tuberogenin | 1333407-05-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: tuberogenin
• CAS: 1333407-05-8
• 化学式: C₂₁H₃₂O₄
• 分子量: 348.483
• InChiKey: VFEQYVNWMXYPSY-PVUCAENGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  25.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  tuberoside l1 在 硫酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 生成 tuberogenin
  参考文献：
  名称：

  8,12;8,20-Diepoxy-8,14-secopregnane glycosides from roots of Asclepias tuberosa and their effect on proliferation of human skin fibroblasts

  摘要：

  A pregnane glycoside fraction from the roots of Asclepias tuberose L. caused normal human skin fibroblasts to proliferate. This fraction contained 21 pregnane glycosides whose structures were established using NMR spectroscopic analysis and chemical evidence. The aglycones of most of these compounds were identified as 8,12;8,20-diepoxy-8,14-secopregnanes, such as tuberogenin or 5,6-didehydrotuberogenin, the same aglycones as constituents of the aerial parts of this plant. Some of these compounds also caused proliferation of skin fibroblasts. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2011.05.012

文献信息

• New 8,12;8,20-diepoxy-8,14-secopregnane hexa- and hepta-glycosides from the roots of Asclepias tuberosa
  作者：Tsutomu Warashina、Toshio Miyase

  DOI：10.1007/s11418-017-1155-9

  日期：2018.1

  Previously, phytochemical investigation of the roots of Asclepias tuberosa (Asclepiadaceae) led to the isolation of some 8,12;8,20-diepoxy-8,14-secopregnane tri-, tetra-, and penta-glycosides. An additional eight new minor 8,12;8,20-diepoxy-8,14-secopregnane glycosides were afforded in the recent investigation of this plant. These glycosides consisted of six or seven 2,6-dideoxy-hexopyranoses together

  以前，对萝摩（Asclepias tuberosa）（萝摩科）的根进行植物化学研究导致分离出约8,12; 8,20-二环氧-8,14-仲高碳烷三，四和五糖苷。在最近对该植物的研究中，还提供了另外八种新的较小的8,12; 8,20-二环氧-8,14-secopregnane糖苷。这些糖苷由六个或七个2,6-二脱氧-己吡喃糖以及糖苷配基，结核菌素组成。这些化合物的结构均使用NMR，质谱分析和化学证据确定。由于仅在结节曲霉中观察到8,12; 8,20-二环氧-8,14-二巯基戊烷型糖苷，这些化合物被认为是该植物的特征植物化学物质。
• 8,12;8,20-Diepoxy-8,14-secopregnane Glycosides from the Aerial Parts of Asclepias tuberosa
  作者：Tsutomu Warashina、Tadataka Noro

  DOI：10.1248/cpb.58.172

  日期：——

  Further study of constituents from the aerial parts of Asclepias tuberosa afforded twenty-two new steroidal glycosides along with tuberoside B(5) and G(5). These glycosides were confirmed to contain 8,12;8,20-diepoxy-8,14-secopregnanes, tuberogenin and its congeners, as their aglycones. The structure of each of these compounds was elucidated based on the interpretation of NMR and MS measurements and

  进一步研究了来自菌核的空中部分的成分，提供了22种新的甾体糖苷以及块茎B（5）和G（5）。确认这些糖苷含有8,12; 8,20-二环氧-8,14-二巯基葡聚糖，结核菌素及其同系物作为糖苷配基。根据NMR和MS测量的解释以及化学证据，阐明了每种化合物的结构。
• 8,14-Secopregnane glycosides from the aerial parts of Asclepias tuberosa
  作者：Tsutomu Warashina、Tadataka Noro

  DOI：10.1016/j.phytochem.2009.07.033

  日期：2009.7

  Twenty pregnane glycosides, tuberoside A(1)-L(5), were isolated from the diethyl ether-soluble fraction of the MeOH extract from the aerial parts of Asclepias tuberosa (Asclepiadaceae). The pregnane glycosides were composed of 8,12;8,20-diepoxy-8,14-secopregnane as aglycon, and D-cymarose, D-oleandrose, D-digitoxose and/or D-glucose as the component sugars. Their structures were established using NMR

  二十种孕烷苷，即马铃薯苷 A(1)-L(5)，是从马蓼（马尾科）地上部分的 MeOH 提取物的乙醚可溶部分中分离出来的。孕烷苷由 8,12;8,20-diepoxy-8,14-secopregnane 作为苷元和 D-cymarose、D-oleandrose、D-digitoxose 和/或 D-glucose 作为成分糖组成。它们的结构是使用核磁共振光谱分析和化学方法确定的。