pregnenolone 3β-D-glucopyranoside | 29685-48-1

• 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: pregnenolone 3β-D-glucopyranoside
• 英文别名: pregnolone 3-O-β-D-glucoside；pregnenolonyl-β-glucoside；3β-pregnenolone-β-D-glucopyranoside；pregnenolone beta-D-glucoside；1-[(3S,8S,9S,10R,13S,14S,17S)-10,13-dimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
• CAS: 29685-48-1
• 化学式: C₂₇H₄₂O₇
• 分子量: 478.626
• InChiKey: KCBQUTGDLFZEIG-KNSPFVISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  116
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  pregnenolone 3β-D-glucopyranoside 在 吡啶 、 水 、 溶剂黄146 作用下， 以 吡啶 为溶剂， 反应 63.0h， 生成 3β-(2,3,6-tri-O-acetyl-β-D-glucopyranosyloxy)-pregn-5-en-20-one
  参考文献：
  名称：

  Synthesis of 5α-Cholestane Type Glycoside Sulfates

  摘要：

  类固醇糖苷硫酸酯的合成，既在类固醇骨架上进行硫酸化，又在糖部分进行硫酸化。从3β-(2-四氢吡喃氧基)-5α-胆甾-6α-醇（I）制备了5α-胆甾烷-3β,6α-二醇-6-β-D-葡萄糖苷-3-硫酸盐V和3-β-D-葡萄糖苷-6-硫酸盐XI的钠盐，使用乙酰基和甲氧甲基基团进行临时保护。首先在孕烷系列中检查了糖部分的硫酸化，并制备了3β-(β-D-葡萄糖吡喃基氧基)孕-5-烯-20-酮-6'-硫酸盐XXVI和4'-硫酸盐2',3'-二乙酸酯XXVII的三乙基铵盐。将该方法应用于胆甾衍生物上，得到了5α-胆甾-3β-基β-D-葡萄糖吡喃苷-6-硫酸盐XXXI的三乙基铵盐。

  DOI：

  10.1135/cccc19931180
• 作为产物：
  描述：

  孕烯醇酮 在 甲醇 、 三氟甲磺酸三甲基硅酯 、 sodium 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 pregnenolone 3β-D-glucopyranoside
  参考文献：
  名称：

  NSC12 的化学修饰导致特定的 FGF 陷阱在多发性骨髓瘤中具有抗肿瘤活性

  摘要：

  抑制 FGF/FGFR 信号传导是治疗依赖于 FGF 刺激的恶性肿瘤（包括多发性骨髓瘤 (MM)）的一种很有前景的策略。甾体衍生物NSC12(化合物1 )是具有体内抗肿瘤活性的泛FGF陷阱。探索了化合物1 的化学修饰以研究构效关系，重点关注双（三氟甲基）1,3-丙二醇链的作用、C20 的立体化学和 C3 位置的功能化。我们的研究揭示了化合物25b，即化合物1的孕烷 3-酮 20 R衍生物作为一种有效的药剂，通过抑制 FGF 依赖性受体的激活和减缓体内 MM 的生长，在体外阻断 MM 细胞的增殖。重要的是，C3 处羟基的缺失阻止了与雌激素受体的结合，这可能与对化合物1观察到的抗肿瘤活性一致，导致特定的 FGF/FGFR 系统抑制剂，并进一步支持 FGFR 在 MM 抗癌治疗中的作用.

  DOI：

  10.1016/j.ejmech.2021.113529

文献信息

• Pregnenolonyl-α-glucoside exhibits marked anti-cancer and CYP17A1 enzymatic inhibitory activities
  作者：Feng-Pai Chou、Wen-Chen Hsu、Sheng-Cih Huang、Chin-Yuan Chang、Ya-Sheng Chiou、Chia-Tse Tsai、Jason WenJay Lyu、Wei-Ting Chen、Tung-Kung Wu

  DOI：10.1039/c9cc09415f

  日期：——

  We report here that pregnenolonyl-α-glucoside (2) exhibits significant dose-dependent cytotoxicity against HT29, AGS, and ES-2 cells. The biochemical characterization results indicates the putative mechanism of 2 on the catalytic site of CYP17A1.

  我们在此报告孕酮-α-葡萄糖苷（2）对HT29、AGS和ES-2细胞表现出显著的剂量依赖性细胞毒性。生化特性结果表明，2对CYP17A1的催化位点具有潜在的作用机制。
• UGT74AN1, a Permissive Glycosyltransferase from <i>Asclepias curassavica</i> for the Regiospecific Steroid 3-<i>O</i>-Glycosylation
  作者：Chao Wen、Wei Huang、Xue-Lin Zhu、Xiao-San Li、Fan Zhang、Ren-Wang Jiang

  DOI：10.1021/acs.orglett.7b03619

  日期：2018.2.2

  A permissive steroid glycosyltransferase (UGT74AN1) from Asclepias curassavica exhibited robust capabilities for the regiospecific C3 glycosylation of cardiotonic steroids and C-21 steroid precursors, and unprecedented promiscuity toward 53 structurally diverse natural and unnatural compounds to form O-, N-, and S-glycosides, along with the catalytic reversibility for a one-pot transglycosylation reaction. These findings highlight UGT74AN1 as the first regiospecific catalyst for cardiotonic steroid C3 glycosylation and exhibit significant potential for glycosylation of diverse bioactive molecules in drug discovery.
• Molecular cloning and characterization of one member of 3β-hydroxy sterol glucosyltransferase gene family in Withania somnifera
  作者：Lokendra Kumar Sharma、Bhaskara Reddy Madina、Pankaj Chaturvedi、Rajender Singh Sangwan、Rakesh Tuli

  DOI：10.1016/j.abb.2007.01.024

  日期：2007.4

  Sterol glycosides are constituents of plant cell membranes. Glucosylations of the sterols are catalyzed by sterol glucosyltransferases (SGTs), which are members of family 1 glycosyltransferases. We have identified the family of SGT genes expressed in the leaves of a medicinal plant Withania somnifera. One member (SGTL1) of this gene family was cloned. The full-length cDNA sequence of SGTL1 represents 2532 bp, comprising untranslated regions (UTRs) of 337 and 89 bp at the 5' and 3' ends, respectively. The amino acid sequence deduced from the 2103 bp open reading frame (ORF) showed homology (67-45%) to the reported plant SGTs. The presence of two putative transmembrane domains suggested the association of SGTL1 with membrane. The SGTL1 was expressed in Escherichia coli and recombinant enzyme from the supernatant was partially purified and biochemically characterized. The relative activity and kinetic properties of SGTL1 for different sterols were compared with a recombinant SGT (GenBank Accession No. Z83833) of Arabidopsis thaliana (AtSGT). Both the recombinant enzymes showed activity with 3-beta-OH sterols. The distribution of SGTL1 transcript in W. somnifera, as determined by quantitative PCR, showed higher expression in roots and mature leaves. Expression of the SGTL1 transcript in the leaves of W. somnifera was enhanced following the application of salicylic acid. In contrast, it decreased rapidly on exposure of the plants to heat shock, suggesting functional role of the enzyme in biotic and abiotic stresses. (c) 2007 Elsevier Inc. All rights reserved.
• Purification and physico-kinetic characterization of 3β-hydroxy specific sterol glucosyltransferase from Withania somnifera (L) and its stress response
  作者：Bhaskara Reddy Madina、Lokendra Kumar Sharma、Pankaj Chaturvedi、Rajender Singh Sangwan、Rakesh Tuli

  DOI：10.1016/j.bbapap.2006.12.009

  日期：2007.3

  Sterol glycosyltransferases catalyze the synthesis of diverse glycosteroids in plants, leading to a change in their participation in cellular metabolism. Withania somnifera is a medically important plant, known for a variety of pharmacologically important withanolides and their glycosides. In this study, a cytosolic sterol glucosyltransferase was purified 3406 fold to near homogeneity from W somnifera leaves and studied for its biochemical and kinetic properties. The purified enzyme was active with UDP-glucose but not with UDP-galactose as sugar donor. It exhibited broad sterol specificity by glucosylating a variety of sterols and phytosterols with 3 beta-OH group. It showed a low level of activity with flavonoids and isoflavonoids. The enzyme gave maximum K-cat/K-m value (0.957) for 24-methylenecholesterol that resembles aglycone structure of pharmacologically important sitoindosides VII and VIII from W somnifera. The enzyme follows ordered sequential bisubstrate mechanism of reaction, in which UDP-glucose and sterol are the first and second binding substrates. This is the first detailed kinetic study on purified plant cytosolic sterol glucosyltransferases. Results on peptide mass fingerprinting and substrate specificity suggested that the enzyme belongs to the family of secondary metabolite glucosylating glucosyltransferases. The enzyme activity exhibited a rapid in vivo response to high temperature and salicylic acid treatment of plants, suggesting its physiological role in abiotic and biotic stress. (c) 2007 Elsevier B.V. All rights reserved.