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 | 97564-91-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 中文名称: 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
• 英文名称: pectenotoxin
• 英文别名: pectenotoxin-2；Pectenotoxin 2；(1S,2R,5R,7R,8E,10E,12R,14S,16R,19R,20S,24R,27S,28S,29R,32R,33R,35S)-14-[(2S,3R,4R)-2,3-dihydroxy-4-methyloxan-2-yl]-28-hydroxy-5,7,9,19,29,35-hexamethyl-13,17,38,39,40,41,42,43-octaoxaoctacyclo[31.4.1.11,35.12,5.120,24.124,27.129,32.012,16]tritetraconta-8,10-diene-18,31-dione
• CAS: 97564-91-5
• 化学式: C₄₇H₇₀O₁₄
• 分子量: 859.064
• InChiKey: PTKFEDGHUVZLPL-LLUYWJARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  61
• 可旋转键数：
  1
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  178
• 氢给体数：
  3
• 氢受体数：
  14

反应信息

• 作为反应物：
  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

文献信息

• Assessment of acylation routes and structural characterisation by liquid chromatography/tandem mass spectrometry of semi-synthetic acyl ester analogues of lipophilic marine toxins
  作者：Pablo de la Iglesia、Elena Fonollosa、Jorge Diogène

  DOI：10.1002/rcm.7057

  日期：2014.12.15

  halides as a source of the acyl radical, and several catalysers of the reaction. A series of mass spectrometric experiments involving product ion scans and multiple reaction monitoring (MRM) were used to confirm the identity and to elucidate the fragmentation pathways of the synthesised products. RESULTS Reaction yields regarding reaction time and temperature were examined at sub-nmol scale for the acylation

  理由酯化是贝类中亲脂性海洋毒素最重要的代谢途径之一。在这项工作中，我们评估了几种化学酰化反应，旨在通过从游离毒素进行部分合成来获得酰基酯类似物。所开发的程序包括基于液相色谱/串联质谱（LC / MS / MS）的灵敏和选择性方法，可用于获得参考材料，这些参考材料可用作方法开发和校准的分析标准品（内部/外部）进行体外和体内毒理学研究。方法酰化系统涉及无水和非无水脂肪酸或酰基卤作为酰基自由基的来源，以及该反应的几种催化剂。使用一系列涉及产物离子扫描和多反应监测（MRM）的质谱实验来确认身份，并阐明合成产物的裂解途径。结果在亚nmol规模下，对由棕榈酸酐和4-（二甲基氨基）吡啶（DMAP）在无水吡啶中组成的酰化系统的反应时间和温度进行了检测，结果表明最佳的条件是在75°C下60 min，75环状亚胺，azaspiracid-1和pectenotoxin-2分别在120°C和100°C 270分钟
• Production of 7-<i>epi</i>-Pectenotoxin-2 Seco Acid and Assessment of Its Acute Toxicity to Mice
  作者：Christopher O. Miles、Alistair L. Wilkins、John S. Munday、Rex Munday、Allan D. Hawkes、Dwayne J. Jensen、Janine M. Cooney、Veronica Beuzenberg

  DOI：10.1021/jf0523871

  日期：2006.2.1

  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.