Occurrence of cytotoxic 9-oxononanoyl secosterol aldehydes in human low-density lipoprotein
作者： Noriyuki Miyoshi , Nozomi Iwasaki , Susumu Tomono , Tatsuya Higashi , Hiroshi Ohshima
DOI: 10.1016/J.FREERADBIOMED.2013.01.029
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摘要: Abstract The reaction products of three major cholesteryl esters, palmitate (C16:0-CE), oleate (C18:1-CE), and linoleate (C18:2-CE), present in human low-density lipoprotein (LDL) treated with ozone were isolated characterized. In vitro ozonization C16:0-CE was found to form the palmitoyl ester secosterol-A (3β-hydroxy-5-oxo-5,6-secocholestan-6-al) its aldolization product secosterol-B (3β-hydroxy-5β-hydroxy-B-norcholestane-6β-carboxaldehyde). On other hand, when C18:1-CE C18:2-CE oxidized by ozone, aldehyde 9-oxononanoyl cholesterol (9-ONC) formed as a primary product, which then further (9-ON-secoA) (9-ON-secoB). compounds 9-ON-secoA -B, but not 9-ONC, exhibit strong cytotoxicity against leukemia HL-60 cells. An LC–ESI–MS/MS method developed for detection these ozonolysis derivatizing them dansyl hydrazine. Using this method, we first time that low concentrations secosterols, LDL. These novel probably play important roles pathogenesis several inflammatory disorders such cancer, diabetes, atherosclerosis, neurodegenerative diseases.
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