7-epi-pectenotoxin-2 seco acid | 212502-88-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7-epi-pectenotoxin-2 seco acid
• 英文别名: 7-epi-Pectenotoxin 2 seco acid；(2R)-2-[(2S,5S,9S)-2-[(S)-[(2R,5R)-5-[(1S,3R,5S)-1-[(2R,5R)-5-[(2R,3E,5E)-6-[(2R,3R,5S)-5-[(2S,3R,4R)-2,3-dihydroxy-4-methyloxan-2-yl]-3-hydroxyoxolan-2-yl]-2,4-dimethylhexa-3,5-dienyl]-5-methyloxolan-2-yl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl]-2-methyl-4-oxooxolan-2-yl]-hydroxymethyl]-1,10-dioxaspiro[4.5]decan-9-yl]propanoic acid
• CAS: 212502-88-0
• 化学式: C₄₇H₇₂O₁₅
• 分子量: 877.08
• InChiKey: DGIMWLBARADZNP-RJTHPJNTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  62
• 可旋转键数：
  12
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  209
• 氢给体数：
  5
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  3,4-二脱氧-1-C-[(1S,2R,5R,7R,8E,10E,12R,14S,16R,19R,20S,24R,27S,28S,29R,32R,33R,35S)-28-羟基-5,7,9,19,29,35-六甲基-18,31-二氧代-13,17,38,39,40,41,42,43-八氧杂辛环[31.4.1.11,35.12,5.120,24.124,27.129,32.012,16]三四十碳-8,10-二烯-14-基]-3-甲基-beta-D-赤式-吡喃戊糖 在 phosphate buffered saline 、 digestive gland homogenate 、 Perna canaliculus 作用下， 以 甲醇 为溶剂， 反应 3.67h， 以1.81 mg的产率得到7-epi-pectenotoxin-2 seco acid
  参考文献：
  名称：

  Production of 7-epi-Pectenotoxin-2 Seco Acid and Assessment of Its Acute Toxicity to Mice

  摘要：

  Pectenotoxins (PTXs) accumulate in shellfish feeding on dinoflagellates of the genus Dinophysis, so that humans can be exposed to these toxins through shellfish consumption. Some PTXs are toxic to experimental animals, whereas others are of much lower toxicity. Pectenotoxin-2, the most abundant PTX from most Dinophysis spp., is rapidly metabolized by most shellfish to a mixture of pectenotoxin-2 seco acid (2) and 7-epi-pectenotoxin-2 seco acid (1). A mixture of 1 and 2 was produced during purification of an extract from in vitro enzymatic hydrolysis of pectenotoxin-2. These were separated by preparative HPLC, and the structure of 1 was confirmed by one- and two-dimensional (1)H and (13)C NMR spectroscopy and LC-MS(3) analyses. No toxic changes were recorded in mice injected intraperitoneally with 1 or 2 at a dose of 5000 mu g/kg. PTX seco acids are therefore unlikely to be of consequence to human consumers at the concentrations found in contaminated shellfish.

  DOI：

  10.1021/jf0523871