(20S,22R,25R)-1α,3β-dihydroxyspirost-5-ene | 79037-17-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (20S,22R,25R)-1α,3β-dihydroxyspirost-5-ene
• 英文别名: (25R)-spirostan-5-en-1α,3β-diol；(25R)-spirost-5-ene-1α,3β-diol；epiruscogenin
• CAS: 79037-17-5
• 化学式: C₂₇H₄₂O₄
• 分子量: 430.628
• InChiKey: QMQIQBOGXYYATH-BUQWVDOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.68
• 重原子数：
  31.0
• 可旋转键数：
  0.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  58.92
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (20S,22R,25R)-1α,3β-dihydroxyspirost-5-ene 在 吡啶 、 氢氧化钾 、 N-溴代丁二酰亚胺(NBS) 、 三甲胺盐酸盐 、 三乙胺 、 sodium iodide 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 20.17h， 生成 (2R,4S,8S,9S,12S,13R,14S,16R)-6-[(3R)-4-iodo-3-methylbutyl]-7,9,13-trimethyl-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-1(20),6,18-triene-14,16-diol
  参考文献：
  名称：

  Preparations of vitamin D analogs, spirostanols and furostanols from diosgenin and their cytotoxic activities

  摘要：

  Vitamin D analogs 12 and 13 having a spiro ring in the side chain, various spirostanols 18-21, 26, 27, 29 and 37, and furostanols 34-36 having SCN and SeCN groups at the 26 position were prepared from diosgenin 1 via (20S,22R,25R)-spirost-1 alpha,2 alpha-epoxy-4,6-dien-3-one 19 as a key intermediate. The cytotoxic activities of these derivatives as well as 1 on scarcely P-gp-expressed HCT 116 cells and P-gp-overexpressed Hep G2 cells were examined by MTT assay. Furostanols 34 (IC50 value: 4.9 +/- 0.3 mu M) and 36 (IC50 value: 1.3 +/- 0.2 mu M) exhibited marked cytotoxic effects on HCT 116 cells, and spirostanol 29 (IC50 value: 2.4 0.8 mu M) and furostanol 36 (IC50 value: 2.8 +/- 0.4 mu M) on Hep G2 cells. Furthermore, the effects of vitamin D analog 12, spirostanol 26 and furostanol 36 on apoptosis-signaling pathways were investigated. Compounds 12 and 26 overexpressed p53 and Bax mRNAs, while compound 36 overexpressed only Bax mRNA. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.02.003
• 作为产物：
  描述：

  薯蓣皂素 在 氨 、 双氧水 、 sodium methylate 、 lithium 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 为溶剂， 反应 8.33h， 生成 (20S,22R,25R)-1α,3β-dihydroxyspirost-5-ene
  参考文献：
  名称：

  Synthesis of (25R)-ruscogenin-1-yl β-d-xylopyranosyl-(1→3)-[β-d-glucopyranosyl-(1→2)]-β-d-fucopyranoside

  摘要：

  The synthesis of (25R)-ruscogenin-1-yl beta -D-xylopyranosyl-(1 --> 3)-[beta -D-glucopyranosyl-(1 --> 2)]-beta -D-fucopyranoside, a saponin from the tuber of Liriope muscari (Decne.) Bailey, is described. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00244-5

文献信息

• New Steroidal Glycosides from Rhizomes of<i>Clintonia udensis</i>
  作者：Yukiko MATSUO、Kazuki WATANABE、Yoshihiro MIMAKI

  DOI：10.1271/bbb.80003

  日期：2008.7.23

  A total of 10 steroidal glycosides, together with three new spirostanol glycosides (6–8), a new furostanol glycoside (9), and a new cholestane glycoside (10), were isolated from the rhizomes of Clintonia udensis (Liliaceae). The structures of the new compounds were determined on the basis of extensive spectroscopic analyses, including 2-D nuclear magnetic resonance (NMR) data, and of hydrolytic cleavage followed by chromatographic or spectroscopic analyses. The isolated glycosides were evaluated for their cytotoxic activity against HL-60 leukemia cells. Spirostanol glycosides 1 and 2, and furostanol glycoside 4 showed cytotoxic activity with IC50 values of 3.2±0.02, 2.2±0.12, and 2.2±0.06 μg/ml, respectively. Neither the spirostanol and furostanol saponins with a hydroxy group at C-1 (6 and 9) and C-12 (7 and 8) nor cholestane glycosides (5 and 10) exhibited apparent cytotoxic activity at a sample concentration of 10 μg/ml.

  从百合科植物黄精（Clintonia udensis）的根茎中分离得到了10种甾体糖苷，其中包括3种新的螺甾烷醇类糖苷（6-8）、1种新的呋甾烷醇类糖苷（9）和1种新的胆甾烷醇类糖苷（10）。通过广泛的波谱分析（包括二维核磁共振数据）以及水解断裂后进行的色谱或波谱分析鉴定了新化合物的结构。对分离得到的糖苷进行了对HL-60白血病细胞的细胞毒活性评价。螺甾烷醇类糖苷1和2以及呋甾烷醇类糖苷4显示了细胞毒活性，它们的IC50值分别为3.2±0.02、2.2±0.12和2.2±0.06 μg/ml。C-1（6和9）和C-12位（7和8）有羟基取代的螺甾烷醇类和呋甾烷醇类皂苷以及胆甾烷醇类糖苷（5和10）在样品浓度为10 μg/ml时均未显示出明显的细胞毒活性。
• Conversion of ruscogenin into 1α- and 1β hydroxycholesterol derivatives
  作者：M. Noam、I. Tamir、E. Breuer、R. Mechoulam

  DOI：10.1016/s0040-4020(01)92435-4

  日期：1981.1

  and 3, and mesylation of position 16 followed by LAH reduction. The utility of the shift reagent Eu(dpm)3 to determine the structures of the products was studied. It was shown that the shifts induced are characteristic of the position and orientation of the OH groups, and can facilitate the elucidation of the structures of hydroxylated steroids.

  对ruscogenin（1）的化学性质进行了研究，因为它的结构特征使其可以用作1-羟基维​​生素D类似物的潜在原料。芸香皂苷元被氧化成1-氧代衍生物2，其被还原成芸香苷元（1）和1-表皮环氧菌素（3）的混合物。既1和3通过克莱门森还原转化成相应的四元醇12和21，将其进一步还原成三醇15和25和二醇16和24通过连续的处理与p -甲苯磺酰氯和LAH。通过位置1和3的选择性苯甲酰化，以及位置16的甲磺酸化，然后LAH还原，将三醇15还原为二醇20。研究了转化试剂Eu（dpm）3在确定产物结构方面的用途。结果表明，引起的移位是OH基团的位置和取向的特征，并且可以促进阐明羟基化类固醇的结构。