4BETA-羟基醉茄内酯E | 54334-04-2

• 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: 4BETA-羟基醉茄内酯E
• 中文别名: 4BETA-羟基醉茄内酯 E
• 英文名称: 4β-hydroxywithanolide E
• 英文别名: 4beta-Hydroxywithanolide E；(1S,2R,6S,7R,9R,11R,12R,15S,16S)-15-[(1S)-1-[(2R)-4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl]-1-hydroxyethyl]-6,12,15-trihydroxy-2,16-dimethyl-8-oxapentacyclo[9.7.0.02,7.07,9.012,16]octadec-4-en-3-one
• CAS: 54334-04-2
• 化学式: C₂₈H₃₈O₈
• 分子量: 502.605
• InChiKey: UPBUGICUKQIKTJ-KABTZXSUSA-N

物化性质

• 溶解度：
  氯仿：可溶；乙醇：可溶；甲醇：可溶

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  36
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  137
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4BETA-羟基醉茄内酯E 在 sodium periodate 作用下， 以 甲醇 、 水 为溶剂， 反应 72.0h， 生成 4β,14α-dihydroxy-5β,6β-epoxyandrost-2-ene-1,17-dione
  参考文献：
  名称：

  酸浆中鸢尾酮和雄烷型withanolides的分离和鉴定

  摘要：

  Withanolides是甾醇类内酯，广泛存在于Nightshade植物中，通常具有很强的抗增殖活性。另外，该化合物类别的结构多样性对于发现新的生物活性具有很大的潜力。在这里，我们报道了两个新近表征的醇化物，命名为irinans，来自酸浆（Physalis peruviana），具有截短的截短骨架，类似于哺乳动物的雄烷性激素。基于仿生化学反应，我们提出了一个模型，将这些化合物与醇化物生物合成联系起来。伊立南人具有有效的抗增殖活性，但低于4ß-羟基withanolideE。我们的工作建立了androwithanolides作为withanolides的新子类。

  DOI：

  10.3762/bjoc.15.196

文献信息

• [EN] METHOD OF SENSITIZING CANCER CELLS TO THE CYTOTOXIC EFFECTS OF APOPTOSIS INDUCING LIGANDS IN CANCER TREATMENT<br/>[FR] MÉTHODE DE SENSIBILISATION DE CELLULES CANCÉREUSES AUX EFFETS CYTOTOXIQUES DE LIGANDS INDUISANT L'APOPTOSE DANS LE TRAITEMENT DU CANCER
  申请人：US HEALTH

  公开号：WO2017139485A1

  公开（公告）日：2017-08-17

  Disclosed is a method of enhancing the response of cancer cells in a mammal to treatment with an apoptosis inducing ligand, which method comprises contacting the cancer cells with an apoptosis inducing ligand in conjunction with an effective amount of a compound of the formula: (I), wherein R1-R14 are as described herein. Also disclosed is a method of inducing apoptosis in cancer cells in a mammal, comprising contacting the cancer cells with the compound described herein and also contacting the cancer cells with an apoptosis inducing ligand, whereby apoptosis is induced in the cancer cells.

  本发明公开了一种增强哺乳动物中癌细胞对凋亡诱导配体治疗反应的方法，该方法包括与式(I)化合物的有效量一起接触癌细胞和凋亡诱导配体，其中R1-R14如本文所述。本发明还公开了一种在哺乳动物中诱导癌细胞凋亡的方法，包括与本文所述化合物接触癌细胞，并且与凋亡诱导配体接触癌细胞，从而诱导癌细胞凋亡。
• Withaperuvin E and nicandrin B, withanolides from physalis peruviana and nicandra physaloides
  作者：Anjana Bagchi、Partha Neogi、Mahendra Sahai、Anil B. Ray、Yoshiteru Oshima、Hiroshi Hikino

  DOI：10.1016/s0031-9422(00)85041-4

  日期：1984.4

  Abstract Novel withanolides, withaperuvin E and nicandrin B, isolated respectively, from Physalis peruviana and Nicandra physaloides , were fully characterized by chemical and spectroscopic means.

  摘要 分别从Physalis peruviana 和Nicandra physaloides 中分离得到的新型withanolides，withaperuvin E 和nicandrin B，通过化学和光谱手段进行了充分的表征。
• 17β-Hydroxywithanolides as Sensitizers of Renal Carcinoma Cells to Tumor Necrosis Factor-α Related Apoptosis Inducing Ligand (TRAIL) Mediated Apoptosis: Structure–Activity Relationships
  作者：Ya-Ming Xu、Alan D. Brooks、E. M. Kithsiri Wijeratne、Curtis J. Henrich、Poonam Tewary、Thomas J. Sayers、A. A. Leslie Gunatilaka

  DOI：10.1021/acs.jmedchem.7b00069

  日期：2017.4.13

  Renal cell carcinoma (RCC) is a cancer with poor prognosis, and the 5-year survival rate of patients with metastatic RCC is 5-10%. Consequently, treatment of metastatic RCC represents an unmet clinical need. Screening of a 50 000 member library of natural and synthetic compounds for sensitizers of RCC cells to TRAIL-mediated apoptosis led to identification of the 17 beta-hydroxywithanolide (17-BHW), withanolide E (1), as a promising lead. To explore structure-activity relationships, we obtained natural and semisynthetic withanolides 1, 2a, 2c, and 3-36 and compared their ability to sensitize TRAIL-mediated apoptosis in a panel of renal carcinoma cells. Our findings revealed that 17-BHWs with a alpha-oriented side chain are superior to known TRAIL-sensitizing withanolides belonging to withaferin A class with a beta-oriented side chain and demonstrated that the 17-BHW scaffold can be modified to enhance sensitization of RCCs to TRAIL-mediated apoptosis, thereby assisting development of natural-product-inspired drugs to treat metastatic RCC.