Skip to main content
SpringerLink
Log in

Analysis of vitamin D, its metabolites and structural analogues

  • Chapter
Steroid Analysis

Abstract

Vitamin D*, a secosteroid derived from a sterol precursor by opening of the steroid B ring between carbons 9 and 10, exists in a number of different chemical forms. In the clinical environment, only vitamins D2 and D3 are important. Vitamin D3 (cholecalciferol) arises by the action of UV light on the sterol precursor, 7-dehydrocholesterol, which is found in the upper layers of the skin. The chemical reactions involved are shown in Figure 10.1. It can be seen that apart from the production of the provitamin and subsequent conversion into vitamin D3, a number of other isomers are formed. The proportion of these different products from 7-dehydrocholesterol varies depending upon the conditions under which they are formed. Vitamin D2 (ergocalciferol) arises in a similar fashion in that it derives from the UV irradiation of the 5,7-diene sterol precursor, ergosterol. Ergosterol is widely distributed in plants, yeasts and a number of animals other than humans. Vitamin D2 has an extra methyl (C-28) attached to carbon 24 on the vitamin D side-chain together with an extra double bond at C-22(23), and its structure is given in Figure 10.1. Because the further metabolism of vitamin D involves hydroxylations on the side chain, it is inevitable that the physiological effects of vitamin D2 and vitamin D3 may well be slightly different. For historical reasons, vitamin D2 is more readily available commercially and is used in a number of countries throughout the world to supplement milk and other foodstuffs, and calciferol BP is in fact vitamin D2.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 74.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Similar content being viewed by others

References

  • Aberhart, D.J. and Hsu, A.C.-T. (1976) Studies on the adduct of 4-phenyl-1,2,4-triazoline-3,5dione with vitamin D3. Journal of Organic Chemistry, 41, 2098–2102.

    Article  CAS  Google Scholar 

  • Adams, J.S., Clemens, T.L. and Holick, M.F. (1981) Silica Sep-Pak preparative chromatography for vitamin D and its metabolites. Journal of Chromatography, 226, 198–201.

    Article  CAS  Google Scholar 

  • Agarwal, V.K. (1988) Liquid chromatographic determination of vitamin D in fortified milk. Journal of the Association of Official Analytical Chemists (Journal of Aoac International), 71, 19–22.

    CAS  Google Scholar 

  • Agarwal, V.K. (1989) Liquid chromatographic determination of vitamin D in infant formula. Journal of the Association of Official Analytical Chemists (Journal of Aoac International), 72, 1007–1009.

    CAS  Google Scholar 

  • Agarwal, V.K. (1990) A new procedure for the isomerisation of vitamin D and its metabolites. Journal of Steroid Biochemistry and Molecular Biology, 35, 149–150.

    CAS  Google Scholar 

  • Agarwal, V.K. (1992) Liquid chromatographic determination of vitamin D in animal feeds and premixes. Journal of Aoac International, 75, 812–815.

    CAS  Google Scholar 

  • Andersen, N.R., Buchwald, F.A. and Grue-Soerensen, G. (1992) Identification and synthesis of a metabolite of KH 1060, a new potent lalpha,25-dihydroxyvitamin D3analog. Bioorganic and Medicinal Chemistry Letters, 2, 1713–1716.

    Article  CAS  Google Scholar 

  • Andersson, S., Holmberg, I. and Wikvall, K. (1983) 25-Hydroxylation of C27-steroids and vitamin D3by a constitutive cytochrome P-450 from rat liver microsomes. Journal of Biological Chemistry, 258, 6777–6781.

    Google Scholar 

  • Axelson, M. (1985) Liquid—solid extraction of vitamin D3metabolites from plasma for analysis by HPLC, GC/MS and protein binding techniques. Analytical Letters, 18, 1607–1622. Belsey, R., DeLuca, H.F. and Potts, J.T. (1971) Competitive binding assay for vitamin D and 25-OH vitamin D. Journal of Clinical Endocrinology and Metabolism, 33, 554–557.

    Google Scholar 

  • Berlin, T., Emtestam, L. and Bjorkhem, I. (1986a) Studies on the relationship between vitamin D3status and urinary excretion of calcium in healthy subjects: effects of increased level of 25hydroxyvitamin D3. Scandinavian Journal of Clinical and Laboratory Investigation, 46, 723–729.

    Article  CAS  Google Scholar 

  • Berlin, T., Holmberg, I. and Bjorkhem, I. (1986b) High circulating levels of 25-hydroxyvitamin D3in renal stone formers with hyperabsorptive hypercalciuria. Scandinavian Journal of Clinical and Laboratory Investigation, 46, 367–374.

    Article  CAS  Google Scholar 

  • Berman, E., Luz, Z., Mazur, Y. et al. (1977) Conformational analysis of vitamin D and analogues. 13C and ‘H nuclear magnetic resonance study. Journal of Organic Chemistry, 42, 3325–3330.

    Article  CAS  Google Scholar 

  • Bikle, D.D. (1983) Assay of Calcium Regulating Hormones. Springer-Verlag, New York.

    Book  Google Scholar 

  • Bikle, D.D. (1992) Clinical counterpoint: vitamin D: new actions, new analogs, new therapeutic potential. Endocrine Reviews, 13, 765–784.

    CAS  Google Scholar 

  • Binderup, L. and Kragballe, K. (1992) Origin of the use of calcipotriol in psoriasis treatment. Reviews in Contemporary Pharmacotherapy, 3, 357–365.

    Google Scholar 

  • Bishop, J.E., Norman, A.W., Coburn, J.W. et al. (1980) Studies on the metabolism of calciferol XVI. Determination of the concentration of 25-hydroxyvitamin D, 24,25-dihydroxyvitamin D and 1,25-dihydroxyvitamin D in a single two millilitre plasma sample. Mineral and Electrolyte Metabolism, 3, 181–189.

    CAS  Google Scholar 

  • Bjorkhem, I. and Holmberg, I. (1978). Assay and properties of a mitochondrial 25-hydroxylase active on vitamin D3. Journal of Biological Chemistry,253, 842–849.

    Google Scholar 

  • Bjorkhem, I. and Holmberg, I. (1979) On the 25-hydroxylation of vitamin D3 in vitro studied with a mass fragmentographic technique. Journal of Biological Chemistry, 254, 9518–9524.

    CAS  Google Scholar 

  • Bjorkhem, I. and Holmberg, I. (1980) Mass fragmentographic assay of 25-hydroxyvitamin D3. In Methods in Enzymology, vol. 67, part F (eds D.B. McCormick and L.D. Wright ). Academic Press, New York, pp. 385–393.

    Google Scholar 

  • Bjorkhem, I., Hansson, R., Holmberg, I. et al. (1979a) 25-Hydroxylation of vitamin D3by a reconstituted system from rat liver microsomes. Biochemical and Biophysical Research Communications, 90, 615–622.

    Google Scholar 

  • Bjorkhem, I., Holmberg, I., Kristiansen, T. et al. (1979b) Assay of 1,25-dihydroxy vitamin D3by isotope dilution—mass fragmentography. Clinical Chemistry, 25, 584–588.

    CAS  Google Scholar 

  • Bjorkhem, I., Holmberg, I., Oftebro, H. et al. (1980) Properties of a reconstituted vitamin D325-hydroxylase from rat liver mitochondria. Journal of Biological Chemistry, 255, 5244–5249.

    CAS  Google Scholar 

  • Bligh, E.G. and Dyer, W.J. (1957) A rapid method for total lipid extraction and purification. Canadian Journal of Biochemistry, 37, 911–917.

    Article  Google Scholar 

  • Blunt, J.W., DeLuca, H.F. and Schnoes, H.K. (1968) 25-Hydroxycholecalciferol: a biologically active metabolite of cholecalciferol. Journal of the Chemical Society, Chemical Communications,801.

    Google Scholar 

  • Bosch, R., Versluis, C., Terlouw, J.K. et al. (1985) Isolation and identification of 25-hydroxy-didydrotachysterol2, 1x,25-dihydroxy-dihydrotachysterol2 and lß,25-dihydroxy-dihydrotachysterol2. Journal of Steroid Biochemistry, 23, 223–229.

    Article  CAS  Google Scholar 

  • Bouillon, R., DeMoor, P., Baggiolini, E.G. et al. (1980) A radioimmunoassay for 1,25-dihydroxycholecalciferol. Clinical Chemistry, 26, 562–567.

    CAS  Google Scholar 

  • Bouillon, R., van Herck, E., Jans, I. et al. (1984) Two direct (non-chromatographic) assays for 25hydroxyvitamin D. Clinical Chemistry, 30, 1731–1736.

    CAS  Google Scholar 

  • Bush, I.E. (1961) The Chromatography of Steroids. Pergamon Press, Oxford.

    Google Scholar 

  • Calverley, M.J. (1987) Synthesis of MC903, a biologically active vitamin D metabolite analogue. Tetrahedron, 43, 4609–4619.

    Article  CAS  Google Scholar 

  • Calverley, M.J. and Jones, G. (1992) Vitamin D. In Antitumor Steroids (ed. R.T. Blickenstaff ). Academic Press, San Diego, pp. 193–270.

    Chapter  Google Scholar 

  • Carlberg, C., Bendik, I., Wyss, A. et al. (1993) Two nuclear signalling pathways for vitamin D. Nature, 361, 657–660.

    Google Scholar 

  • Chen, T.C., Shao, Q., Heath, H. et al. (1993) An update on the vitamin D content of fortified milk from the United States and Canada. New England Journal of Medicine, 329, 1507.

    Article  CAS  Google Scholar 

  • Clemens, T.L. (1990). Useful clinical assays for vitamin D metabolites. Trends in Endocrinology and Metabolism, 1, 129–133.

    Article  CAS  Google Scholar 

  • Clemens, T.L., Hendy, G.N., Graham, R.F. et al. (1978) A radioimmunoassay for 1,25-dihydroxycholecalciferol. Clinical Science, 54, 329–332.

    CAS  Google Scholar 

  • Coldwell, R.D., Trafford, D.J.H., Makin, H.L.J. et al. (1984) Specific estimation of 24,25dihydroxyvitamin D in plasma by gas chromatography–mass spectrometry. Clinical Chemistry, 30, 1193–1198.

    CAS  Google Scholar 

  • Coldwell, R.D., Trafford, D.J.H., Makin, H.L.J. et al. (1985) Specific mass fragmentographic assay for 25,26-dihydroxyvitamin D in human plasma using a deuterated internal standard. Journal of Chromatography, 338, 289–302.

    Article  CAS  Google Scholar 

  • Coldwell, R.D., Trafford, D.J.H., Makin, H.L.J. et al. (1986) The estimation of 25-hydroxyvitamin D2, 24,25-dihydroxyvitamin D2, and 25,26-dihydroxyvitamin D2 in a single sample of plasma using gas chromatography–mass spectrometry. Abstracts presented at the 6th International Symposium on Mass Spectrometry in the Life Sciences, Ghent, Belgium, p. 24.

    Google Scholar 

  • Coldwell, R.D., Trafford, D.J.H., Hruska, K. et al. (1987) Plasma 24,25-hydroxyvitamin D3is not raised in hypophosphatemic mice: Results of a mass fragmentographic study, 9th Meeting of the ASBMR, Indianapolis. Journal of Bone and Mineral Research, 2, abstract 457.

    Google Scholar 

  • Coldwell, R.D., Trafford, D.J.H., Varley, M.J. et al. (1989) Measurement of 25-hydroxyvitamin D2, 25-hydroxyvitamin D3, 24,25-dihydroxyvitamin D2 and 25,26-dihydroxyvitamin D2 in a plasma sample by mass framentography. Clinica Chimica Acta, 180, 157–168.

    Article  CAS  Google Scholar 

  • Coldwell, R.D., Trafford, D.J.H., Varley, M.J. et al. (1990) Stable isotope-labeled vitamin D, metabolites and chemical analogs—synthesis and use in mass spectrometric studies. Steroids, 55, 418–432.

    Article  CAS  Google Scholar 

  • Colston, K.W., Mackay, A., James, S.Y. et al. (1992) EB 1089: A new vitamin D analogue that inhibits the growth of breast cancer cells in vivo and in vitro. Biochemical Pharmacology, 44, 2273–2281.

    Article  CAS  Google Scholar 

  • Cunningham, J., Coldwell, R.D., Jones, G. et al. (1990) Plasma 24,25-dihydroxyvitamin-D3 concentrations in X-linked hypophosphatemic mice—studies using mass fragmentographic and radioreceptor assays. Journal of Bone and Mineral Research, 5, 173–177.

    Article  CAS  Google Scholar 

  • Dabek, J.T., Harkonen, M., Wahlroos, O. et al. (1981) Assay for plasma 25-hydroxyvitamin D2 and 25-hydroxyvitamin D3by high-performance liquid chromatography. Clinical Chemistry, 27, 1346–1351.

    Google Scholar 

  • Dame, M.C., Pierce, E.A., Prahl, J.M. et al. (1986) Monoclonal antibodies to the porcine intestinal receptor for 1,25-dihydroxyvitamin D3: Interaction with distinct receptor domains. Biochemistry, 25, 4523–4534.

    Article  CAS  Google Scholar 

  • Delvin, E.E., Dussault, M. and Glorieux, F.H. (1980) A simplified assay for 25-hydroxycalciferol. Clinical Biochemistry, 13, 106–108.

    Article  CAS  Google Scholar 

  • Dueland, S., Holmberg, I., Berg, T. et al. (1981) Uptake and 25-hydroxylation of vitamin D3by isolated rat liver cells. Journal of Biological Chemistry, 256, 10430–10434.

    CAS  Google Scholar 

  • Eisman, J.A., Hamstra, A.J., Kream, B.E. et al. (1976) 1,25-Dihydroxyvitamin D in biological fluids: A simplified and sensitive assay. Science, 193, 1021–1023.

    Google Scholar 

  • Fraher, L.J., Clemens, T.L., Papapoulos, S.E. et al. (1980) Determination of circulating 25,26dihydroxycholecalciferol in man by radioimmunoassay. Clinical Science, 59, 257–263.

    CAS  Google Scholar 

  • Fraher, L.J., Jones, G., Clemens, T.L. et al. (1981) Radioassays of vitamin D2 and D3metabolites. Advance abstracts of papers for the XIIIth Acta Endocrinological Congress, Cambridge, August 1981,. abstract no. 8. Acta Endocrinologica, 97, Suppl. 243.

    Google Scholar 

  • Gaskell, S.J. (1990) Quantification of steroid conjugates using fast atom bombardment mass spectrometry. Steroids, 55, 458–462.

    Article  CAS  Google Scholar 

  • Gaskell, S.J. and Brownsey, B.G. (1983) Immunoadsorption to improve gas chromatography/ high-resolution mass spectrometry of estradiol-17beta in plasma. Clinical Chemistry, 29, 677–680.

    CAS  Google Scholar 

  • Green, A., Dilworth, J., Calverley, M.J. et al. (1993) Studies on the specificity of the enzymes involved in the side chain metabolism of 1,25-dihydroxyvitamin D3: mass spectrometry of metabolites of 1,25-dihydroxy-24-homo-vitamin D3(MC1127). Abstract for the 184th Meeting of the Society for Endocrinology, London, UK. Journal of Endocrinology, 139, suppl. (abstract P7 ).

    Google Scholar 

  • Guo, Y.-D., Strugnell, S., Back, D.W. et al. (1993) Transfected human liver cytochrome P-450 hydroxylates vitamin D analogs at different side-chain positions. Proceedings of the National Academy of Sciences of the USA, 90, 8668–8672.

    Article  CAS  Google Scholar 

  • Hagenfeldt, Y. and Berlin, T. (1992) The human renal 25-hydroxyvitamin D3-lalpha-hydroxylase-properties studied by isotope-dilution mass spectrometry. European Journal of Clinical Investigation, 22, 223–228.

    Article  CAS  Google Scholar 

  • Hagenfeldt, Y., Eriksson, H. and Bjorkhem, I. (1989) Stimulatory effect of testosterone on renal 25-hydroxyvitamin D31-alpha-hydroxylase in guinea pig. Biochimica et Biophysica Acta, 1002, 84–88.

    Article  CAS  Google Scholar 

  • Hagenfeldt, Y., Bjorkhem, I. and Eriksson, H. (1990) Renal 25-hydroxyvitamin-D3-l-alphahydroxylase in guinea pig—activity variations during development and pregnancy. Biochimica et Biophysica Acta, 1042, 94–98.

    Article  CAS  Google Scholar 

  • Hagenfeldt, Y., Pedersen, J.I. and Bjorkhem, I. (1988) Properties of guinea-pig kidney 25hydroxyvitamin D31-alpha-hydroxylase assayed by isotope dilution–mass spectrometry. Biochemical Journal, 250, 521–526.

    CAS  Google Scholar 

  • Halket, J.M., Ganschow, I. and Lisboa, B.P. (1980) Gas chromatographic–mass spectrometric properties of boronate esters of 24R,25-dihydroxycholecalciferol. Journal of Chromatography, 192, 434–440.

    Article  CAS  Google Scholar 

  • Hansson, R., Holmberg, I. and Wikvall, K. (1981) 25-Hydroxylation of vitamin D3and side-chain hydroxylations of 5ß-cholestane-3a,7a,12a-triol by purified rabbit and rat liver microsomal cytochromes P-450. Journal of Biological Chemistry, 256, 4345–4349.

    Google Scholar 

  • Hart, H.E. and Greenwald, A.B. (1979) Scintillation proximity assay (SPA)—a new method of immunoassay. Molecular Immunology, 16, 265–267.

    Article  CAS  Google Scholar 

  • Hart, J.P., Norman, M.D. and Lacey, C.J. (1992) Voltammetric behaviour of vitamin-D2 and vitamin-D3 at a glassy carbon electrode and their determination in pharmaceutical products by using liquid chromatography with amperometric detection. The Analyst, 117, 1441–1445.

    Article  CAS  Google Scholar 

  • Hasegawa, H. (1992) Vitamin-D determination using high-performance liquid chromatography with internal standard redox mode electrochemical detection and its application to medical nutritional products. Journal of Chromatography, 605, 215–220.

    Article  CAS  Google Scholar 

  • Haussler, M.R. (1986) Vitamin D receptors: nature and function. Annual Review of Nutrition, 6, 527–562.

    Article  CAS  Google Scholar 

  • Heyman, R.A., Mangelsdorf, D.J., Dyck, J.A. et al. (1992) 9-cis-Retinoic acid is a high affinity ligand for the retinoid X receptor. Cell, 68, 397–406.

    Google Scholar 

  • Holick, M.F. (1990) The use and interpretation of assays for vitamin-D and its metabolites. Journal of Nutrition, 120, 1464–1469.

    CAS  Google Scholar 

  • Holick, M.F., Shao, Q., Liu, W.W. et al. (1992) The vitamin-D content of fortified milk and infant formula. New England Journal of Medicine, 326, 1178–1181.

    Article  CAS  Google Scholar 

  • Hollis, B.W. (1984) Comparison of equilibrium and dis-equilibrium assay conditions for ergocalciferol, cholecalciferol and their major metabolites. Journal of Steroid Biochemistry, 21, 81–86.

    Article  CAS  Google Scholar 

  • Hollis, B.W. (1986) Assay of circulating 1,25-dihydroxyvitamin D involving a novel single-cartridge extraction and purification procedure. Clinical Chemistry, 32, 2060–2063.

    CAS  Google Scholar 

  • Hollis, B.W. and Frank, N.E. (1985) Solid phase extraction system for vitamin D and its major metabolites in human plasma. Journal of Chromatography, 343, 43–50.

    Article  CAS  Google Scholar 

  • Hollis, B.W. and Napoli, J.L. (1985) Improved radioimmunoassay for vitamin D and its use in assessing vitamin D status. Clinical Chemistry, 31, 1815–1819.

    CAS  Google Scholar 

  • Hollis, B.W., Kamerud, J.Q., Selvaag, S.R. et al. (1993) Determination of vitamin-D status by radioimmunoassay with an I-125-labeled tracer. Clinical Chemistry, 39, 529–533.

    CAS  Google Scholar 

  • Holmberg, I. (1984a) Inhibition of reconstituted vitamin D325-hydroxylase by a protein fraction from rat liver microsomes. Biochemical and Biophysical Research Communications, 123, 1209–1214.

    Article  CAS  Google Scholar 

  • Holmberg, I. (1984b) Differences in the metabolism of vitamin D2 and vitamin D3by subcellular fractions from rat liver. Biochimica et Biophysica Acta, 800, 106–109.

    Article  CAS  Google Scholar 

  • Holmberg, I. and Larsson, A. (1980) Seasonal variation of vitamin D3and 25-hydroxyvitamin D3in human serum. Clinica Chimica Acta, 100, 173–174.

    Article  CAS  Google Scholar 

  • Holmberg, I., Kristiansen, T. and Sturen, M. (1984) Determination of 25-hydroxyvitamin D in serum by high-performance liquid chromatography and isotope dilution mass spectrometry. Scandinavian Journal of Clinical and Laboratory Investigation, 44, 275–282.

    Article  CAS  Google Scholar 

  • Holmberg, I., Berlin, T., Ewerth, S. et al. (1986a) 25-Hydroxylase activity in subcellular fractions from human liver. Evidence for different rates of mitochondria) hydroxylation of vitamin D2 and D3. Scandinavian Journal of Clinical and Laboratory Investigation, 46, 785–790.

    Google Scholar 

  • Holmberg, I., Saarem, K., Pedersen, J.I. et al. (1986b) Assay of 25-hydroxy vitamin D3–1-alphahydroxylase in pig kidney and mitochondria using isotope dilution-mass spectrometry. Analytical Biochemistry, 159, 317–322.

    Article  CAS  Google Scholar 

  • Horst, R.L. (1985) Recent advances in the quantitation of vitamin D and vitamin D metabolites. In Vitamin D: Basic and Clinical Aspects (ed. R. Kumar ). Martinus Nijhoff, Boston, pp. 423–478.

    Google Scholar 

  • Horst, R.L., Reinhardt, T.A. and Hollis, B.W. (1990) Improved methodology for the analysis of plasma vitamin-D metabolites. Kidney International, 38, S28 - S35.

    Article  Google Scholar 

  • Hummer, L. and Christiansen, C. (1984) A sensitive and selective radioimmunoassay for serum 24,25-dihydroxycholecalciferol in man. Clinical Endocrinology, 21, 71–79.

    Article  CAS  Google Scholar 

  • Hummer, L., Nilas, L., Tjellesen, L. et al. (1984) A selective and simplified radioimmunoassay of 25-hydroxyvitamin D3. Scandinavian Journal of Clinical and Laboratory Investigation, 44, 163–167.

    Article  CAS  Google Scholar 

  • Hummer, L., Johansen, J.S. and Christiansen, C. (1985) Radioimmunoassay for 25,26-dihydroxyvitamin D3. In Vitamin D. Chemical, Biochemical and Clinical Update (eds A.W. Norman, K. Schaefer, H.G. Grigoleit and D.V. Herrath ). Walter de Gruyter, Berlin, pp. 830–831.

    Google Scholar 

  • Jardine, I., Scanlan, G.F., Mattox, V.R. et al. (1984) Analysis of steroid and vitamin D glucuronides and sulfates by fast atom bombardment mass spectrometry. Biomedical Mass Spectrometry, 11, 4–9.

    Article  CAS  Google Scholar 

  • Jones, G. (1978) Assay of vitamin D2 and D3, and 25-hydroxyvitamin D2 and D3in human plasma by high-performance liquid chromatography. Clinical Chemistry, 24, 287–294.

    CAS  Google Scholar 

  • Jones, G. (1980) Ternary solvent mixtures for improved resolution of hydroxylated metabolites of vitamin D2 and vitamin D3during high-performance liquid chromatography. Journal of Chromatography, 221, 27–37.

    Article  CAS  Google Scholar 

  • Jones, G. (1983) Chromatographic separation of 24(R),25-dihydroxyvitamin D3and 25-hydroxyvitamin D3–26,23-lactone using a cyano-bonded phase packing. Journal of Chromatography, 276, 69–75.

    Article  CAS  Google Scholar 

  • Jones, G. and Calverley, M.J. (1993) A dialogue on analogues. Newer vitamin-D drugs for use in bone disease, cirrhosis, and cancer. Trends in Endocrinology and Metabolism, 4, 297–303.

    Article  CAS  Google Scholar 

  • Jones, G. and DeLuca, H.F. (1975) High-pressure liquid chromatography: separation of the metabolites of vitamins D2 and D3on small particle silica columns. Journal of Lipid Research, 16, 448–453.

    CAS  Google Scholar 

  • Jones, G. and Tenenhouse, H.S. (1987) Plasma 24,25-dihydroxyvitamin D3levels not elevated in hypophosphatemic mice. 9th Meeting of the ASBMR, Indianapolis, June 1987. Journal of Bone and Mineral Research, 2, abstract 465.

    Google Scholar 

  • Jones, G., Byrnes, B., Palma, F. et al. (1980) Displacement potency of vitamin D2 analogs in competitive protein binding assays for 25-hydroxyvitamin D3, 24,25-dihydroxyvitamin D3, and 1,25-dihydroxyvitamin D3. Journal of Clinical Endocrinology and Metabolism, 50, 773–775.

    Article  CAS  Google Scholar 

  • Jones, G., Seamark, D.A., Trafford, D.J.H. et al. (1985) Vitamin D: cholecalciferol, ergocalciferol and hydroxylated metabolites. In Modern Chromatographic Analysis of Vitamins (eds A.P. De Leenheer, W.E. Lambert and M.G.M. De Ruyter ). Marcel Dekker Inc., New York, pp. 73–128.

    Google Scholar 

  • Jones, G., Edwards, N., Vriezen, D. et al. (1988) Isolation and identification of seven metabolites of 25-hydroxydihydrotachysterol formed in the isolated perfused rat kidney: a model for the study of side chain metabolism of vitamin D. Biochemistry, 27, 7070–7079.

    Article  CAS  Google Scholar 

  • Jones, G., Trafford, D.J.H., Makin, H.L.J. et al. (1992) Vitamin D: cholecalciferol, ergocalciferol and hydroxylated metabolites. In Modern Chromatographic Analysis of Vitamins, 2nd edn (eds A.P. De Leenheer, W.E. Lambert and H.J. Nelis ). Marcel Dekker, New York, pp. 73–151.

    Google Scholar 

  • Jongen, N.J.M., Van Kinkel, F.C., van der Vijgh, W.J.F. et al. (1984) An international comparison of vitamin D metabolite measurements. Clinical Chemistry, 30, 399–403.

    CAS  Google Scholar 

  • Jordan, P.H., Read, G. and Hargreaves, T. (1991) Determination of 25-hydroxyvitamin-D3in human serum by fluorescence labelling and high-performance liquid chromatography. The Analyst, 116, 1347–1351.

    Article  CAS  Google Scholar 

  • Justova, V. and Starka, L. (1981) Separation of functional hydroxymetabolites of vitamin D3by thin layer chromatography. Journal of Chromatography, 209, 337–340.

    Article  CAS  Google Scholar 

  • Justova, V., Wildtova, Z. and Pacovsky, V. (1984) Simplified competitive protein binding assay for 1,25-dihydroxy-cholecalciferol, the most active metabolite of vitamin D. Endocrinologica Experimentalis, 18, 241–247.

    CAS  Google Scholar 

  • Kao, P.C. and Heser, D.W. (1984) Simultaneous determination of 25-hydroxy and 1,25dihydroxyvitamin D from a single sample by dual cartridge extraction. Clinica Chimica Acta, 30, 56–61.

    CAS  Google Scholar 

  • Kirk, D.N., Toms, H.C., Douglas, C. et al. (1990) A survey of the high-field 1H NMR spectra of the steroid hormones, their hydroxylated derivatives, and related compounds. Journal of the Chemical Society, Perkin Transactions 2, 1567–1594.

    Google Scholar 

  • Kobayashi, N., Ueda, K., Hisada, A. et al. (1991) Development of enzyme immunoassay for plasma 25-hydroxyvitamin-D3. Journal of PharmacobioDynamics, 14, S89.

    Google Scholar 

  • Kobayashi, N., Asano, T., Kitahori, J. et al. (1992) Production and specificity of anti-22oxacalcitriol antisera. Chemical and Pharmaceutical Bulletin, 40, 1520–1522.

    Article  CAS  Google Scholar 

  • Kobayashi, N. Ueda, K., Tsutsumi, M. et al. (1993a) Enzyme immunoassay for plasma 25hydroxyvitamin D3 employing immunoaffinity chromatography as a pretreatment method. Journal of Steroid Biochemistry and Molecular Biology,44, 93–100.

    Google Scholar 

  • Kobayashi, N., Hisada, A. and Shimada, K. (1993b) Syntheses of novel 25-hydroxy-vitamin-D3haptens having chemical bridges at the C-1 lalpha-position. Journal of the Chemical Society, Perkin Transactions 1, 31–37.

    Article  Google Scholar 

  • Kobayashi, N., Takama, A., Shiomura, K. et al. (1994a) Production of a group-specific antibody to la,25-dihydroxyvitamin D and its derivatives having 1a,3ß-dihydroxylated A-ring structure. Steroids, 59, 404–411.

    Article  CAS  Google Scholar 

  • Kobayashi, N., Hisada, A. and Shimada, K. (1994b) Specificity of the polyclonal antibodies raised against a novel 25-hydroxyvitamin D3-bovine serum albumin conjugate linked through the C-1 la position. Journal of Steroid Biochemistry and Molecular Biology, 48, 567–572.

    Article  CAS  Google Scholar 

  • Kobayashi, N., Kitahori, J., Mano, H. et al. (1994c) Syntheses of 11a-(3-carboxypropanoyloxy)la,25-dihydroxyvitamin D3and 11a-(4-carboxybutanoyloxy)-1a,25-dihydroxyvitamin D3: novel haptenic derivatives for production of highly specific antibodies to la,25-dihydroxyvitamin D3. Journal of the Chemical Society, Perkin Transactions 1, 1809–1815.

    Article  Google Scholar 

  • Koizumi, N., Fujimoto, Y., Takeshita, T. et al. (1979) Carbon-13 nuclear magnetic resonance of 24-substituted steroids. Chemical and Pharmaceutical Bulletin, 27, 38–42.

    Article  CAS  Google Scholar 

  • Komuro, S., Nakatsuka, I., Yoshitake, A. et al. (1994) Quantitative determination of F-61,25(OH)2vitamin D3in human serum by gas chromatography mass spectrometry with high-resolution selected ion monitoring. Biological Mass Spectrometry, 23, 33–38.

    Article  CAS  Google Scholar 

  • Koszewski, N.J., Reinhardt, T.A., Beitz, D.C. et al. (1987) Use of Fourier transform ‘H NMR in the identification of vitamin D2 metabolites. Analytical Biochemistry, 162, 446–452.

    Article  CAS  Google Scholar 

  • Koszewski, N.J., Reinhardt, T.A., Napoli, J.L. et al. (1988) 24,26-Dihydroxyvitamin D2: A unique physiological metabolite of vitamin D2. Biochemistry, 27, 5785–5790.

    Google Scholar 

  • Kotovych, G., Aarts, G.H.M. and Bock, K. (1980) A proton magnetic resonance nuclear Overhauser enhancement study. Application to vitamin D derivatives D2 and D3. Canadian Journal of Chemistry, 58, 1206–1210.

    Article  CAS  Google Scholar 

  • Koyama, H., Prahl, J.M., Uhland, A. et al. (1992) A new, highly sensitive assay for 1,25dihydroxyvitamin-D not requiring high-performance liquid chromatography—application of monoclonal antibody against vitamin-D receptor to radioreceptor assay. Analytical Biochemistry, 205, 213–219.

    Article  CAS  Google Scholar 

  • La Mar, G.N. and Budd, D.L. (1974) Elucidation of the solution conformation of the A ring in vitamin D using proton coupling constants and a shift reagent. Journal of the American Chemical Society, 96, 7317–7324.

    Article  Google Scholar 

  • Lambert, P.W., DeOreo, P.B., Hollis, B.W. et al. (1981) Concurrent measurement of plasma levels of vitamin D3and five of its metabolites in normal humans, chronic renal failure patients, and anephric subjects. Journal of Laboratory and Clinical Medicine, 98, 536–548.

    CAS  Google Scholar 

  • LeVan, L.W., Knutson, J.C., Valliere, C.R. et al. (1994) A sensitive and specific assay for calcipotriol (MC 903) in serum of plasma. Proceedings of the 9th Workshop on Vitamin D, Orlando, Florida, p. 204.

    Google Scholar 

  • Levin, A.A., Sturzenbecker, L.J., Kazmer, S. et al. (1992) 9-cis-Retinoic acid stereoisomer binds and activates the nuclear receptor RXRa. Nature, 355, 359–361.

    Google Scholar 

  • Liao, J., Ozono, K., Sone, T. et al. (1990) Vitamin D receptor interaction with specific DNA requires a nuclear protein and la,25-dihydroxyvitamin D3. Proceedings of the National Academy of Sciences of the USA, 87, 9751–9755.

    Article  CAS  Google Scholar 

  • Lin, L., Meltzer, N.M., Honigberg, I.L. et al. (1993) Normal phase HPLC with EC detection1,25-dihydroxy vitamin-D(3) and 25-hydroxy-16-ene-23-yne vitamin-D(3. Journal of Liquid Chromatography, 16, 3093–3100.

    Article  CAS  Google Scholar 

  • Lindback, B., Berlin, T. and Bjorkhem, I. (1987) Three commercial kits and one liquid-chromatographic method evaluated for determining 25—hydroxyvitamin D3in serum. Clinical Chemistry, 33, 1226–1227.

    CAS  Google Scholar 

  • Litwiller, R.D., Mattox, V.R., Jardine, I. et al. (1982) Evidence for a monoglucuronide of 1,25dihydroxyvitamin D3in rat bile. Journal of Biological Chemistry, 257, 7491–7494.

    CAS  Google Scholar 

  • MacDonald, P.N., Haussier, C.A., Terpening, C.M. et al. (1991) Baculovirus-mediated expression of the vitamin D receptor. Journal of Biological Chemistry, 266, 18808–18813.

    CAS  Google Scholar 

  • Makin, G., Lohnes, D., Byford, V. et al. (1989) Target cell metabolism of 1,25-dihydroxyvitaminD3to calcitroic acid—Evidence for a pathway in kidney and bone involving 24-oxidation. Biochemical Journal, 262, 173–180.

    CAS  Google Scholar 

  • Makin, H.L.J. and Trafford, D.J.H. (1984) Measurement of vitamin D and its metabolites by gas chromatography—mass spectrometry. In Vitamin D, Basic and Clinical Aspects (ed. R. Kumar ). Martinus Nijhoff, Boston, pp. 497–521.

    Google Scholar 

  • Makin, H.L.J., Coldwell, R.D. and Trafford, D.J.H. (1991) Assays for vitamin D and its metabolites: Do we need to improve accuracy and precision? In Vitamin D. Gene Regulation, Structure—Function Analysis and Clinical Application (eds A.W. Norman, R. Bouillon and M. Thomasset ). Walter de Gruyter, Berlin, pp. 635–643.

    Google Scholar 

  • Manolagas, S.C. (1986) Cytoreceptor assay for 1,25-dihydroxyvitamin D. Methods in Enzymology, 123, 190–199.

    Article  CAS  Google Scholar 

  • Marks, M.S., Hallenbeck, P.L., Nagata, T. et al. (1992) H-2RIIBP (RXRß) heterodimerizes with other nuclear hormone receptors and provides a combinatorial mechanism of gene regulation. European Molecular Biology Organisation Journal, 11, 1419–1435.

    CAS  Google Scholar 

  • Mason, R.S., Lissner, D., Reek, C. et al. (1979) Assay of 1,25- and 24,25-dihydroxycholecalciferol in human serum—some technical considerations. In Vitamin D: Basic Research and Its Clinical Application (eds A.W. Norman, K. Schaefer, D.V. Herrath, H.-G. Grigoleit, J.W. Coburn, H.F. DeLuca, E.B. Mawer and T. Suda ). Walter de Gruyter, Berlin, pp. 243–250.

    Google Scholar 

  • Mason, R.S., Lissner, D., Grunstein, S. et al. (1980) A simplified assay for dihydroxylated vitamin D metabolites in human serum: Application of hyper-and hypo-vitaminosis D. Clinical Chemistry, 26, 444–450.

    CAS  Google Scholar 

  • Masuda, S., Okano, T., Matsuoka, S. et al. (1991) A sensitive method for the determination of 1,25-dihydroxyvitamin-D in plasma by using calf thymus receptor. Journal of PharmacobioDynamics, 14, S88.

    Google Scholar 

  • Masuda, S., Okano, T., Matsuoka, S. et al. (1993) Gross and separative determination of 1alpha,25-dihydroxyvitamin-D2 and 1-alpha,25-dihydroxyvitamin-D3in plasma using calf thymus receptor. Journal of Nutritional Science and Vitaminology, 39, 101–114.

    Article  CAS  Google Scholar 

  • Mawer, E.B. (1980) Clinical implications of measurements of circulating vitamin D metabolites. Clinical Endocrinology and Metabolism, 9, 63–79.

    Article  CAS  Google Scholar 

  • Mawer, E.B., Berry, J.L., Cundall, J.P. et al. (1990) A sensitive radioimmunoassay using a monoclonal antibody that is equipotent for ercalcitriol and calcitriol (1,25-dihydroxyvitaminDz and vitamin-D3). Clinica Chimica Acta, 19, 199–209.

    Article  Google Scholar 

  • Mayer, E. and Schmidt-Gayk, H. (1984) Interlaboratory comparison of 25-hydroxyvitamin D determination. Clinical Chemistry, 30, 1199–1204.

    CAS  Google Scholar 

  • McGraw, C.A. and Hug, G. (1990) Simultaneous measurement of 25-hydroxyvitamin-D, 24,25dihydroxyvitamin-D, and 1,25-dihydroxyvitamin-D without use of HPLC. Medical Laboratory Science, 47, 17–25.

    CAS  Google Scholar 

  • Miyaura, C., Abe, E., Kuribayashi, T. et al. (1981) la,25-Dihydroxyvitamin D3induced differentiation of human myeloid leukemia cells. Biochemical and Biophysical Research Communications, 102, 937–943.

    Google Scholar 

  • Moody, J.P., Humphries, C.A., Allan, S.M. et al. (1990) Determination of 7-dehydrocholesterol in human skin by high-performance liquid chromatography. Journal of Chromatography Biomedical Applications, 530, 19–27.

    Article  CAS  Google Scholar 

  • Nicholson, G.C., Kent, J.C., Gutteridge, D.H. et al. (1985) Estimation of 1,25-dihydroxyvitamin D by cytoreceptor and competitive protein binding assays without high pressure liquid chromatography. Clinical Endocrinology, 22, 597–609.

    Article  CAS  Google Scholar 

  • Oftebro, H., Falch, J.A., Holmberg, I. et al. (1988) Validation of a radioreceptor assay for 1,25dihydroxyvitamin D using selected ion monitoring GC—MS. Clinica Chimica Acta, 176, 157–168.

    Google Scholar 

  • Okano, T., Mizuno, K., Matsuyama, N. et al. (1979) Gas—liquid chromatography—mass spectrometric identification of previtamin D3and vitamin D3in the skin of vitamin D-deficient rats irradiated with ultraviolet light. Receuil des Travaux des Chimiques des Pays-Bas, 98, 253–257.

    Article  CAS  Google Scholar 

  • Parviainen, M.T., Savolainen, K.E., Korhonen, P.H. et al. (1981) An improved method for routine determination of vitamin D and its hydroxylated metabolites in serum from children and adults. Clinica Chimica Acta, 114, 233–247.

    Article  CAS  Google Scholar 

  • Pedersen, J.I., Shobaki, H.H., Holmberg, I. et al. (1983) 25-Hydroxyvitamin D3–24-hydroxylase in rat kidney mitochondria. Journal of Biological Chemistry, 258, 742–746.

    Google Scholar 

  • Pelc, B. and Marshall, D.H. (1978) Thermal transformation of cholecalciferol between 100–170°C. Steroids, 31, 23–29.

    Article  CAS  Google Scholar 

  • Pike, J.W. (1991) Vitamin D3receptors: structure and function in transcription. Annual Review of Nutrition, 11, 189–216.

    Article  CAS  Google Scholar 

  • Poon, P.M.K., Mak, Y.T. and Pang, C.P. (1993) Gas chromatographic mass fragmentographic determination of serum lalpha,25-dihydroxyvitamin D3. Clinical Biochemistry, 26, 461–469.

    Article  CAS  Google Scholar 

  • Porteous, C., Coldwell, R.D., Trafford, D.J.H. et al. (1987) Recent developments in the measurement of vitamin D and its metabolites in human body fluids. Journal of Steroid Biochemistry, 28, 785–801.

    Article  CAS  Google Scholar 

  • Qaw, F., Calverley, M.J., Schroeder, N.J. et al. (1993) In vivo metabolism of the vitamin D analog, dihydrotachysterol: Evidence for formation of la,25- and lß,25-dihydroxy-dihydrotachysterol metabolites and studies of their biological activity. Journal of Biological Chemistry, 268, 282–292.

    CAS  Google Scholar 

  • Reinhardt, T.A. and Hollis, B.W. (1986) A 1,25-dihydroxyvitamin D assay not requiring high-performance liquid chromatography. Methods in Enzymology, 123, 176–185.

    Article  CAS  Google Scholar 

  • Reinhardt, T.A., Horst, R.L., Littledike, E.T. et al. (1982) 1,25-Dihydroxyvitamin D3receptor in bovine thymus gland. Biochemical and Biophysical Research Communications, 106, 1012–1018.

    Google Scholar 

  • Reinhardt, T.A., Horst, R.L., Orf, J. et al. (1984) A microassay for 1,25-dihydroxyvitamin D not requiring high-performance liquid chromatography: Application of clinical studies. Journal of Clinical Endocrinology and Metabolism, 58, 91–98.

    Article  CAS  Google Scholar 

  • Rhodes, C.J., Claridge, P.A., Trafford, D.J.H. et al. (1983) An evaluation of the use of Sep-Pak C18 cartridges for the extraction of vitamin D3and some of its metabolites from plasma and urine. Journal of Steroid Biochemistry, 19, 1349–1354.

    Article  CAS  Google Scholar 

  • Sato, T., Kawakami, Y., Nagai, Y. et al. (1990) Studies on lalpha-hydroxy derivatives of vitamin D3. Part III. Effect of solvents on the thermal isomerization of lalpha-hydroxyprevitamin D3diacetate to lalpha-hydroxyvitamin D3diacetate. Journal of Nutritional Science and Vitaminology, 36, 299–309.

    Article  Google Scholar 

  • Schroeder, N.J., Trafford, D.J.H., Cunningham, J. et al. (1993) In vivo dihydrotachysterolz metabolism in normal man: formation of la,25- and tß,25-dihydroxylated metabolites and effect on endogenous parathyroid hormone and la,25-dihydroxyvitamin D concentration. Abstract for 15th Annual Meeting of the ASBMR, Tampa, Florida, USA. Journal of Bone and Mineral Research, 8, S217.

    Google Scholar 

  • Schroeder, N.J., Trafford, D.J.H., Cunningham, J. et al. (1994) In vivo dihydrotachysterolz metabolism in normal man: formation of la,25- and lß,25-dihydroxylated metabolites and effect on endogenous parathyroid hormone and la,25-dihydroxyvitamin D concentration. Journal of Clinical Endocrinology and Metabolism, 78, 1481–1487.

    Article  CAS  Google Scholar 

  • Seamark, D.A., Trafford, D.J.H. and Makin, H.L.J. (1980a) The estimation of vitamin D and some metabolites in human plasma by mass fragmentography. Clinica Chimica Acta, 106, 51–62.

    Article  CAS  Google Scholar 

  • Seamark, D.A., Trafford, D.J.H. and Makin, H.L.J. (1980b) A new procedure for the formation of isotachysterol derivatives of subnanomole quantities of ergocalciferol, cholecalciferol and its metabolites prior to gas liquid chromatography. Journal of Steroid Biochemistry, 13, 1057–1063.

    Article  CAS  Google Scholar 

  • Seamark, D.A., Trafford, D.J.H., Hiscocks, P.G. et al. (1980c) High-performance liquid chromatography of vitamin D: enhanced ultraviolet absorbance by prior conversion to isotachysterol derivatives. Journal of Chromatography, 197, 271–273.

    Article  CAS  Google Scholar 

  • Seamark, D.A., Trafford, D.J.H. and Makin, H.L.J. (1981) The estimation of vitamin D and its metabolites in human plasma. Journal of Steroid Biochemistry, 14, 111–123.

    Article  CAS  Google Scholar 

  • Shackleton, C.H.L. and Whitney, J.O. (1980) Use of Sep-Pak cartridges for urinary steroid extraction: evaluation of the method for use prior to gas chromatographic analysis. Clinica Chimica Acta, 107, 231–243.

    Article  CAS  Google Scholar 

  • Sheves, M., Berman, E., Mazur, Y. et al. (1979) Use of 2H NMR and mass spectrometry for the investigation of the vitamin D3previtamin D3equilibrium. Journal of the American Chemical Society, 101, 1882–1883.

    Article  CAS  Google Scholar 

  • Shimada, K. and Mizuguchi, T. (1992) Sensitive and stable Cookson-type reagent for derivatization of conjugated dienes for high-performance liquid chromatography with fluorescence detection. Journal of Chromatography, 606, 133–135.

    Article  CAS  Google Scholar 

  • Shimada, K., and Mizuguchi, T. (1991) Cookson-type reagents—highly sensitive derivatization reagents for conjugated dienes in high-performance liquid chromatography. The Analyst, 116, 1393–1397.

    Article  CAS  Google Scholar 

  • Shimada, K., Mitamura, K., Kaji, H. et al. (1994) Retention behaviour of conjugated metabolites of vitamin D and related compounds in high-performance liquid chromatography. Journal of Chromatographic Science, 32, 107–111.

    Article  CAS  Google Scholar 

  • Shimizu, M. and Yamada, S. (1991) New high sensitive, specific, and accurate method for assaying vitamin D metabolites (the first practical fluorometric assay method for vitamin D). In Vitamin D. Gene Regulation, Structure—Function Analysis and Clinical Application (eds A.W. Norman, R. Bouillon and M. Thomasset ). Walter de Gruyter, Berlin, pp. 644–645.

    Google Scholar 

  • Shimizu, M., Kamachi, S., Nishii, Y. et al. (1991) Synthesis of a reagent for fluorescence-labeling of vitamin-D and its use in assaying vitamin-D metabolites. Analytical Biochemistry, 194, 77–81.

    Article  CAS  Google Scholar 

  • Shimizu, M., Gao, Y., Aso, T. et al. (1992) Fluorometric assay of 25-hydroxyvitamin-D(3) and 24R,25-dihydroxyvitamin-Do in plasma. Analytical Biochemistry, 204, 258–264.

    Article  CAS  Google Scholar 

  • Shimizu, M., Yamazaki, T. and Yamada, S. (1993) Fluorescence-labeling reaction of vitamin-D metabolites and analogs with fluorescent 1,2,4-triazoline-3,5-dione (DMEQ-TAD). Bioorganic and Medicinal Chemistry Letters, 3, 1809–1814.

    Article  CAS  Google Scholar 

  • Soerensen, H., Binderup, L., Calverley, M.J. et al. (1990) In vitro metabolism of calcipotriol (MC 903), a vitamin D analogue. Biochemical Pharmacology, 39, 391–393.

    CAS  Google Scholar 

  • Suda, T., DeLuca, H.F., Schnoes, H.K. et al. (1969) The isolation and identification of 25hydroxyergocalciferol. Biochemistry, 8, 3515–3520.

    Article  CAS  Google Scholar 

  • Szejtli, J., Bolla-Pusztai, E., Szabo, P. et al. (1980) Enhancement of stability and biological effect of cholecalciferol by ß-cyclodextrin complexation. Pharmazie, 35, 779–787.

    CAS  Google Scholar 

  • Takamura, K., Hoshino, H., Sugahara, T. et al. (1991a) Determination of vitamin-D2 in shiitake mushroom (Lentinus edodes) by high-performance liquid chromatography. Journal of Chromatography, 545, 201–204.

    Article  CAS  Google Scholar 

  • Takamura, K., Hoshino, H., Harima, N. et al. (1991b) Identification of vitamin-D2 by thermospray-interface mass spectrometry. Journal of Chromatography, 543, 241–243.

    Article  CAS  Google Scholar 

  • Tanabe, M., Harada, M., Odawara, F. et al. (1991) Synthesis and assignment of novel (1–125)-labeled 1-alpha,25-dihydroxyvitamin D3derivatives. Journal of Nutritional Science and Vitaminology, 37, 39–147.

    Article  Google Scholar 

  • Tanner, J.T., Barnett, S.A. and Mountford, M.K. (1993) Analysis of milk-based infant formula. Phase IV. Iodide, linoleic acid, and vitamin-D and vitamin-K. United States Food and Drug Administration Infant Formula Council Collaborative Study. Journal of Aoac International, 76, 1042–1056.

    CAS  Google Scholar 

  • Teegarden, D., Meredith, S.C. and Sitrin, M.D. (1991) Determination of the affinity of vitamin-D metabolites to serum vitamin-D binding protein using assay employing lipid-coated polystyrene beads. Analytical Biochemistry, 199, 293–399.

    Article  CAS  Google Scholar 

  • Thierry-Palmer, M. and Gray, T.K. (1983) Separation of the hydroxylated metabolites of vitamin D3by high-performance thin-layer chromatography. Journal of Chromatography, 262, 460–463.

    Article  CAS  Google Scholar 

  • Thompson, J.N., Hatina, G., Maxwell, W.B. et al. (1982) High-performance liquid chroma-tographic determination of vitamin D in fortified milks, margarine, and infant formulas. Journal of the Association of Official Analytical Chemists, 65, 624–631.

    CAS  Google Scholar 

  • Trafford, D.J.H., Seamark, D.A., Turnbull, H. et al. (1981) High-performance liquid chromatography of 25-hydroxyvitamin D2 and 25-hydroxyvitamin D3in human plasma: use of isotachysterols and a comparison with gas chromatography—mass spectrometry. Journal of Chromatography, 226, 351–360.

    Article  CAS  Google Scholar 

  • Trafford, D.J.H., Coldwell, R.D. and Makin, H.L.J. (1991). Gas chromatography—mass spectro-metry in the investigation of on-column dehydration of steroid hormones during gas—liquid chromatography. Journal of Pharmaceutical and Biomedical Analysis, 9, 1095–1105.

    Article  CAS  Google Scholar 

  • Tsukida, K., Akutsu, K. and Saiki, K. (1975) Carbon-13 nuclear magnetic resonance spectra of vitamins D and related compounds. Journal of Nutritional Science and Vitaminology, 21, 411–420.

    Article  CAS  Google Scholar 

  • Turnbull, H., Trafford, D.J.H. and Makin, H.L.J. (1982) A rapid and simple method for the measurement of plasma 25-hydroxyvitamin D2 and 25-hydroxyvitamin D3using Sep-Pak CI a cartridges and a single high-performance liquid chromatographic step. Clinica Chimica Acta, 120, 65–76.

    Article  CAS  Google Scholar 

  • Umesono, K., Murakami, K.K., Thompson, C.C. et al. (1991) Direct repeats as selective response elements for the thyroid hormone, retinoic acid and vitamin D3receptors. Cell, 65, 1255–1266.

    Article  CAS  Google Scholar 

  • Valliere, C.R., Knutson, J.C., Levan, L.W. et al. (1994) Microcolumn HPLC assay for 1,25(OH)2D3in serum compared to a competitive radioreceptor assay. Proceedings of the 9th Workshop on Vitamin D, Orlando, Florida, p. 203.

    Google Scholar 

  • vanHoof, H.J.C., Swinkels, L.M.J.W., vanStevenhagen, J.J. et al. (1993) Advantages of paper chromatography as a preparative step in the assay of 1,25-dihydroxyvitamin D. Journal of Chromatography, 621, 33–39.

    Article  CAS  Google Scholar 

  • Vicchio, D., Yergey, A. and O’Brien, K. (1993) Quantification and kinetics of 25-hydroxyvitaminD3by isotope dilution liquid chromatography/thermospray mass spectrometry. Biological Mass Spectrometry, 22, 53–58.

    Article  CAS  Google Scholar 

  • Vreeken, R.J., Honing, M., Vanbaar, B.L.M. et al. (1993) On-line post-column Diels—Alder derivatization for the determination of vitamin-D(3) and its metabolites by liquid chromatography/thermospray mass spectrometry. Biological Mass Spectrometry, 22, 621–632.

    Article  CAS  Google Scholar 

  • Walters, M.R. (1992) Newly identified actions of the vitamin-D endocrine system. Endocrine Reviews, 13, 719–764.

    CAS  Google Scholar 

  • Watson, D., Setchell, K.D.R. and Ross, R. (1991) Analysis of vitamin-D and its metabolites using thermospray liquid chromatography/mass spectrometry. Biomedical Chromatography, 5, 153–160.

    Article  CAS  Google Scholar 

  • Wheeler, M.J. (1993) The Immunoassay Kit Directory, vol. 2, part 2, Steroid and Thyroid Hormones. Kluwer Academic, Lancaster.

    Google Scholar 

  • Wildermuth, S., Dittrich, K., Schmidt-Gayk, H. et al. (1993) Scintillation proximity assay for calcitriol in serum without high pressure liquid chromatography. Clinica Chimica Acta, 220, 61–70.

    Article  CAS  Google Scholar 

  • Wilson, S.R., Tulchinsky, M.L. and Wu, Y.H. (1993) Electrospray ionization mass spectrometry of vitamin-D derivatives. Bioorganic and Medicinal Chemistry Letters, 3, 1805–1808.

    Article  CAS  Google Scholar 

  • Wing, R.M., Okamura, W.H., Rego, A. et al. (1975) Studies on vitamin D and its analogs. VII. Solution conformations of vitamin D3and 1a,25-dihydroxyvitamin D3by high-resolution proton magnetic resonance spectroscopy. Journal of the American Chemical Society, 97, 4980–4985.

    Article  CAS  Google Scholar 

  • Yamada, S., Yamamoto, Y., Takayama, H. et al. (1987) Isolation, identification, and chemical synthesis of 8x,25-dihydroxy-9,10-seco-4,6,10(19)-cholestatrien-3-one. Journal of Biological Chemistry, 262, 12939–12944.

    CAS  Google Scholar 

  • Yeung, B., Reddy, G.S. and Vouros, P. (1992) Characterization of vitamin D metabolites by static and dynamic fast atom bombardment tandem mass spectrometry. Abstracts, for the 40th American Society for Mass Spectrometry Conference on Mass Spectrometry and Allied Topics, Washington, DC, pp. 1089–1090.

    Google Scholar 

  • Yeung, B., Vouros, P. and Reddy, G.S. (1993) Characterization of vitamin-D(3) metabolites using continuous-flow fast atom bombardment tandem mass spectrometry and high-performance liquid chromatography. Journal of Chromatography, 645, 115–123.

    Article  CAS  Google Scholar 

  • Yeung, B., Vouros, P., Siu-Caldera, M.L. et al. (1994) Study of the metabolism of 1,25-dihydroxy-16-ene-vitamin D3in rat kidney using capillary HPLC—electrospray tandem mass spectrometry. Proceedings of the 9th Workshop on Vitamin D, Orlando, Florida, p. 203.

    Google Scholar 

  • Zagalak, B., Neuheiser, F., Zagalak, M.J. et al. (1983) Application of mass fragmentography in the study of biosynthesis and excretion of vitamin D in humans. In Chromatography and Mass Spectrometry in Biomedical Sciences, vol. 2 (ed. A. Frigerio ). Elsevier, Amsterdam, pp. 347–359.

    Google Scholar 

  • Zamarreno, M.M.D., Perez, A.S., Perez, C.G. et al. (1992) High-performance liquid chromatography with electrochemical detection for the simultaneous determination of vitamin-A, vitamin-D3 and vitamin-E in milk. Journal of Chromatography, 623, 69–74.

    Article  Google Scholar 

  • Zamarreno, M.M.D., Perez, A.S., Iglesias, M.C.M. et al. (1993) Determination of vitamin-D(3) and 25-hydroxyvitamin-D(3) using liquid chromatography with amperometric detection. Analytical Letters, 26, 2565–2573.

    Article  Google Scholar 

Download references

Authors
  1. H. L. J. Makin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. G. Jones
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. J. Calverley
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Department of Chemical Pathology, The London Hospital Medical College, Turner Street, E1 2AD, London, UK

    H. L. J. Makin  & D. B. Gower  & 

  2. Department of Chemistry, Queen Mary and Westfield College, University of London, Mile End Road, London E1, UK

    D. N. Kirk

Rights and permissions

Reprints and permissions

Copyright information

© 1995 Springer Science+Business Media Dordrecht

About this chapter

Cite this chapter

Makin, H.L.J., Jones, G., Calverley, M.J. (1995). Analysis of vitamin D, its metabolites and structural analogues. In: Makin, H.L.J., Gower, D.B., Kirk, D.N. (eds) Steroid Analysis. Springer, Dordrecht. https://doi.org/10.1007/978-94-017-3078-5_10

Download citation

  • DOI: https://doi.org/10.1007/978-94-017-3078-5_10

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-94-017-3080-8

  • Online ISBN: 978-94-017-3078-5

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation