Chemistry·Jacek W Morzycki, Andrzej Sobkowiak
Aug 26, 2016·Beilstein Journal of Organic Chemistry·Ivan A YaremenkoAlexander O Terent'ev
Feb 9, 2016·Journal of Chemical Biology·Arnold N Onyango
Mar 1, 2014·Biophysics Reviews·Rosangela ItriMaurício S Baptista
Jan 27, 2021·Free Radical Research·Sayuri MiyamotoLucas G Viviani
Jun 16, 2021·Cell Biochemistry and Biophysics·Xueli GaoRao M Uppu
Jan 1, 2020·ACS Omega·Isabel O L Bacellar, Mauricio S Baptista
Feb 23, 2019·Organic Letters·Moreshwar B ChaudhariBoopathy Gnanaprakasam
Jan 31, 2020·The Journal of Organic Chemistry·Moreshwar B ChaudhariBoopathy Gnanaprakasam
Jan 10, 2019·Journal of the American Chemical Society·Zosia A M Zielinski, Derek A Pratt
Feb 6, 2019·Chemical Reviews·Paolo Di MascioJean Cadet
Jun 30, 2009·Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences·William J Griffiths, Yuqin Wang
Jun 16, 2021·American Journal of Respiratory Cell and Molecular Biology·Alexia PerrymanIlona Jaspers
Jun 28, 2011·Chemistry and Physics of Lipids·Luigi Iuliano

❮ Previous
Next ❯

Related Concepts

Related Feeds

Atherosclerosis Disease Progression

Atherosclerosis is the buildup of plaque on artery walls, causing stenosis which can eventually lead to clinically apparent cardiovascular disease. Find the latest research on atherosclerosis disease progression here.