3-O-acetylmaslinic 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: 3-O-acetylmaslinic acid
• 英文别名: (4aS,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-10-acetoxy-11-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid；(4aS,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-10-acetyloxy-11-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• 化学式: C₃₂H₅₀O₅
• 分子量: 514.746
• InChiKey: SFIVNCSFGSWUOR-PROZZQCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  37
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-O-acetylmaslinic acid 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 山楂酸
  参考文献：
  名称：

  来自榄仁树根皮的 3-乙酰山楂酸

  摘要：

  摘要 从榄仁树的根皮中分离到了一种新的三萜酸3-乙酰山楂酸，与齐墩果酸、阿姜酸、阿朱酚酸和熊果苷。

  DOI：

  10.1016/s0031-9422(00)84538-0
• 作为产物：
  描述：

  山楂酸 、 乙酸酐 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以78%的产率得到3-O-acetylmaslinic acid
  参考文献：
  名称：

  三萜酸的若丹明B缀合物即使在纳摩尔浓度下也具有细胞毒性的mitocan

  摘要：

  三萜酸1 - 6显示出在所有非常低的或无细胞毒性，但其相应的2,3-二- ø -乙酰基-哌嗪基酰胺13 - 18显示出低的EC 50值，几种人肿瘤细胞系。但是，它们对非恶性小鼠成纤维细胞NIH 3T3的细胞毒性也很高。甲显著改善，即制备若丹明B色衍生物达到19 - 24。尽管若丹明B没有细胞毒性（最高浓度为30μM–分析的临界值），但三萜类哌嗪间隔的若丹明B衍生物在纳摩尔浓度下却具有细胞毒性。化合物24（一种二乙酰化山梨酸衍生物）对几种人类肿瘤细胞系的毒性最高，而对小鼠成纤维细胞NIH 3T3的毒性较小。染色和双重染色实验表明，有24个充当线粒体。

  DOI：

  10.1016/j.ejmech.2016.12.040

文献信息

• Semi-synthesis of acylated triterpenes from olive-oil industry wastes for the development of anticancer and anti-HIV agents
  作者：Andres Parra、Samuel Martin-Fonseca、Francisco Rivas、Fernando J. Reyes-Zurita、Marta Medina-O'Donnell、Antonio Martinez、Andres Garcia-Granados、Jose A. Lupiañez、Fernando Albericio

  DOI：10.1016/j.ejmech.2013.12.049

  日期：2014.3

  A broad set of potential bioactive conjugate compounds has been semi-synthesized through solution and solid-phase organic procedures, coupling two natural pentacyclic triterpene acids, oleanolic (OA) and maslinic acids (MA), at the hydroxyl groups of the A-ring of the triterpene skeleton, with 10 different acyl groups. These acyl OA and MA derivatives have been tested for their anti-proliferative (against the bl6f10 murine melanoma cancer cells) and antiviral (as inhibitors of the HIV-1-protease) effects. Several derivatives have shown high levels of early and total apoptosis (up to 90%). Most of the compounds that exhibited anti-proliferative effects also generated ROS, probably involving the activation of an intrinsic apoptotic route. The only four compounds that did not cause the release of ROS could be related to the participation of a probable extrinsic activation of the apoptosis mechanism. A great number of these acyl OA and MA derivatives have proved to be potent inhibitors of the HIV-1-protease, the most active inhibitors having IC50 values between 0.31 and 15.6 mu M, these values being between 4 and 186 times lower than their non-acylated precursors. The potent activities exhibited in the apoptosis-activation processes and in the inhibition of the HIV-1-protease by some OA and MA acylated derivatives imply that these compounds could be used as new, safe, and effective anticancer and/or antiviral drugs. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Rhodamine B conjugates of triterpenoic acids are cytotoxic mitocans even at nanomolar concentrations
  作者：Sven Sommerwerk、Lucie Heller、Christoph Kerzig、Annemarie E. Kramell、René Csuk

  DOI：10.1016/j.ejmech.2016.12.040

  日期：2017.2

  Triterpenoic acids 1–6 exhibited very low or no cytotoxicity at all, but their corresponding 2,3-di-O-acetyl-piperazinyl amides 13–18 showed low EC50 values for several human tumor cell lines. Their cytotoxicity, however, was also high for the non-malignant mouse fibroblasts NIH 3T3. A significant improvement was achieved by preparing the rhodamine B derivatives 19–24. While rhodamine B is not cytotoxic

  三萜酸1 - 6显示出在所有非常低的或无细胞毒性，但其相应的2,3-二- ø -乙酰基-哌嗪基酰胺13 - 18显示出低的EC 50值，几种人肿瘤细胞系。但是，它们对非恶性小鼠成纤维细胞NIH 3T3的细胞毒性也很高。甲显著改善，即制备若丹明B色衍生物达到19 - 24。尽管若丹明B没有细胞毒性（最高浓度为30μM–分析的临界值），但三萜类哌嗪间隔的若丹明B衍生物在纳摩尔浓度下却具有细胞毒性。化合物24（一种二乙酰化山梨酸衍生物）对几种人类肿瘤细胞系的毒性最高，而对小鼠成纤维细胞NIH 3T3的毒性较小。染色和双重染色实验表明，有24个充当线粒体。
• 3-acetylmaslinic acid from the root bark of Terminalia alata
  作者：A.S.R. Anjaneyulu、A.V.Raghava Reddy、Gopal R. Mallavarapu、R.S. Chandrasekhara

  DOI：10.1016/s0031-9422(00)84538-0

  日期：1986.1

  Abstract A new triterpene acid, 3-acetylmaslinic acid, has been isolated from the root bark of Terminalia alata together with oleanolic acid, arjunic acid, arjunolic acid and arjunetin.

  摘要 从榄仁树的根皮中分离到了一种新的三萜酸3-乙酰山楂酸，与齐墩果酸、阿姜酸、阿朱酚酸和熊果苷。