Jatrorrhizin | 483-43-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 原小檗碱生物碱及其衍生物
• 英文名称: Jatrorrhizin
• 英文别名: 3-hydroxy-2,9,10-trimethoxy-5,6-dihydro-isoquino[3,2-a]isoquinolinylium; hydroxide；3-Hydroxy-2,9,10-trimethoxy-5,6-dihydro-isochino[3,2-a]isochinolinylium; Hydroxid；Jatrorrhizine hydroxide；2,9,10-trimethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium-3-ol;hydroxide
• CAS: 483-43-2
• 化学式: C₂₀H₂₀NO₄*HO
• 分子量: 355.39
• InChiKey: FLLCSIZPVWDZQO-UHFFFAOYSA-N

物化性质

• 溶解度：
  DMSO（微溶）、甲醇（微溶）、水（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  2.91
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  52.8
• 氢给体数：
  2
• 氢受体数：
  5

制备方法与用途

生物活性

Jatrorrhizine hydroxide 是从黄连中分离得到的生物碱，具有神经保护、抗菌、抗疟原虫和抗氧化活性。Jatrorrhizine hydroxide 是有效的，具有口服活性的乙酰胆碱酯酶 (AChE) (IC50=872 nM) 的抑制剂，是对 BuChE 的选择性为 115 倍。Jatrorrhizine hydroxide 通过抑制 uptake-2 transporter 的活性减少血清素 (5-HT) 和去甲肾上腺素 (NE) 的摄取。

靶点

IC50: 872 nM (AChE)

体外研究

Jatrorrhizine has antiplasmodial and antiamoebic activity, it against Plasmodium falciparum and E. histolytica with IC ₅₀ values of 3.15 and 82.7 µM, respectively.The hOCT2 (organic cation transporter 2), hOCT3, and PMAT (plasma membrane monoamine transporter) are capable of transporting monoamine neurotransmitters in the brain. Jatrorrhizine has the inhibitory potency of jatrorrhizine on 5-HT and NE uptake in hOCT2-, hOCT3-, and PMAT-transfected cells. Jatrorrhizine strongly inhibits PMAT-mediated MPP ⁺ uptake with an IC ₅₀ value of 1.05 μM and reduces 5-HT and NE uptake mediated by hOCT2, hOCT3, and hPMAT with IC ₅₀ values of 0.1-1 μM (for OCT2 and OCT3) and 1-10 μM (for PMAT).Clearance of neurotransmitters released into the synaptic cleft is defined by two distinct processes. Uptake-1, the common target of current applied antidepressants, is comprised of the serotonin transporter (SERT), the “SERT”, had a high affinity but low capacity to take up [3H]5-HT. Uptake-2 transporters are an important supplementary regulation system in monoamine clearancethought to be the “NET”, has low affinity but high capacity to take up [ ³ H]5-HT into brain slices. Jatrorrhizine significantly inhibited 5-HT and NE uptake in synaptosomes at 25 μM and 50 μM.

体内研究

Jatrorrhizine (intraperitoneal injection; 5, 10, 20 mg/kg) can significantly reduce the duration of immobility when compared with vehicle control group in tail suspension test (TST).

Animal Model:	Male ICR albino mice
Dosage:	5, 10, 20 mg/kg
Administration:	Intraperitoneal injection; 5, 10, 20 mg/kg
Result:	Reduced immobility period in tail suspension test.

反应信息

• 作为产物：
  描述：

  5,8,13,13a-四氢-2,9,10-三甲氧基-6H-二苯并[a,g]喹嗪-3-醇 生成 Jatrorrhizin
  参考文献：
  名称：

  AMANN, M.;NAGAKURA, NAOTAKA;ZENK, M. H.

  摘要：

  DOI：

文献信息

• Govindachari et al., Proceedings - Indian Academy of Sciences, Section A, 1958, vol. 47, p. 41,46
  作者：Govindachari et al.

  DOI：——

  日期：——