3β-(formyloxy)-urs-12-en-28-oic acid | 6227-55-0

• 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-(formyloxy)-urs-12-en-28-oic acid
• 英文别名: (1S,2R,4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-formyloxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-4a-carboxylic acid
• CAS: 6227-55-0
• 化学式: C₃₁H₄₈O₄
• 分子量: 484.72
• InChiKey: OECMCPLQZXRLFK-QHQGJMPNSA-N

物化性质

• 沸点：
  562.9±50.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  35
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  甲酸 、 熊果酸 反应 6.0h， 以90%的产率得到3β-(formyloxy)-urs-12-en-28-oic acid
  参考文献：
  名称：

  过氧化氢的立体化学-熊果酸及相关化合物的乙酸氧化。

  摘要：

  使用NMR数据和X射线分析确定了熊果酸的许多氧化衍生物的立体化学。在1 H和13 C NMR光谱中对26种天然和合成的类熊烷三萜类化合物进行了全信号分配。根据原料和某些中间物种的化学行为和分子力学计算，提出了乌索酸和相关化合物被过酸氧化的可能机理，以及次级过程的机理。

  DOI：

  10.1016/s0040-4020(01)89285-1

文献信息

• Ursolic acid derivatives as potential antidiabetic agents: <i>In vitro</i> , <i>in vivo</i> , and <i>in silico</i> studies
  作者：Ricardo Guzmán-Ávila、Virginia Flores-Morales、Paolo Paoli、Guido Camici、Juan José Ramírez-Espinosa、Litzia Cerón-Romero、Gabriel Navarrete-Vázquez、Sergio Hidalgo-Figueroa、Maria Yolanda Rios、Rafael Villalobos-Molina、Samuel Estrada-Soto

  DOI：10.1002/ddr.21422

  日期：2018.3

  Hit, Lead & Candidate Discovery

  命中，线索和候选发现
• Antibacterial and Antioxidant Activities of Ursolic Acid and Derivatives
  作者：Patrícia do Nascimento、Telma Lemos、Ayla Bizerra、Ângela Arriaga、Daniele Ferreira、Gilvandete Santiago、Raimundo Braz-Filho、José Costa

  DOI：10.3390/molecules19011317

  日期：——

  Ursolic acid, an important bioactive compound, was isolated from ethanol extract of aerial parts of Sambucus australis. In order to develop bioactive ursolic acid derivatives, two semi-synthetic compounds were obtained through modification at C-3. The antibacterial activity of the ursolic acid and its derivatives was investigated. The microdilution method was used for determination of the minimal inhibitory concentration (MIC), against twelve bacterial strains. The influence of ursolic acid and its derivatives on the susceptibility of some bacterial pathogens to the aminoglycosides antibiotics neomycin, amikacin, kanamycin and gentamicin was evaluated. The most representative synergistic effect was observed by 3β-formyloxy-urs-12-en-28-oic acid at the concentration of 64 μg/mL in combination with kanamycin against Escherichia coli (27), a multidrug-resistant clinical isolate from sputum, with reduction of MIC value from 128 μg/mL to 8 μg/mL. Ursolic acid and its derivatives were examined for their radical scavenger activity using the DPPH assay, and showed significant activity.

  熊果酸是一种重要的生物活性化合物，它是从三叶草（Sambucus australis）气生部分的乙醇提取物中分离出来的。为了开发具有生物活性的熊果酸衍生物，通过对 C-3 进行修饰，获得了两种半合成化合物。研究了熊果酸及其衍生物的抗菌活性。采用微量稀释法测定了对 12 种细菌菌株的最小抑菌浓度（MIC）。研究还评估了熊果酸及其衍生物对一些细菌病原体对氨基糖苷类抗生素新霉素、阿米卡星、卡那霉素和庆大霉素敏感性的影响。最具代表性的协同作用是 3β-formyloxy-urs-12-en-28-oic acid 与卡那霉素（kanamycin）联用（浓度为 64 μg/mL）对大肠埃希菌（27）（一种从痰中分离出来的耐多种药物的临床菌株）的作用，其 MIC 值从 128 μg/mL 降至 8 μg/mL。熊果酸及其衍生物采用 DPPH 法检测其自由基清除剂活性，结果表明它们具有显著的活性。
• Hemodialysis-associated hypertension: Pathophysiology and therapy
  作者：Matthias P. Hörl、Walter H. Hörl

  DOI：10.1053/ajkd.2002.30542

  日期：2002.2

  The majority of end-stage renal disease (ESRD) patients are hypertensive. Hypertension in the hemodialysis patient population is multifactorial. Further, hypertension is associated with an increased risk for left ventricular hypertrophy, coronary artery disease, congestive heart failure, cerebrovascular complications, and mortality. Anti hypertensive medications alone do not adequately control blood pressure (BP) in hemodialysis patients. There are, however, several therapeutic options available to normalize BP in these patients, often without the need for additional drug therapy (eg, long, slow hemodialysis; short, daily hemodialysis; nocturnal hemodialysis; or, most effectively, dietary salt and fluid restriction in combination with reduction of dialysate sodium concentration). Optimal BP in dialysis patients is not different from recommendations for the general population, even though definite evidence is not yet available. Predialysis systolic and diastolic BPs are of particular importance. Left ventricular mass correlates with predialysis systolic BP. Survival is better in hemodialysis patients with a mean arterial pressure below 99 mm Hg as compared with those with higher BP. Low predialysis systolic BP (<110 mm Hg) and low predialysis diastolic BP (<70 mm Hg) are associated with increased mortality, primarily because of severe congestive heart failure or coronary artery disease. Patients that experience repeated intradialytic hypotensive episodes should also be viewed with caution, and predialytic BP values should be reevaluated. A possible treatment option for these patients may be slow, long hemodialysis; short, daily hemodialysis; or nocturnal hemodialysis. Among the anti hypertensive agents currently available, angiotensin-converting enzyme (ACE) inhibitors appear to have the greatest ability to reduce left ventricular mass. Pressure load can be satisfactorily determined by using the average value of predialysis BP measurements over 1 month. In selected hemodialysis patients, interdialytic ambulatory blood pressure monitoring (ABPM) may help to determine if the patient is in fact hypertensive. In addition, ABPM provides important information about the change in BP between day and night. Regular home BP monitoring, yearly echocardiography, and treatment of traditional risk factors for cardiovascular disease are recommended. (C) 2002 by the National Kidney Foundation, Inc.