An alternative pathway of vitamin D2 metabolism: Cytochrome P450scc (CYP11A1)‐mediated conversion to 20‐hydroxyvitamin D2 and 17,20‐dihydroxyvitamin D2

Slominski, Andrzej; Semak, Igor; Wortsman, Jacobo; Zjawiony, Jordan; Li, Wei; Zbytek, Blazej; Tuckey, Robert C.

doi:10.1111/j.1742-4658.2006.05302.x

Cited by 98Vitamin D Research StudiesSteroid Chemistry and BiochemistryPharmacogenetics and Drug Metabolism

An alternative pathway of vitamin D2 metabolism: Cytochrome P450scc (CYP11A1)‐mediated conversion to 20‐hydroxyvitamin D2 and 17,20‐dihydroxyvitamin D2

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Slominski, Andrzej, Semak, Igor, Wortsman, Jacobo, Zjawiony, Jordan, Li, Wei, Zbytek, Blazej, Tuckey, Robert C.·2006·The FEBS Journal

DOI 10.1111/j.1742-4658.2006.05302.xPMC PMC1893115

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Abstract

We report an alternative, hydroxylating pathway for the metabolism of vitamin D 2 in a cytochrome P450 side chain cleavage (P450scc; CYP11A1) reconstituted system. NMR analyses identified solely 20‐hydroxyvitamin D 2 and 17,20‐dihydroxyvitamin D 2 derivatives. 20‐Hydroxyvitamin D 2 was produced at a rate of 0.34 mol·min−1·mol−1 P450scc, and 17,20‐dihydroxyvitamin D 2 was produced at a rate of 0.13 mol·min−1·mol−1. In adrenal mitochondria, vitamin D 2 was metabolized to six monohydroxy products. Nevertheless, aminoglutethimide (a P450scc inhibitor) inhibited this adrenal metabolite formation. Initial testing of metabolites for biological activity showed that, similar to vitamin D 2, 20‐hydroxyvitamin D 2 and 17,20‐dihydroxyvitamin D 2 inhibited DNA synthesis in human epidermal HaCaT keratinocytes, although to a greater degree. 17,20‐Dihydroxyvitamin D 2 stimulated transcriptional activity of the involucrin promoter, again to a significantly greater extent than vitamin D 2, while the effect of 20‐hydroxyvitamin D 2 was statistically insignificant. Thus, P450scc can metabolize vitamin D 2 to generate novel products, with intrinsic biological activity (at least in keratinocytes).

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Purified CYP11A1 hydroxylates the vitamin D2 side chain without cleavage, with the preferred initial site at C20.
“purified CYP11A1 can also hydroxylate the side chain of vitamin D2 without its cleavage, with the preferred site for the initial hydroxylation being at C20”
From The role of CYP11A1 in the production of vitamin D metabolites and their role in the regulation of epidermal functions (2014) · cites this paper as [58]
The major products of vitamin D2 metabolism by CYP11A1 are 20(OH)D2 and 17,20(OH)2D2, with lesser production of 17,20,24(OH)3D2 and an unidentified dihydroxyvitamin D2 metabolite.
“The major products were identified as 20(OH)D2 and 17,20(OH)2D2, with lesser production of 17,20,24(OH)3D2 and another unidentified dihydroxyvitamin D2 metabolite.”
From The role of CYP11A1 in the production of vitamin D metabolites and their role in the regulation of epidermal functions (2014) · cites this paper as [58]
Catalytic activity of CYP11A1 on non-traditional substrates such as vitamin D and ergosterol does not result in side chain cleavage, but involves sequential hydroxylations of the side chain including at C17.
“Importantly, catalytic activity on non-traditional substrates such as vitamin D and ergosterol does not result in side chain cleavage, but involves sequential hydroxylations of the side chain including at C17 [[10,24–30], and see below].”
From Novel activities of CYP11A1 and their potential physiological significance (2015) · cites this paper as [29]
The activity of CYP11A1 is affected by substrate structure: sterols with steroidal or Δ7-steroidal structures undergo side chain cleavage following hydroxylations at C22 and C20, whereas vitamin D metabolism involves sequential hydroxylations starting at C20 without cleavage.
“The activity of CYP11A1 is affected by the structure of the substrate with sterols having steroidal or Δ7-steroidal structures undergoing side chain cleavage following hydroxylations at C22 and C20. In contrast, metabolism of vitamin D involves sequential hydroxylations that start at C20 but do not lead to cleavage.”
From Novel activities of CYP11A1 and their potential physiological significance (2015) · cites this paper as [29]
Recombinant human CYP11A1 shows a similar sequence of reactions for vitamin D2, with 20(OH)D2 as the major product and lower production of 17,20(OH)2D2 and 17,20,24(OH)3D2 and another unidentified D2 metabolite.
“A similar sequence of reactions was seen for recombinant human CYP11A1 [9]. The major product was 20(OH)D2 with lower production of 17,20(OH)2D2 and 17,20,24 (OH)3D2 and another unidentified D2 metabolite [28,29].”
From Novel activities of CYP11A1 and their potential physiological significance (2015) · cites this paper as [29]

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Slominski, A. T., Zmijewski, M. A., Semak, I. V., Zbytek, B., Pisarchik, A. V., Li, W., Zjawiony, J. K., & Tuckey, R. C. (2014) · Anti-Cancer Agents in Medicinal Chemistry · doi:10.2174/18715206113139990308 · Cited by 91 · see citing works
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Sequential metabolism of 7-dehydrocholesterol to steroidal 5, 7-dienes in adrenal glands and its biological implication in the skin
Slominski, A. T., Zmijewski, M. A., Semak, I., Sweatman, T., Janjetovic, Z., Li, W., Zjawiony, J. K., & Tuckey, R. C. (2009) · PLoS ONE · doi:10.1371/journal.pone.0004309 · Cited by 90 · see citing works
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20S-Hydroxyvitamin D3, Noncalcemic Product of CYP11A1 Action on Vitamin D3, Exhibits Potent Antifibrogenic Activity in Vivo
Slominski, A., Janjetovic, Z., Tuckey, R. C., Nguyen, M. N., Bhattacharya, K. G., Wang, J., Li, W., Jiao, Y., Gu, W., Brown, M., et al. (2013) · The Journal of Clinical Endocrinology & Metabolism · doi:10.1210/jc.2012-3074 · Cited by 89 · see citing works
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Production of 22-hydroxy metabolites of vitamin D3 by cytochrome p450scc (CYP11A1) and analysis of their biological activities on skin cells
Tuckey, R. C., Li, W., Shehabi, H. Z., Janjetovic, Z., Nguyen, M. N., Kim, T.-K., Chen, J., Howell, D. E., Benson, H. A. E., Sweatman, T., et al. (2011) · Drug Metabolism and Disposition · doi:10.1124/dmd.111.040071 · Cited by 88 · see citing works
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Vitamin D Signaling in Psoriasis: Pathogenesis and Therapy
Brożyna, A. A., Slominski, R. M., Nedoszytko, B., Zmijewski, M. A., & Slominski, A. T. (2022) · International Journal of Molecular Sciences · doi:10.3390/ijms23158575 · Cited by 84 · see citing works
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Novel vitamin D hydroxyderivatives inhibit melanoma growth and show differential effects on normal melanocytes.
Slominski, A. T., Janjetović, Z., Kim, T., Wright, A. C., Grese, L., Riney, S. J., Nguyen, M. N., & Tuckey, R. C. (2012) · PubMed · Cited by 84 · see citing works
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Characterization of a new pathway that activates lumisterol in vivo to biologically active hydroxylumisterols
Slominski, A. T., Kim, T.-K., Hobrath, J. V., Janjetovic, Z., Oak, A. S. W., Postlethwaite, A., Lin, Z., Li, W., Takeda, Y., Jetten, A. M., et al. (2017) · Scientific Reports · doi:10.1038/s41598-017-10202-7 · Cited by 82 · see citing works
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Cytochrome P450scc-dependent metabolism of 7-dehydrocholesterol in placenta and epidermal keratinocytes
Slominski, A. T., Kim, T.-K., Chen, J., Nguyen, M. N., Li, W., Yates, C. R., Sweatman, T., Janjetovic, Z., & Tuckey, R. C. (2012) · The International Journal of Biochemistry & Cell Biology · doi:10.1016/j.biocel.2012.07.027 · Cited by 81 · see citing works
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Novel non-calcemic secosteroids that are produced by human epidermal keratinocytes protect against solar radiation
Slominski, A. T., Janjetovic, Z., Kim, T.-K., Wasilewski, P., Rosas, S., Hanna, S., Sayre, R. M., Dowdy, J. C., Li, W., & Tuckey, R. C. (2015) · The Journal of Steroid Biochemistry and Molecular Biology · doi:10.1016/j.jsbmb.2015.01.014 · Cited by 77 · see citing works
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Novel vitamin D photoproducts and their precursors in the skin
Slominski, A., Kim, T.-K., Zmijewski, M. A., Janjetovic, Z., Li, W., Chen, J., Kusniatsova, E. I., Semak, I., Postlethwaite, A., Miller, D. D., et al. (2013) · Dermato-Endocrinology · doi:10.4161/derm.23938 · Cited by 76 · see citing works
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Melanocyte Receptors: Clinical Implications and Therapeutic Relevance
Carlson, J. A., Linette, G. P., Aplin, A. E., Ng, B., & Slominski, A. T. (2007) · Dermatologic Clinics · doi:10.1016/j.det.2007.06.005 · Cited by 75 · see citing works
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20-hydroxyvitamin D₃ inhibits proliferation of cancer cells with high efficacy while being non-toxic.
Wang, J., Slominski, A. T., Tuckey, R. C., Janjetović, Z., Kulkarni, A. L., Chen, J., Postlethwaite, A. E., Miller, D. D., & Li, W. (2012) · UWA Profiles and Research Repository (UWA) · Cited by 74 · see citing works
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Neuroendocrinology of the skin
Zmijewski, M. A., & Slominski, A. T. (2011) · Dermato-Endocrinology · doi:10.4161/derm.3.1.14617 · Cited by 73 · see citing works
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Chemical synthesis of 20S-hydroxyvitamin D3, which shows antiproliferative activity
Li, W., Chen, J., Janjetovic, Z., Kim, T.-K., Sweatman, T., Lu, Y., Zjawiony, J., Tuckey, R. C., Miller, D., & Slominski, A. (2010) · Steroids · doi:10.1016/j.steroids.2010.05.021 · Cited by 68 · see citing works
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Evolutionary formation of melatonin and vitamin D in early life forms: insects take centre stage
Kim, T., Slominski, R. M., Pyza, E., Kleszczyński, K., Tuckey, R. C., Reiter, R. J., Holick, M. F., & Slominski, A. T. (2024) · Biological reviews/Biological reviews of the Cambridge Philosophical Society · doi:10.1111/brv.13091 · Cited by 68 · see citing works
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COVID‐19 and Vitamin D: A lesson from the skin
Slominski, R. M., Stefan, J., Athar, M., Holick, M. F., Jetten, A. M., Raman, C., & Slominski, A. T. (2020) · Experimental Dermatology · doi:10.1111/exd.14170 · Cited by 62 · see citing works
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Metabolic activation of tachysterol 3 to biologically active hydroxyderivatives that act on VDR , AhR , LXRs, and PPARγ receptors
Slominski, A. T., Kim, T., Slominski, R. M., Song, Y., Janjetović, Z., Podgórska, E., Reddy, S. B., Song, Y., Raman, C., Tang, E. K. Y., et al. (2022) · The FASEB Journal · doi:10.1096/fj.202200578r · Cited by 61 · see citing works
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Non-Musculoskeletal Benefits of Vitamin D beyond the Musculoskeletal System
Zhang, S., Miller, D. D., & Li, W. (2021) · International Journal of Molecular Sciences · doi:10.3390/ijms22042128 · Cited by 56 · see citing works
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Novel vitamin D analogs as potential therapeutics: metabolism, toxicity profiling, and antiproliferative activity.
Chen, J., Wang, J., Kim, T., Tieu, E. W., Tang, E. K. Y., Lin, Z., Kovacic, D., Miller, D. D., Postlethwaite, A. E., Tuckey, R. C., et al. (2014) · PubMed · Cited by 55 · see citing works
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Human cytochrome P450 enzymes 5–51 as targets of drugs and natural and environmental compounds: mechanisms, induction, and inhibition – toxic effects and benefits
Rendić, S., & Guengerich, F. P. (2018) · Drug Metabolism Reviews · doi:10.1080/03602532.2018.1483401 · Cited by 54 · see citing works
The Role of Classical and Novel Forms of Vitamin D in the Pathogenesis and Progression of Nonmelanoma Skin Cancers
Slominski, A. T., Brożyna, A. A., Zmijewski, M. A., Janjetović, Z., Kim, T., Slominski, R. M., Tuckey, R. C., Mason, R. S., Jetten, A. M., Guroji, P., et al. (2020) · Advances in experimental medicine and biology · doi:10.1007/978-3-030-46227-7_13 · Cited by 54 · see citing works
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The osteogenic transcription factor runx2 controls genes involved in sterol/steroid metabolism, including CYP11A1 in osteoblasts
Teplyuk, N. M., Zhang, Y., Lou, Y., Hawse, J. R., Hassan, M. Q., Teplyuk, V. I., Pratap, J., Galindo, M., Stein, J. L., Stein, G. S., et al. (2009) · Molecular Endocrinology · doi:10.1210/me.2008-0270 · Cited by 52 · see citing works
Synthesis and photochemical transformation of 3β,21-dihydroxypregna-5,7-dien-20-one to novel secosteroids that show anti-melanoma activity
Zmijewski, M. A., Li, W., Chen, J., Kim, T.-K., Zjawiony, J. K., Sweatman, T. W., Miller, D. D., & Slominski, A. T. (2011) · Steroids · doi:10.1016/j.steroids.2010.10.009 · Cited by 51 · see citing works
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Differential antitumor effects of vitamin D analogues on colorectal carcinoma in culture
Wierzbicka, J., Binek, A., Ahrends, T., KA, J. D. N., SZYDŁOWSKA, A., Turczyk, L., Wasiewicz, T., Wierzbicki, P., Sądej, R., Tuckey, R. C., et al. (2015) · International Journal of Oncology · doi:10.3892/ijo.2015.3088 · Cited by 51 · see citing works
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Antitumor Effects of Vitamin D Analogs on Hamster and Mouse Melanoma Cell Lines in Relation to Melanin Pigmentation
Wasiewicz, T., Szyszka, P., Cichorek, M., Janjetović, Z., Tuckey, R. C., Slominski, A. T., & Zmijewski, M. A. (2015) · International Journal of Molecular Sciences · doi:10.3390/ijms16046645 · Cited by 49 · see citing works
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Kinetics of vitamin D3 metabolism by cytochrome P450scc (CYP11A1) in phospholipid vesicles and cyclodextrin
Tuckey, R. C., Nguyen, M. N., & Slominski, A. T. (2008) · The International Journal of Biochemistry & Cell Biology · doi:10.1016/j.biocel.2008.05.006 · Cited by 49 · see citing works
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Metabolism of vitamin D2 to 17, 20,24-trihydroxyvitamin D2 by cytochrome p450scc (CYP11A1)
Nguyen, M. N., Slominski, A., Li, W., Ng, Y. R., & Tuckey, R. C. (2009) · Drug Metabolism and Disposition · doi:10.1124/dmd.108.025619 · Cited by 48 · see citing works
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Metabolism of 1α-hydroxyvitamin D3 by cytochrome P450scc to biologically active 1α,20-dihydroxyvitamin D3
Tuckey, R. C., Janjetovic, Z., Li, W., Nguyen, M. N., Zmijewski, M. A., Zjawiony, J., & Slominski, A. (2008) · The Journal of Steroid Biochemistry and Molecular Biology · doi:10.1016/j.jsbmb.2008.10.005 · Cited by 48 · see citing works
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The renaissance of vitamin D.
Wierzbicka, J., Piotrowska, A., & Zmijewski, M. A. (2014) · Acta Biochimica Polonica · doi:10.18388/abp.2014_1830 · Cited by 48 · see citing works
Tissue-Specific Profiling of Oxidative Stress-Associated Transcriptome in a Healthy Mouse Model
Kim, J. M., Kim, H.-G., & Son, C. (2018) · International Journal of Molecular Sciences · doi:10.3390/ijms19103174 · Cited by 45 · see citing works
New vitamin D analogs as potential therapeutics in melanoma
Szyszka, P., Zmijewski, M. A., & Slominski, A. T. (2012) · Expert Review of Anticancer Therapy · doi:10.1586/era.12.40 · Cited by 45 · see citing works
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Rat CYP24A1 acts on 20-hydroxyvitamin D3 producing hydroxylated products with increased biological activity
Tieu, E. W., Tang, E. K. Y., Chen, J., Li, W., Nguyen, M. N., Janjetovic, Z., Slominski, A., & Tuckey, R. C. (2012) · Biochemical Pharmacology · doi:10.1016/j.bcp.2012.09.032 · Cited by 44 · see citing works
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Steroidogenic enzyme Cyp11a1 regulates Type 2 CD8 + T cell skewing in allergic lung disease
Jia, Y., Domenico, J. M., Takeda, K., Han, J., Wang, M., Armstrong, M., Reisdorph, N. A., O’Connor, B. P., Lucas, J. J., & Gelfand, E. W. (2013) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.1216671110 · Cited by 44 · see citing works
Lumisterol is metabolized by CYP11A1: discovery of a new pathway
Tuckey, R. C., Slominski, A. T., Cheng, C. Y. S., Chen, J., Kim, T.-K., Xiao, M., & Li, W. (2014) · The International Journal of Biochemistry & Cell Biology · doi:10.1016/j.biocel.2014.08.004 · Cited by 43 · see citing works
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Hydroxylation of CYP11A1-derived products of vitamin D3 metabolism by human and mouse CYP27B1
Tang, E. K. Y., Chen, J., Janjetovic, Z., Tieu, E. W., Slominski, A. T., Li, W., & Tuckey, R. C. (2013) · Drug Metabolism and Disposition · doi:10.1124/dmd.113.050955 · Cited by 42 · see citing works
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Isotope-Labeling Studies Support the Electrophilic Compound I Iron Active Species, FeO3+, for the Carbon–Carbon Bond Cleavage Reaction of the Cholesterol Side-Chain Cleavage Enzyme, Cytochrome P450 11A1
Yoshimoto, F. K., Jung, I.-J., Goyal, S., Gonzalez, E. R., & Guengerich, F. P. (2016) · Journal of the American Chemical Society · doi:10.1021/jacs.6b04437 · Cited by 42 · see citing works
Purified Mouse CYP27B1 Can Hydroxylate 20,23-Dihydroxyvitamin D3, Producing 1α,20,23-Trihydroxyvitamin D3, Which Has Altered Biological Activity
Tang, E. K. Y., Li, W., Janjetovic, Z., Nguyen, M. N., Wang, Z., Slominski, A., & Tuckey, R. C. (2010) · Drug Metabolism and Disposition · doi:10.1124/dmd.110.034389 · Cited by 40 · see citing works
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CYP11A1‑derived vitamin D hydroxyderivatives as candidates for therapy of basal and squamous cell carcinomas
Slominski, A. T., Brożyna, A. A., Kim, T., Elsayed, M., Janjetović, Z., Qayyum, S., Slominski, R. M., Oak, A. S. W., Li, C., Podgórska, E., et al. (2022) · International Journal of Oncology · doi:10.3892/ijo.2022.5386 · Cited by 39 · see citing works
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Detection of 7-Dehydrocholesterol and Vitamin D3 Derivatives in Honey
Kim, T., Atigadda, V. R., Brzeminski, P., Fabisiak, A., Tang, E. K. Y., Tuckey, R. C., & Slominski, A. T. (2020) · Molecules · doi:10.3390/molecules25112583 · Cited by 36 · see citing works
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Vitamin D and Skin Cancer
Burns, E. M., Elmets, C. A., & Yusuf, N. (2014) · Photochemistry and Photobiology · doi:10.1111/php.12382 · Cited by 35 · see citing works
Human cytochrome P450scc (CYP11A1) catalyzes epoxide formation with ergosterol
Tuckey, R. C., Nguyen, M. N., Chen, J., Slominski, A. T., Baldisseri, D. M., Tieu, E. W., Zjawiony, J. K., & Li, W. (2012) · Drug Metabolism and Disposition · doi:10.1124/dmd.111.042515 · Cited by 32 · see citing works
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Corrigendum
(2006) · FEBS Journal · doi:10.1111/j.1742-4658.2006.05447.x · Cited by 31 · see citing works
Antifibrogenic Activities of CYP11A1-derived Vitamin D3-hydroxyderivatives Are Dependent on RORγ
Janjetović, Z., Postlethwaite, A. E., Kang, H. S., Kim, T., Tuckey, R. C., Crossman, D. K., Qayyum, S., Jetten, A. M., & Slominski, A. T. (2020) · Endocrinology · doi:10.1210/endocr/bqaa198 · Cited by 26 · see citing works
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CYP11A1 expression in bone is associated with aromatase inhibitor-related bone loss
Rodríguez-Sanz, M., García‐Giralt, N., Prieto‐Alhambra, D., Servitja, S., Balcells, S., Pecorelli, R., Díez‐Pérez, A., Grinberg, D., Tusquets, I., & Nogués, X. (2015) · Journal of Molecular Endocrinology · doi:10.1530/jme-15-0079 · Cited by 26 · see citing works
Vitamin D from UV-Irradiated Mushrooms as a Way for Vitamin D Supplementation: A Systematic Review on Classic and Nonclassic Effects in Human and Animal Models
Rondanelli, M., Moroni, A., Zese, M., Gasparri, C., Riva, A., Petrangolini, G., Perna, S., & Mazzola, G. (2023) · Antioxidants · doi:10.3390/antiox12030736 · Cited by 25 · see citing works
Cytochrome P450 Vitamin D Hydroxylases in Inflammation and Cancer
Gröschel, C., Tennakoon, S., & Kállay, E. (2015) · Advances in pharmacology · doi:10.1016/bs.apha.2015.03.002 · Cited by 25 · see citing works
2β- and 16β-hydroxylase activity of CYP11A1 and direct stimulatory effect of estrogens on pregnenolone formation
Mosa, A., Neunzig, J., Gerber, A., Zapp, J., Hannemann, F., Pilak, P., & Bernhardt, R. (2015) · The Journal of Steroid Biochemistry and Molecular Biology · doi:10.1016/j.jsbmb.2015.02.014 · Cited by 25 · see citing works
Pediatric Hypovitaminosis D
Ariganjoye, R. (2017) · Global Pediatric Health · doi:10.1177/2333794x16685504 · Cited by 24 · see citing works
Adaptive evolution of mammalian aromatases: lessons from Suiformes
Conley, A. J., Corbin, C. J., & Hughes, A. L. (2008) · Journal of Experimental Zoology Part A Ecological Genetics and Physiology · doi:10.1002/jez.451 · Cited by 23 · see citing works
Beneficial health effects of ultraviolet radiation: expert review and conference report
Riedmann, U., Dibben, C. J. L., de Gruijl, F. R., Gorman, S., Hart, P. H., Hoel, D. G., Levy, C., Lindqvist, P. G., Norval, M., Parikh, S., et al. (2025) · Photochemical & Photobiological Sciences · doi:10.1007/s43630-025-00743-6 · Cited by 22 · see citing works
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Photobiology of vitamin D
Holick, M. F., & Slominski, A. T. (2023) · Elsevier eBooks · doi:10.1016/b978-0-323-91386-7.00006-4 · Cited by 22 · see citing works
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The potential role of vitamin D in the progression of benign and malignant melanocytic neoplasms
Pinczewski, J., & Slominski, A. T. (2010) · Experimental Dermatology · doi:10.1111/j.1600-0625.2010.01169.x · Cited by 21 · see citing works
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Alternative pathways for vitamin D metabolism
Slominski, A. T., Tuckey, R. C., Jenkinson, C., Li, W., & Jetten, A. M. (2023) · Elsevier eBooks · doi:10.1016/b978-0-323-91386-7.00001-5 · Cited by 21 · see citing works
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Metabolism of 20-hydroxyvitamin D3 and 20,23-dihydroxyvitamin D3 by rat and human CYP24A1
Tieu, E. W., Li, W., Chen, J., Kim, T., Ma, D., Slominski, A. T., & Tuckey, R. C. (2015) · The Journal of Steroid Biochemistry and Molecular Biology · doi:10.1016/j.jsbmb.2015.02.010 · Cited by 20 · see citing works
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Updates on Mechanisms of Cytochrome P450 Catalysis of Complex Steroid Oxidations
Guengerich, F. P., Tateishi, Y., McCarty, K. D., & Yoshimoto, F. K. (2024) · International Journal of Molecular Sciences · doi:10.3390/ijms25169020 · Cited by 19 · see citing works
17,20S(OH)2pD Can Prevent the Development of Skin Fibrosis in the Bleomycin-Induced Scleroderma Mouse Model
Lobbins, M. L. B., Scott, I.-S. O., Slominski, A. T., Hasty, K. A., Zhang, S., Miller, D. D., Li, W., Kim, T., Janjetović, Z., Patel, T. S., et al. (2021) · International Journal of Molecular Sciences · doi:10.3390/ijms22168926 · Cited by 17 · see citing works
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Vitamin D as a regulator of steroidogenic enzymes
Lundqvist, J. (2014) · F1000Research · doi:10.12688/f1000research.4714.1 · Cited by 16 · see citing works
Impacts of deficiency in vitamin D derivatives on disease severity in adult bronchial asthma patients
Althagfan, S. S., Alolayan, S. O., Ahmed, S., Emara, M. M., & Awadallah, M. F. (2021) · Pulmonary Pharmacology & Therapeutics · doi:10.1016/j.pupt.2021.102073 · Cited by 15 · see citing works
Total synthesis of biologically active 20S-hydroxyvitamin D3
Wang, Q., Lin, Z., Kim, T., Slominski, A. T., Miller, D. D., & Li, W. (2015) · Steroids · doi:10.1016/j.steroids.2015.09.009 · Cited by 15 · see citing works
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22-NBD-cholesterol as a novel fluorescent substrate for cholesterol-converting oxidoreductases
Faletrov, Y. V., Bialevich, K. I., Edimecheva, I. P., Kostsin, D. G., Rudaya, E. V., Slobozhanina, E. I., & Shkumatov, V. M. (2012) · The Journal of Steroid Biochemistry and Molecular Biology · doi:10.1016/j.jsbmb.2012.09.035 · Cited by 14 · see citing works
Synthesis of Chiral Building Blocks for Oxygenated Terpenoids through a Simultaneous and Stereocontrolled Construction of Contiguous Quaternary Stereocenters by an Ireland–Claisen Rearrangement
Akahori, Y., Yamakoshi, H., Sawayama, Y., Hashimoto, S., & Nakamura, S. (2013) · The Journal of Organic Chemistry · doi:10.1021/jo402537u · Cited by 14 · see citing works
Propranolol-Loaded Trehalosome as Antiproliferative Agent for Treating Skin Cancer: Optimization, Cytotoxicity, and In Silico Studies
Younis, M. K., Elakkad, Y. E., Eldeen, R. R. F., Ali, I. H., & Khalil, I. A. H. (2023) · Pharmaceutics · doi:10.3390/pharmaceutics15082033 · Cited by 13 · see citing works
Placenta-specific CYP11A1 overexpression lead to autism-like symptom in offspring with altered steroid hormone biosynthesis in the placenta-brain axis and rescued by vitamin D intervention
Yin, H., Zhang, J., Chen, Y., Guo, J., Li, Q., Dinnyés, A., Sun, Q., Liu, X., He, G., Zhu, B., et al. (2024) · Brain Behavior and Immunity · doi:10.1016/j.bbi.2024.07.012 · Cited by 11 · see citing works
Role of microsomal steroid hydroxylases in Δ7-steroid biosynthesis
Sushko, T. A., Gilep, A. A., Yantsevich, A. V., & Usanov, S. A. (2013) · Biochemistry (Moscow) · doi:10.1134/s0006297913030103 · Cited by 10 · see citing works
Cytochrome P450BM-3 and P450 11A1 retain Compound I (FeO3+) chemistry with electrophilic substrates poised for Compound 0 (Fe3+O2−) reactions
McCarty, K. D., Tateishi, Y., & Guengerich, F. P. (2025) · Journal of Biological Chemistry · doi:10.1016/j.jbc.2025.110378 · Cited by 6 · see citing works
Retrospective Analysis of Vitamin D Deficiency in an Adult Population of Arad County, Western Romania (2019–2022)
Marti, D. T., Neşiu, A., Baltă, C., Olariu, T. R., Mihu, A. G., Hermenean, A. O., & Oatis, D. A. (2024) · Life · doi:10.3390/life14020274 · Cited by 4 · see citing works
Vitamin D3, cholecalciferol via its hydroxylmetabolites, receptors and metabolizing enzymes modulates male reproductive functions
Oluwole, D. T., & Ajayi, A. F. (2025) · Life Sciences · doi:10.1016/j.lfs.2025.123680 · Cited by 3 · see citing works
In Vitro and In Vivo characterization of CYP11A1, CYP17A1 and cChloramphenicol acetyltransferase-dependent steroid conversion
Mosa, A. A. (2015) · Publications of the UdS (Saarland University) · doi:10.22028/d291-23081 · Cited by 1 · see citing works
Evolución de la DMO durante el tratamiento con inhibidores de aromatasa y su relación con el gen CYP11A1: estudio prospectivo de la cohorte B-ABLE
Rodríguez-Sanz, M., Prieto‐Alhambra, D., Servitja, S., García‐Giralt, N., Garrigós, L., Albanell, J., Martinez‐García, M., González, I., Martos, T., Díez‐Pérez, A., et al. (2015) · Revista de Osteoporosis y Metabolismo Mineral · doi:10.4321/s1889-836x2015000400004
Comparing diene derivatisation methods of dry blood spot samples for vitamin D metabolites quantification by liquid chromatography-tandem mass spectrometry
Rapholo, A. A. F. (2017) · UpSpace Institutional Repository (University of Pretoria)
The Biosynthesis of Vitamins
Zhao, X., Zhang, T., Qi, Y., Liu, X., Ren, X., Chen, S., Meng, Z., Lin, W., Yang, S., Wang, L., et al. (2026) · Elsevier eBooks · doi:10.1016/b978-0-443-24738-5.00078-1
VDR Activation Suppresses Pancreatic Cancer Metastasis Through Inhibition of the ERK Signaling Pathway
Zhang, D., Ding, W., Fang, Y., Xu, H., Zhang, X., Li, C., & Wang, Y. (2026) · Cancers · doi:10.3390/cancers18142296

Metabolism of vitamin D2 to 17, 20,24-trihydroxyvitamin D2 by cytochrome p450scc (CYP11A1)
Nguyen, M. N., Slominski, A., Li, W., Ng, Y. R., & Tuckey, R. C. (2009) · Drug Metabolism and Disposition · doi:10.1124/dmd.108.025619 · Cited by 48 · see citing works
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The cytochrome P450scc system opens an alternate pathway of vitamin D3 metabolism
Slominski, A., Semak, I., Zjawiony, J., Wortsman, J., Li, W., Szczesniewski, A., & Tuckey, R. C. (2005) · The FEBS Journal · doi:10.1111/j.1742-4658.2005.04819.x · Cited by 155 · see citing works
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Metabolism of 1α-hydroxyvitamin D3 by cytochrome P450scc to biologically active 1α,20-dihydroxyvitamin D3
Tuckey, R. C., Janjetovic, Z., Li, W., Nguyen, M. N., Zmijewski, M. A., Zjawiony, J., & Slominski, A. (2008) · The Journal of Steroid Biochemistry and Molecular Biology · doi:10.1016/j.jsbmb.2008.10.005 · Cited by 48 · see citing works
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In vivo evidence for a novel pathway of vitamin D 3 metabolism initiated by P450scc and modified by CYP27B1
Slominski, A. T., Kim, T., Shehabi, H. Z., Semak, I., Tang, E. K. Y., Nguyen, M. N., Benson, H. A. E., Korik, E., Janjetovic, Z., Chen, J., et al. (2012) · The FASEB Journal · doi:10.1096/fj.12-208975 · Cited by 266 · see citing works
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Production of 22-hydroxy metabolites of vitamin D3 by cytochrome p450scc (CYP11A1) and analysis of their biological activities on skin cells
Tuckey, R. C., Li, W., Shehabi, H. Z., Janjetovic, Z., Nguyen, M. N., Kim, T.-K., Chen, J., Howell, D. E., Benson, H. A. E., Sweatman, T., et al. (2011) · Drug Metabolism and Disposition · doi:10.1124/dmd.111.040071 · Cited by 88 · see citing works
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Authors: Slominski, A., Semak, I., Wortsman, J., Zjawiony, J., Li, W., Zbytek, B., & Tuckey, R. C.
Affiliations: University of Tennessee Health Science Center (US)
Belarusian State University (BY)
SIU Medicine (US)
University of Mississippi (US)
The University of Western Australia (AU)
ORCID: Slominski, Andrzej
Semak, Igor
Zjawiony, Jordan
Tuckey, Robert C.
Venue: The FEBS Journal
Publisher: Wiley
Published: 2006-06-05
Volume: 273
Issue: 13
Pages: 2891-2901
ISSN: 1742-464X (ISSN-L)
1742-4658
DOI: 10.1111/j.1742-4658.2006.05302.x
PMC: PMC1893115
OpenAlex: W2028177638
Cited by: 98
References: 41
Citations by year: 2026: 2 · 2025: 3 · 2024: 5 · 2023: 4 · 2022: 3 · 2021: 4 · 2020: 6 · 2019: 1 · 2018: 5 · 2017: 5 · 2016: 2 · 2015: 12 · 2014: 9 · 2013: 7 · 2012: 7
FWCI: 3.26
Type: journal article
Language: en
Open access: bronze
doi.org
Licence: onlinelibrary.wiley.com/termsAndConditions#vor (vor)
Locations: FEBS Journal (publishedVersion)
PubMed (publishedVersion)
PubMed Central (acceptedVersion)
UWA Profiles and Research Repository (UWA) (submittedVersion)
Funders: National Institutes of Health
National Institute of Arthritis and Musculoskeletal and Skin Diseases (AR-052190, R01AR052190)
Topics: Health Sciences › Medicine › Pathology and Forensic Medicine › Vitamin D Research Studies
Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Steroid Chemistry and Biochemistry
Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Pharmacology › Pharmacogenetics and Drug Metabolism
Keywords: CYP11A1, cytochrome P450 side-chain cleavage, adrenal mitochondria, aminoglutethimide, keratinocytes, DNA synthesis inhibition
MeSH terms: Aminoglutethimide, Animals, Cattle, Cholesterol Side-Chain Cleavage Enzyme, Ergocalciferols, Humans, Hydroxycholecalciferols, Male, Magnetic Resonance Spectroscopy, Promoter Regions, Genetic, Protein Precursors, Keratinocytes, 25-Hydroxyvitamin D 2, Rats, Wistar, Rats

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An alternative pathway of vitamin D2 metabolism: Cytochrome P450scc (CYP11A1)‐mediated conversion to 20‐hydroxyvitamin D2 and 17,20‐dihydroxyvitamin D2

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