3β-hydroxyoleana-9(11),12-dien-28-oic acid | 226562-46-5

• 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-hydroxyoleana-9(11),12-dien-28-oic acid
• 英文别名: 3β-hydroxyolean-9(11),12-dien-28-oic acid；3β-hydroxyolean-9,12-dien-28-oic acid；eucalyptanoic acid；eucalytptanoic acid；3β-hydroxy-oleanadien-(9(11).12)-oic acid-(28)；3β-Hydroxy-oleanadien-(9(11).12)-saeure-(28)；(4aS,6aR,6bS,8aR,10S,12aS,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,14b-dodecahydropicene-4a-carboxylic acid
• CAS: 226562-46-5
• 化学式: C₃₀H₄₆O₃
• 分子量: 454.693
• InChiKey: KICUTMUDQMLBSF-GWKPGGNQSA-N

物化性质

• 沸点：
  567.0±50.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  33
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3β-hydroxyoleana-9(11),12-dien-28-oic acid 在 吡啶 作用下， 以 甲醇 、 乙醚 为溶剂， 生成 methyl (4aS,6aR,6bS,8aR,10S,12aS,14bS)-10-acetoxy-2,2,6a,6b,9,9,12a-heptamethyl -1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14b-hexadecahydropicene-4a(2H)-carboxylate
  参考文献：
  名称：

  Structure and Spasmolytic Activity of Eucalyptanoic Acid from Eucalyptus camaldulensis var. obtusa and Synthesis of Its Active Derivative from Oleanolic Acid

  摘要：

  A new triterpenoid acid named eucalyptanoic acid (1) has been isolated from the fresh uncrushed leaves of Eucalyptus camaldulensis var. obtusa along with two known constituents, beta-sitosterol (2) and betulinic acid (3). The structure of 1 has been established as 3beta-hydroxyolean-9(11),12-dien-28-oic acid through spectral studies including 1D and 2D NMR. 1 and its acetyl (1a) and acetylmethyl (1b) derivatives were tested for spasmolytic activity. 1b was found to be the most active spasmolytic, mediated through blockade of calcium influx at 1 mg/mL. In the present study lb was also prepared starting from oleanolic acid (4). Acetylation. of 4 gave 4a, which on methylation afforded 4b. Reaction of 4b with N-bromosuccinimide (NBS) furnished 1b. Hence 4 may be regarded as the biogenetic precursor of 1. Compounds 4 and 4a were found inactive at 1 mg/mL,while 4b was moderately active in showing spasmolytic activity.

  DOI：

  10.1021/np020127x
• 作为产物：
  描述：

  齐墩果酸 在 lead(IV) tetraacetate 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以20%的产率得到3β-hydroxyoleana-9(11),12-dien-28-oic acid
  参考文献：
  名称：

  通过靶向Brk / Paxillin / Rac1轴发现齐墩果酸及其类似物作为乳腺癌细胞迁移和侵袭抑制剂的类似物的发现，优化和药理学建模

  摘要：

  生物测定指导的Terminalia bentzoe L.的叶分离甲醇提取物确定了已知的三萜齐墩果酸（1）是其主要的乳腺癌细胞迁移抑制剂。进一步的化学优化，得到了五个新（9 - 12和15）和七个已知的（4 - 8，13，和14）的半合成类似物。测试所有化合物抑制人乳腺癌MDA-MB-231细胞迁移，增殖和侵袭的能力。结果显示3‐ O‐ [ N‐（3′‐氯苯磺酰基）‐氨基甲酰基】‐油酸（11）和3‐O‐ö - [ ñ - （5'-氟苯磺酰基） -氨基甲酰基] -oleanolic酸（12）是在低温的最活跃的命中μ米浓度。Western blot分析表明活性1，11，和12可能至少部分与抑制Brk / Paxillin / Rac1信号通路有关。进行了药理学建模研究，以更好地了解对于抗迁移活性重要的常见结构结合表位。具有最佳体积的缺电子苯环的磺酰基氨基甲酰基部分与改善的活性有关。这项研究是第一个通过靶向Brk

  DOI：

  10.1111/cbdd.12380

文献信息

• Semi-synthesis of taraxerane triterpenoids from oleanolic acid
  作者：Antonio Martinez、Alberto Perojil、Francisco Rivas、Marta Medina-O'Donnell、Andres Parra

  DOI：10.1016/j.tet.2014.12.064

  日期：2015.2

  The semi-syntheses of taraxerane triterpenoids by diverse bromination processes and other reactions, from oleanolic acid and some closely related derivatives, have been performed. For all the reactions performed, suitable mechanisms to explain the formation of these derivatives have been proposed.

  已经通过齐墩果酸和一些密切相关的衍生物通过不同的溴化过程和其他反应进行了塔拉蒽烷三萜类化合物的半合成。对于所有进行的反应，已经提出了解释这些衍生物形成的合适机理。
• A Series of Oleanolic Acid Derivatives as Anti-Hepatitis B Virus Agents: Design, Synthesis, and in Vitro and in Vivo Biological Evaluation
  作者：Wenqiang Yan、Chenze Zhang、Bi Li、Xin Xu、Miao Liang、Shun Gu、Fuhao Chu、Bing Xu、Jian Ren、Penglong Wang、Haimin Lei

  DOI：10.3390/molecules21040402

  日期：——

  introduction of conjugated alkadiene and epoxy ring moieties formed by means of photosensitized oxidation. Eosin Y was used as photosensitizer during this process. Next the cytotoxicity of the products was evaluated on HepG2.2.15 cells to determine the appropriate treatment concentration for the subsequent experiments. Most of the OA derivatives exhibited anti-HBV antigens secretion activity in HepG2.2.15 cells

  通过多种反应合成了一系列齐墩果酸衍生物，包括引入共轭二烯和通过光敏氧化形成的环氧环部分。在此过程中，曙红 Y 用作光敏剂。接下来在HepG2.2.15细胞上评估产物的细胞毒性以确定后续实验的合适处理浓度。大多数OA衍生物在HepG2.2.15细胞中表现出抗HBV抗原分泌活性。在测试的化合物中，OA-4 (3.13 µg/mL) 对 HBsAg、HBeAg 和 HBV DNA 复制的分泌显示出显着的活性，抑制率为 90.52% ± 1.78%、31.55% ± 3.65% 和 94.57% ± 3.11 % 分别在 6 天后。此外，在DHBV感染的鸭模型中进一步研究了OA-4。当 OA-4 以 500 mg/kg 的剂量给药时，结果显示在第 5、10 和 3 天对 DHBV 的显着抑制作用分别为 19.94% ± 2.87%、28.80% ± 3.62% 和 29.25% ± 2.65% OA-4
• Kitasato, Acta Phytochimica, 1936, vol. 9, p. 43,61, 75
  作者：Kitasato

  DOI：——

  日期：——
• Midazolam attenuates ketamine-induced abnormal perception and thought process but not mood changes
  作者：Manzo Suzuki、Kentaro Tsueda、Peter S. Lansing、Merritt M. Tolan、Thomas M Fuhrman、Rachel A. Sheppard、Harrell E. Hurst、Steven B. Lippmann

  DOI：10.1007/bf03019666

  日期：2000.9

  Purpose: To determine the effects of midazolam, 30 ng.mL(-1), on altered perception, mood, and cognition induced by ketamine.Methods: After ketamine was administered to achieve target concentrations of 50, 100, or 150 ng.mL(-1) in 11 volunteers, perception, mood, and thought process were assessed by a visual analog scale. Mini-Mental State examination (MMSE) assessed cognition. Boluses of midazolam, 30, 14.5, and 12 mu g.kg(-1), were injected every 30 min to maintain the plasma concentration at 30 ng.mL(-1), which was reached 30 min after each injection.Results: Ketamine produced changes in perception about the body (P < 0.01, 0.001, and 0.0001 at 30, 60, and 90 min), surroundings (P < 0.01 and 0.0001 at 60 and 90 min), time (P < 0.002 and 0.0001 at 60 and 90 min), reality (P < 0.001 and 0.0001 at 60 and 90 min), sounds (P < 0.002 at 90 min), and meaning(P < 0.05 at 30 min), Subjects felt less energetic and clearheaded (P < 0.02 and 0.05) during ketamine, midazolam, and their coadministration. Ketamine impaired thought process (P < 0.003 and 0.0001 at 60 and 90 min). Ketamine and midazolam decreased mean total MMSE and recall scores (P < 0.001 for both). Go-administration reduced the number of subjects with perceptual (body, P < 0.01 and 0.001 at 30 and 60 min) and thought process abnormalities. Within the range of observation, co-administration did not affect the changes in mood or recall.Conclusion: Midazolam attenuates ketamine-induced changes in perception and thought process.
• Structure and Spasmolytic Activity of Eucalyptanoic Acid from <i>Eucalyptus camaldulensis</i> var. <i>obtusa</i> and Synthesis of Its Active Derivative from Oleanolic Acid
  作者：Sabira Begum、Ishrat Sultana、Bina S. Siddiqui、Farhana Shaheen、Anwar H. Gilani

  DOI：10.1021/np020127x

  日期：2002.12.1

  A new triterpenoid acid named eucalyptanoic acid (1) has been isolated from the fresh uncrushed leaves of Eucalyptus camaldulensis var. obtusa along with two known constituents, beta-sitosterol (2) and betulinic acid (3). The structure of 1 has been established as 3beta-hydroxyolean-9(11),12-dien-28-oic acid through spectral studies including 1D and 2D NMR. 1 and its acetyl (1a) and acetylmethyl (1b) derivatives were tested for spasmolytic activity. 1b was found to be the most active spasmolytic, mediated through blockade of calcium influx at 1 mg/mL. In the present study lb was also prepared starting from oleanolic acid (4). Acetylation. of 4 gave 4a, which on methylation afforded 4b. Reaction of 4b with N-bromosuccinimide (NBS) furnished 1b. Hence 4 may be regarded as the biogenetic precursor of 1. Compounds 4 and 4a were found inactive at 1 mg/mL,while 4b was moderately active in showing spasmolytic activity.