ent-8β-cyanomethyl-13-methyl-12-podocarpene-19-hydroxyethyl ester | 1308669-13-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: ent-8β-cyanomethyl-13-methyl-12-podocarpene-19-hydroxyethyl ester
• 英文别名: 2-hydroxyethyl (1R,4aS,4bR,8aR,10aS)-8a-(cyanomethyl)-1,4a,7-trimethyl-3,4,4b,5,8,9,10,10a-octahydro-2H-phenanthrene-1-carboxylate
• CAS: 1308669-13-7
• 化学式: C₂₂H₃₃NO₃
• 分子量: 359.509
• InChiKey: IYYLGQKNLYVERW-HJWIKWMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  70.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4α-carboxy-13α-amino-13,16-seco-ent-19-norbeyeran-16-oic acid lactam 在 Aspergillus niger BCRC 32720 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 144.0h， 以28 mg的产率得到ent-8β-cyanomethyl-7α-hydroxy-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

文献信息

• Transformation of Isosteviol Lactam by Fungi and the Suppressive Effects of Its Transformed Products on LPS-Induced iNOS Expression in Macrophages
  作者：Bo-Hon Chou、Li-Ming Yang、Shwu-Fen Chang、Feng-Lin Hsu、Li-Hsuan Wang、Wen-Kuang Lin、Pan-Chun Liu、Shwu-Jiuan Lin

  DOI：10.1021/np100915q

  日期：2011.6.24

  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.