Egenine; (6R,8S)-6,8-二氢-6-[(5S)-5,6,7,8-四氢-6-甲基-1,3-二氧杂环戊并[4,5-g]异喹啉-5-基]呋喃并[3,4-e]-1,3-苯并二氧杂环戊烯-8-醇 | 6883-44-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 中文名称: Egenine; (6R,8S)-6,8-二氢-6-[(5S)-5,6,7,8-四氢-6-甲基-1,3-二氧杂环戊并[4,5-g]异喹啉-5-基]呋喃并[3,4-e]-1,3-苯并二氧杂环戊烯-8-醇
• 中文别名: (6R,8S)-6,8-二氢-6-[(5S)-5,6,7,8-四氢-6-甲基-1,3-二氧杂环戊并[4,5-g]异喹啉-5-基]呋喃并[3,4-e]-1,3-苯并二氧杂环戊烯-8-醇；Egenine;(6R,8S)-6,8-二氢-6-[(5S)-5,6,7,8-四氢-6-甲基-1,3-二氧杂环戊并[4,5-g]异喹啉-5-基]呋喃并[3,4-e]-1,3-苯并二氧杂环戊烯-8-醇；(6R,8S)-6,8-二氢-6-[(5S)-5,6,7,8-四氢-6-甲基-1,3-二氧杂环戊并[4,5-g]异喹啉-5-基]呋喃并[3,4-e
• 英文名称: (+)-egenine
• 英文别名: Egenine；(6R,8S)-6-[(5S)-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-6,8-dihydrofuro[3,4-g][1,3]benzodioxol-8-ol
• CAS: 6883-44-9
• 化学式: C₂₀H₁₉NO₆
• 分子量: 369.374
• InChiKey: YMHFBUOKLSWOQF-NSHGMRRFSA-N

物化性质

• 沸点：
  511.3±50.0 °C(Predicted)
• 密度：
  1.478

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  69.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Egenine; (6R,8S)-6,8-二氢-6-[(5S)-5,6,7,8-四氢-6-甲基-1,3-二氧杂环戊并[4,5-g]异喹啉-5-基]呋喃并[3,4-e]-1,3-苯并二氧杂环戊烯-8-醇 在 双氧水 作用下， 以 甲醇 为溶剂， 反应 48.0h， 以8.1 mg的产率得到egenine-α-N-oxide
  参考文献：
  名称：

  Alkaloids from Corydalis decumbens suppress neuronal excitability in primary cultures of mouse neocortical neurons

  摘要：

  Eight previously undescribed alkaloids, named corydemine, dihydrocorydemine, corydedine, 8,13-dioxo-14-hydroxytetrahydropalmatine, egenine-alpha-N-oxide, egenine-beta-N-oxide, 7'-O-ethylegenine-alpha-N-oxide, and 7'-O-ethylegenine-beta-N-oxide, together with three known ones, muramine, L-tetrahydropalmatine, and (+)-egenine, were isolated from the bulbs of Corydalis decumbens. Their structures were elucidated by comprehensive spectroscopic analysis and chemical correlation. The isolated compounds were tested for their ability to modulate neuronal excitability in primary cultured neocortical neurons. Four of the compounds, corydemine, dihydrocorydemine, muramine, and L-tetrahydropalmatine, inhibited neuronal excitability with IC50 values of 3.6, 16.7, 13.5 and 14.0 mu M, respectively. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2018.03.006

文献信息

• Compounds and Compositions for Modulating Lipid Levels and Methods of Preparing Same
  申请人：Liu Haiyan

  公开号：US20110009628A1

  公开（公告）日：2011-01-13

  The present technology relates to compounds of Formulas I-VI and methods of making and using such compounds. Methods of use include prevention and treatment of hyperlipidemia, hypercholesterolemia, hypertriglyceridemia, hepatic steatosis, and metabolic syndrome. Compounds disclosed herein also increase HDL-C, lower total cholesterol, LDL-cholesterol, and triglycerides and increase hepatic LDL receptor expression, inhibit PCSK9 expression, and activate AMP-activated protein kinase.

  目前的技术涉及到公式I-VI的化合物以及制备和使用这些化合物的方法。使用方法包括预防和治疗高脂血症、高胆固醇血症、高甘油三酯血症、肝脂肪变性和代谢综合征。本文披露的化合物还可以增加高密度脂蛋白胆固醇（HDL-C），降低总胆固醇、低密度脂蛋白胆固醇（LDL-C）和甘油三酯，并增加肝LDL受体表达，抑制PCSK9表达，并激活AMP激活蛋白激酶。
• Phthalideisoquinoline Hemiacetal Alkaloids from <i>Corydalis decumbens</i> That Inhibit Spontaneous Calcium Oscillations, Including Alkyl Derivatives of (+)-Egenine That Are Strikingly Levorotatory
  作者：Chun-Lei Zhang、Qi-Long Huang、Juan Chen、Wan-Jin Zhang、Hai-Xiao Jin、Hong-Bo Wang、C. Benjamin Naman、Zheng-Yu Cao

  DOI：10.1021/acs.jnatprod.9b00247

  日期：2019.10.25

  The new phthalideisoquinoline hemiacetal alkaloids (2-7) and the known analogues (1 and 8) were isolated from the bulbs of Corydalis decumbens. The new compounds were characterized by analysis of their NMR spectroscopic data, chemical degradation syntheses, X-ray crystallography, and comparison of experimental and calculated ECD data. All the isolates were screened in vitro for inhibitory activity

  从延胡索球茎中分离出新的邻苯二甲酰喹啉半缩醛生物碱（2-7）和已知类似物（1和8）。通过分析其NMR光谱数据，化学降解合成，X射线晶体学以及对实验数据和计算得出的ECD数据进行比较，对这些新化合物进行了表征。体外筛选所有分离物对原代培养的新皮层神经元中自发钙振荡的抑制活性。发现化合物1-3和5-7具有抑制自发性钙振荡的活性，IC50值分别为6.8、5.6、11.6、10.2、8.3和3.1μM。还观察到在远端立体中心C-7'处存在羟基，甲氧基和乙氧基。一些分离的邻苯二甲酰异喹啉半缩醛生物碱可以改变优选的构象并反转旋光的迹象，而不是由C-1或C-9处的构型异构现象引起的，并且这些类似物的3J1,9耦合常数也随之变化。例如，化合物1和6是左旋的，尽管这些分子具有与（+）-丁香碱相同的碳骨架和绝对构型。当将新化合物的数据与已知类似物的文献值进行比较时，尤其是在此类分子内，这强调了仅根据观察到的偶
• [EN] BERBERINE DERIVATIVES USEFUL FOR MODULATING LIPID LEVELS AND THEIR METHODS OF SYNTHESIS<br/>[FR] DÉRIVÉS DE LA BERBÉRINE UTILES POUR MODULER LES NIVEAUX LIPIDIQUES ET LEURS PROCÉDÉS DE SYNTHÈSE
  申请人：LIU HAIYAN

  公开号：WO2011006000A1

  公开（公告）日：2011-01-13

  The present technology relates to compounds of Formulas I-VI and methods of making and using such compounds. Methods of use include prevention and treatment of hyperlipidemia, hypercholesterolemia, hypertriglyceridemia, hepatic steatosis, and metabolic syndrome. Compounds disclosed herein also increase HDL-C, lower total cholesterol, LDL-cholesterol, and triglycerides and increase hepatic LDL receptor expression, inhibit PCSK9 expression, and activate AMP-activated protein kinase.