metatacarboline A | 1420845-86-8

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: metatacarboline A
• 英文别名: Metatacarboline A；1-[3-[(2S)-2-carboxypyrrolidin-1-yl]-3-oxopropyl]-9H-pyrido[3,4-b]indole-3-carboxylic acid
• CAS: 1420845-86-8
• 化学式: C₂₀H₁₉N₃O₅
• 分子量: 381.388
• InChiKey: VSQKKTIEHWELDM-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  metatacarboline A 在 盐酸 、 三甲基氯硅烷 、 水 作用下， 反应 9.0h， 生成 L-脯氨酸甲酯
  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
• 作为产物：
  描述：

  N-Chloroacetyl-D-proline ethyl ester 在 lithium hydroxide monohydrate 、 palladium 10% on activated carbon 、 氢气 、 sodium methylate 作用下， 以 甲醇 、 乙醇 、 乙腈 为溶剂， 反应 3.08h， 生成 metatacarboline A
  参考文献：
  名称：

  水溶性metacarboline A，C，D，E和F的简明全合成及其抗癌活性

  摘要：

  报道了Metatacarboline生物碱（简称为Mc）的简单，简洁，无保护基团的首次全部合成。Mc A，C，D，E和F。通过经典的维蒂希反应（Wittig reaction）已构建了metacarboline生物碱的核心结构，这是从容易获得的起始原料中获得的关键步骤，该原料的总收率为40-75％。使用C6神经胶质瘤细胞系对这些合成的化合物进行了抗癌活性评估。Mc D和Mc F显示出显着的抗增殖活性，这已通过MTT和Clonogenic分析得以证实。FACS分析表明，Mc D和Mc F分别将细胞周期停滞在亚细胞周期的G0 / G1和G2 / M期。此外，蛋白质印迹分析和Mc D处理的细胞的免疫组织化学显示，caspase依赖性下游信号传导被激活，从而导致细胞凋亡。

  DOI：

  10.1016/j.ejmech.2016.02.033

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.
• Concise total synthesis of water soluble metatacarboline A, C, D, E and F and its anticancer activity
  作者：Badher Naveen、Anwita Mudiraj、Geeviman Khamushavalli、Phanithi Prakash Babu、Rajagopal Nagarajan

  DOI：10.1016/j.ejmech.2016.02.033

  日期：2016.5

  The simple, concise, protecting group free and first total synthesis of Metatacarboline alkaloids (abbreviated as Mc) Mc A, C, D, E and F are reported. The core structure of metatacarboline alkaloids has been constructed by the classical Wittig reaction as key step from easily accessible starting materials with 40–75% overall yields. These synthesized compounds have been subjected to evaluate for their

  报道了Metatacarboline生物碱（简称为Mc）的简单，简洁，无保护基团的首次全部合成。Mc A，C，D，E和F。通过经典的维蒂希反应（Wittig reaction）已构建了metacarboline生物碱的核心结构，这是从容易获得的起始原料中获得的关键步骤，该原料的总收率为40-75％。使用C6神经胶质瘤细胞系对这些合成的化合物进行了抗癌活性评估。Mc D和Mc F显示出显着的抗增殖活性，这已通过MTT和Clonogenic分析得以证实。FACS分析表明，Mc D和Mc F分别将细胞周期停滞在亚细胞周期的G0 / G1和G2 / M期。此外，蛋白质印迹分析和Mc D处理的细胞的免疫组织化学显示，caspase依赖性下游信号传导被激活，从而导致细胞凋亡。