Effect of substituting fluorine for hydrogen at C-26 and C-27 on the side chain of 1,25-dihydroxyvitamin D3

1993 ◽  
Vol 45 (11) ◽  
pp. 2331-2336 ◽  
Author(s):  
Masaaki Inaba ◽  
Senji Okuno ◽  
Yoshiki Nishizawa ◽  
Yasuo Imanishi ◽  
Takashi Katsumata ◽  
...  
Keyword(s):  
Side Chain ◽  
Dihydroxyvitamin D3 ◽  
1,25 Dihydroxyvitamin D3

Synthesis of Tetracyclic Analogues of Calcitriol (1,25-Dihydroxyvitamin D3) with Side-Chain-Locked Spatial Orientations at C(20)

2002 ◽  
Vol 85 (10) ◽  
pp. 3251-3261 ◽  
Author(s):  
Carmen Varela ◽  
Kristina Nilsson ◽  
Mercedes Torneiro ◽  
Antonio Mouriño
Keyword(s):  
Side Chain ◽  
Dihydroxyvitamin D3 ◽  
1,25 Dihydroxyvitamin D3

Unique rearrangement of ergocalciferol side chain in vitro: production of a biologically highly active homologue of 1,25-dihydroxyvitamin D3

Biochemistry ◽  
1986 ◽  
Vol 25 (19) ◽  
pp. 5512-5518 ◽  
Author(s):  
Yoko Tanaka ◽  
Rafal R. Sicinski ◽  
Hector F. DeLuca ◽  
Hiroshi Sai ◽  
Nobuo Ikekawa
Keyword(s):  
Side Chain ◽  
In Vitro Production ◽  
Dihydroxyvitamin D3 ◽  
1,25 Dihydroxyvitamin D3 ◽  
Highly Active ◽  
Vitro Production

scholarly journals Detection of 7-Dehydrocholesterol and Vitamin D3 Derivatives in Honey

Molecules ◽  
2020 ◽  
Vol 25 (11) ◽  
pp. 2583
Author(s):  
Tae-Kang Kim ◽  
Venkatram Atigadda ◽  
Pawel Brzeminski ◽  
Adrian Fabisiak ◽  
Edith K. Y. Tang ◽  
...  
Keyword(s):  
Vitamin D3 ◽  
Cytochromes P450 ◽  
Ultraviolet B ◽  
Human Epidermis ◽  
Side Chain ◽  
Hydroxylase Activity ◽  
Dihydroxyvitamin D3 ◽  
1,25 Dihydroxyvitamin D3 ◽  
Clear Peak ◽  
Anti Inflammatory

20(S)-Hydroxyvitamin D3 (20(OH)D3) is an endogenous metabolite produced by the action of CYP11A1 on the side chain of vitamin D3 (D3). 20(OH)D3 can be further hydroxylated by CYP11A1, CYP27A1, CYP24A1 and/or CYP27B1 to several hydroxyderivatives. CYP11A1 also hydroxylates D3 to 22-monohydroxyvitamin D3 (22(OH)D3), which is detectable in the epidermis. 20-Hydroxy-7-dehydrocholesterol (20(OH)-7DHC) has been detected in the human epidermis and can be phototransformed into 20(OH)D3 following the absorption of ultraviolet B (UVB) energy by the B-ring. 20(OH)D3 and its hydroxyderivatives have anti-inflammatory, pro-differentiation and anti-proliferative effects, comparable to 1,25-dihydroxyvitamin D3 (1,25(OH)2D3). Since cytochromes P450 with 20- or 25-hydroxylase activity are found in insects participating in ecdysone synthesis from 7-dehydrocholesterol (7DHC), we tested whether D3-hydroxyderivatives are present in honey, implying their production in bees. Honey was collected during summer in the Birmingham area of Alabama or purchased commercially and extracted and analyzed using LC-MS. We detected a clear peak of m/z = 423.324 [M + Na]+ for 20(OH)D3 corresponding to a concentration in honey of 256 ng/g. We also detected peaks of m/z = 383.331 [M + H − H2O]+ for 20(OH)-7DHC and 25(OH)D3 with retention times corresponding to the standards. We further detected species with m/z = 407.329 [M + Na]+ corresponding to the RT of 7DHC, D3 and lumisterol3 (L3). Similarly, peaks with m/z = 399.326 [M + H − H2O]+ were detected at the RT of 1,25(OH)2D3 and 1,20-dihydroxyvitamin D3 (1,20(OH)2D3). Species corresponding to 20-monohydroxylumisterol3 (20(OH)L3), 22-monohydroxyvitamin D3 (22(OH)D3), 20,23-dihydroxyvitamin D3 (20,23(OH)2D3), 20,24/25/26-dihydroxyvitamin D3 (20,24/25/26(OH)2D3) and 1,20,23/24/25/26-trihydroxyvitamin D3 (1,20,23/24/25/26(OH)3D3) were not detectable above the background. In conclusion, the presence of 7DHC and D3 and of species corresponding to 20(OH)-7DHC, 20(OH)D3, 1,20(OH)2D3, 25(OH)D3 and 1,25(OH)2D3 in honey implies their production in bees, although the precise biochemistry and photochemistry of these processes remain to be defined.

Metabolism of 1,25-dihydroxyvitamin D3: evidence for side-chain oxidation

Biochemistry ◽  
1976 ◽  
Vol 15 (11) ◽  
pp. 2420-2423 ◽  
Author(s):  
Rajiv Kumar ◽  
Deborah Harnden ◽  
Hector F. DeLuca
Keyword(s):  
Side Chain ◽  
Dihydroxyvitamin D3 ◽  
Chain Oxidation ◽  
1,25 Dihydroxyvitamin D3

Low-calcium diets increase both production and clearance of 1,25-dihydroxyvitamin D3 in rats

1990 ◽  
Vol 258 (2) ◽  
pp. E282-E287 ◽  
Author(s):  
J. Fox ◽  
J. E. Bunker ◽  
M. Kamimura ◽  
P. F. Wong
Keyword(s):  
Side Chain ◽  
Small Intestinal Mucosa ◽  
Metabolic Clearance ◽  
Elevated Plasma ◽  
Metabolic Clearance Rate ◽  
Deficient Diet ◽  
Dihydroxyvitamin D3 ◽  
Glucuronyl Transferase ◽  
1,25 Dihydroxyvitamin D3 ◽  
Small Intestinal

Administration of large doses of 1,25-dihydroxyvitamin D3 [1,25(OH)2D3] to animals induces 1,25(OH)2D3 side-chain oxidative pathways. This study determined if the elevated plasma 1,25(OH)2D3 seen in rats fed low-Ca diets is associated not only with an increased production rate (PR) but also with an increased metabolic clearance rate (MCR) of the hormone. In vitamin D-replete rats fed a Ca-deficient diet for 3-4 wk, the PR increased 21-fold, plasma levels 15-fold, and the MCR by 37%. The increased MCR in Ca-deficient rats was associated with a 48% increase in hepatic microsomal UDP glucuronyl transferase enzyme activity, whereas 1,25(OH)2D3 catabolism by homogenates of liver and small intestinal mucosa was unchanged. In contrast to the effects of low-Ca diets, acute (7 h) pharmacological elevation of plasma 1,25(OH)2D3 to 1.5 ng/ml in normal rats did not influence the MCR. Thus chronically elevated 1,25(OH)2D3 levels are necessary to stimulate clearance. In conclusion, 1,25(OH)2D3 clearance in rats can be stimulated not only by chronic pharmacological doses of 1,25(OH)2D3 but also by the physiological stimulus of a low-Ca diet. Hence, plasma 1,25(OH)2D3 levels can be regulated by changes in both PR and MCR.

Increased potency of 1,25-dihydroxyvitamin D3 on human osteoblast-like cells following structural side-chain modification

Bone ◽  
1990 ◽  
Vol 11 (6) ◽  
pp. 439-443 ◽  
Author(s):  
D.B. Evans ◽  
M. Thavarajah ◽  
M.R. Uskokovic ◽  
J.A. Kanis
Keyword(s):  
Side Chain ◽  
Human Osteoblast ◽  
Dihydroxyvitamin D3 ◽  
1,25 Dihydroxyvitamin D3
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