gypsogenin 28-O-α-D-galactopyranosyl-(1->6)-β-D-glucopyranosyl-(1->6)-[β-D-glucopyranosyl-(1->3)]-β-D-glucopyranosyl ester | 1028100-31-3

• 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: gypsogenin 28-O-α-D-galactopyranosyl-(1->6)-β-D-glucopyranosyl-(1->6)-[β-D-glucopyranosyl-(1->3)]-β-D-glucopyranosyl ester
• 英文别名: gypsogenin 28-O-α-D-galactopyranosyl’-(1→6)-β-D-glucopyranosyl-(1 →6)[β-D-glucopyranosyl-(1→3)]-β-D-glucopyranosylester；[(2S,3R,4S,5R,6R)-3,5-dihydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxymethyl]oxan-2-yl] (4aS,6aR,6aS,6bR,8aR,9S,10S,12aR,14bS)-9-formyl-10-hydroxy-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• CAS: 1028100-31-3
• 化学式: C₅₄H₈₆O₂₄
• 分子量: 1119.26
• InChiKey: JLSIUEOHGXDDEP-BIRCXJCDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  78
• 可旋转键数：
  14
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  391
• 氢给体数：
  14
• 氢受体数：
  24

反应信息

• 作为反应物：
  描述：

  gypsogenin 28-O-α-D-galactopyranosyl-(1->6)-β-D-glucopyranosyl-(1->6)-[β-D-glucopyranosyl-(1->3)]-β-D-glucopyranosyl ester 在 盐酸 作用下， 反应 4.0h， 生成 可得然胶 、 β-半乳糖苷酶 、 (3β, 4α)-3-羟基-23-氧代齐墩果-12-烯-28-酸
  参考文献：
  名称：

  New triterpenoid saponins with strong α-glucosidase inhibitory activity from the roots of Gypsophila oldhamiana

  摘要：

  Seven new triterpenoid saponins (1-7), have been isolated and elucidated from the roots of Gypsophila oldhamiana together with five known triterpenoid saponins (8-12). These saponins which could be classified into three series: 3-O-monoglucosides (1, 8, 9), 28-O-monoglucosides (24, 12) and 3, 28-O-bidesmosides (5-7, 10, 11), have been evaluated for their a-glucosidase inhibition activity. As a result, the preliminary structure-activity relationships were discussed based on the position of sugar linkage attached to the aglycone, and 28-O-monoglucosides 2-4 and 12 showed significant inhibitory activities on a-glucosidase. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.12.053
• 作为产物：
  描述：

  3-O-acetyl gypsogenin 28-O-2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl’-(1→6)-2,3,4-tri-O-benzoyl-β-D-glucopyranosyl-(1→6)[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1→3)]-2,4-O-acetyl-β-D-glucopyranoside 在 甲醇 、 sodium methylate 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以56%的产率得到gypsogenin 28-O-α-D-galactopyranosyl-(1->6)-β-D-glucopyranosyl-(1->6)-[β-D-glucopyranosyl-(1->3)]-β-D-glucopyranosyl ester
  参考文献：
  名称：

  从满天星满天星及其衍生物作为α-葡萄糖苷酶抑制剂 的根源中合成新的三萜皂苷

  摘要：

  以无味的2-甲基-5-叔丁基苯基（Mbp）硫代糖苷和N-苯基三氟乙酰亚氨酸酯供体为关键步骤，有效而有效地实现了三萜皂苷1及其衍生物2-3的首次合成，和它们对α葡糖苷酶和α淀粉酶抑制活性进行评价体外。初步的结构-活性关系研究表明，C4-CHO和C4-CH 2 OH对α-葡萄糖苷酶抑制活性不是必需的。在这三种化合物中，化合物3表现出对α-葡萄糖苷酶的显着抑制活性，IC 50为值为9.17μM。根据Dixon图上的截距确定为9.35μM的K i，抗α-葡萄糖苷酶的更强皂苷3可能是非竞争性抑制模式。同时，计算化合物1-3的亲脂性，作为药理效力的预测。根据预测的log  P值，亲脂性可能与评估的生物学潜能相关。

  DOI：

  10.1039/c6nj01602b

文献信息

• Concise synthesis of a new triterpenoid saponin from the roots of Gypsophila oldhamiana and its derivatives as α-glucosidase inhibitors
  作者：Qingchao Liu、Tiantian Guo、Fahui Li、Dong Li

  DOI：10.1039/c6nj01602b

  日期：——

  The first synthesis of the triterpenoid saponin 1 and its derivatives 2–3 was efficiently achieved in an efficient and practical strategy with an odourless 2-methyl-5-tert-butylphenyl (Mbp) thioglycoside and a N-phenyltrifluoroacetimidate donor as a key step, and their inhibitory activities against α-glucosidase and α-amylase were evaluated in vitro. The preliminary structure–activity relationship

  以无味的2-甲基-5-叔丁基苯基（Mbp）硫代糖苷和N-苯基三氟乙酰亚氨酸酯供体为关键步骤，有效而有效地实现了三萜皂苷1及其衍生物2-3的首次合成，和它们对α葡糖苷酶和α淀粉酶抑制活性进行评价体外。初步的结构-活性关系研究表明，C4-CHO和C4-CH 2 OH对α-葡萄糖苷酶抑制活性不是必需的。在这三种化合物中，化合物3表现出对α-葡萄糖苷酶的显着抑制活性，IC 50为值为9.17μM。根据Dixon图上的截距确定为9.35μM的K i，抗α-葡萄糖苷酶的更强皂苷3可能是非竞争性抑制模式。同时，计算化合物1-3的亲脂性，作为药理效力的预测。根据预测的log  P值，亲脂性可能与评估的生物学潜能相关。
• New triterpenoid saponins with strong α-glucosidase inhibitory activity from the roots of Gypsophila oldhamiana
  作者：Jian-Guang Luo、Li Ma、Ling-Yi Kong

  DOI：10.1016/j.bmc.2007.12.053

  日期：2008.3.15

  Seven new triterpenoid saponins (1-7), have been isolated and elucidated from the roots of Gypsophila oldhamiana together with five known triterpenoid saponins (8-12). These saponins which could be classified into three series: 3-O-monoglucosides (1, 8, 9), 28-O-monoglucosides (24, 12) and 3, 28-O-bidesmosides (5-7, 10, 11), have been evaluated for their a-glucosidase inhibition activity. As a result, the preliminary structure-activity relationships were discussed based on the position of sugar linkage attached to the aglycone, and 28-O-monoglucosides 2-4 and 12 showed significant inhibitory activities on a-glucosidase. (C) 2008 Elsevier Ltd. All rights reserved.