macrophin

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: macrophin
• 英文别名: [5-(Hydroxymethyl)-4-methoxy-6-(3-methoxy-3-oxoprop-1-enyl)-2-oxopyran-3-yl]methyl 3-methylbut-2-enoate；[5-(hydroxymethyl)-4-methoxy-6-(3-methoxy-3-oxoprop-1-enyl)-2-oxopyran-3-yl]methyl 3-methylbut-2-enoate
• 化学式: C₁₇H₂₀O₈
• 分子量: 352.341
• InChiKey: YVTIJGPTRUSDKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  丁酸酐 、 macrophin 在 吡啶 作用下， 反应 4.0h， 生成
  参考文献：
  名称：

  Isolation, structural modification of macrophin from endophytic fungus Phoma macrostoma and their cytotoxic potential

  摘要：

  Four known metabolites, macrophin (1), rosellisin (2), 2-(2-hydroxy-5-6-methoxy-3-methylene-1,4-benzodioxin-2(3H)-one (3), and methoxyphenoxyacrylic acid (4) were isolated, for the first time, from an endophytic fungus, Phoma macrostoma inhabiting the inner tissue of medicinal plant Glycyrrhiza glabra Linn. Their structures were characterized by comparison of their NMR data with literature data, and X-ray diffraction data of macrophin (1) as described herein for the first time. The compounds (1-4) were evaluated for their growth-inhibitory activities against a panel of cancer cell lines. Of these substances, macrophin (1) showed prominent cytotoxic activity against the MDA-MB-231, T47D, MCF-7, and MIAPaCa-2 cancer-cell lines with IC50 values of 14.8, 8.12, 13.0, and 0.9M, respectively. This biological significance has prompted us to generate a series of five acylated analogs (1a-1e) of 1 to conduct structure-activity relationship (SAR) study. The result illustrates all the analogues (1a-1e) were more potent than 1 against MDMB-231 and MIAPaCa-2 cancer cell lines. The compound 1d, an n-butanoyl substituent, has been proven to be three-fold more potent than 1 with IC50 values of 0.3 and 3.7 mu M against MIAPaCa-2 and MDMB-231 cell lines, respectively.

  DOI：

  10.1007/s00044-018-2281-y

文献信息

• Isolation, structural modification of macrophin from endophytic fungus Phoma macrostoma and their cytotoxic potential
  作者：Yedukondalu Nalli、Palak Arora、Sameer Khan、Fayaz Malik、Syed Riyaz-Ul-Hassan、Vivek Gupta、Asif Ali

  DOI：10.1007/s00044-018-2281-y

  日期：2019.3

  Four known metabolites, macrophin (1), rosellisin (2), 2-(2-hydroxy-5-6-methoxy-3-methylene-1,4-benzodioxin-2(3H)-one (3), and methoxyphenoxyacrylic acid (4) were isolated, for the first time, from an endophytic fungus, Phoma macrostoma inhabiting the inner tissue of medicinal plant Glycyrrhiza glabra Linn. Their structures were characterized by comparison of their NMR data with literature data, and X-ray diffraction data of macrophin (1) as described herein for the first time. The compounds (1-4) were evaluated for their growth-inhibitory activities against a panel of cancer cell lines. Of these substances, macrophin (1) showed prominent cytotoxic activity against the MDA-MB-231, T47D, MCF-7, and MIAPaCa-2 cancer-cell lines with IC50 values of 14.8, 8.12, 13.0, and 0.9M, respectively. This biological significance has prompted us to generate a series of five acylated analogs (1a-1e) of 1 to conduct structure-activity relationship (SAR) study. The result illustrates all the analogues (1a-1e) were more potent than 1 against MDMB-231 and MIAPaCa-2 cancer cell lines. The compound 1d, an n-butanoyl substituent, has been proven to be three-fold more potent than 1 with IC50 values of 0.3 and 3.7 mu M against MIAPaCa-2 and MDMB-231 cell lines, respectively.