5-stigmasten-3β,7β-diol | 4863-54-1

• 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: 5-stigmasten-3β,7β-diol
• 英文别名: (24R)-24-ethyl-cholest-5-en-3β,7β-diol；stigmast-5-ene-3β,7β-diol；7-β-hydroxy-β-sitosterol；stigmast-5-en-3β,7β-diol；7β-hydroxy-β-sitosterol；sitost-5-ene-3β,7β-diol；7beta-Hydroxysitosterol；(3S,7R,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-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: 4863-54-1；15140-59-7；34427-61-7；75521-67-4；145163-98-0；145985-29-1
• 化学式: C₂₉H₅₀O₂
• 分子量: 430.715
• InChiKey: SXJVFYZNUGGHRG-PZHNMUJHSA-N

物化性质

• 沸点：
  535.0±38.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.93
• 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：

  5-stigmasten-3β,7β-diol 在 吡啶 、 苯 作用下， 生成 Vitamin D5
  参考文献：
  名称：

  Wunderlich, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1936, vol. 241, p. 116,119, 123

  摘要：

  DOI：
• 作为产物：
  描述：

  豆甾醇 在 sodium tetrahydroborate 、 氧气 、 hematoporphyrin 作用下， 以 吡啶 、 甲醇 、 乙醚 、 氯仿 为溶剂， 反应 125.0h， 生成 5-stigmasten-3β,7β-diol
  参考文献：
  名称：

  β-谷甾醇，菜油甾醇，豆甾醇和芸苔甾醇的5alpha-，7alpha-和7beta-羟基衍生物的质谱表征。

  摘要：

  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。

  DOI：

  10.1021/jf9812580

文献信息

• Synthesis, isolation and characterisation of β-sitosterol and β-sitosterol oxide derivatives
  作者：Florence O. McCarthy、Jay Chopra、Alan Ford、Sean A. Hogan、Joe P. Kerry、Nora M. O'Brien、Eileen Ryan、Anita R. Maguire

  DOI：10.1039/b505069c

  日期：——

  β-Sitosterol is the most prevalent plant cholesterol derivative (phytosterol) and can undergo similar oxidation to cholesterol, leading to β-sitosterol oxides. The biological impact of phytosterol oxides has only been evaluated in a phytosterol blend (usually of β-sitosterol, campesterol, stigmasterol and dihydrobrassicasterol). The lack of pure phytosterols, including β-sitosterol, hinders the collection of significant toxicity data on the individual β-sitosterol oxides. An efficient synthetic route to multi-gram quantities of pure β-sitosterol is described here, together with the first syntheses and characterisation of pure β-sitosterol oxides.

  δ-谷甾醇是最常见的植物胆固醇衍生物（植物甾醇），可发生与胆固醇类似的氧化作用，生成δ-谷甾醇氧化物。植物固醇氧化物的生物影响只在植物固醇混合物（通常包括δ-谷甾醇、坎贝酯醇、豆甾醇和二氢巴西甾醇）中进行过评估。由于缺乏纯植物甾醇（包括δ-谷甾醇），因此无法收集有关单个δ-谷甾醇氧化物的重要毒性数据。本文介绍了多克纯δ-谷甾醇的高效合成路线，以及纯δ-谷甾醇氧化物的首次合成和表征。
• Inhibitory Effect of Some Oxygenated Stigmastane-Type Sterols on 12-O-Tetradecanoylphorbol-13-acetate-Induced Inflammation in Mice.
  作者：Yumiko KIMURA、Ken YASUKAWA、Michio TAKIDO、Toshihiro AKIHISA、Toshitake TAMURA

  DOI：10.1248/bpb.18.1617

  日期：——

  The oxygenated stigmastane-type sterols stigmastane-3β, 6α-diol, stigmastane-3β, 6β-diol, 7α-hydroxysitosterol and its diacetyl derivative, 7β-hydroxysitosterol and its diacetyl derivative, 7-oxositosterol, 4β-hydroxysitosterol, and stigmast-4-ene-3β, 6β-diol were evaluated with respect to their anti-inflammatory activity against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation in mice. All of the sterols, with the exception of 7α-hydroxysitosterol and its diacetyl derivative, were found to possess marked inhibitory activity. The 50% inhibitory dose of these compounds for TPA-inflammation (1 μg) was 0.5-1.0 mg/ear.

  氧化的甾烷型固醇（stigmastane-3β, 6α-diol、stigmastane-3β, 6β-diol、7α-羟基甾醇及其二乙酰衍生物、7β-羟基甾醇及其二乙酰衍生物、7-氧代甾醇、4β-羟基甾醇和stigmast-4-ene-3β, 6β-diol）对小鼠体内12-O-十四烷酰基-13-乙酰基-7-羟基-4-甲基-10-羟基-1-磷酰基-5-胆甾烯酸（TPA）引起的炎症的抗炎活性进行了评估。除7α-羟基甾醇及其二乙酰衍生物外，所有固醇均具有明显的抑制活性。这些化合物对TPA炎症的50%抑制剂量（1微克）为0.5-1.0毫克/耳。
• Sterols as Anticancer Agents: Synthesis of Ring-B Oxygenated Steroids, Cytotoxic Profile, and Comprehensive SAR Analysis
  作者：João F. S. Carvalho、M. Manuel Cruz Silva、João N. Moreira、Sérgio Simões、M. Luisa Sá e Melo

  DOI：10.1021/jm1007769

  日期：2010.11.11

  The cytotoxicity of oxysterols was systematically studied in tumor and normal cells. Synthetic strategies to prepare this library included oxidations at ring B and a new method to yield 6 beta-hemiphthalates directly from Delta(5)-steroids. Most oxysterols were cytotoxic and showed selectivity toward cancer cells, LAMA-84 cells (leukemia) being particularly sensitive to 4, 8, 22, and 27 (IC50 < 5.6 mu M). The structural requirements to induce selective toxicity are discussed to shed light on the development of new anticancer drugs.
• 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.
• DE701601
  申请人：——

  公开号：——

  公开（公告）日：——