oleanolic acid monomethyl ether

• 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: oleanolic acid monomethyl ether
• 英文别名: (3β)-3-methoxyolean-12-en-28-oic acid；3β-methoxyolean-12-en-28-oic acid；3β-methoxyoleanolic acid；(4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-methoxy-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: C₃₁H₅₀O₃
• 分子量: 470.736
• InChiKey: CFDOCMGYUBAVED-JBYJGCOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  34
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  oleanolic acid monomethyl ether 在 chromium(VI) oxide 、 甲醇 、 potassium carbonate 、 溶剂黄146 、 sodium hydroxide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 (2α, 3β) methyl 3,12-dihydroxy-11-oxo-olean-12-en-28-oate
  参考文献：
  名称：

  齐墩果酸吲哚衍生物作为新型抗炎药的体外和体内研究：合成、生物学评价和机理分析

  摘要：

  齐墩果酸（OA）是一种众所周知的天然产物，具有许多重要的药理活性；然而，其微弱的生物活性严重限制了其在药物开发中的潜在应用。齐墩果酸的结构修饰是增强其生物活性且毒性较低的有效手段，但具有挑战性。在本研究中，我们系统地合成了一系列新的11 oxooleanolic酸衍生物，并用感应的LPS评价了它们的抗炎活性BV2细胞炎症模型和12- ö十四烷诱导的耳炎症佛波醇-13-乙酸酯（TPA）小鼠模型。发现化合物8和9显示出比 OA 更有效的抗炎作用，并表现出低细胞毒性。还研究了可能的作用机制。在体外和体内结果表明，这两种新的 11-氧代齐墩果酸衍生物可能通过抑制 NO、促炎细胞因子和趋化因子（IL-1β、IL-6、IL-12、TNF-α、MCP-1 和MIP-1α) 和抗炎细胞因子 (IL-10) 的上调，这可能与抑制 NF-κB、MAPKs 和 PI3K/Akt 相关炎症信号通路的激活和 Nrf2/HO-1

  DOI：

  10.1016/j.bioorg.2021.104981
• 作为产物：
  描述：

  oleanolic acid 3-O-β-D-galactosyl(1->4)-O-β-D-galactopyranoside 在 硫酸 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 oleanolic acid monomethyl ether
  参考文献：
  名称：

  来自决明花的两种鼠李素双半乳糖苷和一种齐墩果酸双半乳糖苷

  摘要：

  摘要 来自决明子的花，两​​种新的鼠李素苷，3-半乳糖基(1→4)-吡喃半乳糖苷和相关的3-半乳糖基(1→6)吡喃半乳糖苷，以及齐墩果酸3-半乳糖基(1→4)-吡喃半乳糖苷已被隔离。这三种糖苷早期尚未从任何植物来源中分离出来。还获得了已知的化合物槲皮素、二十二烷醇、巴西棕榈醇、蜡醇和二十八烷醇。

  DOI：

  10.1016/s0031-9422(82)85087-5

文献信息

• Bismuth(III) Triflate-Based Catalytic Direct Opening of Oleanolic Hydroxy-γ-lactones to Afford 12-Oxo-28-carboxylic Acids
  作者：Jorge A. R. Salvador、Vânia M. Moreira、Rui M. A. Pinto、Ana S. Leal、Christophe Le Roux

  DOI：10.1002/adsc.201100155

  日期：2011.10

  The bismuth(III) triflate-based catalytic direct opening of oleanolic hydroxy-γ-lactones affords the corresponding 12-oxo-28-carboxylic acid derivatives, in both acetonitrile and dichloromethane, at reflux, in high yields. Participation of an in situ generated Brønsted acid species from bismuth(III) triflate is most likely involved in the reaction mechanism. Full structural elucidation of the products

  齐墩果酸羟基-γ-内酯的基于三氟甲磺酸铋（III）的催化直接打开以高收率在乙腈和二氯甲烷中提供了相应的在乙腈和二氯甲烷中的12-氧代-28-羧酸衍生物。的参与原位生成从铋（III），三氟甲磺酸是最有可能参与反应机理布朗斯台德酸物质。已通过1D和2D NMR技术对所得产物进行了完整的结构阐明。
• Efficient oxidation of oleanolic acid derivatives using magnesium bis(monoperoxyphthalate) hexahydrate (MMPP): A convenient 2-step procedure towards 12-oxo-28-carboxylic acid derivatives
  作者：Jorge A R Salvador、Vânia M Moreira、Rui M A Pinto、Ana S Leal、José A Paixão

  DOI：10.3762/bjoc.8.17

  日期：——

  straightforward and high yielding procedure to convert oleanolic acid derivatives into the corresponding delta-hydroxy-gamma-lactones, by using the convenient oxidizing agent magnesium bis(monoperoxyphthalate) hexahydrate (MMPP) in refluxing acetonitrile, is reported. In addition, a two-step procedure for the preparation of oleanolic 12-oxo-28-carboxylic acid derivatives directly from Delta(12)-oleananes

  报道了通过在回流乙腈中使用方便的氧化剂双（单过氧邻苯二甲酸酯）六水合物 (MMPP) 镁，将齐墩果酸衍生物转化为相应的 δ-羟基-γ-内酯的一种新的、直接且高产的方法。此外，直接从 Delta(12)-齐墩果烷制备齐墩果酸 12-氧代-28-羧酸衍生物的两步程序，无需中间后处理，并在两个步骤中保持相同的反应溶剂, 被描述为应用于 3,12-dioxoolean-28-oic 酸的合成。
• Synthesis of oleanolic acid derivatives: In vitro, in vivo and in silico studies for PTP-1B inhibition
  作者：Juan José Ramírez-Espinosa、Maria Yolanda Rios、Paolo Paoli、Virginia Flores-Morales、Guido Camici、Vianey de la Rosa-Lugo、Sergio Hidalgo-Figueroa、Gabriel Navarrete-Vázquez、Samuel Estrada-Soto

  DOI：10.1016/j.ejmech.2014.09.036

  日期：2014.11

  Non-insulin dependent diabetes mellitus is a multifactorial disease that links different metabolic routes: a point of convergence is the enzyme PTP-1B which turns off insulin and leptin receptors involved in glucose and lipid metabolism, respectively. Pentacyclic acid triterpenes such as oleanolic acid (OA) have proved to be excellent PTP-1B inhibitors, thus, the purpose of current work was to generate a series of derivatives that improve the pharmacological effect of OA. Our findings suggest that the presence of the carboxylic acid and/or its corresponding reduction product carbinol derivative (H-bond donor) in C-28 is required to maintain the inhibitory activity: moreover, this is further enhanced by ester or ether formation on C-3. The most active derivatives were cinnamoyl ester (6) and ethyl ether (10). Compound 6 showed potent in vitro inhibitory activity and significantly decrease of blood glucose levels on in vivo experiments. Meanwhile, 10 showed contrasting outcomes, since it was the compound with higher inhibitory activity and selectivity over PTP-1B and has improved interaction with site B, according with docking studies, the in vivo antidiabetic effect was similar to oleanolic acid. In conclusion, oleanolic acid derivatives have revealed an enhanced inhibitory effect over PTP-1B activity by increasing molecular interactions with either catalytic or allosteric sites and producing a hypoglycaemic effect on non insulin dependent diabetes mellitus rat model. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Two rhamnetin digalactosides and an oleanolic acid digalactoside from the flowers of Cassia laevigata
  作者：J. Singh

  DOI：10.1016/s0031-9422(82)85087-5

  日期：1982.1

  Abstract From the flowers of Cassia laevigata , two new rhamnetin glycosides, the 3-galactosyl(1→4)- galactopyranoside and the related 3-galactosyl(1→6)galactopyranoside, and oleanolic acid 3-galactosyl(1→4)- galactopyranoside have been isolated. These three glycosides have not been isolated earlier from any plant source. The known compounds quercetin, docosyl alcohol, carnaubyl alcohol, ceryl alcohol

  摘要 来自决明子的花，两​​种新的鼠李素苷，3-半乳糖基(1→4)-吡喃半乳糖苷和相关的3-半乳糖基(1→6)吡喃半乳糖苷，以及齐墩果酸3-半乳糖基(1→4)-吡喃半乳糖苷已被隔离。这三种糖苷早期尚未从任何植物来源中分离出来。还获得了已知的化合物槲皮素、二十二烷醇、巴西棕榈醇、蜡醇和二十八烷醇。
• The in vitro and in vivo study of oleanolic acid indole derivatives as novel anti-inflammatory agents: Synthesis, biological evaluation, and mechanistic analysis
  作者：Jingwei Jin、Hao He、Xinyue Zhang、Rihui Wu、Lishe Gan、Dongli Li、Yujing Lu、Panpan Wu、Wing-Leung Wong、Kun Zhang

  DOI：10.1016/j.bioorg.2021.104981

  日期：2021.8

  is challenging. In the present study, we systematically synthesized a series of new 11-oxooleanolic acid derivatives and evaluated their anti-inflammatory activities with a LPS induced BV2 cells inflammation model and a 12-O-tetradecanoyl phorbol-13-acetate (TPA) induced ear inflammation mice model. It was found that compounds 8 and 9 show more potent anti-inflammatory effects than OA and exhibit a

  齐墩果酸（OA）是一种众所周知的天然产物，具有许多重要的药理活性；然而，其微弱的生物活性严重限制了其在药物开发中的潜在应用。齐墩果酸的结构修饰是增强其生物活性且毒性较低的有效手段，但具有挑战性。在本研究中，我们系统地合成了一系列新的11 oxooleanolic酸衍生物，并用感应的LPS评价了它们的抗炎活性BV2细胞炎症模型和12- ö十四烷诱导的耳炎症佛波醇-13-乙酸酯（TPA）小鼠模型。发现化合物8和9显示出比 OA 更有效的抗炎作用，并表现出低细胞毒性。还研究了可能的作用机制。在体外和体内结果表明，这两种新的 11-氧代齐墩果酸衍生物可能通过抑制 NO、促炎细胞因子和趋化因子（IL-1β、IL-6、IL-12、TNF-α、MCP-1 和MIP-1α) 和抗炎细胞因子 (IL-10) 的上调，这可能与抑制 NF-κB、MAPKs 和 PI3K/Akt 相关炎症信号通路的激活和 Nrf2/HO-1