9-Demethoxy-9-benzoyloxyberberin

• 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: 9-Demethoxy-9-benzoyloxyberberin
• 英文别名: Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium, 9-(benzoyloxy)-5,6-dihydro-10-methoxy-；(17-methoxy-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(13),2,4(8),9,14,16,18,20-octaen-16-yl) benzoate
• 化学式: C₂₆H₂₀NO₅
• 分子量: 426.449
• InChiKey: OUUPORLAIMDZBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  57.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  盐酸小檗碱 在 吡啶 作用下， 以 乙腈 为溶剂， 生成 9-Demethoxy-9-benzoyloxyberberin
  参考文献：
  名称：

  小檗碱9-O-苯甲酸衍生物的合成及抗氧化活性

  摘要：

  虽然小檗碱（BBR）具有抗氧化活性，但其活性有限。我们合成了 9 - O-苯甲酸小檗碱衍生物，并通过ABTS、DPPH、HOSC 和 FRAP 测定筛选了它们的抗氧化活性。苯甲酸环上的对位被卤素元素修饰，从而增强了抗氧化活性，并且发现邻位上的取代基优于间位。化合物8p , 8c , 8d , 8i , 8j , 8l , 尤其是8p显示出显着更高的抗氧化活性，这可归因于电子供体基团。所有小檗碱衍生物均具有适当的亲油性。总之，化合物8p是一种很有前途的抗氧化剂候选物，具有显着提高的抗氧化活性和中等的亲脂性。

  DOI：

  10.1039/d1ra01339d

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。
• COMPOUNDS, COMPOSITIONS AND METHODS FOR REDUCING LIPID LEVELS
  申请人：Liu Haiyan

  公开号：US20090048246A1

  公开（公告）日：2009-02-19

  Compositions comprising extracts or isolated or purified compounds from plants of the genus Corydalis provide prevention and treatment of hyperlipidemia, hypercholesterolemia, hypertriglyceridemia, hepatic steatosis, and metabolic syndrome. Corydalis compounds and their derivatives of natural and synthetic origins lower total cholesterol, LDL-cholesterol, and triglycerides and increase hepatic LDL receptor expression and activate AMP-activated protein kinase. Specific stereoisomers of Corydalis compounds with lipid lowering activity include 14R-(+)-corypalmine, 14R,13S-(+)-corydaline, 14R-(+)-tetrahydropalmatin, (+)-corlumidin, d-(+)-bicuculline, and (+)-egenine.

  从黄堇属植物提取物或分离纯化的化合物构成的组合物可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。黄堇化合物及其天然和合成来源的衍生物可降低总胆固醇、LDL-胆固醇和甘油三酯，增加肝LDL受体表达并激活AMP激活蛋白激酶。具有降脂活性的黄堇化合物的特定立体异构体包括14R-(+)-可丹碱、14R,13S-(+)-可丹啉、14R-(+)-四氢棕榈碱、(+)-可鲁米丁、d-(+)-比库枯碱和(+)-艾根碱。
• Crystal structure-guided design of berberine-based novel chitinase inhibitors
  作者：Lei Chen、Ling Zhu、Jinli Chen、Wei Chen、Xuhong Qian、Qing Yang

  DOI：10.1080/14756366.2020.1837123

  日期：2020.1.1

  model GH18 chitinase from the bacterium Serratia marcescens. Based on the berberine-binding mode, a hydrophobic cavity-based optimisation strategy was developed to increase their inhibitory activity. A series of berberine derivatives were designed and synthesised, and their inhibitory activities against GH18 chitinases were evaluated. The compound 4c showed 80-fold-elevated inhibitory activity against

  摘要 糖苷水解酶家族18（GH18）几丁质酶在从细菌到哺乳动物的各种生物中起着重要作用。几丁质酶抑制剂作为农药，杀真菌剂和抗哮喘药具有潜在的应用。黄连素，植物来源的异喹啉生物碱，先前被报道对各种GH18几丁质酶抑制与仅具有中等ķ 我值范围μM20和70之间。在本报告中，我们首次展示了Sm ChiB的小ber碱复合晶体结构，Sm ChiB是一种来自粘质沙雷氏菌的模型GH18几丁质酶。。基于小ber碱结合模式，开发了基于疏水腔的优化策略以增加其抑制活性。设计并合成了一系列小碱衍生物，并评估了它们对GH18几丁质酶的抑制活性。化合物4c对Sm ChiB和人几丁质酶hAMCase的抑制活性提高了80倍，K i值在亚微摩尔水平。提出了抑制活性提高的机理。这项工作为开发新型几丁质酶抑制剂提供了新的策略。
• Method and composition for controlling oral pathogens
  申请人：Wu D. Christine

  公开号：US20070098649A1

  公开（公告）日：2007-05-03

  A composition and method of controlling oral and other human pathogens is disclosed. The composition and method utilize an antimicrobial or antibiotic and a berberine as active agents to treat mammals, including humans.
• COMPOUNDS AND COMPOSITIONS FOR REDUCING LIPID LEVELS
  申请人：Liu Haiyan

  公开号：US20110269754A1

  公开（公告）日：2011-11-03

  Compositions comprising extracts or isolated or purified compounds from plants of the genus Corydalis provide prevention and treatment of hyperlipidemia, hypercholesterolemia, hypertriglyceridemia, hepatic steatosis, and metabolic syndrome. Corydalis compounds and their derivatives of natural and synthetic origins lower total cholesterol, LDL-cholesterol, and triglycerides and increase hepatic LDL receptor expression and activate AMP-activated protein kinase. Specific stereoisomers of Corydalis compounds with lipid lowering activity include 14R-(+)-corypalmine, 14R,13S-(+)-corydaline, 14R-(+)-tetrahydropalmatin, (+)-corlumidin, d-(+)-bicuculline, and (+)-egenine.