(24ξ)-24¹-methoxy-24-methylcycloartane-3β,24-diol

• 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: (24ξ)-24¹-methoxy-24-methylcycloartane-3β,24-diol
• 英文别名: (24R,S)-24¹-methoxy-24-methylcycloartane-3β,24-diol；(1S,3R,6S,8R,11S,12S,15R,16R)-15-[(2R)-5-hydroxy-5-(methoxymethyl)-6-methylheptan-2-yl]-7,7,12,16-tetramethylpentacyclo[9.7.0.01,3.03,8.012,16]octadecan-6-ol
• 化学式: C₃₂H₅₆O₃
• 分子量: 488.795
• InChiKey: BGKDKAMMXBHXAE-YGBPDJJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  24-亚甲基环阿屯醇 在 Glomerella fusarioides IFO 8831 mycelium 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 240.0h， 以2.6%的产率得到(24ξ)-24¹-methoxy-24-methylcycloartane-3β,24-diol
  参考文献：
  名称：

  Biotransformation of Cycloartane-Type Triterpenes by the Fungus Glomerella fusarioides

  摘要：

  Biotransformation of three cycloartane-type triterpenes, cycloartenol (1), 24-methylenecycloartanol (2), and cycloartenone (3), by the fungus Glomerella fusarioides was studied. Compound 1 was converted to 3, cycloart-25-ene-3 beta, 24-diol (4), and cycloartane-3 beta, 24,25-triol (5). Compound 2 was metabolized to cycloeucalenol (6) and two new compounds, 24-methylcycloartane-3 beta,24,24(1)-triol (7) and 24(1)-methoxy-24-methylcycloartane-3 beta, 24-diol (8). Compound 3 was converted into two new metabolites, 4 alpha,4 beta,14 alpha-trimethyl-9 beta, 19-cyclopregnane-3,20-dione (9) and 25-hydroxy-24-methoxycycloartan-3-one (14), and four known compounds, viz., cycloartane-3,24-dione (10), 24-hydroxycycloart-25-en-3-one (11), (23E)-25-hydroxycycloart-23-en-3-one (12), and 24,25-dihydroxycycloartan-3-one (13). The structures of four new metabolites, 7, 8, 9, and 14, were established by spectroscopic methods.

  DOI：

  10.1021/np058120d

文献信息

• Biotransformation of Cycloartane-Type Triterpenes by the Fungus <i>Glomerella </i><i>f</i><i>usarioides</i>
  作者：Toshihiro Akihisa、Kenji Watanabe、Risa Yoneima、Takashi Suzuki、Yumiko Kimura

  DOI：10.1021/np058120d

  日期：2006.4.1

  Biotransformation of three cycloartane-type triterpenes, cycloartenol (1), 24-methylenecycloartanol (2), and cycloartenone (3), by the fungus Glomerella fusarioides was studied. Compound 1 was converted to 3, cycloart-25-ene-3 beta, 24-diol (4), and cycloartane-3 beta, 24,25-triol (5). Compound 2 was metabolized to cycloeucalenol (6) and two new compounds, 24-methylcycloartane-3 beta,24,24(1)-triol (7) and 24(1)-methoxy-24-methylcycloartane-3 beta, 24-diol (8). Compound 3 was converted into two new metabolites, 4 alpha,4 beta,14 alpha-trimethyl-9 beta, 19-cyclopregnane-3,20-dione (9) and 25-hydroxy-24-methoxycycloartan-3-one (14), and four known compounds, viz., cycloartane-3,24-dione (10), 24-hydroxycycloart-25-en-3-one (11), (23E)-25-hydroxycycloart-23-en-3-one (12), and 24,25-dihydroxycycloartan-3-one (13). The structures of four new metabolites, 7, 8, 9, and 14, were established by spectroscopic methods.

表征谱图