Highly sensitive quantification of key regulatory oxysterols in biological samples by LC-ESI-MS/MS

Journal of Lipid Research

Volumn 50, Issue 2, 2009, Pages 350-357

  Honda, Akira ^a   Yamashita, Kouwa ^b   Hara, Takashi ^c   Ikegami, Tadashi ^a   Miyazaki, Teruo ^a   Shirai, Mutsumi ^c   Xu, Guorong ^d   Numazawa, Mitsuteru ^b   Matsuzaki, Yasushi ^a  

^a TOKYO MEDICAL UNIVERSITY   (Japan)

^b TOHOKU PHARMACEUTICAL UNIVERSITY   (Japan)

^c Ibaraki Prefectural Institute of Public Health   (Japan)

^d RUTGERS NEW JERSEY MEDICAL SCHOOL   (United States)

Author keywords

22R hydroxycholesterol; 24S,25 epoxycholesterol; 24S hydroxycholesterol; 25 hydroxycholesterol; 27 hydroxycholesterol; 4 hydroxycholesterol; 7 hydroxycholesterol; Electrospray ionization; Liquid chromatography tandem mass spectrometry

Indexed keywords

22 HYDROXYCHOLESTEROL; 24,25 EPOXYCHOLESTEROL; 26 HYDROXYCHOLESTEROL; 4BETA HYDROXYCHOLESTEROL; 7ALPHA HYDROXYCHOLESTEROL; ALKALINE EARTH METAL; CHOLESTEROL DERIVATIVE; OXYSTEROL; PICOLINIC ACID DERIVATIVE; STABLE ISOTOPE; UNCLASSIFIED DRUG; 22-HYDROXYCHOLESTEROL; 24 HYDROXYCHOLESTEROL; 24-HYDROXYCHOLESTEROL; 25 HYDROXYCHOLESTEROL; 25-HYDROXYCHOLESTEROL; 27-HYDROXYCHOLESTEROL; CHOLEST 5 EN 3 BETA,7 ALPHA DIOL; CHOLEST 5 ENE 3,4 DIOL; CHOLEST-5-EN-3 BETA,7 ALPHA-DIOL; CHOLEST-5-ENE-3,4-DIOL;

ANALYTIC METHOD; ANIMAL CELL; ARTICLE; BLOOD SAMPLING; CEREBROTENDINOUS XANTHOMATOSIS; CONTROLLED STUDY; DILUTION; ELECTROSPRAY MASS SPECTROMETRY; EXTRACTION; HUMAN; HYDROLYSIS; LIPID ANALYSIS; LIQUID CHROMATOGRAPHY; LIVER MICROSOME; MEASUREMENT; NONHUMAN; PRIORITY JOURNAL; RAT; SENSITIVITY AND SPECIFICITY; SERUM; SIGNAL NOISE RATIO; VOLUNTEER; ANIMAL; CALIBRATION; CHEMISTRY; EVALUATION; METHODOLOGY; REPRODUCIBILITY; TANDEM MASS SPECTROMETRY;

ANIMALS; CALIBRATION; CHROMATOGRAPHY, LIQUID; HUMANS; HYDROXYCHOLESTEROLS; MICROSOMES, LIVER; RATS; REPRODUCIBILITY OF RESULTS; SENSITIVITY AND SPECIFICITY; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TANDEM MASS SPECTROMETRY;

EID: 64749098311     PISSN: 00222275     EISSN: 15397262     Source Type: Journal    
DOI: 10.1194/jlr.D800040-JLR200     Document Type: Article

References (35)

1. Dzeletovic, S., O. Breuer, E. Lund, and U. Diczfalusy. 1995. Determination of cholesterol oxidation products in human plasma by isotope dilution-mass spectrometry. Anal. Biochem. 225: 73-80.
2. Bodin, K., L. Bretillon, Y. Aden, L. Bertilsson, U. Broome, C. Einarsson, and U. Diczfalusy. 2001. Antiepileptic drugs increase plasma levels of 4β-hydroxycholesterol in humans: evidence for involvement of cytochrome p450 3A4. J. Biol. Chem. 276: 38685-38689.
3. Pikuleva, I. A. 2006. Cholesterol-metabolizing cytochromes P450. Drug Metab. Dispos. 34: 513-520.
4. Lund, E. G., T. A. Kerr, J. Sakai, W. P. Li, and D. W. Russell. 1998. cDNA cloning of mouse and human cholesterol 25-hydroxylases, polytopic membrane proteins that synthesize a potent oxysterol regulator of lipid metabolism. J. Biol. Chem. 273: 34316-34327.
5. Lund, E. G., J. M. Guileyardo, and D. W. Russell. 1999. cDNA cloning of cholesterol 24-hydroxylase, a mediator of cholesterol homeostasis in the brain. Proc. Natl. Acad. Sci. USA. 96: 7238-7243.
6. Li, X., W. M. Pandak, S. K. Erickson, Y. Ma, L. Yin, P. Hylemon, and S. Ren. 2007. Biosynthesis of the regulatory oxysterol, 5-cholesten3β, 25-diol 3-sulfate, in hepatocytes. J. Lipid Res. 48: 2587-2596.
7. Smith, L. L. 1981. Cholesterol Autoxidation. Plenum Press, New York.
8. Nelson, J. A., S. R. Steckbeck, and T. A. Spencer. 1981. Biosynthesis of 24,25-epoxycholesterol from squalene 2,3;22,23-dioxide. J. Biol. Chem. 256: 1067-1068.
9. Janowski, B. A., P. J.Willy, T. R. Devi, J. R. Falck, and D. J.Mangelsdorf. 1996. An oxysterol signalling pathway mediated by the nuclear receptor LXRα. Nature. 383: 728-731.
10. Janowski, B. A., M. J. Grogan, S. A. Jones, G. B. Wisely, S. A. Kliewer, E. J. Corey, and D. J. Mangelsdorf. 1999. Structural requirements of ligands for the oxysterol liver X receptors LXRα and LXRβ. Proc. Natl. Acad. Sci. USA. 96: 266-271.
11. Fu, X., J. G. Menke, Y. Chen, G. Zhou, K. L. MacNaul, S. D. Wright, C. P. Sparrow, and E. G. Lund. 2001. 27-Hydroxycholesterol is an endogenous ligand for liver X receptor in cholesterol-loaded cells. J. Biol. Chem. 276: 38378-38387.
12. Axelson, M., and O. Larsson. 1995. Low density lipoprotein (LDL) cholesterol is converted to 27-hydroxycholesterol in human fibroblasts. J. Biol. Chem. 270: 15102-15110.
13. Krieger, M., J. L. Goldstein, and M. S. Brown. 1978. Receptor-mediated uptake of low density lipoprotein reconstituted with 25-hydroxycholesteryl oleate suppresses 3-hydroxy-3-methylglutarylcoenzyme A reductase and inhibits growth of human fibroblasts. Proc. Natl. Acad. Sci. USA. 75: 5052-5056.
14. Spencer, T. A., A. K. Gayen, S. Phirwa, J. A. Nelson, F. R. Taylor, A. A. Kandutsch, and S. K. Erickson. 1985. 24(S),25-Epoxycholesterol. Evidence consistent with a role in the regulation of hepatic cholesterogenesis. J. Biol. Chem. 260: 13391-13394.
15. Breuer, O., and I. Björkhem. 1990. Simultaneous quantification of several cholesterol autoxidation and monohydroxylation products by isotope-dilution mass spectrometry. Steroids. 55: 185-192.
16. 4-3-ketone derivatives by HPLC and response to physiological perturbations. J. Lipid Res. 42: 649-658.
17. Ogishima, T., and K. Okuda. 1986. An improved method for assay of cholesterol 7α-hydroxylase activity. Anal. Biochem. 158: 228-232.
18. 14C]cholesterol as substrate. Anal. Biochem. 182: 212-216.
19. 4-3-ketone derivatives. J. Chromatogr. A. 691: 247-254.
20. Burkard, I., K. M. Rentsch, and A. von Eckardstein. 2004. Determination of 24S- and 27-hydroxycholesterol in plasma by high-performance liquid chromatography-mass spectrometry. J. Lipid Res. 45: 776-781.
21. Saldanha, T., A. C. Sawaya, M. N. Eberlin, and N. Bragagnolo. 2006. HPLC separation and determination of 12 cholesterol oxidation products in fish: comparative study of RI, UV, and APCI-MS detectors. J. Agric. Food Chem. 54: 4107-4113.
22. McDonald, J. G., B. M. Thompson, E. C. McCrum, and D.W. Russell. 2007. Extraction and analysis of sterols in biological matrices by high performance liquid chromatography electrospray ionization mass spectrometry. Methods Enzymol. 432: 145-170.
23. Honda, A., K. Yamashita, H. Miyazaki, M. Shirai, T. Ikegami, G. Xu, M. Numazawa, T. Hara, and Y. Matsuzaki. 2008. Highly sensitive analysis of sterol profiles in human serum by LC-ESI-MS/MS. J. Lipid Res. 49: 2063-2073.
24. Honda, A., G. Salen, Y. Matsuzaki, A. K. Batta, G. Xu, E. Leitersdorf, G. S. Tint, S. K. Erickson, N. Tanaka, and S. Shefer. 2001. Differences in hepatic levels of intermediates in bile acid biosynthesis between Cyp272/2 mice and CTX. J. Lipid Res. 42: 291-300.
25. Honda, A., Y. Mizokami, Y. Matsuzaki, T. Ikegami, M. Doy, and H. Miyazaki. 2007. Highly sensitive assay of HMG-CoA reductase activity by LC-ESI-MS/MS. J. Lipid Res. 48: 1212-1220.
26. Taguchi, G. 1986. Introduction to Quality Engineering-Designing Quality into Products and Process. Asian Productivity Organization, Tokyo, Japan.
27. Yamashita, K., S. Kobayashi, S. Tsukamoto, and M. Numazawa. 2007. Synthesis of pyridine-carboxylate derivatives of hydroxysteroids for liquid chromatography-electrospray ionization-mass spectrometry. Steroids. 72: 50-59.
28. Griffiths, W. J., Y. Wang, G. Alvelius, S. Liu, K. Bodin, and J. Sjövall. 2006. Analysis of oxysterols by electrospray tandem mass spectrometry. J. Am. Soc. Mass Spectrom. 17: 341-362.
29. Karu, K., M. Hornshaw, G. Woffendin, K. Bodin, M. Hamberg, G. Alvelius, J. Sjövall, J. Turton, Y.Wang, andW. J. Griffiths. 2007. Liquid chromatography-mass spectrometry utilizing multi-stage fragmentation for the identification of oxysterols. J. Lipid Res. 48: 976-987.
30. Jiang, X., D. S. Ory, and X. Han. 2007. Characterization of oxysterols by electrospray ionization tandem mass spectrometry after one-step derivatization with dimethylglycine. Rapid Commun. Mass Spectrom. 21: 141-152.
31. Yamashita, K., M. Okuyama, Y. Watanabe, S. Honma, S. Kobayashi, and M. Numazawa. 2007. Highly sensitive determination of estrone and estradiol in human serum by liquid chromatography-electrospray ionization tandem mass spectrometry. Steroids. 72: 819-827.
32. Honda, A., G. Salen, Y. Matsuzaki, A. K. Batta, G. Xu, T. Hirayama, G. S. Tint, M. Doy, and S. Shefer. 2005. Disrupted coordinate regulation of farnesoid X receptor target genes in a patient with cerebrotendinous xanthomatosis. J. Lipid Res. 46: 287-296.
33. Oda, H., H. Yamashita, K. Kosahara, S. Kuroki, and F. Nakayama. 1990. Esterified and total 7α-hydroxycholesterol in human serum as an indicator for hepatic bile acid synthesis. J. Lipid Res. 31: 2209-2218.
34. Kudo, K., G. T. Emmons, E. W. Casserly, D. P. Via, L. C. Smith, J. St Pyrek, and G. J. Schroepfer, Jr. 1989. Inhibitors of sterol synthesis. Chromatography of acetate derivatives of oxygenated sterols. J. Lipid Res. 30: 1097-1111.
35. Honda, A., K. Yamashita, H. Miyazaki, M. Shirai, T. Ikegami, G. Xu, M. Numazawa, T. Hara, and Y. Matsuzaki. 2008. Highly sensitive analysis of sterol profiles in human serum by LC-ESI-MS/MS. J. Lipid Res. 49: 2063-2073.