6β,16α-dihydroxyhederagenin 3-O-β-D-glucuronopyranoside | 1350446-53-5

• 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: 6β,16α-dihydroxyhederagenin 3-O-β-D-glucuronopyranoside
• 英文别名: (2S,3S,4S,5R,6R)-6-[[(3S,4R,4aR,5R,6aR,6bS,8R,8aR,12aS,14aR,14bR)-8a-carboxy-5,8-dihydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• CAS: 1350446-53-5
• 化学式: C₃₆H₅₆O₁₂
• 分子量: 680.833
• InChiKey: BHTVLQLEKSLXBO-ITSBEUCGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  48
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  214
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  6β,16α-dihydroxyhederagenin 3-O-β-D-glucuronopyranoside 在 盐酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 3.0h， 生成 D-葡萄糖醛酸
  参考文献：
  名称：

  Effect of triterpenes and triterpene saponins from the stem bark of Kalopanax pictus on the transactivational activities of three PPAR subtypes

  摘要：

  Kalopanax pictus (Araliaceae) is a deciduous tree that grows in East Asian countries. Its stem bark and leaves have been used in traditional medicine to treat rheumatic arthritis, neurotic pain, and diabetes mellitus. A phytochemical study on a methanol extract of the stem bark of K. pictus resulted in the isolation of three new compounds, 6 beta,16 alpha-dihydroxy-hederagenin 3-O-beta-D-glucuronopyranoside (1), 3-O-beta-D-glucuronopyranosyl-28-O-beta-D-glucopyranosyl-6 beta,16 alpha-dihydroxy-oleanolic acid (2), and 3-O-beta-D-galactopyranosyl(1 -> 3)-alpha-L-arabinopyranosyl hederagenin 28-O-beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranosyl ester (3), along with eight known compounds (4-11). Their structures were established on the basis of chemical and spectroscopic methods (IR, 1D and 2D NMR, and HRESITOFMS). Compounds 1-6 and 8-10 upregulated PPARs transcriptional activity in a dose-dependent manner in HepG2 cells, with EC50 values in the range 0.20-15.5 mu M. Moreover, the specific PPAR transactivational effects of compounds 1-6 and 8-10 on separate PPAR subtypes, PPAR alpha, -gamma, and -beta(delta) were further investigated. Compounds 4,5,8, and 10 showed significant PPAR alpha transactivational activity, with EC50 values of 7.8, 8.0, 10.3, and 17.3 mu M. respectively. Compounds 2,4,6, and 8-10 exhibited PPAR7 dose-dependent transactivational activity, with EC50 values of 14.7, 15.5, 14.8, 10.9, 17.1, and 16.3 mu M, whereas compounds 8 and 10 significantly upregulated PPAR beta(delta) transcriptional activity, with EC50 values of 15.7 and 17.7 mu M, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.08.029