13(S)-HODE cholesteryl ester | 33783-77-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 13(S)-HODE cholesteryl ester
• 英文别名: [(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] (9Z,11E,13S)-13-hydroxyoctadeca-9,11-dienoate
• CAS: 33783-77-6；141554-21-4
• 化学式: C₄₅H₇₆O₃
• 分子量: 665.097
• InChiKey: RZXYPSUQZUUHPD-XFIJILBJSA-N

物化性质

• 溶解度：
  DMF：>50mg/mL； DMSO：>50mg/mL；乙醇：>50mg/mL；乙醇:PBS (1:10): <10 μg/ml

计算性质

• 辛醇/水分配系数(LogP)：
  14.7
• 重原子数：
  48
• 可旋转键数：
  21
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  胆甾醇亚油酸酯 在 soybean 15-lipoxygenase 作用下， 生成 13(S)-HODE cholesteryl ester
  参考文献：
  名称：

  Electrospray MS/MS reveals extensive and nonspecific oxidation of cholesterol esters in human peripheral vascular lesions

  摘要：

  Although LDL is rendered proatherogenic by various experimental treatments (e. g., acetylation), the exact structural changes that drive LDL transformation in vivo remain enigmatic. Among the many hypothesized targets of oxidative modification are cholesterol esters (CE). This family of neutral lipids, which carries a highly unsaturated pool of fatty acyl groups, is the main component of both LDL particles and atherosclerotic plaques. Tandem mass spectrometry (MS/MS) was employed to reveal abundant and diverse oxidized CEs (oxCE), including novel oxidation products, within human peripheral vascular lesions. These oxCE species composed up to 40% of the total CE pool, with cholesteryl linoleate being oxidized to the greatest extent. Imaging mass spectrometry studies showed that oxCE was entirely confined within the plaque, along with unmodified CE and triacylglyceride (TAG). Interestingly, we found no evidence for TAG oxidation, although polyunsaturated species were abundant. Enzymatic oxidation of cholesteryl linoleate by 15-lipoxygenase (15-LO), an enzyme often invoked in CE oxidation, initially results in a regio- and stereospecific product. Analysis of intact cholesteryl hydroxyoctadecadienoate isomers in human atheromata revealed no regio- or stereospecificity, indicating 15-LO was either not a major source of oxCE or nonenzymatic processes had eroded any product specificity.-Hutchins, P. M., E. E. Moore, and R. C. Murphy. Electrospray MS/MS reveals extensive and nonspecific oxidation of cholesterol esters in human peripheral vascular lesions. J. Lipid Res. 2011. 52: 2070-2083.

  DOI：

  10.1194/jlr.m019174

文献信息

• Baba, Naomichi; Tahara, Shoichi; Nakajima, Shuhei, Bioscience, Biotechnology and Biochemistry, 1992, vol. 56, # 2.3.4, p. 540
  作者：Baba, Naomichi、Tahara, Shoichi、Nakajima, Shuhei、Iwasa, Junkichi、Kaneko, Takao、Matsuo, Mitsuyoshi

  DOI：——

  日期：——
• Electrospray MS/MS reveals extensive and nonspecific oxidation of cholesterol esters in human peripheral vascular lesions
  作者：Patrick M. Hutchins、Ernest E. Moore、Robert C. Murphy

  DOI：10.1194/jlr.m019174

  日期：2011.11

  Although LDL is rendered proatherogenic by various experimental treatments (e. g., acetylation), the exact structural changes that drive LDL transformation in vivo remain enigmatic. Among the many hypothesized targets of oxidative modification are cholesterol esters (CE). This family of neutral lipids, which carries a highly unsaturated pool of fatty acyl groups, is the main component of both LDL particles and atherosclerotic plaques. Tandem mass spectrometry (MS/MS) was employed to reveal abundant and diverse oxidized CEs (oxCE), including novel oxidation products, within human peripheral vascular lesions. These oxCE species composed up to 40% of the total CE pool, with cholesteryl linoleate being oxidized to the greatest extent. Imaging mass spectrometry studies showed that oxCE was entirely confined within the plaque, along with unmodified CE and triacylglyceride (TAG). Interestingly, we found no evidence for TAG oxidation, although polyunsaturated species were abundant. Enzymatic oxidation of cholesteryl linoleate by 15-lipoxygenase (15-LO), an enzyme often invoked in CE oxidation, initially results in a regio- and stereospecific product. Analysis of intact cholesteryl hydroxyoctadecadienoate isomers in human atheromata revealed no regio- or stereospecificity, indicating 15-LO was either not a major source of oxCE or nonenzymatic processes had eroded any product specificity.-Hutchins, P. M., E. E. Moore, and R. C. Murphy. Electrospray MS/MS reveals extensive and nonspecific oxidation of cholesterol esters in human peripheral vascular lesions. J. Lipid Res. 2011. 52: 2070-2083.