胆甾-5,7,9-三烯-3beta-醇 | 51982-45-7

• 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
• 中文名称: 胆甾-5,7,9-三烯-3beta-醇
• 中文别名: 4-吡啶甲醛,5-氨基-2-(三氟甲基)-
• 英文名称: Δ^5,7,9-cholestatrien-3β-ol
• 英文别名: cholesta-5,7,9(11)-trien-3-β-ol；cholesta-5,7,9(11)-trien-3β-ol；cholesta-5,7,9(11)-trien-3-ol；cholestatrienol；cholestatrien-(5.7.9(11))-ol-(3β)；(10S)-3c-Hydroxy-10r.13c-dimethyl-17c-((R)-1.5-dimethyl-hexyl)-(14tH)-2.3.4.10.12.13.14.15.16.17-decahydro-1H-cyclopenta[a]phenanthren；Cholesta-5,7,9(11)-trien-3-ol, (3beta)-；(3S,10S,13R,14R,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,12,14,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS: 51982-45-7
• 化学式: C₂₇H₄₂O
• 分子量: 382.63
• InChiKey: YQYYDLWKDGKMKI-BXAZICILSA-N

物化性质

• 沸点：
  513.3±39.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  胆甾-5,7,9-三烯-3beta-醇 在 乙酸酐 作用下， 生成 Δ^5,7,9-cholestatrien-3β-ol acetate
  参考文献：
  名称：

  Δ^{5, 7}-Steroids. VII. The Conversion of Δ^{5, 7}- to Δ^{5, 7, 9}-Steroidal Hormones

  摘要：

  DOI：

  10.1021/jo50001a021
• 作为产物：
  描述：

  7-脱氢醋酸胆固醇 在 sodium hydroxide 、 mercury(II) diacetate 、 溶剂黄146 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 19.5h， 生成 胆甾-5,7,9-三烯-3beta-醇
  参考文献：
  名称：

  Cyclodextrin-catalyzed extraction of fluorescent sterols from monolayer membranes and small unilamellar vesicles

  摘要：

  This study examined the kinetics of sterol desorption from monolayer and small unilamellar vesicle membranes to 2-hydroxypropyl-beta-cyclodextrin. The sterols used include cholesterol, dehydroergosterol (ergosta-5,7,9,(11),22-tetraen-3 beta-ol) and cholestatrienol (cholesta-5,7,9,(11)-trien-3 beta-ol). Desorption rates of dehydroergosterol and cholestatrienol from pure sterol monolayers were faster (3.3-4.6-fold) than the rate measured for cholesterol. In mixed monolayers (sterol: 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine 30:70 mol%), both dehydroergosterol and cholestatrienol desorbed faster than cholesterol, clearly indicating a difference in interfacial behavior of these sterols. In vesicle membranes desorption of dehydroergosterol was slower than desorption of cholestatrienol, and both rates were markedly affected by the phospholipid composition. Desorption of sterols was slower from sphingomyelin as compared to phosphatidylcholine vesicles. Desorption of fluorescent sterols was also faster from vesicles prepared by ethanol-injection as compared to extruded vesicles. The results of this study suggest that dehydroergosterol and cholestatrienol differ from cholesterol in their membrane behavior, therefore care should be exercised when experimental data derived with these probes are interpreted. (C) 2000 Elsevier Science Ireland Ltd. All rights reserved.

  DOI：

  10.1016/s0009-3084(00)00122-5

文献信息

• Enzymatic Production or Chemical Synthesis and Uses for 5,7-Dienes and UVB Conversion Products Thereof
  申请人：Slominski Andrej

  公开号：US20120258938A1

  公开（公告）日：2012-10-11

  Provided herein are steroidal compounds that are androsta-5,7-dienes or pregna-5,7-dienes and ultraviolet B (UVB) conversion products thereof and cholecalciferol derivatives hydroxylated at one or more of C1, C17, C20, C23, C24, C25, and C26 which includes pharmaceutical, cosmeceutical or nutraceutical compositions of the steroidal compounds as shown in Tables 1A, 2A and 3. Also provided is a method for producing hydroxylated metabolites of cholecalciferol via CYP11A1, CYP24, CYP27A1, or CYP27B1 enzyme systems where the hydroxylase has an activity to hydroxylate position C1 or C20 or other position of the sidechain of a secosteroid or its 5,7-dieneal precursor and the hydroxylated metabolites so produced. Methods are provided for inhibiting proliferation of either a normally or abnormally proliferating cell, for modifying immune activity, or for treating a condition associated with the proliferating or quiescent cell or immune cells by contacting the cell with or administering any of the compounds described herein.

  本文提供的是雄甾-5,7-二烯或孕甾-5,7-二烯及其紫外线B（UVB）转化产物和羟化在C1、C17、C20、C23、C24、C25和C26上的胆钙醇衍生物，其中包括表1A、2A和3中所示的雄甾类化合物的制药、化妆品或营养品组合物。同时，本文还提供了一种通过CYP11A1、CYP24、CYP27A1或CYP27B1酶系统产生羟化代谢产物的方法，其中羟化酶具有羟化分裂素或其5,7-二烯前体的侧链的C1或C20或其他位置的活性，以及由此产生的羟化代谢产物。本文还提供了一种通过接触或给予本文所述的任何化合物来抑制正常或异常增殖细胞的增殖，修饰免疫活性或治疗与增殖或静止细胞或免疫细胞相关的疾病的方法。
• Enzymatic production or chemical synthesis and uses for 5,7-dienes and UVB conversion products thereof
  申请人：Slominski Andrzej

  公开号：US20110118228A1

  公开（公告）日：2011-05-19

  Provided herein are steroidal compounds that are androsta-5,7-dienes or a pregna-5,7-dienes and ultraviolet B (UVB) conversion products thereof which includes pharmaceutical compositions of the steroidal compounds as shown in Tables 1 and 2. Also provided is a method for producing hydroxylated metabolites of cholecalciferol or ergocalciferol via the P450scc (CYP11A1) or CYP27B1 enzyme systems where the hydroxylase has an activity to hydroxylate position C20 of a secosteroid or its 5,7-dieneal precursor and the hydroxylated metabolites so produced. In addition, a method for inhibiting proliferation of either a normally or abnormally proliferating cell by contacting the cell with any of the compounds described herein. A related method is provided of treating a condition associated with the proliferating cell such as a cancer, a skin disorder, a defect in cell differentiation, cosmetic, prophylaxsis, or healthy cell maintenance.

  本文提供的是雄甾-5,7-二烯或孕甾-5,7-二烯及其紫外线B（UVB）转化产物的类固醇化合物，其中包括所示的表1和表2的类固醇化合物的药物组成。此外，还提供了一种通过P450scc（CYP11A1）或CYP27B1酶系统产生维生素D3或维生素D2的羟化代谢产物的方法，其中羟化酶具有羟化一个类固醇的C20位置或其5,7-二烯前体的活性，以及所产生的羟化代谢产物。此外，还提供了一种通过接触任何本文所述的化合物来抑制正常或异常增殖细胞增殖的方法。还提供了一种相关的方法，用于治疗与增殖细胞相关的疾病，例如癌症，皮肤疾病，细胞分化缺陷，美容，预防或维持健康的细胞。
• Formation of a Tight Complex between Amphidinol 3 and Sterols in Lipid Bilayers Revealed by Short-Range Energy Transfer
  作者：Manami Hieda、Koya Tsujimura、Masanao Kinoshita、Nobuaki Matsumori

  DOI：10.1246/bcsj.20220273

  日期：2022.12.15

  The exploration of molecular recognition in lipid bilayers is still extremely difficult. In this report, we leveraged short-range energy transfer (ET) that enabled detection of close contacts within 1 nm distance, and applied it to the interaction of natural products with sterols in lipid bilayers. Amphidinol 3 (AM3), a polyhydroxy–polyene metabolite from a marine dinoflagellate, possesses potent antifungal activity by forming membrane pores in a sterol-dependent manner. Although AM3 was shown to interact directly with membrane sterols, the mode of interaction is yet to be fully elucidated. Herein, we found that AM3 and cholestatrienol (CTL), a fluorescent sterol, can be an ET pair because the emission spectrum of the former overlaps with the excitation of the latter. We further confirmed that CTL exerts the sterol-dependent pore formation of AM3 as in the case of cholesterol. Then, titration using intermolecular ET in bilayers revealed that AM3 and CTL form a 1:1 complex with a dissociation constant of 1.4 × 10−5 M. The distance between the AM3 polyene and CTL triene was estimated to be less than 1 nm. Based on this information, we proposed a tight binding model between AM3 and the sterol in lipid bilayers.

  脂质双分子层中分子识别的探索仍然非常困难。在这份报告中，我们利用短程能量转移（ET）技术检测了1纳米距离内的紧密接触，并将其应用于天然产物与脂质双分子层中固醇的相互作用。Amphidinol 3（AM3）是一种来自海洋双鞭毛藻的多羟基聚烯代谢产物，通过形成膜孔以依赖固醇的方式具有强大的抗真菌活性。尽管AM3被证明与膜固醇直接相互作用，但相互作用的模式尚未完全阐明。在这里，我们发现AM3和胆甾三烯醇（CTL）是一种荧光固醇，可以成为ET对，因为前者的发射光谱与后者的激发光谱重叠。我们进一步证实，CTL像胆固醇一样，对AM3发挥固醇依赖性孔形成的作用。然后，在双分子层中使用分子间ET滴定显示，AM3和CTL形成1：1的复合物，解离常数为1.4×10-5M。AM3聚烯和CTL三烯之间的距离估计小于1纳米。基于这些信息，我们提出了AM3与脂质双分子层中固醇之间的紧密结合模型。
• Synthesis of steroid phosphates via monomeric metaphosphate
  作者：Fausto Ramirez、James F. Marecek、Shrishailam S. Yemul

  DOI：10.1021/jo00157a005

  日期：1983.5
• Minor and trace sterols in marine invertebrates. 26. Isolation and structure elucidation of nine new 5.alpha.,8.alpha.-epidoxy sterols from four marine organisms
  作者：A. A. Leslie Gunatilaka、Yalamanchili Gopichand、Francis J. Schmitz、Carl Djerassi

  DOI：10.1021/jo00332a020

  日期：1981.9