lagunamide B | 1255709-52-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: lagunamide B
• 英文别名: (3S,6S,12R,15S,18R,21E,24S,25S,26R)-12-benzyl-6-[(2R)-butan-2-yl]-18-[(2S)-butan-2-yl]-26-[(E)-but-2-en-2-yl]-24-hydroxy-3,4,10,13,15,21,25-heptamethyl-1,19-dioxa-4,7,10,13,16-pentazacyclohexacos-21-ene-2,5,8,11,14,17,20-heptone
• CAS: 1255709-52-4
• 化学式: C₄₅H₆₉N₅O₁₀
• 分子量: 840.07
• InChiKey: AEOXIHQSVQNFCU-PCOXENEKSA-N

物化性质

• 沸点：
  1051.9±65.0 °C(Predicted)
• 密度：
  1.065±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  60
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  192
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  lagunamide B 、 (R)-methoxytrifluoromethylphenylacetyl chloride 在 盐酸 、 水 、 吡啶 作用下， 以 水 为溶剂， 反应 28.0h， 生成
  参考文献：
  名称：

  Lagunamides A and B: Cytotoxic and Antimalarial Cyclodepsipeptides from the Marine Cyanobacterium Lyngbya majuscula

  摘要：

  Lagunamides A (1) and B (2) are new cyclic depsipeptides isolated from the marine cyanobacterium Lyngbya majuscula obtained from Pulau Hantu Besar, Singapore. The planar structural characterization of these molecules was achieved by extensive spectroscopic analysis, including 2D NMR experiments. In addition to Marfey's method and (3)J(H-H) coupling constant values, a modified method based on Mosher's reagents and analysis using LC-MS was deployed for the determination of the absolute configuration. Lagunamides A and B displayed significant antimalarial properties, with IC50 values of 0.19 and 0.91 mu M, respectively, when tested against Plasmodium falciparum. Lagunamides A and B also possessed potent cytotoxic activity against P388 murine leukemia cell lines, with IC50 values of 6.4 and 20.5 nM, respectively. Furthermore, these cyanobacterial compounds exhibited moderate antiswarming activities when tested against Pseudomonas aeruginosa PA01.

  DOI：

  10.1021/np100442x

文献信息

• Lagunamides A and B: Cytotoxic and Antimalarial Cyclodepsipeptides from the Marine Cyanobacterium <i>Lyngbya majuscula</i>
  作者：Ashootosh Tripathi、Jonathan Puddick、Michèle R. Prinsep、Matthias Rottmann、Lik Tong Tan

  DOI：10.1021/np100442x

  日期：2010.11.29

  Lagunamides A (1) and B (2) are new cyclic depsipeptides isolated from the marine cyanobacterium Lyngbya majuscula obtained from Pulau Hantu Besar, Singapore. The planar structural characterization of these molecules was achieved by extensive spectroscopic analysis, including 2D NMR experiments. In addition to Marfey's method and (3)J(H-H) coupling constant values, a modified method based on Mosher's reagents and analysis using LC-MS was deployed for the determination of the absolute configuration. Lagunamides A and B displayed significant antimalarial properties, with IC50 values of 0.19 and 0.91 mu M, respectively, when tested against Plasmodium falciparum. Lagunamides A and B also possessed potent cytotoxic activity against P388 murine leukemia cell lines, with IC50 values of 6.4 and 20.5 nM, respectively. Furthermore, these cyanobacterial compounds exhibited moderate antiswarming activities when tested against Pseudomonas aeruginosa PA01.