102(P52) 活性型ビタミンD_4の代謝研究(ポスター発表の部)
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概要
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To investigate the effect of the methyl group at C-24 position in the side chain on the metabolism of active form of vitamin D compound, active form of vitamin D_4 (3) was synthesized and the structure of the metabolites of 3 in bile acid of rat was studied on the basis of spectral data and the oxidative cleavage of the metabolites. Three metabolites (M1,M2,M3) were isolated. One of the metabolites (M1) was determinned as calcitroic acid (4) by comparing the spectral data reported in the literature. The structures of the other two metabolites (M2, M3) was elucidated by ^1H, ^<13>C and 2D-NMR (^1H-^1H,^1H-^<13>C,^1H-^<13>C long range COSY) (Table 2), UV and mass spectra (Fig.1, Fig.2). M2 and M3 have the same molecular ion (m/z, 490) indicating the metabolites are the structual isomers each other and hydroxyl group and carboxylic acid are attached to the intact molecule (3). ^<13>C-NMR spectra showed that the signals due to the tertiary carbon atom disappeared and new signals attributable to the quarternary carbon atom at C-24 position appeared. No signals due to the hydroxymethyl group was observed in the ^1H-NMR spectra. It is suggested that the hydroxyl group was introduced to the C-24 position. Oxidative cleavage of the proposed vicinal diol structure of M2 and M3 gave the expected 24-oxo products, 5 and 6. From the results described above, the structures of M2 and M3 were determined as (24R)-9,10-secoergosta-5,7,10(19)-triene-1α 3β,24,25-tetrol-26-oic acid (7) and (24R)-9,10-secoergosta-5,7,10(19)-triene-1α 3β,24,25-tetrol-28-oic acid (8). Precursors of M2, 3β,24,25-trihydroxyergosta-5,7-dien-26-oic acid (9) and M3, 3β,24,25-trihydroxyergosta-5,7-dien-28-oic acid (10) were synthesized and the conversion of respective 9 and 10 into 7 and 8 is now under way.
- 天然有機化合物討論会の論文
- 1999-09-01
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関連論文
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- 102(P52) 活性型ビタミンD_4の代謝研究(ポスター発表の部)
- 活性型ビタミンD誘導体の合成研究
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