enniatin A1 | 4530-21-6

• 物质功能分类: 分析化学 - 标准品
• 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: enniatin A1
• 英文别名: (3s,6r,9s,12r,15s,18r)-3,6,12,18-Tetraisopropyl-4,10,16-trimethyl-9,15-disec-butyl-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone；(3S,6R,9S,12R,15S,18R)-3,9-di(butan-2-yl)-4,10,16-trimethyl-6,12,15,18-tetra(propan-2-yl)-1,7,13-trioxa-4,10,16-triazacyclooctadecane-2,5,8,11,14,17-hexone
• CAS: 4530-21-6
• 化学式: C₃₅H₆₁N₃O₉
• 分子量: 667.884
• InChiKey: OWUREPXBPJFMOK-BRGCSTNASA-N

物化性质

• 熔点：
  116-117 °C
• 沸点：
  840.5±65.0 °C(Predicted)
• 密度：
  1.027±0.06 g/cm3(Predicted)
• 溶解度：
  在DMSO中的溶解度为10mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  47
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  9

安全信息

• 危险等级：
  6.1(a)

制备方法与用途

简介

Enniatin A1 是从镰刀菌霉菌毒素 (Fusarium) 中分离出来的，由交替的 D-α-羟基异戊酸和 N-甲基-L-氨基酸组成的环状十六肽。这种化合物具有抗癌特性，通过诱导细胞凋亡和破坏 ERK 信号通路发挥作用。Enniatin A1 在大鼠肝微粒体中抑制 ACAT 的 IC50 值为 49 μM。

生物活性

Enniatin A1 同样是由镰刀菌霉菌毒素 (Fusarium) 分离出来的化合物，由交替的 D-α-羟基异戊酸和 N-甲基-L-氨基酸组成。它通过诱导细胞凋亡和破坏 ERK 信号通路表现出抗癌特性，并且在大鼠肝微粒体中抑制 ACAT 的 IC50 值为 49 μM。

靶点

ERK

反应信息

• 作为反应物：
  描述：

  enniatin A1 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 30.0h， 生成 Subenniatin B
  参考文献：
  名称：

  Induced production of depsipeptides by co-culturing Fusarium tricinctum and Fusarium begoniae

  摘要：

  A co-culture of Fusarium tricinctum and Fusarium begoniae induced the production of two new linear depsipeptides, subenniatins A and B (1-2), which were not detected when either of the two fungi was cultured alone. The structures of the new compounds were unambiguously determined by analysis of 1D, 2D NMR, and mass spectra, as well as by chemical transformation. Complex NMR spectra were observed for compounds 1 and 2, which were attributed to the presence of rotamers as revealed by 1D NOE and ROESY measurements. Structurally, compounds 1 and 2 are biogenetic building blocks of the cytotoxic enniatins B, B1, A1, and A, which are the major metabolites of F. tricinctum when this fungus is cultured alone. Compounds 1 and 2 were found to be inactive in cytotoxic and antibacterial assays. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.005

文献信息

• Induced production of depsipeptides by co-culturing Fusarium tricinctum and Fusarium begoniae
  作者：Jian-ping Wang、Wenhan Lin、Victor Wray、Daowan Lai、Peter Proksch

  DOI：10.1016/j.tetlet.2013.03.005

  日期：2013.5

  A co-culture of Fusarium tricinctum and Fusarium begoniae induced the production of two new linear depsipeptides, subenniatins A and B (1-2), which were not detected when either of the two fungi was cultured alone. The structures of the new compounds were unambiguously determined by analysis of 1D, 2D NMR, and mass spectra, as well as by chemical transformation. Complex NMR spectra were observed for compounds 1 and 2, which were attributed to the presence of rotamers as revealed by 1D NOE and ROESY measurements. Structurally, compounds 1 and 2 are biogenetic building blocks of the cytotoxic enniatins B, B1, A1, and A, which are the major metabolites of F. tricinctum when this fungus is cultured alone. Compounds 1 and 2 were found to be inactive in cytotoxic and antibacterial assays. (C) 2013 Elsevier Ltd. All rights reserved.