12-O-benzoyllineolon | 19308-48-6

• 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: 12-O-benzoyllineolon
• 英文别名: 12β-benzoyloxy-3β,8,14-trihydroxy-14β,17βH-pregn-5-en-20-one；12β-Benzoyloxy-3β,8,14-trihydroxy-14β,17βH-pregn-5-en-20-on；12-O-Benzoyl-lineolon；[(3S,8S,9R,10R,12R,13S,14R,17R)-17-acetyl-3,8,14-trihydroxy-10,13-dimethyl-2,3,4,7,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-12-yl] benzoate
• CAS: 19308-48-6
• 化学式: C₂₈H₃₆O₆
• 分子量: 468.59
• InChiKey: QYGCNWGDTWSRCZ-XYCCFREGSA-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：
  0.64
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  12-O-benzoyllineolon 在 氢氧化钾 作用下， 生成 lineolon
  参考文献：
  名称：

  的根的糖苷Pachycarpus线纹（DECNE。）BULLOCK（或P. Schweinfurthii（NE BR。）BULLOCK）苷和苷元，第一部分201 †往最‡

  摘要：

  Pachycarpus lineolatus（DECNE。）BULLOCK的根包含复杂的酯糖苷混合物，可通过温和的酸水解将其分解为糖和genin-糖苷混合物。这些糖主要由D-cymarose和一种新的生物玫瑰组成，可以被认为是thevetosido-cymarose。

  DOI：

  10.1002/hlca.19590420340
• 作为产物：
  描述：

  12-O-benzoyllineolon 3-O-β-D-glucopyranosyl-(1->4)-O-β-D-diginopyranosyl-(1->4)-O-β-D-cymaropyranosyl-(1->4)-β-D-cymaropyranoside 在 盐酸 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.5h， 以3.8 mg的产率得到12-O-benzoyllineolon
  参考文献：
  名称：

  Amurensiosides A–K, 11 new pregnane glycosides from the roots of Adonis amurensis

  摘要：

  Five new pregnane tetraglycosides, amurensiosides A-E (1-5), two new pregnane hexaglycosides, amurensiosides F(6) and 1(9), two new 18-norpregnane hexaglycosides,amurensiosides G (7) and H (8), and two new pregnane octaglycosides, amurensiosides J (10) and K(11), were isolated from the MeOH extract of the roots of Adonis amurensis. The structures of the new compounds were determined on the basis of extensive spectroscopic analysis, including two-dimensional (2D) NMR data, and the results of hydrolytic cleavage. The isolated compounds were evaluated for their cytotoxic activity against HSC-2 human oral squamous cell carcinoma cells. (C) 2009 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2009.10.008

文献信息

• Indonesian Medicinal Plants. I. Chemical Structures of Calotroposides A and B, Two New Oxypregnane-Oligoglycosides from the Root of Calotropis gigantea (Asclepiadaceae).
  作者：Isao KITAGAWA、Ru-song ZHANG、Jong Dae PARK、Nam In BAEK、Yasuyuki TAKEDA、Masayuki YOSHIKAWA、Hirotaka SHIBUYA

  DOI：10.1248/cpb.40.2007

  日期：——

  Two new oxypregnane-oligoglycosides named calotroposides A (1) and B (2) have been isolated from the root of Calotropis gigantea (Asclepiadaceae), an Indonesian medicinal plant, and their chemical structures have been elucidated by chemical and spectroscopic methods as 12-O-benzoyllineolon 3-O-β-D-cymaropyranosyl(1→4)-β-D-oleandropyranosyl(1→4)-β-D-oleandropyranosyl(1→4)-β-D-cymaropyranosyl(1→4)-β-D-cymaropyranoside and 12-O-benzoylde-acetylmetaplexigenin 3-O-β-D-cymaropyranosyl(1→4)-β-D-oleandropyranosyl(1→4)-β-D-oleandropyranosyl(1→4)-β-D-cymaropyranosyl(1→4)-β-D-cymaropyranoside, respectively.

  从印度尼西亚药用植物Calotropis gigantea（夷果科）的根中分离出两种新型氧孕烷寡糖苷，分别命名为calotroposides A (1) 和B (2)。通过化学和光谱方法阐明了它们的化学结构，分别为12-O-苯甲酰林诺酮 3-O-β-D-醋酸甲酰基(1→4)-β-D-油菜糖基(1→4)-β-D-油菜糖基(1→4)-β-D-醋酸甲酰基(1→4)-β-D-醋酸甲酰基苷和12-O-苯甲酰-去乙酰基甲基生物雌激素 3-O-β-D-醋酸甲酰基(1→4)-β-D-油菜糖基(1→4)-β-D-油菜糖基(1→4)-β-D-醋酸甲酰基(1→4)-β-D-醋酸甲酰基苷。