Literature DB >> 19462099

The ratio of cholesterol 5,6-secosterols formed from ozone and singlet oxygen offers insight into the oxidation of cholesterol in vivo.

Anita D Wentworth1, Byeong-Doo Song, Jorge Nieva, Asher Shafton, Sangeetha Tripurenani, Paul Wentworth.   

Abstract

Ongoing efforts to unravel the origins of the cholesterol 5,6-secosterols (1a and 1b) in biological systems have revealed that the two known chemical routes to these oxysterols, ozonolysis of cholesterol (3) and Hock-cleavage of 5-alpha-hydroperoxycholesterol (4a), are distinguishable based upon the ratio of the hydrazone derivatives (2a and 2b) formed in each case and this ratio offers an insight into the chemical origin of the secosterols in vivo.

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Year:  2009        PMID： 19462099      PMCID： PMC2819220          DOI： 10.1039/b821584g

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  14 in total

Review 1.  Free radical biology and medicine: it's a gas, man!

Authors:  William A Pryor; Kendall N Houk; Christopher S Foote; Jon M Fukuto; Louis J Ignarro; Giuseppe L Squadrito; Kelvin J A Davies
Journal:  Am J Physiol Regul Integr Comp Physiol       Date:  2006-04-20       Impact factor: 3.619

2.  Cholesterol seco-sterol-induced aggregation of methylated amyloid-beta peptides--insights into aldehyde-initiated fibrillization of amyloid-beta.

Authors:  Johanna C Scheinost; Hong Wang; Grant E Boldt; John Offer; Paul Wentworth
Journal:  Angew Chem Int Ed Engl       Date:  2008       Impact factor: 15.336

3.  Cholesterol photodynamic oxidation by ultraviolet irradiation and cholesterol ozonization by ozone exposure.

Authors:  K Osada; A Sevanian
Journal:  Methods Enzymol       Date:  2000       Impact factor: 1.600

4.  Cholesterol as a singlet oxygen detector in biological systems.

Authors:  A W Girotti; W Korytowski
Journal:  Methods Enzymol       Date:  2000       Impact factor: 1.600

5.  Elevated levels of oxidized cholesterol metabolites in Lewy body disease brains accelerate alpha-synuclein fibrilization.

Authors:  Daryl A Bosco; Douglas M Fowler; Qinghai Zhang; Jorge Nieva; Evan T Powers; Paul Wentworth; Richard A Lerner; Jeffery W Kelly
Journal:  Nat Chem Biol       Date:  2006-03-26       Impact factor: 15.040

6.  Quantitative determination of cholesterol 5alpha-, 7alpha-, and 7beta-hydroperoxides in rat skin.

Authors:  S Yamazaki; N Ozawa; A Hiratsuka; T Watanabe
Journal:  Free Radic Biol Med       Date:  1999-07       Impact factor: 7.376

Review 7.  Small molecule oxidation products trigger disease-associated protein misfolding.

Authors:  Jan Bieschke; Qinghai Zhang; Daryl A Bosco; Richard A Lerner; Evan T Powers; Paul Wentworth; Jeffery W Kelly
Journal:  Acc Chem Res       Date:  2006-09       Impact factor: 22.384

8.  Lipid-derived aldehydes accelerate light chain amyloid and amorphous aggregation.

Authors:  Jorge Nieva; Asher Shafton; Laurence J Altobell; Sangeetha Tripuraneni; Joseph K Rogel; Anita D Wentworth; Richard A Lerner; Paul Wentworth
Journal:  Biochemistry       Date:  2008-06-26       Impact factor: 3.162

9.  Evidence for ozone formation in human atherosclerotic arteries.

Authors:  Paul Wentworth; Jorge Nieva; Cindy Takeuchi; Roger Galve; Anita D Wentworth; Ralph B Dilley; Giacomo A DeLaria; Alan Saven; Bernard M Babior; Kim D Janda; Albert Eschenmoser; Richard A Lerner
Journal:  Science       Date:  2003-11-07       Impact factor: 47.728

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

Authors:  Johan Brinkhorst; Susheel J Nara; Derek A Pratt
Journal:  J Am Chem Soc       Date:  2008-08-23       Impact factor: 15.419
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  11 in total

1.  Formation of cholesterol ozonolysis products in vitro and in vivo through a myeloperoxidase-dependent pathway.

Authors:  Susumu Tomono; Noriyuki Miyoshi; Hidemi Shiokawa; Tomoe Iwabuchi; Yasuaki Aratani; Tatsuya Higashi; Haruo Nukaya; Hiroshi Ohshima
Journal:  J Lipid Res       Date:  2010-10-04       Impact factor: 5.922

2.  Alternatives to the 'water oxidation pathway' of biological ozone formation.

Authors:  Arnold N Onyango
Journal:  J Chem Biol       Date:  2015-06-16

Review 3.  Rearrangements of organic peroxides and related processes.

Authors:  Ivan A Yaremenko; Vera A Vil'; Dmitry V Demchuk; Alexander O Terent'ev
Journal:  Beilstein J Org Chem       Date:  2016-08-03       Impact factor: 2.883

4.  Ozone-derived Oxysterols Affect Liver X Receptor (LXR) Signaling: A POTENTIAL ROLE FOR LIPID-PROTEIN ADDUCTS.

Authors:  Adam M Speen; Hye-Young H Kim; Rebecca N Bauer; Megan Meyer; Kymberly M Gowdy; Michael B Fessler; Kelly E Duncan; Wei Liu; Ned A Porter; Ilona Jaspers
Journal:  J Biol Chem       Date:  2016-10-04       Impact factor: 5.157

5.  Inhibition of endothelial- and neuronal-type, but not inducible-type, nitric oxide synthase by the oxidized cholesterol metabolite secosterol aldehyde: Implications for vascular and neurodegenerative diseases.

Authors:  Ying-Ling Lai; Susumu Tomono; Noriyuki Miyoshi; Hiroshi Ohshima
Journal:  J Clin Biochem Nutr       Date:  2011-09-02       Impact factor: 3.114

6.  Evidence for prehistoric origins of Egyptian mummification in late Neolithic burials.

Authors:  Jana Jones; Thomas F G Higham; Ron Oldfield; Terry P O'Connor; Stephen A Buckley
Journal:  PLoS One       Date:  2014-08-13       Impact factor: 3.240

Review 7.  The Contribution of Singlet Oxygen to Insulin Resistance.

Authors:  Arnold N Onyango
Journal:  Oxid Med Cell Longev       Date:  2017-09-07       Impact factor: 6.543

Review 8.  Endogenous Generation of Singlet Oxygen and Ozone in Human and Animal Tissues: Mechanisms, Biological Significance, and Influence of Dietary Components.

Authors:  Arnold N Onyango
Journal:  Oxid Med Cell Longev       Date:  2016-03-06       Impact factor: 6.543

Review 9.  Biochemical properties of cholesterol aldehyde secosterol and its derivatives.

Authors:  Noriyuki Miyoshi
Journal:  J Clin Biochem Nutr       Date:  2018-02-07       Impact factor: 3.114

10.  Cholesterol secosterol aldehyde adduction and aggregation of Cu,Zn-superoxide dismutase: Potential implications in ALS.

Authors:  Lucas S Dantas; Adriano B Chaves-Filho; Fernando R Coelho; Thiago C Genaro-Mattos; Keri A Tallman; Ned A Porter; Ohara Augusto; Sayuri Miyamoto
Journal:  Redox Biol       Date:  2018-08-16       Impact factor: 11.799
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