Lumisterol is metabolized by CYP11A1: Discovery of a new pathway

International Journal of Biochemistry and Cell Biology

Volumn 55, Issue , 2014, Pages 24-34

  Tuckey, Robert C ^a   Slominski, Andrzej T ^b   Cheng, Chloe Y S ^a   Chen, Jianjun ^b,c   Kim, Tae Kang ^b   Xiao, Min ^b   Li, Wei ^b  

^a UNIVERSITY OF WESTERN AUSTRALIA   (Australia)

^b UNIVERSITY OF TENNESSEE HEALTH SCIENCE CENTER   (United States)

^c South College School of Pharmacy   (United States)

Author keywords

CYP11A1; Cytochrome P450scc; Hydroxylation; Lumisterol; Vitamin D3

Indexed keywords

BETA CYCLODEXTRIN DERIVATIVE; CHOLESTEROL; CHOLESTEROL MONOOXYGENASE (SIDE CHAIN CLEAVING); COLECALCIFEROL; LUMISTEROL; ERGOSTEROL; 2 HYDROXYPROPYL BETA CYCLODEXTRIN; 20,22 DIHYDROXYLUMISTEROL3; 22 HYDROXYLUMISTEROL3; 24 HYDROXYLUMISTEROL3; DRUG METABOLITE; LUMISTEROL3 DERIVATIVE; PREGNALUMISTEROL; TRIHYDROXYLUMISTEROL3 DERIVATIVE; UNCLASSIFIED DRUG;

ADRENAL GLAND; ANIMAL TISSUE; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHOLESTEROL METABOLISM; CONTROLLED STUDY; EX VIVO STUDY; EXPERIMENTAL CATTLE; EXPERIMENTAL PIG; HETERONUCLEAR MULTIPLE BOND CORRELATION; HETERONUCLEAR SINGLE QUANTUM COHERENCE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HYDROXYLATION; IN VITRO STUDY; INCUBATION TIME; MASS SPECTROMETRY; METABOLITE; MICHAELIS MENTEN KINETICS; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; PURIFICATION; STEROL METABOLISM; VITAMIN D METABOLISM; ANIMAL; BOVINE; CHEMICAL MODEL; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; FEMALE; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PIG; DRUG HYDROXYLATION; DRUG METABOLISM; DRUG RETENTION; DRUG SOLUBILITY; DRUG STRUCTURE; LIQUID CHROMATOGRAPHY; PROTEIN CLEAVAGE; STEROIDOGENESIS;

ADRENAL GLANDS; ANIMALS; CATTLE; CHOLESTEROL SIDE-CHAIN CLEAVAGE ENZYME; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ERGOSTEROL; FEMALE; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; METABOLIC NETWORKS AND PATHWAYS; MODELS, CHEMICAL; MOLECULAR STRUCTURE; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SWINE;

EID: 84906776632     PISSN: 13572725     EISSN: 18785875     Source Type: Journal    
DOI: 10.1016/j.biocel.2014.08.004     Document Type: Article

References (40)

1. M.W. Clarke, R.C. Tuckey, S. Gorman, B. Holt, and P.H. Hart Optimized 25-hydroxyvitamin D analysis using liquid-liquid extraction with 2D separation with LC/MS/MS detection, provides superior precision compared to conventional assays Metabolomics 9 2013 1031 1040
2. J. De Caprio, J. Yun, and N.B. Javitt Bile acid and sterol solubilization in 2-hydroxypropyl-β-cyclodextrin J Lipid Res 33 1992 441 443
3. K.M. Dixon, A.W. Norman, V.B. Sequeira, R. Mohan, M.S. Rybchyn, and V.E. Reeve et al. 1alpha, 25(OH)-vitamin D and a nongenomic vitamin D analogue inhibit ultraviolet radiation-induced skin carcinogenesis Cancer Prev Res 4 2011 1485 1494
4. O. Guryev, R.A. Carvalho, S. Usanov, A. Gilep, and R.W. Estabrook A pathway for the metabolism of vitamin D3: unique hydroxylated metabolites formed during catalysis with cytochrome P450scc (CYP11A1) Proc Natl Acad Sci U S A 100 2003 14754 14759 (Pubitemid 37517963)
5. M.F. Holick Vitamin D: a millennium perspective J Cell Biochem 88 2003 296 307
6. M.F. Holick, J.A. MacLaughlin, M.B. Clark, S.A. Holick, J.T. Potts Jr., and R.R. Anderson et al. Photosynthesis of previtamin D3 in human skin and the physiologic consequences Science 210 1980 203 205 (Pubitemid 11252464)
7. 3 photosynthesis in man: skin pigment in not an essential regulator Science 211 1981 590 593 (Pubitemid 11188172)
8. 3 and its photoisomers in human skin Science 216 1982 1001 1003 (Pubitemid 12025041)
9. M.T. Mizwicki, D. Keidel, C.M. Bula, J.E. Bishop, L.P. Zanello, and J.M. Wurtz et al. Identification of an alternative ligand-binding pocket in the nuclear vitamin D receptor and its functional importance in 1alpha, 25(OH)2-vitamin D3 signaling Proc Natl Acad Sci U S A 101 2004 12876 12881 (Pubitemid 39167551)
10. M.N. Nguyen, A. Slominski, W. Li, Y.R. Ng, and R.C. Tuckey Metabolism of vitamin D2 to 17,20,24-trihydroxyvitamin D2 by cytochrome P450scc (CYP11A1) Drug Metab Dispos 37 2009 761 767
11. 3 in human skin correct? Photochem Photobiol 9 2010 11 17
12. M.C. Rebsamen, J. Sun, A.W. Norman, and J.K. Liao 1alpha, 25-dihydroxyvitamin D3 induces vascular smooth muscle cell migration via activation of phosphatidylinositol 3-kinase Circ Res 91 2002 17 24 (Pubitemid 34778937)
13. A. Slominski, G. Ermak, and M. Mihm ACTH receptor, CYP11A1, CYP17 and CYP21A2 genes are expressed in skin J Clin Endocrinol Metab 81 1996 2746 2749 (Pubitemid 26240307)
14. A.T. Slominski, Z. Janjetovic, B.E. Fuller, M.A. Zmijewski, R.C. Tuckey, and M.N. Nguyen et al. Products of vitamin D3 or 7-dehydrocholesterol metabolism by cytochrome P450scc show anti-leukemia effects, having low or absent calcemic activity PLoS ONE 5 3 2010 e9907
15. A. Slominski, Z. Janjetovic, R.C. Tuckey, M.N. Nguyen, K.G. Bhattacharya, and J. Wang et al. 20S-Hydroxyvitamin D3, noncalcemic product of CYP11A1 action on vitamin D3, exhibits potent antifibrogenic activity in vivo J Clin Endocrinol Metab 98 2013 E298 E303
16. A.T. Slominski, T.K. Kim, J. Chen, M.N. Nguyen, W. Li, and C.R. Yates et al. Cytochrome P450scc-dependent metabolism of 7-dehydrocholesterol in placenta and epidermal keratinocytes Int J Biochem Cell Biol 44 2012 2003 2018
17. A.T. Slominski, T.K. Kim, W. Li, A.K. Yi, A. Postlethwaite, and R.C. Tuckey The role of CYP11A1 in the production of vitamin D metabolites and their role in the regulation of epidermal functions J Steroid Biochem Mol Biol 2014 10.1016/j.jsbmb.2013.10.012
18. 3 metabolism initiated by P450scc and modified by CYP27B1 FASEB J 26 2012 3901 3915
19. A.T. Slominski, T.K. Kim, H.Z. Shehabi, E.K.Y. Tang, H.A.E. Benson, and I. Semak et al. In vivo production of novel vitamin D2 hydroxy-derivatives by human placentas, epidermal keratinocytes, Caco-2 colon cells and the adrenal gland Mol Cell Endocrinol 383 2014 181 192
20. A.T. Slominski, T.K. Kim, Y. Takeda, Z. Janjetovic, A.A. Brozyna, and C. Skobowiat et al. RORα and RORγ are expressed in human skin and serve as receptors for endogenously produced noncalcemic 20-hydroxy- and 20,23-dihydroxyvitamin D FASEB J 28 2014 2775 2789
21. A. Slominski, I. Semak, J. Wortsman, J. Zjawiony, W. Li, and B. Zbytek et al. An alternate pathway of vitamin D2 metabolism: cytochrome P450scc (CYP11A1) mediated conversion to 20-hydroxyvitamin D2 and 17,20-dihydroxyvitamin D2 FEBS J 273 2006 2891 2901
22. A. Slominski, I. Semak, J. Zjawiony, J. Wortsman, M.N. Gandy, and J. Li et al. Enzymatic metabolism of ergosterol by cytochrome P450scc (CYP11A1) to biologically active 17α,24-dihydroxyergosterol Chem Biol 12 2005 931 939 (Pubitemid 41206807)
23. A. Slominski, I. Semak, J. Zjawiony, J. Wortsman, W. Li, and A. Szczesniewski et al. The cytochrome P450scc system opens an alternate pathway of vitamin D3 metabolism FEBS J 272 2005 4080 4090 (Pubitemid 41160916)
24. A. Slominski, J. Zjawiony, J. Wortsman, I. Semak, J. Stewart, and A. Pisarchik et al. A novel pathway for sequential transformation of 7-dehydrocholesterol and expression of the P450scc system in mammalian skin Eur J Biochem 271 2004 4178 4188 (Pubitemid 39506746)
25. A. Slominski, M.A. Zmijewski, I. Semak, T. Sweatman, Z. Janjetovic, and W. Li et al. Sequential metabolism of 7-dehydrocholesterol to steroidal 5,7-dienes in adrenal glands and its biological implication in the skin PLoS ONE 4 2 2009 e4309 10.1371/journal.pone.0004309
26. N. Strushkevich, F. MacKenzie, T. Cherkesova, I. Grabovec, S. Usanov, and H. Park Structural basis for pregnenolone biosynthesis by the mitochondrial monooxygenase system Proc Natl Acad Sci U S A 108 2011 10139 10143
27. D. Thiboutot, S. Jabar, J.M. McAllister, A. Sivarajah, K. Gilliland, and Z. Cong et al. Human skin is a steroidogenic tissue: steroidogenic enzymes and cofactors are expressed in epidermis, normal sebocytes, and an immortalized sebocyte cell line (SEB-1) J Invest Dermatol 120 2003 905 914 (Pubitemid 36702897)
28. R.C. Tuckey Progesterone synthesis by the human placenta Placenta 26 2005 273 281 (Pubitemid 40485864)
29. 3 by cytochrome P450scc (CYP11A1) and analysis of their biological activities on skin cells Drug Metab Dispos 39 2011 1577 1588
30. R.C. Tuckey, W. Li, J.K. Zjawiony, M.A. Zmijewski, M.N. Nguyen, and T. Sweatman et al. Pathways and products for the metabolism of vitamin D3 by cytochrome P450scc (CYP11A1) FEBS J 275 2008 2585 2596 (Pubitemid 351600097)
31. R.C. Tuckey, M.N. Nguyen, J. Chen, A.T. Slominski, D.M. Baldisseri, and E.W. Tieu et al. Human cytochrome P450scc (CYP11A1) catalyses epoxide formation with ergosterol Drug Metab Dispos 40 2012 436 444
32. R.C. Tuckey, M.N. Nguyen, and A. Slominski Kinetics of vitamin D3 metabolism by cytochrome P450scc (CYP11A1) in phospholipid vesicles and cyclodextrin Int J Biochem Cell Biol 40 2008 2619 2626
33. R.C. Tuckey, and J. Sadleir The concentration of adrenodoxin reductase limits cytochrome P450scc activity in the human placenta Eur J Biochem 263 1999 319 325 (Pubitemid 29337021)
34. R.C. Tuckey, and P.M. Stevenson Properties of bovine luteal cytochrome P-450scc incorporated into artificial phospholipid vesicles Int J Biochem 16 1984 497 503 (Pubitemid 14100092)
35. M. Wacker, and M.F. Holick Sunlight and vitamin D. A global perspective for health Dermatoendocrinology 5 2013 1 58
36. J. Wang, A. Slominski, R.C. Tuckey, Z. Janjetovic, A. Kulkarni, and J. Chen et al. 20-Hydroxyvitamin D3 inhibits proliferation of cancer cells with high efficacy while being non-toxic Anticancer Res 32 2012 739 746
37. S.T. Woods, J. Sadleir, T. Downs, T. Triantopoulos, M.J. Headlam, and R.C. Tuckey Expression of catalytically active human cytochrome P450scc in Escherichia coli and mutagenesis of isoleucine-462 Arch Biochem Biophys 353 1998 109 115 (Pubitemid 28373035)
38. M.A. Zmijewski, W. Li, J. Chen, T.K. Kim, J.K. Zjawiony, and T.W. Sweatman et al. Synthesis and photochemical transformation of 3beta, 21-dihydroxypregna-5,7-dien-20-one to novel secosteroids that show anti-melanoma activity Steroids 76 2011 193 203
39. M.A. Zmijewski, W. Li, J.K. Zjawiony, T.W. Sweatman, J. Chen, and D.D. Miller et al. Synthesis and photo-conversion of androsta- and pregna-5,7-dienes to vitamin D3-like derivatives Photochem Photobiol Sci 7 2008 1570 1576
40. M.A. Zmijewski, W. Li, J.K. Zjawiony, T.W. Sweatman, J. Chen, and D.D. Miller et al. Photo-conversion of two epimers (20R and 20S) of pregna-5,7-diene-3beta, 17alpha, 20-triol and their bioactivity in melanoma cells Steroids 74 2009 218 228