(10alpha)-2beta,16alpha,20,25-四羟基-9beta-甲基-19-去甲羊毛甾-5-烯-3,11,22-三酮 | 55903-92-9

• 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
• 中文名称: (10alpha)-2beta,16alpha,20,25-四羟基-9beta-甲基-19-去甲羊毛甾-5-烯-3,11,22-三酮
• 英文名称: 23,24-dihydrocucurbitacin D
• 英文别名: 23,24-dihydro-cucurbitacin D；dihydrocucurbitacin D；cucurbitacin R；2β,16α,20,25-tetrahydroxy-10α-cucurbit-5-ene-3,11,22-trione；2β,16α,20,25-Tetrahydroxy-10α-cucurbit-5-en-3,11,22-trion；(2S,8S,9R,10R,13R,14S,16R,17R)-17-[(2R)-2,6-dihydroxy-6-methyl-3-oxoheptan-2-yl]-2,16-dihydroxy-4,4,9,13,14-pentamethyl-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthrene-3,11-dione
• CAS: 55903-92-9
• 化学式: C₃₀H₄₆O₇
• 分子量: 518.691
• InChiKey: ITMUUFDDBRYVNJ-VOKXYEOFSA-N

物化性质

• 熔点：
  124 °C
• 沸点：
  682.6±55.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  37
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  132
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (10alpha)-2beta,16alpha,20,25-四羟基-9beta-甲基-19-去甲羊毛甾-5-烯-3,11,22-三酮 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 72.0h， 生成 tetrahydrocucurbitacin F
  参考文献：
  名称：

  Sasamori, Hiroshi; Reddy, K. Sambi; Kirkup, Michael P., Journal of the Chemical Society. Perkin transactions I, 1983, # 7, p. 1333 - 1347

  摘要：

  DOI：
• 作为产物：
  描述：

  葫芦素 D 在 5%-palladium/activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 (10alpha)-2beta,16alpha,20,25-四羟基-9beta-甲基-19-去甲羊毛甾-5-烯-3,11,22-三酮
  参考文献：
  名称：

  Cucurbitacin D Is a Disruptor of the HSP90 Chaperone Machinery

  摘要：

  Heat shock protein 90 (Hsp90) facilitates the maturation of many newly synthesized and unfolded proteins (clients) via the Hsp90 chaperone cycle, in which Hsp90 forms a heteroprotein complex and relies upon cochaperones, immunophilins, etc., for assistance in client folding. Hsp90 inhibition has emerged as a strategy for anticancer therapies due to the involvement of clients in many oncogenic pathways. Inhibition of chaperone function results in client ubiquitinylation and degradation via the proteasome, ultimately leading to tumor digression. Small molecule inhibitors perturb ATPase activity at the N-terminus and include derivatives of the natural product geldanamycin. However, N-terminal inhibition also leads to induction of the pro-survival heat shock response (HSR), in which displacement of the Hsp90-bound transcription factor, heat shock factor-1, translocates to the nucleus and induces transcription of heat shock proteins, including Hsp90. An alternative strategy for Hsp90 inhibition is disruption of the Hsp90 heteroprotein complex. Disruption of the Hsp90 heteroprotein complex is an effective strategy to prevent client maturation without induction of the HSR. Cucurbitacin D, isolated from Cucurbita texana, and 3-epi-isocucurbitacin D prevented client maturation without induction of the HSR. Cucurbitacin D also disrupted interactions between Hsp90 and two cochaperones, Cdc37 and p23.

  DOI：

  10.1021/acs.jnatprod.5b00054

文献信息

• Anti-Diabetic Effects of Cucurbitacins from Ibervillea lindheimeri on Induced Mouse Diabetes
  作者：Sonia E. Hernández Navia、José L. Figueroa-Hernández、José S. Rodríguez-Zavala、Miriam Rodriguez-Sosa、Mariano Martínez-Vázquez

  DOI：10.1155/2022/3379557

  日期：2022.6.25

  Mexico has a great tradition of using medicinal plants against diabetes. For example, species from the genus Ibervillea traditionally known as “wereque” in Mexican popular medicine have a long ethnobotanical history as anti-diabetic agents. Previous studies by our group indicated that ethyl acetate extract from Ibervillea lindheimeri (I. lindheimeri) roots reduced glucose in mice with chemically induced

  墨西哥在使用药用植物治疗糖尿病方面有着悠久的传统。例如，在墨西哥流行医学中传统上被称为“wereque”的伊比利亚属植物作为抗糖尿病药物具有悠久的民族植物学历史。我们小组先前的研究表明，来自Ibervillea lindheimeri ( I. lindheimeri ) 根的乙酸乙酯提取物可降低化学诱导糖尿病小鼠的葡萄糖。在这项工作中， I. lindheimeri乙酸乙酯提取物的主要代谢物；23,24-二氢葫芦素 D (1); 2-O- β吡喃葡萄糖基-23,24-二氢葫芦素 D (2) 以及分别从 1 和 2 获得的乙酰化化合物 (3) 和 (4) 在化学诱导的糖尿病小鼠模型中作为抗高血糖剂进行了评估。我们的研究结果表明，与对照组相比，葫芦素 1、2 和 4 降低了糖尿病 CD1 小鼠的血糖。此外，结果表明化合物 1、2 和 4 主要在附睾脂肪组织 (EAT) 中促进 4 型葡萄糖转运蛋白
• JACOBS, HELEN;SINGH, TAMAR;REYNOLDS, WILLIAM F.;MCLEAN, STEWART, J. NATUR. PROD., 53,(1990) N, C. 1600-1605
  作者：JACOBS, HELEN、SINGH, TAMAR、REYNOLDS, WILLIAM F.、MCLEAN, STEWART

  DOI：——

  日期：——
• The Constitutents of Ecballium elaterium L. VI. The Functions of Elatericin A^1,2
  作者：David Lavie、Youval Shvo

  DOI：10.1021/ja01521a037

  日期：1959.6
• CHEMOSENSORY RECEPTOR LIGAND-BASED THERAPIES
  申请人：Anji Pharma (US) LLC

  公开号：EP2661266B1

  公开（公告）日：2020-09-16
• Chemosensory Receptor Ligand-Based Therapies
  申请人：BARON Alain D.

  公开号：US20120177730A1

  公开（公告）日：2012-07-12

  Provided herein are methods for treating conditions associated with a chemosensory receptor, including diabetes, obesity, and other metabolic diseases, disorders or conditions by administrating a composition comprising a chemosensory receptor ligand, such as a bitter receptor ligand. Also provided herein are chemosensory receptor ligand compositions, including bitter receptor ligand compositions, and methods for the preparation thereof for use in the methods of the present invention. Also provided herein are compositions comprising metformin and salts thereof and methods of use.