11-氧代熊果酸 | 105870-59-5

• 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
• 中文名称: 11-氧代熊果酸
• 英文名称: 11-oxoursolic acid
• 英文别名: Obtusilin；(1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bS)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-13-oxo-1,2,3,4,5,6,6a,7,8,8a,10,11,12,14b-tetradecahydropicene-4a-carboxylic acid
• CAS: 105870-59-5
• 化学式: C₃₀H₄₆O₄
• 分子量: 470.693
• InChiKey: MDQJVSLVPQYJLP-HUWCOUCRSA-N

物化性质

• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  34
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

制备方法与用途

Obtusilin 是一种天然产物，可以从赤桉（Eucalyptus camaldulensis）的叶子中分离获得。

反应信息

• 作为反应物：
  描述：

  11-氧代熊果酸 在 chromium(VI) oxide 、 硫酸 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 13.0h， 生成 methyl 3,11-dioxo-urs-12-en-28-oate
  参考文献：
  名称：

  具有胆碱酯酶抑制潜力的熊果酸和齐墩果酸衍生物。

  摘要：

  三萜类化合物是科学关注的焦点，并且在许多药理学应用中对三萜类化合物进行了评估，其中它们具有充当胆碱酯酶抑制剂的能力。这些抑制剂仍然是令人感兴趣的药物，它们可以改善患有与年龄有关的痴呆症（尤其是阿尔茨海默氏病）的痴呆症患者的生活质量。本文中，我们制备了熊果酸和齐墩果酸的几种衍生物，并在Ellman分析中对其抑制乙酰胆碱酯酶和/或丁酰胆碱酯酶的能力进行了筛选，并确定了每种活性化合物的抑制类型。结果，即使在微摩尔范围内，几种化合物也被证明是乙酰胆碱酯酶和丁酰胆碱酯酶的良好抑制剂。熊果酸衍生的羟基-丙烯酰基衍生物10是丁酰胆碱酯酶的竞争性抑制剂，其抑制常数为Ki = 4.29μM，因此，其活性是金标准加兰他敏氢溴酸盐的两倍。然而，最好的乙酰胆碱酯酶抑制剂是2-甲基-3-氧代甲基熊果酸酯（18），它是一种混合型抑制剂，分别显示Ki = 1.72 µM和Ki'= 1.28 µM。

  DOI：

  10.1016/j.bioorg.2018.12.013
• 作为产物：
  描述：

  methyl 3β-acetyloxy-11-oxo-urs-12-en-28-oate 在 氢氧化钾 、 sodium hydroxide 、 乙醇 作用下， 生成 11-氧代熊果酸
  参考文献：
  名称：

  An ocular cat-scratch disease patient positive for cytoplasmic anti-neutrophil cytoplasmic antibody

  摘要：

  Background: We report a case of ocular cat-scratch disease with permanent vision reduction in a patient who was cytoplasmic antineutrophil cytoplasmic antibody (C-ANCA) positive. Methods: Case report and review of the literature. Results: While taking steroids and antibiotics, a 52-year-old man with uveitis associated with cat-scratch disease developed retinal vein occlusion and a macular exudate. His final visual acuity was poor because of residual macular degeneration and optic atrophy. Serum C-ANCA increased and decreased in parallel with ocular inflammatory activity. Conclusion: C-ANCA is an indicator of vasculitis and may be useful as an indicator of severe cat-scratch disease.

  DOI：

  10.1007/s004170100374

文献信息

• Auxiliary-directed oxidation of ursolic acid by ‘Ru’-porphyrins: chemical modulation of cytotoxicity against tumor cell lines
  作者：Katsunori Tanaka、Kishor Mazumder、Eric R.O. Siwu、Satoshi Nozaki、Yasuyoshi Watanabe、Koichi Fukase

  DOI：10.1016/j.tetlet.2012.01.107

  日期：2012.4

  Derivatization of ursolic acid, one of the natural ursene-type pentacyclic triterpenes, was investigated by the oxidation with dioxoruthenium(VI) tetraphenylporphyrins. Oxidation selectivity on the terpene structure was modulated by the auxiliaries introduced on the tetraphenylporphyrin. Chemical oxidation of the ursolic acid affected the cytotoxic activity against tumor cell lines.

  熊果酸（一种天然的熊果型五环三萜烯）的衍生化是通过用二氧合钌（VI）四苯基卟啉进行氧化研究的。通过在四苯基卟啉上引入的助剂调节萜​​烯结构上的氧化选择性。熊果酸的化学氧化影响了针对肿瘤细胞系的细胞毒性活性。
• Preparation of certain derivatives of ursolic acid and their antimicrobial activity
  作者：N. I. Zaletova、A. N. Shchavlinskii、O. N. Tolkachev、S. A. Vichkanova、T. V. Fateeva、N. M. Krutikova、I. V. Yartseva、N. A. Klyuev

  DOI：10.1007/bf00758617

  日期：1986.5

  The authors studied the industrial wastes from the production of an antitumorigenic preparation rosevin, in which about 18% of ursolic acid was found. They obtained several oxygen-substituted derivatives of ursolic acid by oxidation with chromic acid and KMnO/sub 4/ in different media to study their biological activity. The structure of the compounds obtained was confirmed by the data of IR and PMR

  作者研究了生产抗肿瘤制剂 Rosevin 的工业废物，其中发现了约 18% 的熊果酸。他们通过在不同介质中用铬酸和 KMnO/sub 4/ 氧化获得了几种熊果酸的氧取代衍生物，以研究它们的生物活性。所得化合物的结构由IR和PMR光谱数据以及分子质谱数据证实，其中分子在电子撞击下电离。
• Complete assignments of1H and13C NMR resonances of oleanolic acid, 18?-oleanolic acid, ursolic acid and their 11-oxo derivatives
  作者：Werner Seebacher、Nebojsa Simic、Robert Weis、Robert Saf、Olaf Kunert

  DOI：10.1002/mrc.1214

  日期：2003.8

  Complete assignments of 1H and 13C NMR chemical shifts for oleanolic acid, 18α-oleanolic acid, ursolic acid and their 11-oxo derivatives based on 1H, 13C, 2D DQF-COSY, NOESY, HSQC, HMBC and HSQC-TOCSY experiments were achieved. Copyright © 2003 John Wiley & Sons, Ltd.

  基于 1H、13C、2D DQF-COSY、NOESY、HSQC、HMBC 和 HSQC-TOCSY 实验，实现了齐墩果酸、18α-齐墩果酸、熊果酸及其 11-oxo 衍生物 1H 和 13C NMR 化学位移的完整分配。Copyright © 2003 John Wiley & Sons, Ltd. All Rights Reserved.
• Sulfamates of methyl triterpenoates are effective and competitive inhibitors of carbonic anhydrase II
  作者：Stefan Schwarz、Sven Sommerwerk、Susana D. Lucas、Lucie Heller、René Csuk

  DOI：10.1016/j.ejmech.2014.08.051

  日期：2014.10

  Carbonic anhydrase II, belonging to one of the most important enzyme groups of the human body, is a well-studied isozyme from the family of the carbonic anhydrases. Since it is involved in several physiological processes, it has been a pharmaceutical target for many years. In this study we synthesized a number of sulfamates derived from pentacyclic methyl triterpenoates, and we demonstrate their potential as carbonic anhydrase II inhibitors using the well-established photometric 4-nitrophenyl acetate assay. Inhibition constants, as an indicator of their inhibition strength, were in the micromolar range; one compound (10, methyl (3 beta) 3-(aminosulfonyloxy)-oleanoate) showed a K-i value as low as 0.3 mu M. This K-i value is comparable to that of acetazolamide which is a potent carbonic anhydrase inhibitor and a drug for the treatment of glaucoma. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Rusconi,P., Diss. <E.T.H. Zuerich 1940> S. 23
  作者：Rusconi,P.

  DOI：——

  日期：——