4-hydroxy-3,4-secolupane-3,28-dioic acid 3,4-lactone

• 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: 4-hydroxy-3,4-secolupane-3,28-dioic acid 3,4-lactone
• 英文别名: 6-dehydroxy-20,29-dihydroviburolide；(1R,2R,5S,8S,9R,10R,13R,14R,20R)-1,2,14,19,19-pentamethyl-17-oxo-8-propan-2-yl-18-oxapentacyclo[11.9.0.02,10.05,9.014,20]docosane-5-carboxylic acid
• 化学式: C₃₀H₄₈O₄
• 分子量: 472.709
• InChiKey: DQRICWBOKMAKMT-SVAFSPIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  34
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-hydroxy-3,4-secolupane-3,28-dioic acid 3,4-lactone 在 硫酸 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 生成 (3S,4S,5R,8R,9R,10R,13S,14R,15S)-4-(2-carboxyethyl)-4,9,10-trimethyl-15-propan-2-yl-3-prop-1-en-2-yl-2,3,5,6,7,8,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-13-carboxylic acid
  参考文献：
  名称：

  A-ring modified betulinic acid derivatives as potent cancer preventive agents

  摘要：

  Ten new 3,4-seco betulinic acid (BA) derivatives were designed and synthesized. Among them, compounds 7-15 exhibited enhanced chemopreventive ability in an in vitro short-term 12-O-tetradecanoylphorbol- 13-acetate (TPA) induced Epstein-Barr virus early antigen (EBV-EA) activation assay in Raji cells. Specifically, analogs with a free C-28 carboxylic acid, including 7, 8, 11, and 13, inhibited EBV-EA activation significantly. The most potent compound 8 displayed 100% inhibition at 1 x 10(3) mol ratio/TPA and 73.4%, 35.9%, and 8.4% inhibition at 5 x 10(2), 1 x 10(2), and 1 x 10 mol ratio/TPA, respectively, comparable with curcumin at high concentration and better than curcumin at low concentration. The potent chemopreventive activity of novel seco A-ring BAs (8 and 11) was further confirmed in an in vivo mouse skin carcinogenesis assay. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.041
• 作为产物：
  描述：

  路路通酸 在 palladium on activated charcoal 、 氢气 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 溶剂黄146 为溶剂， 生成 4-hydroxy-3,4-secolupane-3,28-dioic acid 3,4-lactone
  参考文献：
  名称：

  A-ring modified betulinic acid derivatives as potent cancer preventive agents

  摘要：

  Ten new 3,4-seco betulinic acid (BA) derivatives were designed and synthesized. Among them, compounds 7-15 exhibited enhanced chemopreventive ability in an in vitro short-term 12-O-tetradecanoylphorbol- 13-acetate (TPA) induced Epstein-Barr virus early antigen (EBV-EA) activation assay in Raji cells. Specifically, analogs with a free C-28 carboxylic acid, including 7, 8, 11, and 13, inhibited EBV-EA activation significantly. The most potent compound 8 displayed 100% inhibition at 1 x 10(3) mol ratio/TPA and 73.4%, 35.9%, and 8.4% inhibition at 5 x 10(2), 1 x 10(2), and 1 x 10 mol ratio/TPA, respectively, comparable with curcumin at high concentration and better than curcumin at low concentration. The potent chemopreventive activity of novel seco A-ring BAs (8 and 11) was further confirmed in an in vivo mouse skin carcinogenesis assay. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.041

文献信息

• A Novel Secobetulinic Acid 3,4-Lactone from Viburnum aboricolum
  作者：Yuan-Ling Ku、G. Venkateswara Rao、Chung-Hsiung Chen、Chi Wu、Jih-Hwa Guh、Shoei-Sheng Lee

  DOI：10.1002/hlca.200390068

  日期：2003.3

  Bio-assay-guided fractionation of the CHCl3-soluble extract from the leaves of Viburnum aboricolum led to the isolation of a novel secobetulinic acid 3,4-lactone, viburolide (=(6β)-4,6-dihydroxy-3,4-secolup-20(29)-ene-3,28-dioic acid 3,4-lactone; 1). This is the first lupane-type compound possessing such a lactone skeleton from natural products. Its structure was elucidated by spectral analysis and

  生物测定引导的氯仿的分馏3可溶提取物的叶荚蒾aboricolum导致了新颖secobetulinic酸3,4-内酯的隔离，viburolide（=（6 β）-4,6-二羟基-3-， 4-secolup-20（29）-烯-3,28-二酸3,4-内酯; 1）。这是第一种具有这种来自天然产物的内酯骨架的紫杉烷型化合物。通过光谱分析阐明了其结构，并与由桦木酸苄酯（2）制得的6-脱羟基-20,29-二氢维布洛利（6）进行了比较。发现化合物6以12.3μM的IC 50抑制非雄激素依赖性人前列腺癌细胞（PC-3）。
• A-ring modified betulinic acid derivatives as potent cancer preventive agents
  作者：Hsin-Yi Hung、Kyoko Nakagawa-Goto、Harukuni Tokuda、Akira Iida、Nobutaka Suzuki、Ibrahim D. Bori、Keduo Qian、Kuo-Hsiung Lee

  DOI：10.1016/j.bmcl.2013.12.041

  日期：2014.2

  Ten new 3,4-seco betulinic acid (BA) derivatives were designed and synthesized. Among them, compounds 7-15 exhibited enhanced chemopreventive ability in an in vitro short-term 12-O-tetradecanoylphorbol- 13-acetate (TPA) induced Epstein-Barr virus early antigen (EBV-EA) activation assay in Raji cells. Specifically, analogs with a free C-28 carboxylic acid, including 7, 8, 11, and 13, inhibited EBV-EA activation significantly. The most potent compound 8 displayed 100% inhibition at 1 x 10(3) mol ratio/TPA and 73.4%, 35.9%, and 8.4% inhibition at 5 x 10(2), 1 x 10(2), and 1 x 10 mol ratio/TPA, respectively, comparable with curcumin at high concentration and better than curcumin at low concentration. The potent chemopreventive activity of novel seco A-ring BAs (8 and 11) was further confirmed in an in vivo mouse skin carcinogenesis assay. (C) 2013 Elsevier Ltd. All rights reserved.