cholesta-5,7,22-trien-3β-ol | 22643-62-5

• 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: cholesta-5,7,22-trien-3β-ol
• 英文别名: (22E)-cholesta-5,7,22-trien-3β-ol；(3β,22E)-ergosta-5,7,22-trien-3-ol；5,7,22-Cholestatrien-3beta-ol；(3S,9S,10R,13R,14R,17R)-10,13-dimethyl-17-[(E,2R)-6-methylhept-3-en-2-yl]-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS: 22643-62-5
• 化学式: C₂₇H₄₂O
• 分子量: 382.63
• InChiKey: RQOCXCFLRBRBCS-LNOGQBHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  28
• 可旋转键数：
  4
• 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：

  cholesta-5,7,22-trien-3β-ol 在 氧气 、 亚甲兰 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 5α,8α-epidioxycholesta-6,22-dien-3β-ol
  参考文献：
  名称：

  The Antiplasmodial Activity of Isolates from Ajuga remota

  摘要：

  Ajuga remota is the most frequently used medicinal herb for malaria treatment in Kenya. Its two known isolates ajugarin-1 (1) and ergosterol-5,8-endoperoxide (3) and a new isolate 8-O-acetylharpagide (2) were evaluated for their in vitro antiplasmodial activity. Ajugarin-1 was moderately active, with an IC50 of 23.0 +/- 3.0 muM, as compared to chloroquine (IC50 = 0.041 +/- 0.003 muM) against the chloroquine-sensitive (FCA 20/GHA) strain of Plasmodium falciparum. Ergosterol-5,8-endoperoxide was about 3x as potent (IC50 = 8.2 +/- 1.1 muM), while 8-O-acetylharpagide, whose structure was established by spectroscopic evidence, was inactive. Both ajugarin-1 and ergosterol-5,8-endoperoxide did not exhibit cytotoxicity against A431 (skin carcinoma) cell line, but 8-O-acetylharpagide was significantly cytotoxic. This iridoid glucoside, which has been formerly isolated from Ajuga decumbens, was identified in A. remota for the first time.

  DOI：

  10.1021/np0104626
• 作为产物：
  描述：

  在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 cholesta-5,7,22-trien-3β-ol
  参考文献：
  名称：

  甾醇侧链对脂质双层中两性霉素B离子通道形成的影响

  摘要：

  两性霉素B（AmB）是临床实践中使用的最有效的抗真菌药物之一。AmB与膜固醇相互作用，增加真菌膜的通透性；但是，尚不清楚AmB相对于细胞膜中的其他固醇如何选择性地识别真菌固醇麦角固醇（Erg）。在这项研究中，我们通过测试一系列与Erg脂环结构相同但在侧链结构上变化的Erg类似物（通过使用K +来研究），对Erg侧链对AmB活性的影响进行了研究。流入分析。结果清楚地表明，固醇侧链对于AmB对Erg的选择性和AmB-固醇离子通道的活性至关重要。与我们先前的发现表明药物与Erg之间存在直接相互作用的结果一致，这些数据表明AmB直接识别固醇侧链结构，从而促进AmB形成离子通道。此外，Erg侧链中的C24甲基和Δ22双键对于与AmB的相互作用同样重要。构象分析表明，C24甲基可通过增加侧链的范德华（VDW）接触面积来促进相互作用，而Δ22双键会限制侧链构型，以使VDW与刚性AmB糖苷配基的接触最大化。

  DOI：

  10.1021/bi500122c

文献信息

• [EN] 1 alpha -HYDROXYVITAMIN D2 ANALOGS AND PROCESS FOR PREPARING SAME
  申请人：WISCONSIN ALUMNI RESEARCH FOUNDATION

  公开号：WO1985003939A1

  公开（公告）日：1985-09-12

  (EN) Novel vitamin D derivatives, analogs of vitamin D2 compounds which lack the 24-methyl substituent and are identified as 1$g(a)-hydroxy-28-norvitamin D2 and 1$g(a),25-dihydroxy-28-norvitamin D2. The compounds of the invention are characterized by unexpectedly high vitamin D-like activity as well as a novel activity pattern. Because of such activity they would find ready application as substitutes for vitamin D or various of the known vitamin D metabolites in their various application for the treatment of calcium disorders.(FR) Nouveaux dérivés de la vitamine D qui sont des analogues de composés de la vitamine D2 auxquels fait défaut le composant méthyle 24 et qui sont identifiés comme 1 $(a)-hydroxy-28-norvitamine D2 et 1$g(a), 25-dihydroxy-28-norvitamine D2. Les composés de la présente invention sont caractérisés par une activité similaire à la vitamine D surprenament élevée ainsi que par un nouveau spectre d'activité. En raison d'une telle activité, ils trouveraient facilement une application en tant que substituants de la vitamine D ou de divers métabolites connus de la vitamide D dans leurs différentes applications pour le traitement des affections en relation avec le calcium.
• Effect of Sterol Side Chain on Ion Channel Formation by Amphotericin B in Lipid Bilayers
  作者：Yasuo Nakagawa、Yuichi Umegawa、Tetsuro Takano、Hiroshi Tsuchikawa、Nobuaki Matsumori、Michio Murata

  DOI：10.1021/bi500122c

  日期：2014.5.20

  by AmB. Furthermore, the C24 methyl group and Δ22 double bond in the side chain of Erg are equally important for the interaction with AmB. Conformational analysis revealed that the C24 methyl group contributes to the interaction by increasing the van der Waals (VDW) contact area of the side chain, while the Δ22 double bond restricts the side chain conformation to maximize the VDW contact with the rigid

  两性霉素B（AmB）是临床实践中使用的最有效的抗真菌药物之一。AmB与膜固醇相互作用，增加真菌膜的通透性；但是，尚不清楚AmB相对于细胞膜中的其他固醇如何选择性地识别真菌固醇麦角固醇（Erg）。在这项研究中，我们通过测试一系列与Erg脂环结构相同但在侧链结构上变化的Erg类似物（通过使用K +来研究），对Erg侧链对AmB活性的影响进行了研究。流入分析。结果清楚地表明，固醇侧链对于AmB对Erg的选择性和AmB-固醇离子通道的活性至关重要。与我们先前的发现表明药物与Erg之间存在直接相互作用的结果一致，这些数据表明AmB直接识别固醇侧链结构，从而促进AmB形成离子通道。此外，Erg侧链中的C24甲基和Δ22双键对于与AmB的相互作用同样重要。构象分析表明，C24甲基可通过增加侧链的范德华（VDW）接触面积来促进相互作用，而Δ22双键会限制侧链构型，以使VDW与刚性AmB糖苷配基的接触最大化。
• The Antiplasmodial Activity of Isolates from <i>Ajuga </i><i>r</i><i>emota</i>
  作者：Kimani A. M. Kuria、Hezekiah Chepkwony、Cindy Govaerts、Eugene Roets、Roger Busson、Peter de Witte、Istvan Zupko、Georges Hoornaert、Ludo Quirynen、Louis Maes、Leen Janssens、Jos Hoogmartens、Gert Laekeman

  DOI：10.1021/np0104626

  日期：2002.5.1

  Ajuga remota is the most frequently used medicinal herb for malaria treatment in Kenya. Its two known isolates ajugarin-1 (1) and ergosterol-5,8-endoperoxide (3) and a new isolate 8-O-acetylharpagide (2) were evaluated for their in vitro antiplasmodial activity. Ajugarin-1 was moderately active, with an IC50 of 23.0 +/- 3.0 muM, as compared to chloroquine (IC50 = 0.041 +/- 0.003 muM) against the chloroquine-sensitive (FCA 20/GHA) strain of Plasmodium falciparum. Ergosterol-5,8-endoperoxide was about 3x as potent (IC50 = 8.2 +/- 1.1 muM), while 8-O-acetylharpagide, whose structure was established by spectroscopic evidence, was inactive. Both ajugarin-1 and ergosterol-5,8-endoperoxide did not exhibit cytotoxicity against A431 (skin carcinoma) cell line, but 8-O-acetylharpagide was significantly cytotoxic. This iridoid glucoside, which has been formerly isolated from Ajuga decumbens, was identified in A. remota for the first time.