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Vitamin D


DATA No : VVD0300 INFORMANT : Sachiko Yamada

NAME : (5Z,7E)-(3S,24R)-9,10-seco-5,7,10(19)-cholestatriene-3,24,25-triol

COMMON NAME: (24R)-24,25-dihydroxyvitamin D3 / (24R)-24,25-dihydroxycholecalciferol
SYMBOL: 24R,25-(OH)2D3
FORMULA: C27H44O3 MOL.WT (average) : 416.636


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BIOLOGICAL ACTIVITY
The increase in serum calcium concentration and intestinal calcium transport in response to the isomers of 24,25-(OH)2D3.: Table (Ref. 0089)
Serum inorganic phosphorus and epiphyseal plate calcification response to the 24,25-(OH)2D3: Table (Ref. 0089)
HL-60 human promyelocytes differentiation : ED50 in nitro blue tetrazplium reduction, phagocytic activity, and nonspecific acid esterase activity are 1.1 times 10-6 M, 9.5 times 10-7 M and 9.5 times 10-7 M, respectively, when 1,25-(OH)2D3 shows the respective ED50 values of 1.0 times 10-8 M, 1.0 times 10-8 M and 1.1 times 10-8 M, respectively. (Ref. 0228)
PHYSICAL AND CHEMICAL PROPERTIES
MELTING POINT:

BOILING POINT:

REFRACTIVE INDEX:

OPTICAL ROTATION:

DENSITY:

SOLUBILITY:
SPECTRAL DATA
UV SPECTRA:lmax (nm) 265 (Ref. 0088/0090)

IR SPECTRA:

NMR SPECTRA:1H-NMR (d, CDCl3) 0.55 (3H, s), 0.93 (3H, d, J = 4 Hz) , 1.17 (3H, s), 1.22 (3H, s), 3.33 (1H, m), 3.95 (1H, m), 4.85 (1H, bs), 5.07 (1H, bs), 6.08 (1H, d, J = 11 Hz), 6.25 (1H, d, J = 11 Hz) (Ref. 0090)

MASS SPECTRA:m/z 416 (M+), 271, 253, 136, 118; spectrum (Ref. 0088)
m/z 416, 136, 118 (Ref. 0090)

OTHER SPECTRA:
CHROMATOGRAM DATA
HPLC: The stereochemistry at C(24) of the natural 24,25-(OH)2D3 was determined to be R by co-chromatography on HPLC with synthetic (24R)- and (24S)- 24,25-(OH)2D3 in a form of tris-trimethylsilyl ether.(Ref. 0089) .
SOURCE
Isolation and identification: from chicken kidney homogenates incubated with 24-OHD3. (Ref. 0088)
CHEMICAL SYNTHESIS
Stereoselective synthesis from dinor-5,7-choladien-3b-ol and a chiral side-chain fragment. (Ref. 0090)
Synthesis of epimeric mixture of 24x,25-(OH)2D3 from 3b-acetoxy-27-nor-5-cholesten-25-one. (Ref. 0091)
The stereochemistry at C(24) of the natural 24,25-(OH)2D3 was determined to be R by Co-chromatography on HPLC with synthetic (24R)- and (24S)-24,25-(OH)2D3. (Ref. 0089)
METABOLISM
In vitro, 24R,25-(OH)2D3 is oxidized at C(24) to yield 25-hydroxy-24-oxovitamin D3 (Ref. 0096) , then hydroxylated at C(23) to give 23S,25-dihydroxy-24-oxovitamin D3 (Ref. 0102) , and cleaved at 23,24-bond to afford 23-hydroxy-24,25,26,27-tetranorvitamin D3 (Ref. 0105) . All these metabolic transformations were demonstrated to be catalyzed by vitamin D3 24-hydroxylase (CYP24)(Ref. 0266) . In vivo, 24R,25-(OH)2D3 has long half-life (17 days in dog) and metabolized similarly as found in the in vitro studies up to 23S,25-(OH)2-24-oxo-D3. However in vivo 23S,25-(OH)2-24-oxo-D3 is conjugated as it is produced in a form of 23b-glucuronide and excreted to bile (Ref. 0106) .
GENETIC INFORMATION
Cloning of the enzyme to produce 24R,25-dihydroxyvitamin D3 from 25-hydroxyvitamin D3, vitamin D-24-hydroxylase (Ref. 0031/0033)
NOTE

REFERENCES
[0031]
AUTHOR:Shinki, T., Shimada, H., Wakino, S., Anazawa, H., Hayashi, M., Saruta, T., DeLuca, H. F., and Suda, T.
TITLE:Cloning and expression of rat 25-hydroxyvitamin D3-1alpha-hydroxylase cDNA PubMed ID:9371776
JOURNAL:Proc Natl Acad Sci U S A.
VOL:94 PAGE : 12920-12925 (1997)
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[0033]
AUTHOR:Chen, K. S., Prahl, J. M., and DeLuca, H. F.
TITLE:Isolation and expression of human 1,25-dihydroxyvitamin D3 24-hydroxylase cDNA PubMed ID:8506296
JOURNAL:Proc Natl Acad Sci U S A.
VOL:90 PAGE : 4543-4547 (1993)
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[0088]
AUTHOR:Holick, M. F., Schnoes, H. K., DeLuca, H. F., Gray, R. W., Boyle, I. T., and Suda, T.
TITLE:Isolation and identification of 24,25-dihydroxycholecalciferol, a metabolite of vitamin D made in the kidney PubMed ID:4342902
JOURNAL:Biochemistry.
VOL:11 PAGE : 4251-4255 (1972)
[TOP]

[0089]
AUTHOR:Tanaka, Y., DeLuca, H. F., Ikekawa, N., Morisaki, M., and Koizumi, N.
TITLE:Determination of stereochemical configuration of the 24-hydroxyl group of 24,25-dihydroxyvitamin D3 and its biological importance PubMed ID:1190783
JOURNAL:Arch Biochem Biophys.
VOL:170 PAGE : 620-626 (1975)
[TOP]

[0090]
AUTHOR:Takayama, H.; Ohmori, M.; Yamada, S.
TITLE:Facile, Stereoselective Synthesis of (24R)-24,25-Dihydroxyvitamin D3 Using D-Glyceric Acid as A Chiral Synthon.
JOURNAL:Tetrahedron Lett.
VOL:21 PAGE : 5027 -5028 (1980)
[TOP]

[0091]
AUTHOR:Lam, H. Y., Schnoes, H. K., DeLuca, H. F., and Chen, T. C.
TITLE:24,25-Dihydroxyvitamin D3. Synthesis and biological activity PubMed ID:4761971
JOURNAL:Biochemistry.
VOL:12 PAGE : 4851-4855 (1973)
[TOP]

[0096]
AUTHOR:Takasaki, Y., Suda, T., Yamada, S., Takayama, H., and Nishii, Y.
TITLE:Isolation, identification, and biological activity of 25-hydroxy-24-oxovitamin D3: a new metabolite of vitamin D3 generated by in vitro incubations with kidney homogenates PubMed ID:7225351
JOURNAL:Biochemistry.
VOL:20 PAGE : 1681-1686 (1981)
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[0102]
AUTHOR:Yamada, S., Ohmori, M., Takayama, H., Takasaki, Y., and Suda, T.
TITLE:Isolation and identification of 1 alpha- and 23-hydroxylated metabolites of 25-hydroxy-24-oxovitamin D3 from in vitro incubates of chick kidney homogenates PubMed ID:6848514
JOURNAL:J Biol Chem.
VOL:258 PAGE : 457-463 (1983)
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[0105]
AUTHOR:Jones, G., Kano, K., Yamada, S., Furusawa, T., Takayama, H., and Suda, T.
TITLE:Identification of 24,25,26,27-tetranor-23-hydroxyvitamin D3 as a product of the renal metabolism of 24,25-dihydroxyvitamin D3 PubMed ID:6332645
JOURNAL:Biochemistry.
VOL:23 PAGE : 3749-3754 (1984)
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[0106]
AUTHOR:Shimoyamada, A., Tomiyama, S., Shimizu, M., Yamamoto, K., Kunii, S., and Yamada, S.
TITLE:In vivo metabolism of 24R,25-dihydroxyvitamin D3: structure of its major bile metabolite PubMed ID:9219897
JOURNAL:Biochim Biophys Acta.
VOL:1346 PAGE : 147-157 (1997)
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[0228]
AUTHOR:Ostrem, V. K., Lau, W. F., Lee, S. H., Perlman, K., Prahl, J., Schnoes, H. K., and DeLuca, H. F.
TITLE:Induction of monocytic differentiation of HL-60 cells by 1,25-dihydroxyvitamin D analogs PubMed ID:3477545
JOURNAL:J Biol Chem.
VOL:262 PAGE : 14164-14171 (1987)
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[0266]
AUTHOR:Beckman, M. J., Tadikonda, P., Werner, E., Prahl, J., Yamada, S., and DeLuca, H. F.
TITLE:Human 25-hydroxyvitamin D3-24-hydroxylase, a multicatalytic enzyme PubMed ID:8679605
JOURNAL:Biochemistry.
VOL:35 PAGE : 8465-8472 (1996)
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Last updated June 19, 2007. Copyright © 1989-2007 Japanese Conference on the Biochemistry of Lipids (JCBL). All rights reserved.