desmethylisaridin E | 1445952-23-7

• 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: desmethylisaridin E
• 英文别名: Desmethylisaridin E；(3S,10S,13S,16S,19S)-16-benzyl-11-methyl-3-(2-methylpropyl)-10,13-di(propan-2-yl)-4-oxa-1,8,11,14,17-pentazabicyclo[17.3.0]docosane-2,5,9,12,15,18-hexone
• CAS: 1445952-23-7
• 化学式: C₃₄H₅₁N₅O₇
• 分子量: 641.808
• InChiKey: RCPWUQRPXYBTHY-PWOFSUAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  46
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  154
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  desmethylisaridin E 、 N-A-(2,4-二硝基-5-氟苯基)-L-丙氨酸 在 盐酸 、 碳酸氢钠 作用下， 以 水 、 丙酮 为溶剂， 反应 25.0h， 生成 L-FDAA-L-Pro 、 L-Phe-L-FDAA 、 (S)-2-(5-((S)-1-amino-1-oxopropan-2-ylamino)-2,4-dinitrophenylamino)-3-methylbutanoic acid 、 (S)-2-((5-((S)-1-amino-1-oxopropan-2-ylamino)-2,4-dinitrophenyl)(methyl)amino)-3-methylbutanoic acid
  参考文献：
  名称：

  Suberoylanilide Hydroxamic Acid, a Histone Deacetylase Inhibitor, Induces the Production of Anti-inflammatory Cyclodepsipeptides from Beauveria felina

  摘要：

  The addition of the histone deacetylase inhibitor suberoylanilide hydroxamic acid to a culture of the filamentous fungus Beauveria felina significantly changed its secondary metabolite profile and led to the isolation of eight compounds, including three new cyclodepsipeptides, desmethylisaridin E (1), desmethylisaridin C2 (2), and isaridin F (3), along with five known cyclodepsipeptide compounds. Isaridin F (3) possesses a cyclodepsipeptide ring with N-methylbutyric acid, which is rare in natural peptides. Absolute configurations of the new cyclodepsipeptides were achieved by Marfey's method. The anti-inflammatory activity of the isolated compounds was investigated through evaluating their effect on superoxide anion production and elastase release by FMLP-induced human neutrophils. Among the tested compounds, desmethylisaridin E (1) inhibited superoxide anion production and desmethylisaridin C2 (2) inhibited elastase release, with IC50 values of 10.00 +/- 0.80 and 10.01 +/- 0.46 mu M, respectively.

  DOI：

  10.1021/np400143j

文献信息

• Suberoylanilide Hydroxamic Acid, a Histone Deacetylase Inhibitor, Induces the Production of Anti-inflammatory Cyclodepsipeptides from <i>Beauveria felina</i>
  作者：Yu-Ming Chung、Mohamed El-Shazly、Da-Wei Chuang、Tsong-Long Hwang、Teigo Asai、Yoshiteru Oshima、Mohamed L. Ashour、Yang-Chang Wu、Fang-Rong Chang

  DOI：10.1021/np400143j

  日期：2013.7.26

  The addition of the histone deacetylase inhibitor suberoylanilide hydroxamic acid to a culture of the filamentous fungus Beauveria felina significantly changed its secondary metabolite profile and led to the isolation of eight compounds, including three new cyclodepsipeptides, desmethylisaridin E (1), desmethylisaridin C2 (2), and isaridin F (3), along with five known cyclodepsipeptide compounds. Isaridin F (3) possesses a cyclodepsipeptide ring with N-methylbutyric acid, which is rare in natural peptides. Absolute configurations of the new cyclodepsipeptides were achieved by Marfey's method. The anti-inflammatory activity of the isolated compounds was investigated through evaluating their effect on superoxide anion production and elastase release by FMLP-induced human neutrophils. Among the tested compounds, desmethylisaridin E (1) inhibited superoxide anion production and desmethylisaridin C2 (2) inhibited elastase release, with IC50 values of 10.00 +/- 0.80 and 10.01 +/- 0.46 mu M, respectively.