3β,6β,23-trihydroxyolean-12-en-28-oic acid 28-O-β-D-glucopyranoside | 1332859-40-1

• 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: 3β,6β,23-trihydroxyolean-12-en-28-oic acid 28-O-β-D-glucopyranoside
• 英文别名: 3beta,6beta,23-trihydroxyolean-12-en-28-oic acid 28-O-beta-D-glucopyranoside；[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (4aS,6aR,6aS,6bR,8R,8aR,9R,10S,12aR,14bS)-8,10-dihydroxy-9-(hydroxymethyl)-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: 1332859-40-1
• 化学式: C₃₆H₅₈O₁₀
• 分子量: 650.851
• InChiKey: ACQGRYACYVKOBB-ONXNPAKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  46
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  177
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  3β,6β,23-trihydroxyolean-12-en-28-oic acid 28-O-β-D-glucopyranoside 在 盐酸 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 生成 3β,6β,23- trihydroxyolean-12-en-28-oic acid 、 葡萄糖
  参考文献：
  名称：

  Anti-inflammatory Triterpenoid Saponins from the Stem Bark of Kalopanax pictus

  摘要：

  Five new compounds, 16,23,29-trihydroxy-3-oxo-olean-12-en-28-oic acid (1), 4,23,29-trihydroxy-3,4-seco-olean-12-en-3-oate-28-oic acid (2), 3 beta,6 beta,23-trihydroxyolean-12-en-28-oic acid 28-O-beta-D-glucopyranoside (3), 3-O-[2,3-di-O-acetyl-alpha-L-arabinopyranosyl]hederagenin 28-O-alpha-L-rhamnopyranosyl-(1 -> 4)-beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranoside (4), and 3-O-[3,4-di-O-acetyl-alpha-L-arabinopyranosyl]hederagenin 28-O-alpha-L-rhamnopyranosyl-(1 -> 4)-beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranoside (5), as well as 10 known compounds (6-15), were isolated from the stem bark of Kalopanax pictus. Compounds 1-5 and 7-14 inhibited TNF alpha-induced NF-kappa B transcriptional activity in HepG2 cells in a dose-dependent manner, with IC(50) values ranging from 0.6 to 16.4 mu M. Furthermore, the transcriptional inhibitory function of these compounds was confirmed on the basis of decreases in COX-2 and iNOS gene expression in HepG2 cells. The structure activity relationship of the compounds with respect to anti-inflammatory activity is also discussed.

  DOI：

  10.1021/np200382s

文献信息

• Anti-inflammatory Triterpenoid Saponins from the Stem Bark of <i>Kalopanax pictus</i>
  作者：Tran H. Quang、Nguyen T. T. Ngan、Chau V. Minh、Phan V. Kiem、Nguyen X. Nhiem、Bui H. Tai、Nguyen P. Thao、Nguyen H. Tung、Seok B. Song、Young H. Kim

  DOI：10.1021/np200382s

  日期：2011.9.23

  Five new compounds, 16,23,29-trihydroxy-3-oxo-olean-12-en-28-oic acid (1), 4,23,29-trihydroxy-3,4-seco-olean-12-en-3-oate-28-oic acid (2), 3 beta,6 beta,23-trihydroxyolean-12-en-28-oic acid 28-O-beta-D-glucopyranoside (3), 3-O-[2,3-di-O-acetyl-alpha-L-arabinopyranosyl]hederagenin 28-O-alpha-L-rhamnopyranosyl-(1 -> 4)-beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranoside (4), and 3-O-[3,4-di-O-acetyl-alpha-L-arabinopyranosyl]hederagenin 28-O-alpha-L-rhamnopyranosyl-(1 -> 4)-beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranoside (5), as well as 10 known compounds (6-15), were isolated from the stem bark of Kalopanax pictus. Compounds 1-5 and 7-14 inhibited TNF alpha-induced NF-kappa B transcriptional activity in HepG2 cells in a dose-dependent manner, with IC(50) values ranging from 0.6 to 16.4 mu M. Furthermore, the transcriptional inhibitory function of these compounds was confirmed on the basis of decreases in COX-2 and iNOS gene expression in HepG2 cells. The structure activity relationship of the compounds with respect to anti-inflammatory activity is also discussed.