isosteviol 16-oxime | 131420-75-2

• 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: isosteviol 16-oxime
• 英文别名: isosteviol oxime
• CAS: 131420-75-2
• 化学式: C₂₀H₃₁NO₃
• 分子量: 333.471
• InChiKey: VAPPWLUSZRLUPV-XGBBNYNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  69.89
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  isosteviol 16-oxime 在 氯化亚砜 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 144.0h， 生成 ent-8β-cyanomethyl-12β-methoxy-13-methyl-13-podocarpen-19-oic acid
  参考文献：
  名称：

  Transformation of Isosteviol Lactam by Fungi and the Suppressive Effects of Its Transformed Products on LPS-Induced iNOS Expression in Macrophages

  摘要：

  From the screening of 21 microbial strains, Absidia pseudocylindrospora ATCC 24169 and Aspergillus niger BCRC 32720 were found to reproducibly transform isosteviollactam (4 alpha-carboxy-13 alpha-amino-13,16-seco-ent-19-norbeyeran-16-oic acid 13,16-lactam) (3) into various compounds. Preparative-scale transformation of 3 with Abs. pseudocylindrospora yielded two new hydroxylated compounds (4 and 5), with conservation of the lactam ring. Preparative-scale transformation of 3 with Asp. niger afforded seven new compounds, 6 and 9-14, together with the known compounds 7 and 8. A single-crystal X-ray diffraction experiment confirmed the structure of 14. The suppressive effects of compounds 1-14 on the lipopolysaccharide-induced expression of the inducible nitric oxide synthase gene in RAW 264.7 macrophages were examined by a reverse-transcription real-time PCR analysis. With the exception of 7, all other compounds significantly reduced levels of iNOS mRNA relative to control cells, which were induced by LPS alone. Compounds 2, 3, and 5 were similar in activity to dexamethasone, while 9 was more potent.

  DOI：

  10.1021/np100915q
• 作为产物：
  描述：

  异甜菊醇 在 吡啶 、 盐酸羟胺 作用下， 生成 isosteviol 16-oxime
  参考文献：
  名称：

  A Natural Plant-Derived Dihydroisosteviol Prevents Cholera Toxin-Induced Intestinal Fluid Secretion

  摘要：

  甜菊糖及其主要代谢产物甜菊醇据称会影响多种组织（如肾脏、胰腺和肠道）中的离子传输。研究人员对甜菊糖、甜菊醇及其类似物对肠道氯离子分泌的影响进行了研究，实验对象为人类T84上皮细胞系。短路电流测量显示，甜菊醇及其类似物异甜菊醇、二氢异甜菊醇和异甜菊醇16-肟以剂量依赖性方式抑制了毛喉素诱导的氯离子分泌，IC50值分别为101、100、9.6和50μM，而母体化合物甜菊糖则没有影响。顶端氯离子电流测量表明

  DOI：

  10.1124/jpet.107.129288