(3β)-3-3,4,5-trimethoxyphenacyl-20(29)-lupaene-28-oic acid

• 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)-3-3,4,5-trimethoxyphenacyl-20(29)-lupaene-28-oic acid
• 英文别名: (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-9-(3,4,5-trimethoxybenzoyl)oxy-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
• 化学式: C₄₀H₅₈O₇
• 分子量: 650.896
• InChiKey: KJXFOVDPXHPXLU-LWDDMNJASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.4
• 重原子数：
  47
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  白桦脂酸 、 3,4,5-三甲氧基苯甲酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 以27.6%的产率得到(3β)-3-3,4,5-trimethoxyphenacyl-20(29)-lupaene-28-oic acid
  参考文献：
  名称：

  Synthesis of triterpenoid derivatives and their anti-tumor and anti-hepatic fibrosis activities

  摘要：

  Oleanolic acid (1), ursolic acid (2), hederagenin (3), betulinol (4), betulinic acid (5), and glycyrrhetinic acid (6) are obtained from acorn/licorice industrial wastes with common triterpenoid structure as a model set for esterification. Eight 3,4,5-methoxybenzoyl triterpenoid derivatives (1a-6a), including four new derivatives (1a, 3a-1, 3a-2, and 3a-3), are synthesized by classical procedures. Their antitumor and anti-hepatic fibrosis activities are evaluated on four human tumor cell lines and t-HSC/Cl-6 cells. Derivative 1a shows maximum antiproliferative effects against all cell lines, especially against tumor cells with IC50 values in the range of 5.32-15.23 mu M, but does not affect the viability of normal cells. The anti-tumor mechanisms of 1a are also investigated by western blot and docking studies. The 3,4,5-methoxybenzoyl triterpenoids offers an intriguing solution for naturally derived antitumor drugs and may be invaluable for further development of cancer therapy.

  DOI：

  10.1080/14786419.2018.1499642

文献信息

• New betulinic acid derivatives as potent proteasome inhibitors
  作者：Keduo Qian、Sang-Yong Kim、Hsin-Yi Hung、Li Huang、Chin-Ho Chen、Kuo-Hsiung Lee

  DOI：10.1016/j.bmcl.2011.07.072

  日期：2011.10

  study, 22 new betulinic acid (BA) derivatives were synthesized and tested for their inhibition of the chymotrypsin-like activity of 20S proteasome. From the SAR study, we concluded that the C-3 and C-30 positions are the pharmacophores for increasing the proteasome inhibition effects, and larger lipophilic or aromatic side chains are favored at these positions. Among the BA derivatives tested, compounds

  在这项研究中，合成了 22 种新的桦木酸 (BA) 衍生物并测试了它们对 20S 蛋白酶体的胰凝乳蛋白酶样活性的抑制作用。从 SAR 研究中，我们得出结论，C-3 和 C-30 位置是增加蛋白酶体抑制作用的药效团，并且在这些位置有利于较大的亲脂或芳香侧链。在测试的BA衍生物，化合物13，20，和21显示出最好的蛋白酶体抑制活性，IC 50个分别1.42，1.56，和1.80μM，的值，它是三至四倍比蛋白酶体抑制控制LLM-F更有效和乳胱氨酸。
• Tobacco Caterpillar Antifeedent from the Gotti Stem Wood Triterpene Betulinic Acid
  作者：S. G. Jagadeesh、G. L. David Krupadanam、G. Srimannarayana、S. Samba Murthy、Amarjit Kaur、S. S. Raja

  DOI：10.1021/jf970768b

  日期：1998.7.1

  Betulinic acid (I), a pentacyclic triterpene, on derivatization gives six compounds: 3 beta-hydroxylup-20(29)-en-28 oic acid methyl ester (II), 3 beta-acetoxylup-20(29)-en-28-oic acid (III), 3 beta-allyloxylup-20(29)-en-28-oic acid (TV), 3 beta-p-methylcinnamatoxylup-20(29)-en-28-oic acid (V), 3 beta-p-methoxycinnamatoxylup-20(29)-en-28-oic acid (VI), and 3 beta-tri-O-methylgallotoxylup-20(29)-en-28 acid (VII). Their antifeedent activity against the agricultural pest tobacco caterpillar larvae (Spodoptera litura F) in a no-choice laboratory study showed the active compounds are V, VI, and VII.
• Synthesis of triterpenoid derivatives and their anti-tumor and anti-hepatic fibrosis activities
  作者：Jing Xu、Xude Wang、Hongyu Zhang、Jiayin Yue、Yuanyuan Sun、Xiaoshu Zhang、Yuqing Zhao

  DOI：10.1080/14786419.2018.1499642

  日期：2020.3.18

  Oleanolic acid (1), ursolic acid (2), hederagenin (3), betulinol (4), betulinic acid (5), and glycyrrhetinic acid (6) are obtained from acorn/licorice industrial wastes with common triterpenoid structure as a model set for esterification. Eight 3,4,5-methoxybenzoyl triterpenoid derivatives (1a-6a), including four new derivatives (1a, 3a-1, 3a-2, and 3a-3), are synthesized by classical procedures. Their antitumor and anti-hepatic fibrosis activities are evaluated on four human tumor cell lines and t-HSC/Cl-6 cells. Derivative 1a shows maximum antiproliferative effects against all cell lines, especially against tumor cells with IC50 values in the range of 5.32-15.23 mu M, but does not affect the viability of normal cells. The anti-tumor mechanisms of 1a are also investigated by western blot and docking studies. The 3,4,5-methoxybenzoyl triterpenoids offers an intriguing solution for naturally derived antitumor drugs and may be invaluable for further development of cancer therapy.