isopimara-7,15-dien-19-ol 19-O-α-L-arabinofuranoside

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: isopimara-7,15-dien-19-ol 19-O-α-L-arabinofuranoside
• 英文别名: (2R,3R,4R,5S)-2-[[(1S,4aR,4bS,7S,10aR)-7-ethenyl-1,4a,7-trimethyl-3,4,4b,5,6,8,10,10a-octahydro-2H-phenanthren-1-yl]methoxy]-5-(hydroxymethyl)oxolane-3,4-diol
• 化学式: C₂₅H₄₀O₅
• 分子量: 420.59
• InChiKey: DBECRELNMQGQOD-ZIJANGFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  79.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  isopimara-7,15-dien-19-ol 19-O-α-L-arabinofuranoside 在 盐酸 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.75h， 以7 g的产率得到isopimara-7,15-dien-19-ol
  参考文献：
  名称：

  LC-MS- and ¹H NMR Spectroscopy-Guided Identification of Antifungal Diterpenoids from Sagittaria latifolia

  摘要：

  Antifungal screening of small-molecule natural product libraries showed that a column fraction (CF) derived from the plant extract of Sagittaria latifolia was active against the fungal pathogen Cryptococcus neoformans. Dereplication analysis by liquid chromatography mass spectrometry (LC-MS) and proton nuclear magnetic resonance spectroscopy (H-1 NMR) indicated the presence of new compounds in this CF. Subsequent fractionation of the plant extract resulted in the identification of two new isopimaradiene-type diterpenoids, 1 and 2. The structures of 1 and 2 were determined by chemical methods and spectroscopic analysis as isopimara-7,15-dien-19-ol 19-O-alpha-L-arabinofuranoside and isopimara-7,15-dien-19-ol 19-O-alpha-L-(5'-acetoxy)-arabinofuranoside, respectively. Compound 1 exhibited IC50 values of 3.7 and 1.8 mu g/mL, respectively, against C. neoformans and C. gattii. Its aglycone, isopimara-7,15-dien-19-ol (3), resulting from acid hydrolysis of 1, was also active against the two fungal pathogens, with IC50 values of 9.2 and 6.8 mu g/mL, respectively. This study demonstrates that utilization of the combined LC-MS and H-1 NMR analytical tools is an improved chemical screening approach for hit prioritization in natural product drug discovery.

  DOI：

  10.1021/acs.jnatprod.5b00470
• 作为产物：
  描述：

  isopimara-7,15-dien-19-ol 19-O-α-L-(5′-acetoxy)arabinofuranoside 在 甲醇 、 potassium hydroxide 作用下， 反应 0.25h， 生成 isopimara-7,15-dien-19-ol 19-O-α-L-arabinofuranoside
  参考文献：
  名称：

  LC-MS- and ¹H NMR Spectroscopy-Guided Identification of Antifungal Diterpenoids from Sagittaria latifolia

  摘要：

  Antifungal screening of small-molecule natural product libraries showed that a column fraction (CF) derived from the plant extract of Sagittaria latifolia was active against the fungal pathogen Cryptococcus neoformans. Dereplication analysis by liquid chromatography mass spectrometry (LC-MS) and proton nuclear magnetic resonance spectroscopy (H-1 NMR) indicated the presence of new compounds in this CF. Subsequent fractionation of the plant extract resulted in the identification of two new isopimaradiene-type diterpenoids, 1 and 2. The structures of 1 and 2 were determined by chemical methods and spectroscopic analysis as isopimara-7,15-dien-19-ol 19-O-alpha-L-arabinofuranoside and isopimara-7,15-dien-19-ol 19-O-alpha-L-(5'-acetoxy)-arabinofuranoside, respectively. Compound 1 exhibited IC50 values of 3.7 and 1.8 mu g/mL, respectively, against C. neoformans and C. gattii. Its aglycone, isopimara-7,15-dien-19-ol (3), resulting from acid hydrolysis of 1, was also active against the two fungal pathogens, with IC50 values of 9.2 and 6.8 mu g/mL, respectively. This study demonstrates that utilization of the combined LC-MS and H-1 NMR analytical tools is an improved chemical screening approach for hit prioritization in natural product drug discovery.

  DOI：

  10.1021/acs.jnatprod.5b00470

文献信息

• LC-MS- and ¹H NMR Spectroscopy-Guided Identification of Antifungal Diterpenoids from <i>Sagittaria latifolia</i>
  作者：Ranga Rao Ravu、Melissa R. Jacob、Cynthia Jeffries、Ying Tu、Shabana I. Khan、Ameeta K. Agarwal、R. Kiplin Guy、Larry A. Walker、Alice M. Clark、Xing-Cong Li

  DOI：10.1021/acs.jnatprod.5b00470

  日期：2015.9.25

  Antifungal screening of small-molecule natural product libraries showed that a column fraction (CF) derived from the plant extract of Sagittaria latifolia was active against the fungal pathogen Cryptococcus neoformans. Dereplication analysis by liquid chromatography mass spectrometry (LC-MS) and proton nuclear magnetic resonance spectroscopy (H-1 NMR) indicated the presence of new compounds in this CF. Subsequent fractionation of the plant extract resulted in the identification of two new isopimaradiene-type diterpenoids, 1 and 2. The structures of 1 and 2 were determined by chemical methods and spectroscopic analysis as isopimara-7,15-dien-19-ol 19-O-alpha-L-arabinofuranoside and isopimara-7,15-dien-19-ol 19-O-alpha-L-(5'-acetoxy)-arabinofuranoside, respectively. Compound 1 exhibited IC50 values of 3.7 and 1.8 mu g/mL, respectively, against C. neoformans and C. gattii. Its aglycone, isopimara-7,15-dien-19-ol (3), resulting from acid hydrolysis of 1, was also active against the two fungal pathogens, with IC50 values of 9.2 and 6.8 mu g/mL, respectively. This study demonstrates that utilization of the combined LC-MS and H-1 NMR analytical tools is an improved chemical screening approach for hit prioritization in natural product drug discovery.