Journal of Lipid Research p. 87 - 97 (2011)
Update date:2022-08-02
Topics:
Tomono, Susumu
Miyoshi, Noriyuki
Shiokawa, Hidemi
Iwabuchi, Tomoe
Aratani, Yasuaki
Higashi, Tatsuya
Nukaya, Haruo
Ohshima, Hiroshi
1 3 β-Hydroxy-5-oxo-5,6-secocholestan-6-al (sec osterol- A) and its aldolization product 3 β-hydroxy-5 β- hydroxy-B-norcholestane-6 β-carboxaldehyde (secosterol-B) were recently detected in human atherosclerotic tissues and brain specimens, and they may play pivotal roles in the pathogenesis of atherosclerosis and neurodegenerative diseases. However, as their origin remains unidentifi ed, we examined the formation mechanism, the stability, and the fate of secosterols in vitro and in vivo. About 40% of secosterol-A remained unchanged after 3 h incubation in the FBS-free medium, whereas 20% and 40% were converted to its aldehyde-oxidation product, 3 β-hydroxy-5-oxo-secocholestan- 6-oic acid, and secosterol-B, respectively. In the presence of FBS, almost all secosterol-A was converted immediately to these compounds. Secosterol-B in the medium, with and without FBS, was relatively stable, but β30% was converted to its aldehyde-oxidation product, 3 β-hydroxy-5 β-hydroxy- B-norcholestane-6-oic acid (secoB-COOH). When neutrophillike differentiated human leukemia HL-60 (nHL-60) cells activated with PMA were cultured in the FBS-free medium containing cholesterol, significantly increased levels of secosterol-A and its aldehyde-oxidation product, but not secosterol-B, were formed. This secosterol-A formation was decreased in the culture of PMA-activated nHL-60 cells containing several reactive oxygen species (ROS) inhibitors and scavengers or in the culture of PMA-activated neutrophils isolated from myeloperoxidase (MPO)-defi cient mice. Our results demonstrate that secoterol-A is formed by an ozone-like oxidant generated with PMA-activated neutrophils through the MPO-dependent mechanism. - Tomono, S., N. Miyoshi, H. Shiokawa, T. Iwabuchi, Y. Aratani, T. Higashi, H. Nukaya, and H. Ohshima. Formation of cholesterol ozonolysis products in vitro and in vivo through amyeloperoxidase-dependent pathway.
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