tigogenin 3β-O-(β-D-glucopyranoside) | 35068-81-6

• 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: tigogenin 3β-O-(β-D-glucopyranoside)
• 英文别名: 3-O-[β-D-glucopyranosyl]tigogenin；tigogenine 3-O-(β-D-glucopyranoside)；tigogenin 3-O-beta-D-glucopyranoside；(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[(1R,2S,4S,5'R,6R,7S,8R,9S,12S,13S,16S,18S)-5',7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2'-oxane]-16-yl]oxyoxane-3,4,5-triol
• CAS: 35068-81-6
• 化学式: C₃₃H₅₄O₈
• 分子量: 578.787
• InChiKey: ZNEIIZNXGCIAAL-WILLDVSMSA-N

物化性质

• 沸点：
  695.5±55.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  41
• 可旋转键数：
  3
• 环数：
  7.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  118
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tigogenin 3β-O-(β-D-glucopyranoside) 、 1-(苯甲酰基氧基)-1H-1,2,3-苯并噻唑 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以40%的产率得到tigogenin 3β-O-(3,6-di-O-benzoyl-β-D-glucopyranoside)
  参考文献：
  名称：

  Synthesis of the Cytotoxic Gitogenin 3β-O-[2-O-(α-l-Rhamnopyranosyl)-β-d-galactopyranoside] and its Congeners

  摘要：

  (25R)-5a-螺甾-2a,3b-二醇 (gitogenin) 3β-O-[2-O-(α-l-鼠李吡喃糖基)-β-d-半乳吡喃糖苷] (1)，一种从长茎黄精（百合科）地下部分分离得到的细胞毒性螺甾皂苷，被简明地合成出来。在此过程中，其类似物2-4也被制备出来。所有四个化合物在抑制癌细胞生长方面与薯蓣皂苷具有相当的效力。

  DOI：

  10.1055/s-2006-926316
• 作为产物：
  描述：

  薯蓣皂素 在 palladium on activated charcoal 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 氢气 、 sodium methylate 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 氯仿 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 生成 tigogenin 3β-O-(β-D-glucopyranoside)
  参考文献：
  名称：

  Synthesis of the Cytotoxic Gitogenin 3β-O-[2-O-(α-l-Rhamnopyranosyl)-β-d-galactopyranoside] and its Congeners

  摘要：

  (25R)-5a-螺甾-2a,3b-二醇 (gitogenin) 3β-O-[2-O-(α-l-鼠李吡喃糖基)-β-d-半乳吡喃糖苷] (1)，一种从长茎黄精（百合科）地下部分分离得到的细胞毒性螺甾皂苷，被简明地合成出来。在此过程中，其类似物2-4也被制备出来。所有四个化合物在抑制癌细胞生长方面与薯蓣皂苷具有相当的效力。

  DOI：

  10.1055/s-2006-926316

文献信息

• A novel glucosyltransferase involved in steroid saponin biosynthesis in Solanum aculeatissimum
  作者：Atsuko Kohara、Chiharu Nakajima、Kimiko Hashimoto、Toshihiko Ikenaga、Hiroyuki Tanaka、Yukihiro Shoyama、Shigeo Yoshida、Toshiya Muranaka

  DOI：10.1007/s11103-004-7204-2

  日期：2005.1

  UDP-glucosyltransferase activity. This is the first cloned glucosyltransferase involved in steroidal saponin biosynthesis. SaGT4A catalyzes the 3-O-glucosylation of steroidal sapogenins, such as diosgenin, nuatigenin, and tigogenin. This enzyme also glucosylates steroidal alkaloids, such as solanidine, solasodine, and tomatidine. Gene expression analysis revealed that the accumulation of SaGT4A transcripts showed

  甾体皂苷广泛分布于许多植物物种中。它们的不同结构导致了广泛的应用，包括药物和药物生产。已经提出，皂苷分子的非糖和寡糖部分的性质均有助于单个皂苷的特性。尽管对甾族皂苷的发生，化学结构和不同的药物活性进行了大量研究，但对它们的生物合成途径的了解却很少。糖基化被认为是甾体皂苷生物合成的最后一步，并且被认为参与调节皂苷的生物活性。催化糖分子向甾体化合物转移的糖基转移酶的分离将有助于阐明产生多种皂苷并控制其在植物中的活性的机制。在这项研究中，我们获得了三个从茄茄中推定的糖基转移酶的cDNA。SaGT4A是三者之一，显示UDP-葡萄糖基转移酶活性。这是参与甾体皂苷生物合成的第一个克隆的葡糖基转移酶。SaGT4A催化甾体皂苷元（如薯os皂苷元，纽替丁宁和tigogenin）的3-O-糖基化。该酶还将葡糖基化甾体生物碱，例如茄碱，索拉索定和番茄碱。
• Steriodal glycosides for treating hypercholesterolemia
  申请人：PFIZER INC.

  公开号：EP0796862A2

  公开（公告）日：1997-09-24

  The invention provides the use of a spirostanyl glycoside of formula I, wherein Q1, Q4 and Q5 are each methylene; Q2 is carbonyl, methylene, Q3 is and R1 is a specified glycosidic group; with various provisos; in the manufacture of a medicament for the treatment of hypercholesterolemia or atherosclerosis.

  本发明提供了式 I 的螺烷苷的用途、 其中 Q1、Q4 和 Q5 各为亚甲基； Q2 是羰基、亚甲基、 Q3 是 和 R1 是特定的糖苷基团； 附带各种但书； 用于制造治疗高胆固醇血症或动脉粥样硬化的药物。
• Steroidal glycosides for treating hypercholesterolemia
  申请人：PFIZER INC.

  公开号：EP0796863A2

  公开（公告）日：1997-09-24

  The invention provides spirostanyl glycosides of formula I, wherein Q1, Q4 and Q5 are each methylene; Q2 is Q3 is and R1 is a specified glycosidic group. The comopunds are useful in the treatment of hypercholesterolemia or atherosclerosis.

  本发明提供了式 I 的螺烷基糖苷、 其中 Q1、Q4 和 Q5 各为亚甲基； Q2 是 Q3 为 和 R1 是一个特定的糖苷基团。 这些组合物可用于治疗高胆固醇血症或动脉粥样硬化。
• Antifungal activity of 2α,3β-functionalized steroids stereoselectively increases with the addition of oligosaccharides
  作者：Amy Cammarata、Sunil Kumar Upadhyay、Branko S. Jursic、Donna M. Neumann

  DOI：10.1016/j.bmcl.2011.10.015

  日期：2011.12

  Invasive fungal infections pose a significant problem to the immune-compromised. Moreover, increased resistance to common antifungals requires development of novel compounds that can be used to treat invasive fungal infections. Naturally occurring steroidal glycosides have been shown to possess a range of functional antimicrobial properties, but synthetic methodology for their development hinders thorough exploration of this class of molecules and the structural components required for broad spectrum antifungal activity. In this report, we outline a novel approach to the synthesis of glycoside-linked functionalized 2 alpha,3 beta-cholestane and spirostane molecules and present data from in vitro screenings of the antifungal activities against human fungal pathogens and as well as mammalian cell toxicity of these derivatives. (C) 2011 Elsevier Ltd. All rights reserved.
• Effect of C-ring modifications on the cytotoxicity of spirostan saponins and related glycosides
  作者：Karell Pérez-Labrada、Ignacio Brouard、Sara Estévez、María Teresa Marrero、Francisco Estévez、Daniel G. Rivera

  DOI：10.1016/j.bmc.2012.05.018

  日期：2012.7

  Twelve C-ring modified spirostanyl glycosides were synthesized and evaluated for their cytotoxicity against the human myeloid leukemia cell line (HL-60). With the aim of assessing the influence of the hydrophobic character, the conformational flexibility and the stereochemistry of the C-ring functionalities on the cytotoxic activity, a variety of spirostanic aglycones incorporating methylene, methoxyl, alpha,beta-unsaturated ketone and lactone groups were subjected to a linear glycosylation strategy leading to glycosides derived from the 3,6-dipivaloylated beta-D-glucoside and the beta-chacotrioside moieties. The 3,6-dipivaloylated spirostanyl beta-D-glucosides showed moderate to good cytotoxic activity against HL-60, but no significant cytotoxicity against benign blood cells. However, the cytotoxicity of spirostanyl beta-chacotriosides was highly dependent on the nature of the C-ring functional groups of the steroidal aglycones. Actually, the chacotrioside-based saponins either with no functionality or bearing a hydrophobic methylene group at C-12 were the most cytotoxic ones against both HL-60 and benign blood cells. On the other hand, the incorporation of very polar functionalities and the opening of the ring C with the consequent loss of rigidity led to a significant drop in the cytotoxicity against HL-60. These results confirm that spirostanyl beta-chacotriosides including very lipophilic aglycones are the most cytotoxic ones among their congeners. (C) 2012 Elsevier Ltd. All rights reserved.