(24S)-stigmasta-5,22E-diene-3β,7β-diol | 64998-20-5

• 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: (24S)-stigmasta-5,22E-diene-3β,7β-diol
• 英文别名: (24S)-stigmasta-5,22-dien-3β,7β-diol；stigmasta-5,22-diene-3β,7β-diol；stigmast-5,22-diene-3β,7β-diol；7α-hydroxylstigmasterol；7β-hydroxystigmasterol；stigmastadiene-(5,22t)-diol-(3β,7β)；7beta-Hydroxystigmasterol；(3S,7R,8S,9S,10R,13R,14S,17R)-17-[(E,2R,5S)-5-ethyl-6-methylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol
• CAS: 64998-20-5
• 化学式: C₂₉H₄₈O₂
• 分子量: 428.699
• InChiKey: DPNNWDOFSGOYEK-IWIJBSIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (24S)-stigmasta-5,22E-diene-3β,7β-diol 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 23.0h， 以42%的产率得到(24S)-5α,6α-epoxystigmast-22-en-3β,7β-diol
  参考文献：
  名称：

  摘要：

  The toxicity of 7-substituted steroids 1-8 for Colorado beetle (Leptinotarsa decemlineata Say.) larvae was studied. The most active compound is 3-acetoxy-Delta(5)-7-ketone 2b.

  DOI：

  10.1023/a:1019696132738
• 作为产物：
  描述：

  豆甾醇 在 sodium tetrahydroborate 、 chromium trioxide-pyridine complex 作用下， 以 1,4-二氧六环 、 吡啶 、 甲醇 、 氯仿 为溶剂， 反应 62.0h， 生成 (24S)-stigmasta-5,22E-diene-3β,7β-diol
  参考文献：
  名称：

  豆甾醇的 7-氧代-和 7-羟基-衍生物的合成

  摘要：

  植物甾体 3ß-羟基-(24S)-stigmast-5, 22E-dien-7-one 和 (24S)-stigmasta-5, 22E-diene-3\, 7ß-diol 已由豆甾醇合成。

  DOI：

  10.1007/bf01373854

文献信息

• Mass Spectrometry Characterization of the 5α-, 7α-, and 7β-Hydroxy Derivatives of β-Sitosterol, Campesterol, Stigmasterol, and Brassicasterol
  作者：Renzo Bortolomeazzi、Michela De Zan、Lorena Pizzale、Lanfranco S. Conte

  DOI：10.1021/jf9812580

  日期：1999.8.1

  chromatography mobilities, specific color reactions, and mass spectral data with those of the corresponding hydroxy derivatives of cholesterol, which were synthesized in the same manner. The phytosterols had the same behavior to photooxidation as cholesterol and, moreover, the different phytosterols photooxidized at about the same rate. The mass spectra of the trimethylsilyl ethers of the hydroxy derivatives

  β-谷甾醇，菜油甾醇，豆甾醇和芸苔甾醇的5α-氢过氧化物是通过在吡啶并以血卟啉为敏化剂的条件下将各甾醇在吡啶中进行光氧化而获得的。氢过氧化物的还原得到相应的5α-羟基衍生物。通过使等分的5α-氢过氧化物异构化为7α-氢过氧化物而获得固醇的7α-氢过氧化物和7β-氢过氧化物，其继而异构化为7β-氢过氧化物。还原得到相应的7α-和7β-羟基衍生物。通过比较薄层色谱的迁移率，特定的颜色反应，确定了β-谷甾醇，菜油甾醇，豆甾醇和芸苔甾醇的5α-，7α-和7β-羟基衍生物。质谱数据与相应的胆固醇羟基衍生物的质谱数据相同。植物甾醇对光氧化的行为与胆固醇相同，而且，不同的植物甾醇以大约相同的速率光氧化。研究的植物甾醇的羟基衍生物的三甲基甲硅烷基醚和胆固醇的相应羟基衍生物的质谱具有相同的裂解模式和相似的相对离子丰度。
• Synthesis of 7-oxo- and 7-hydroxy- derivatives of stigmasterol
  作者：N. V. Kovganko、Yu. G. Chernov

  DOI：10.1007/bf01373854

  日期：1996.3

  The phytosteroids 3ß-hydroxy-(24S)-stigmast-5, 22E-dien-7-one and (24S)-stigmasta-5, 22E-diene-3\, 7ß-diol have been synthesized from stigmasterol.

  植物甾体 3ß-羟基-(24S)-stigmast-5, 22E-dien-7-one 和 (24S)-stigmasta-5, 22E-diene-3\, 7ß-diol 已由豆甾醇合成。
• Synthesis and Characterization of Stigmasterol Oxidation Products
  作者：David A. Foley、Yvonne O’Callaghan、Nora M. O’Brien、Florence O. McCarthy、Anita R. Maguire

  DOI：10.1021/jf9024745

  日期：2010.1.27

  The synthesis and structural characterization of a series of oxides of stigmasterol is described providing a valuable series of reference standards for these oxides, analogous to the cholesterol oxidation products (COPs) which have been shown to have detrimental biological effects. Biological evaluation of the oxides of phytosterols is significant in the context of increased dietary use of phytosterols

  描述了一系列豆甾醇的氧化物的合成和结构表征，为这些氧化物提供了一系列有价值的参考标准，类似于已证明具有有害生物作用的胆固醇氧化产物（COP）。在饮食中增加植物甾醇的使用以降低胆固醇吸收的情况下，对植物甾醇的氧化物的生物学评估是重要的。
• Dehydro-sterol compounds and manufacture thereof
  申请人：WINTHROP CHEM CO INC

  公开号：US02098984A1

  公开（公告）日：1937-11-16
• Oxyphytosterols as Active Ingredients in Wheat Bran Suppress Human Colon Cancer Cell Growth: Identification, Chemical Synthesis, and Biological Evaluation
  作者：Yingdong Zhu、Dominique Soroka、Shengmin Sang

  DOI：10.1021/jf506361r

  日期：2015.3.4

  Consumption of whole grains has been reported to be associated with a lower risk of colorectal cancer. Recent studies illustrated that phytochemicals in wheat bran (WB) may protect against colorectal cancer. There is a growing interest in the phytosterol contents of foods as either intrinsic or added components due to their beneficial health effects. However, little is known whether phytosterols in WB contribute the observed chemopreventative activity of the grain. In the present study, we directly purified and identified four oxyphytosterols 1-4 from sterol-enriched fraction of WB, and also successfully synthesized five sterol oxides 5-8 and 13. Using these nine compounds as references, we outlined a comprehensive profile of steroids in WB using tandem liquid chromatography mass spectrometry with electrospray ionization (LC-ESI/MSn, n = 23) techniques for the first time. Among them, three sterol oxides 13, 14, and 18 are novel compounds, and 14 compounds 3, 4, 6-11, 13, 14, 16, and 18-20 were reported in WB for the first time. Our results on the inhibitory effects of available sterol oxides 18 and 13 against the growth of human colon cancer cells HCT-116 and HT-29 showed that compounds 2-8 exerted significant antiproliferative effects, with oxysterol 8 being the most active one in both cells. We further demonstrated that four most active sterol oxides 5-8 could induce cell death through the apoptosis pathway. Our results showed that phytosterols, particularly oxyphytosterols, in WB possess significant antiproliferative properties, and thereby may greatly contribute the observed chemoprevention of the whole grain wheat.