astraisoolesaponin A₁

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: astraisoolesaponin A₁
• 英文别名: (2S,3S,4S,5R,6R)-6-[[(1S,2R,5R,6S,7S,10R,11R,13S,17S)-17-carboxy-13-hydroxy-6-(hydroxymethyl)-1,2,6,10,17-pentamethyl-19-oxo-7-pentacyclo[12.9.0.02,11.05,10.015,21]tricosa-14,20-dienyl]oxy]-5-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxyoxane-2-carboxylic acid
• 化学式: C₄₈H₇₂O₂₁
• 分子量: 985.087
• InChiKey: VPYLFAXATJMRTE-VBUWARIUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  69
• 可旋转键数：
  10
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  349
• 氢给体数：
  12
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  astraisoolesaponin A₁ 在 硫酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 1.0h， 生成 L-鼠李糖 、 葡萄糖 、 D-葡萄糖醛酸
  参考文献：
  名称：

  Rearranged oleanane type saponins, astraisoolesaponins A 1 –A 3 and B, from the stems of Astragalus membranaceus (Fisch.) Bge. var. mongholicus (Bge.) Hsiao

  摘要：

  Four novel saponins, astraisoolesaponins A(1)-A(3) and B (1-4) were isolated from the stems of Astragalus membranaceus (Fisch.) Bge. var. mongholicus (Bge.) Hsiao. Spectroscopic analysis indicated that 1-4 are the first example of saponins possessing a 28-methyl-rearranged carbon skeleton. Their absolute configurations were determined by electronic circular dichroism (ECD) calculations. Both 3 and 4 displayed triglyceride accumulation inhibitory effects in HepG2 cells and glucose uptake increase effects on L6 cells. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2016.09.034

文献信息

• Rearranged oleanane type saponins, astraisoolesaponins A 1 –A 3 and B, from the stems of Astragalus membranaceus (Fisch.) Bge. var. mongholicus (Bge.) Hsiao
  作者：Yi Zhang、Yuan-Qiang Guo、Xiao-Xia Li、Jing-Ya Ruan、Ting-Ting Wang、Jian Li、Li-Feng Han、Hai-Yang Yu、Tao Wang

  DOI：10.1016/j.tet.2016.09.034

  日期：2016.11

  Four novel saponins, astraisoolesaponins A(1)-A(3) and B (1-4) were isolated from the stems of Astragalus membranaceus (Fisch.) Bge. var. mongholicus (Bge.) Hsiao. Spectroscopic analysis indicated that 1-4 are the first example of saponins possessing a 28-methyl-rearranged carbon skeleton. Their absolute configurations were determined by electronic circular dichroism (ECD) calculations. Both 3 and 4 displayed triglyceride accumulation inhibitory effects in HepG2 cells and glucose uptake increase effects on L6 cells. (C) 2016 Elsevier Ltd. All rights reserved.