6-hydroxymetatacarboline H | 1420845-93-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 6-hydroxymetatacarboline H
• 英文别名: (2S)-1-[3-[3-[[(1S)-1-carboxy-2-phenylethyl]carbamoyl]-6-hydroxy-9H-pyrido[3,4-b]indol-1-yl]propanoyl]pyrrolidine-2-carboxylic acid
• CAS: 1420845-93-7
• 化学式: C₂₉H₂₈N₄O₇
• 分子量: 544.564
• InChiKey: VZSNMDLSRQBMCL-ZEQRLZLVSA-N

物化性质

• 沸点：
  953.4±65.0 °C(Predicted)
• 密度：
  1.480±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  173
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  6-hydroxymetatacarboline H 在 盐酸 、 水 作用下， 反应 1.0h， 生成 L-苯丙氨酸
  参考文献：
  名称：

  HR-MALDI-MS Imaging Assisted Screening of β-Carboline Alkaloids Discovered from Mycena metata

  摘要：

  Fruiting bodies of Mycena metata were screened for the presence of new secondary metabolites by means of HPLC-UV, LC-HR-ESIMS, and high-resolution matrix-assisted laser desorption/ionization mass spectrometry imaging (HR-MALDI-MS imaging). Thus, a new beta-carboline alkaloid, 6-hydroxymetatacarboline D (1d), was isolated from fruiting bodies of M. metata. 6-Hydroxymetatacarboline D consists of a highly substituted beta-carboline skeleton, which is likely to be derived biosynthetically from L-tryptophan, 2-oxoglutaric acid, L-threonine, and L-proline. The structure of the alkaloid was established by 2D NMR spectroscopic methods and HR-ESIMS. Moreover, by extensive application of LC-HR-ESIMS, LC-HR-ESIMS/MS, and LC-HR-ESIMS3 techniques we were able to elucidate the structures of a number of accompanying beta-carboline alkaloids, 1a-1c, 1e-1i, and 2a-2g, structurally closely related to 6-hydroxymetatacarboline D, which are present in M. metata in minor amounts. The absolute configuration of the stereogenic centers of the beta-carboline alkaloids was determined by GC-MS comparison with authentic synthetic samples after hydrolytic cleavage and derivatization of the resulting amino acids.

  DOI：

  10.1021/np300455a

文献信息

• HR-MALDI-MS Imaging Assisted Screening of β-Carboline Alkaloids Discovered from <i>Mycena metata</i>
  作者：Robert J. R. Jaeger、Marc Lamshöft、Sebastian Gottfried、Michael Spiteller、Peter Spiteller

  DOI：10.1021/np300455a

  日期：2013.2.22

  Fruiting bodies of Mycena metata were screened for the presence of new secondary metabolites by means of HPLC-UV, LC-HR-ESIMS, and high-resolution matrix-assisted laser desorption/ionization mass spectrometry imaging (HR-MALDI-MS imaging). Thus, a new beta-carboline alkaloid, 6-hydroxymetatacarboline D (1d), was isolated from fruiting bodies of M. metata. 6-Hydroxymetatacarboline D consists of a highly substituted beta-carboline skeleton, which is likely to be derived biosynthetically from L-tryptophan, 2-oxoglutaric acid, L-threonine, and L-proline. The structure of the alkaloid was established by 2D NMR spectroscopic methods and HR-ESIMS. Moreover, by extensive application of LC-HR-ESIMS, LC-HR-ESIMS/MS, and LC-HR-ESIMS3 techniques we were able to elucidate the structures of a number of accompanying beta-carboline alkaloids, 1a-1c, 1e-1i, and 2a-2g, structurally closely related to 6-hydroxymetatacarboline D, which are present in M. metata in minor amounts. The absolute configuration of the stereogenic centers of the beta-carboline alkaloids was determined by GC-MS comparison with authentic synthetic samples after hydrolytic cleavage and derivatization of the resulting amino acids.