5α,8α-epidioxycholesta-6,22-dien-3β-ol | 75246-76-3

• 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: 5α,8α-epidioxycholesta-6,22-dien-3β-ol
• 英文别名: 5α,8α-epidioxy-(22E,22R)-ergosta-6,22-dien-3β-ol；(1S,2R,5R,6R,9R,10R,13S,15S)-6,10-dimethyl-5-[(E,2R)-6-methylhept-3-en-2-yl]-16,17-dioxapentacyclo[13.2.2.01,9.02,6.010,15]nonadec-18-en-13-ol
• CAS: 75246-76-3
• 化学式: C₂₇H₄₂O₃
• 分子量: 414.629
• InChiKey: WISOACODKWCRQK-XRLZFMEMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  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