8-hydroxy-7,8-dihydrocoptisine

• 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: 8-hydroxy-7,8-dihydrocoptisine
• 英文别名: 5,7,17,19-Tetraoxa-13-azahexacyclo[11.11.0.02,10.04,8.015,23.016,20]tetracosa-1(24),2,4(8),9,15(23),16(20),21-heptaen-14-ol；5,7,17,19-tetraoxa-13-azahexacyclo[11.11.0.02,10.04,8.015,23.016,20]tetracosa-1(24),2,4(8),9,15(23),16(20),21-heptaen-14-ol
• 化学式: C₁₉H₁₅NO₅
• 分子量: 337.332
• InChiKey: PADCSDOTWTYKDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  60.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  8-hydroxy-7,8-dihydrocoptisine 以 氘代二甲亚砜 为溶剂， 反应 4383.0h， 生成 8-氧代黄连碱; 8-氧黄连碱
  参考文献：
  名称：

  Berberine and coptisine free bases

  摘要：

  The free bases of protoberberine alkaloids berberine and coptisine and related compounds have been examined. The H-1 and C-13 NMR data of 8-hydroxy-7,8-dihydroberberine (2a), 8-hydroxy-7,8-dihydrocoptisine (2b), bis(7,8-dihydroberberin-8-yl) ether (3a), 8-oxoberberine (5a), and 8-oxocoptisine (5b) as well as X-ray data of compounds 2a, 5a, and 5b are reported and discussed. (C) 2003 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2003.09.018
• 作为产物：
  描述：

  氯化黄连碱 在 sodium hydroxide 作用下， 以 乙醚 、 水 为溶剂， 反应 48.0h， 生成 8-hydroxy-7,8-dihydrocoptisine
  参考文献：
  名称：

  Berberine and coptisine free bases

  摘要：

  The free bases of protoberberine alkaloids berberine and coptisine and related compounds have been examined. The H-1 and C-13 NMR data of 8-hydroxy-7,8-dihydroberberine (2a), 8-hydroxy-7,8-dihydrocoptisine (2b), bis(7,8-dihydroberberin-8-yl) ether (3a), 8-oxoberberine (5a), and 8-oxocoptisine (5b) as well as X-ray data of compounds 2a, 5a, and 5b are reported and discussed. (C) 2003 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2003.09.018

文献信息

• Simanek,V. et al., Collection of Czechoslovak Chemical Communications, 1972, vol. 37, p. 2746 - 2763
  作者：Simanek,V. et al.

  DOI：——

  日期：——
• Anti-inflammatory activity of coptisine free base in mice through inhibition of NF-κB and MAPK signaling pathways
  作者：Han-bin Chen、Chao-dan Luo、Jia-li Liang、Zhen-biao Zhang、Guo-sheng Lin、Jia-zhen Wu、Cai-lan Li、Li-hua Tan、Xiao-bo Yang、Zi-ren Su、Jian-hui Xie、Hui-fang Zeng

  DOI：10.1016/j.ejphar.2017.06.027

  日期：2017.9

  Coptisine is one of the main constituents of Coptis chinensis which has been widely used for the remedy of inflammatory disorders. Although the biological activities of coptisine have been well known, the pharmacological properties of its free base have seldomly been elucidated thus far. The aim of this study was to investigate the potential anti-inflammatory properties of coptisine free base (CFB, 8-hydroxy-7,8-dihydrocoptisine) on three animal models, namely xylene-induced ear edema, acetic acid-induced vascular permeability and carrageenan-induced paw edema. The results exhibited that CFB exerted a dose-dependent suppression on ear edema induced by xylene, significantly mitigated the aggravation of vascular permeability caused by acetic acid and paw edema induced by carrageenan. Additionally, CFB significantly suppressed the productions of interleukin-1 beta (IL-1 beta), interleukin-6 (IL-6), prostaglandinE2 (PGE(2)) and tumor necrosis factor (TNF-alpha) in the drug-treated groups as compared with the vehicle group after treatment with carrageenan. Signaling events of nuclear factor-kappa B (NF-kappa B) translocation, such as p-IKK alpha, p-IKK beta, p-I kappa B alpha and p65 (nucleus) were significantly inactivated, while inhibitor of nuclear factor kappa Ba (I kappa Ba) and p65 (cytosolic) were markedly up-regulated by CFB. Furthermore, CFB also significantly suppressed the mitogen-activated protein kinase (MAPK) pathway by blocking the phosphorylation of p-p38 (phospho-p38 mitogen-activated protein kinases) and p-JNK (phosphoc-jun N-terminal kinase) but not p-ERK (phospho-extracellular signal-regulated kinase). Hence, CFB efficiently prevented inflammation, at least partially, via inhibition of NF-kappa B and MAPK pathways. These findings provided a pioneering pharmacological basis for the anti-inflammatory effect of CFB and suggested CFB might be a potential candidate for the therapy of inflammatory disorders.
• Berberine and coptisine free bases
  作者：Jiřı́ Dostál、Stanislav Man、Pavlı́na Sečkářová、Dagmar Hulová、Marek Nečas、Milan Potáček、Jaromı́r Toušek、Roger Dommisse、Walter Van Dongen、Radek Marek

  DOI：10.1016/j.molstruc.2003.09.018

  日期：2004.1

  The free bases of protoberberine alkaloids berberine and coptisine and related compounds have been examined. The H-1 and C-13 NMR data of 8-hydroxy-7,8-dihydroberberine (2a), 8-hydroxy-7,8-dihydrocoptisine (2b), bis(7,8-dihydroberberin-8-yl) ether (3a), 8-oxoberberine (5a), and 8-oxocoptisine (5b) as well as X-ray data of compounds 2a, 5a, and 5b are reported and discussed. (C) 2003 Elsevier B.V. All rights reserved.