6β-hydroxyolean-18-en-3β-yl acetate

• 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: 6β-hydroxyolean-18-en-3β-yl acetate
• 英文别名: 3β-acetoxy-6β-hydroxy-olean-18-ene；[(3S,4aR,5R,6aS,6aR,6bR,8aR,14aR,14bR)-5-hydroxy-4,4,6a,6b,8a,11,11,14b-octamethyl-1,2,3,4a,5,6,6a,7,8,9,10,13,14,14a-tetradecahydropicen-3-yl] acetate
• 化学式: C₃₂H₅₂O₃
• 分子量: 484.763
• InChiKey: AREVFNRRRYVDPO-WKLSDETGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  35
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.91
• 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：

  3β,6β-dihidroxy-olean-18-ene 、 乙酸酐 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以4.2 mg的产率得到6β-hydroxyolean-18-en-3β-yl acetate
  参考文献：
  名称：

  Olean-18-ene triterpenoids from Celastraceae species inhibit HIV replication targeting NF-kB and Sp1 dependent transcription

  摘要：

  In the present study we report the isolation of nine new olean-18-ene triterpenes (1-9), along with three known ones (10-12), from Cassine xylocarpa and Maytenus jelskii. Their stereostructures have been elucidated on the basis of spectroscopic analysis, including 1D and 2D NMR techniques (COSY, ROESY, HSQC and HMBC), and spectrometric methods. The natural compounds and derivatives 13-15 have been tested for their potential as inhibitors of human immunodeficiency virus type 1 replication. Five compounds from this series displayed potent antiviral activity with IC(50)s in the micromolar range (1, 3, 4, 7 and 8) being 1 and 8 the most active compounds. The target of these compounds was different from antiretroviral drugs currently licensed as they act as inhibitors of enhancer-dependent transcription. The structure-activity relationships were established based on the regiosubstitution and oxidation degree of the triterpene scaffold, revealing that these aspects were able to modulate the selectivity and intensity of HIV inhibition. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.035

文献信息

• Acid-catalyzed Backbone Rearrangement of 5,6-Epoxyalnusanes and Preparation of Daturadiol
  作者：Motoo Tori、Masaki Takai、Yuzo Matsumoto、Yoshihiko Moriyama、Takahiko Tsuyuki、Takeyoshi Takahashi、Hiraku Ohnishi、Akiko Itai、Yoichi Iitaka

  DOI：10.1246/bcsj.57.2490

  日期：1984.9

  Epoxidation of alnus-5-en-3β-yl acetate with m-chloroperbenzoic acid gave a 5β,6β-epoxide as a main product together with a 5α,6α-epoxide as a minor product. Treatment of the α-epoxide with BF3·OEt2 afforded a 1(10),5-diene and a mixture of 6α-hydroxy-12- and -18-ene derivatives. The 12-ene was converted into daturadiol (=olean-12-ene-3β,6β-diol).

  用间氯过苯甲酸环氧化 alnus-5-en-3β-yl 乙酸酯得到 5β,6β-环氧化物作为主要产物和 5α,6α-环氧化物作为次要产物。用BF3·OEt2 处理α-环氧化物得到1(10),5-二烯和6α-羟基-12-和-18-烯衍生物的混合物。12-烯转化为曼陀罗二醇（=olean-12-ene-3β,6β-diol）。
• Olean-18-ene triterpenoids from Celastraceae species inhibit HIV replication targeting NF-kB and Sp1 dependent transcription
  作者：Alex A. Osorio、Alejandro Muñóz、David Torres-Romero、Luis M. Bedoya、Nayra R. Perestelo、Ignacio A. Jiménez、José Alcamí、Isabel L. Bazzocchi

  DOI：10.1016/j.ejmech.2012.03.035

  日期：2012.6

  In the present study we report the isolation of nine new olean-18-ene triterpenes (1-9), along with three known ones (10-12), from Cassine xylocarpa and Maytenus jelskii. Their stereostructures have been elucidated on the basis of spectroscopic analysis, including 1D and 2D NMR techniques (COSY, ROESY, HSQC and HMBC), and spectrometric methods. The natural compounds and derivatives 13-15 have been tested for their potential as inhibitors of human immunodeficiency virus type 1 replication. Five compounds from this series displayed potent antiviral activity with IC(50)s in the micromolar range (1, 3, 4, 7 and 8) being 1 and 8 the most active compounds. The target of these compounds was different from antiretroviral drugs currently licensed as they act as inhibitors of enhancer-dependent transcription. The structure-activity relationships were established based on the regiosubstitution and oxidation degree of the triterpene scaffold, revealing that these aspects were able to modulate the selectivity and intensity of HIV inhibition. (C) 2012 Elsevier Masson SAS. All rights reserved.