85(P-42) 神経突起伸長作用を有するジクチオステロール及び関連化合物の立体選択的合成と構造活性相関(ポスター発表の部)
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In the course of screening for low molecular weight natural product being able to exhibit the neurite outgrowth in the neurons of the hypothalamus of rat, an active compound was isolated from the culture broth of the cellular slime mold Dictyostelium purpureum K1001. ^<13>C-NMR spectrum of the hydrogenated product of the compound was agreed with that of poriferastanol (1) (not stigmastanol (2)). The compound was finally identified as dictyosterol (3) by comparing ^1H-NMR spectrum with that of synthetic dictyosterol. The coupling of the phenyl sulfone derivative (8) derived from optically active epoxy alcohol (4) with C-22 aldehyde (9) from stigmasterol (12) in the presence of LDA, the deprotection of the hydroxyl group and the reductive desulfonylation with Na-Hg afforded 3. The epimer (11) of 3 was synthesized in a similar manner as described for 3. The compound (11) was obtained more easily from 12 by the elimination of the hydroxyl group of 6-hydroxystigmasterol (13) derived from the hydroboration of 12. In application to this method, the coupling of 10 with the C-22 aldehyde (15) or the C-22 iodo (18) produced provitamin D_6 (20) or D_5 (23) respectively. Similarly, the reaction of 8 with 14 gave clionesterol (19). The coupling of 10 with 17 produced β-sitosterol (22). It was shown that the double bond between C-22/C-23 and the free hydroxyl group are essential to exhibit the neurite outgrowth. Dictyosterol (3) and the diastereomeric mixture of 3 and 11 showed the same biological activity indicating that the configration of ethyl group at C-24 position is not important. In connection with the effect of the alkyl group at C-24 position, the activity of the neurite outgrowth was decreased in the order of C_2H_5>CH_3>H. However, the steroid derivatives having bulky alkyl groups in the side chain such as propyl or butyl group at C-24 position showed no activity of neurite outgrowth.
- 天然有機化合物討論会の論文
- 2001-09-01
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