12α-hydroxybufalin | 852831-45-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 12α-hydroxybufalin
• 英文别名: 12alpha-Hydroxybufalin；5-[(3S,5R,8R,9S,10S,12S,13S,14S,17R)-3,12,14-trihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one
• CAS: 852831-45-9
• 化学式: C₂₄H₃₄O₅
• 分子量: 402.531
• InChiKey: MDAMKPSXKUKLHO-KVQYNQLBSA-N

物化性质

• 沸点：
  595.8±50.0 °C(Predicted)
• 密度：
  1.289±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  29
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  87
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  尿苷(5')二氢二磷酰(1)-alpha-D-葡萄糖 、 12α-hydroxybufalin 在 Bacillus subtilis glycosyltransferase YjiC₁ 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以82%的产率得到12α-hydroxybufalin 3-O-β-D-glucoside
  参考文献：
  名称：

  使用微生物糖基转移酶酶促合成丁二酸内酯O-糖苷作为有效的抗肿瘤药

  摘要：

  丁二烯内酯是一类天然的强心类固醇，以其抗肿瘤活性而闻名。不良的水溶性阻碍了它们的临床应用。酶促糖基化是改善天然产物的溶解度的有利方法。在这项工作中，我们描述了高效的一步法合成布法地那利O-葡萄糖苷和O-半乳糖苷使用微生物糖基转移酶YjiC1，转化率从63％到99％。从14种底物中获得了总共24种糖苷，包括17种新化合物，并通过广泛的NMR和高分辨率电喷雾电离质谱（HR-ESI-MS）分析鉴定了它们的结构。这些产物属于五种类型：3β-OH，7β-OH，3β，7β-di-OH，11α-OH和12β-OH的糖基化。的C-7β或C-11α Ö bufadienolide的-glycosides报道首次。此外，3- O-糖苷对A549和MCF7人癌细胞系表现出显着的细胞毒活性，并显示出对Na + / K + -ATPase的有效抑制活性（IC 50）值在0.053-0.76μM范围内。特别是，bufalin

  DOI：

  10.1002/adsc.201700777
• 作为产物：
  描述：

  蟾毒灵 在 mycelia of Cunninghamella blakesleana AS 3.970 作用下， 以 乙醇 为溶剂， 反应 96.0h， 以52.7 mg的产率得到12α-hydroxybufalin
  参考文献：
  名称：

  Microbial Hydroxylation of Bufalin by Cunninghamella blakesleana and Mucor spinosus

  摘要：

  The microbial transformation of a cytotoxic bufadienolide, bufalin (1), was carried out using two strains of filamentous fungi. Cunninghamella blakesleana catalyzed the specific 12 alpha-hydroxylation of bufalin and produced 12 alpha-hydroxybufalin (2) and 7 beta,12 alpha-dihydroxybufalin (3) as the major metabolites, together with 7 beta-hydroxybufalin (4) and 12 beta-hydroxybufalin (5) in low yields. Two minor products were isolated from the culture broth of Mucor spinosus and were identified as 7 beta,15 alpha-dihydroxybufalin (6) and 5 beta,7 beta-dihydroxybufalin (7), respectively. Metabolites 2, 3, 6, and 7 are new compounds, and their structures were fully characterized by NMR and MS spectroscopy.

  DOI：

  10.1021/np0500023

文献信息

• Enzymatic Synthesis of Bufadienolide<i>O</i>-Glycosides as Potent Antitumor Agents Using a Microbial Glycosyltransferase
  作者：Kai Li、Jin Feng、Yi Kuang、Wei Song、Meng Zhang、Shuai Ji、Xue Qiao、Min Ye

  DOI：10.1002/adsc.201700777

  日期：2017.11.10

  significant cytotoxic activities against A549 and MCF7 human cancer cell lines, and showed potent inhibitory activities against Na+/K+‐ATPase with IC50 values in the range 0.053–0.76 μM. In particular, bufalin 3‐O‐β‐d‐glucoside showed enhanced water solubility (25‐fold increase from bufalin) and potent antitumor activities (30% inhibition rate, 1.4 mg kg−1, i.p.) on A549 human lung cancer xenograft Balb/c

  丁二烯内酯是一类天然的强心类固醇，以其抗肿瘤活性而闻名。不良的水溶性阻碍了它们的临床应用。酶促糖基化是改善天然产物的溶解度的有利方法。在这项工作中，我们描述了高效的一步法合成布法地那利O-葡萄糖苷和O-半乳糖苷使用微生物糖基转移酶YjiC1，转化率从63％到99％。从14种底物中获得了总共24种糖苷，包括17种新化合物，并通过广泛的NMR和高分辨率电喷雾电离质谱（HR-ESI-MS）分析鉴定了它们的结构。这些产物属于五种类型：3β-OH，7β-OH，3β，7β-di-OH，11α-OH和12β-OH的糖基化。的C-7β或C-11α Ö bufadienolide的-glycosides报道首次。此外，3- O-糖苷对A549和MCF7人癌细胞系表现出显着的细胞毒活性，并显示出对Na + / K + -ATPase的有效抑制活性（IC 50）值在0.053-0.76μM范围内。特别是，bufalin
• Microbial Hydroxylation of Bufalin by <i>Cunninghamella </i><i>b</i><i>lakesleana </i>and<i> Mucor </i><i>s</i><i>pinosus</i>
  作者：Min Ye、Jian Han、Guangzhong Tu、Dongge An、Dean Guo

  DOI：10.1021/np0500023

  日期：2005.4.1

  The microbial transformation of a cytotoxic bufadienolide, bufalin (1), was carried out using two strains of filamentous fungi. Cunninghamella blakesleana catalyzed the specific 12 alpha-hydroxylation of bufalin and produced 12 alpha-hydroxybufalin (2) and 7 beta,12 alpha-dihydroxybufalin (3) as the major metabolites, together with 7 beta-hydroxybufalin (4) and 12 beta-hydroxybufalin (5) in low yields. Two minor products were isolated from the culture broth of Mucor spinosus and were identified as 7 beta,15 alpha-dihydroxybufalin (6) and 5 beta,7 beta-dihydroxybufalin (7), respectively. Metabolites 2, 3, 6, and 7 are new compounds, and their structures were fully characterized by NMR and MS spectroscopy.