acremine P | 1448507-16-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: acremine P
• 英文别名: Acremine P；(1S,2S,4R,8R,9R)-8-hydroxy-4,10,10-trimethyl-3,11,12,13-tetraoxatetracyclo[7.3.1.01,7.02,4]tridec-6-en-5-one
• CAS: 1448507-16-1
• 化学式: C₁₂H₁₄O₆
• 分子量: 254.24
• InChiKey: VRVCIBRMPZDPKI-FBHFSLSBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  77.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  acremine P 在 palladium on activated charcoal 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 以0.5 mg的产率得到acremine A
  参考文献：
  名称：

  Secondary Metabolites of the Sponge-Derived Fungus Acremonium persicinum

  摘要：

  This study reports the isolation and characterization of six new acremine metabolites, 5-chloroacremine A (4), 5-chloroacremine H (5), and acremines 0 (6), P (7), Q(8), and R (9), together with the known acremines A (1), F (2), and N (3) from the fungus Acremonium persicinum cultured from the marine sponge Anomoianthella rubra. The relative configuration of acremine F (2) was determined by analyses of proton coupling constant values and NOESY data, and the absolute configuration confirmed as (IS, 4S, 6R) by X-ray crystallographic analysis of the borate ester derivative 15. Acremines O, P, and R were each shown to be of 8R configuration by H-1 NMR analyses of MPA esters. The relative configurations suggested for acremines P and Q were each deduced by molecular modeling together with NOESY and coupling constant data. The (3)J(H-C) values in acremine P were measured using the pulse sequence EXSIDE, and the observed (3)J(H8-C4) of 5.4 Hz and small (3)J(H-C) values (<1.5 Hz) from H-8 to C-10 and C-11 were fully consistent with stereoisomer 7a. For acremine Q NOESY data combined with molecular modeling established the preferred diastereomer 8a.

  DOI：

  10.1021/np4002114

文献信息

• Secondary Metabolites of the Sponge-Derived Fungus <i>Acremonium persicinum</i>
  作者：Suciati、James A. Fraser、Lynette K. Lambert、Gregory K. Pierens、Paul V. Bernhardt、Mary J. Garson

  DOI：10.1021/np4002114

  日期：2013.8.23

  This study reports the isolation and characterization of six new acremine metabolites, 5-chloroacremine A (4), 5-chloroacremine H (5), and acremines 0 (6), P (7), Q(8), and R (9), together with the known acremines A (1), F (2), and N (3) from the fungus Acremonium persicinum cultured from the marine sponge Anomoianthella rubra. The relative configuration of acremine F (2) was determined by analyses of proton coupling constant values and NOESY data, and the absolute configuration confirmed as (IS, 4S, 6R) by X-ray crystallographic analysis of the borate ester derivative 15. Acremines O, P, and R were each shown to be of 8R configuration by H-1 NMR analyses of MPA esters. The relative configurations suggested for acremines P and Q were each deduced by molecular modeling together with NOESY and coupling constant data. The (3)J(H-C) values in acremine P were measured using the pulse sequence EXSIDE, and the observed (3)J(H8-C4) of 5.4 Hz and small (3)J(H-C) values (<1.5 Hz) from H-8 to C-10 and C-11 were fully consistent with stereoisomer 7a. For acremine Q NOESY data combined with molecular modeling established the preferred diastereomer 8a.