3β-hydroxy-18α-oleanen-(12)-one-(11) | 38242-02-3

• 物质功能分类: 天然产物 - 萜类
• 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-hydroxy-18α-oleanen-(12)-one-(11)
• 英文别名: 3β-Hydroxy-18α-oleanen-(12)-on-(11)；(4aR,6aR,6aS,6bR,8aR,10S,12aS,14bS)-10-hydroxy-2,2,4a,6a,6b,9,9,12a-octamethyl-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picen-13-one
• CAS: 38242-02-3
• 化学式: C₃₀H₄₈O₂
• 分子量: 440.71
• InChiKey: UKAIYBGRLWQHDQ-VEAZXVKRSA-N

物化性质

• 熔点：
  175 °C
• 沸点：
  524.0±49.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  32
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

制备方法与用途

生物活性

β-阿米烯农醇（11-氧代-β-阿马烯）是一种甘草根中的齐墩果型三萜，是甘草次酸的前体。它具有抗增殖和抗炎活性，并可作为合成许多三萜类化合物的骨架。

体外研究

β-阿米烯农醇（11-氧代-β-阿马烯）抑制HL60细胞生长，其IC50值为26.3 μM。在THP-1细胞中，β-阿米烯农醇（11-氧代-β-阿马烯）（100 μM）显著减少了脂多糖诱导的TNFα释放。

CYP88D6 通过体外酶活性测定被表征，并显示出催化 β-阿马烯在 C-11 的逐步两步氧化生成 β-阿米烯农醇（11-氧代-β-阿马烯）的能力。将 CYP88D6 和 β-阿马烯合成酶共表达于酵母中，也催化了 β-阿马烯的体内氧化生成 β-阿米烯农醇。

反应信息

• 作为反应物：
  描述：

  3β-hydroxy-18α-oleanen-(12)-one-(11) 、 苯甲酰氯 在 吡啶 作用下， 生成 3β-Benzoyloxyolean-12-en-11-on
  参考文献：
  名称：

  三萜。第三十六部分 18α-油精-12-en-3β-ol衍生物的反应及α-amyrin的立体化学观察

  摘要：

  DOI：

  10.1039/jr9550002125
• 作为产物：
  描述：

  3β-hydroxyolean-12-en-11-one acetate 在 氢氧化钾 作用下， 生成 3β-hydroxy-18α-oleanen-(12)-one-(11)
  参考文献：
  名称：

  Long-term glycemic control measurements in diabetic patients receiving hemodialysis

  摘要：

  Cardiovascular morbidity is increased in patients with diabetes mellitus and there is a great prevalence of diabetes and cardiovascular disease among patients with end-stage renal disease (ESRD). Control of glycemia can decrease cardiovascular and end-organ damage. Because the validity of glycemic control tests have not been rigorously studied in patients with ESRD, we evaluated the value of various measures in these patients. The overall clinical goal was to investigate whether hemoglobin A(1)C (A(1)C) accurately reflects actual glycemic control as compared with other measures in light of the importance of attaining appropriately controlled blood glucose (BG). The commonly used tests of total glycated hemoglobin (GHb) and A(1)C may be unreliable in patients with ESRD because of the presence of anemia, shortened red blood cell (RBC) survival, and assay interferences from uremia. The primary aim of this study was to assess the relationship of capillary BG measurements to A(1)C, GHb, total glycated plasma proteins (GPP), and fructosamine (Fr) in diabetic patients receiving hemodialysis. Twenty-three patients were instructed to obtain BG evaluations twice daily for 7 days by using the Elite glucometer (Bayer Corporation, Elkhart, IN). These determinations included 6 fasting, 6 preprandial, and 3 separate 2-hour postprandial levels. Blood was obtained on day 7 for measurement of A(1)C, GHb, GPP, and Fr. A(1)C was analyzed by an immunoassay, GPP and GHb were assayed by affinity high-performance liquid chromatography (HPLC), and Fr by automated nitroblue colorimetric assay. Scatter plots were generated by plotting the average BG versus A(1)C, GHb, GPP, or Fr. Linear regression was performed for each plot showing the following relationships: A(1)C = 0.0174 (BG) + 4.76 (r = 0.58; P < 0.05): GHb = 0.0371 (BG) + 3.57 (r = 0.584; P < 0.05): GPP = 0.0083 (BG) + 26.13 (r = 0.065; P = 0.77): Fr = 0.6865 (BG) + 250 (r = 0.345; P = 0.11). Despite anemia and shortened RBC lifespan in patients with ESRD, A(1)C in the range of 6% to 7% estimates glycemic control similarly to patients without severe renal impairment. A(1)C values above 7.5% may overestimate hyperglycemia in patients with ESRD. Thus, diabetic patients receiving hemodialysis may have long-term BG that are more properly controlled than previously determined, reducing their risks of the macro- and microvascular complications of diabetes mellitus. (C) 2002 by the National Kidney Foundation, Inc.

  DOI：

  10.1053/ajkd.2002.30549

文献信息

• 736. Triterpene resinols and related acids. Part XXIV. 18-iso-β-Amyranol
  作者：Richard Budziarek、William Manson、F. S. Spring

  DOI：10.1039/jr9510003336

  日期：——
• Long-term glycemic control measurements in diabetic patients receiving hemodialysis
  作者：Melanie S. Joy、William T. Cefalu、Susan L. Hogan、Patrick H. Nachman

  DOI：10.1053/ajkd.2002.30549

  日期：2002.2

  Cardiovascular morbidity is increased in patients with diabetes mellitus and there is a great prevalence of diabetes and cardiovascular disease among patients with end-stage renal disease (ESRD). Control of glycemia can decrease cardiovascular and end-organ damage. Because the validity of glycemic control tests have not been rigorously studied in patients with ESRD, we evaluated the value of various measures in these patients. The overall clinical goal was to investigate whether hemoglobin A(1)C (A(1)C) accurately reflects actual glycemic control as compared with other measures in light of the importance of attaining appropriately controlled blood glucose (BG). The commonly used tests of total glycated hemoglobin (GHb) and A(1)C may be unreliable in patients with ESRD because of the presence of anemia, shortened red blood cell (RBC) survival, and assay interferences from uremia. The primary aim of this study was to assess the relationship of capillary BG measurements to A(1)C, GHb, total glycated plasma proteins (GPP), and fructosamine (Fr) in diabetic patients receiving hemodialysis. Twenty-three patients were instructed to obtain BG evaluations twice daily for 7 days by using the Elite glucometer (Bayer Corporation, Elkhart, IN). These determinations included 6 fasting, 6 preprandial, and 3 separate 2-hour postprandial levels. Blood was obtained on day 7 for measurement of A(1)C, GHb, GPP, and Fr. A(1)C was analyzed by an immunoassay, GPP and GHb were assayed by affinity high-performance liquid chromatography (HPLC), and Fr by automated nitroblue colorimetric assay. Scatter plots were generated by plotting the average BG versus A(1)C, GHb, GPP, or Fr. Linear regression was performed for each plot showing the following relationships: A(1)C = 0.0174 (BG) + 4.76 (r = 0.58; P < 0.05): GHb = 0.0371 (BG) + 3.57 (r = 0.584; P < 0.05): GPP = 0.0083 (BG) + 26.13 (r = 0.065; P = 0.77): Fr = 0.6865 (BG) + 250 (r = 0.345; P = 0.11). Despite anemia and shortened RBC lifespan in patients with ESRD, A(1)C in the range of 6% to 7% estimates glycemic control similarly to patients without severe renal impairment. A(1)C values above 7.5% may overestimate hyperglycemia in patients with ESRD. Thus, diabetic patients receiving hemodialysis may have long-term BG that are more properly controlled than previously determined, reducing their risks of the macro- and microvascular complications of diabetes mellitus. (C) 2002 by the National Kidney Foundation, Inc.
• Triterpenoids. Part XXXVI. Reactions of 18α-olean-12-en-3β-ol derivatives and observations on the stereochemistry of α-amyrin
  作者：G. G. Allan、F. S. Spring

  DOI：10.1039/jr9550002125

  日期：——