秦艽甲素 | 439-89-4

• 物质功能分类: 生物化工 - 提取物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃吡啶类
• 中文名称: 秦艽甲素
• 英文名称: gentianine
• 英文别名: erythricin；gentianin；5-vinyl-3,4-dihydro-pyrano[3,4-c]pyridin-1-one；5-Vinyl-3,4-dihydro-pyrano[3,4-c]pyridin-1-on；5-vinyl-3,4-dihydro-pyrano[3,4-c]pyridine-1-one；5-vinyl-3,4-dihydro-pyrano[3,4-c]pyridine-1-on；5-ethenyl-3,4-dihydropyrano[3,4-c]pyridin-1-one
• CAS: 439-89-4
• 化学式: C₁₀H₉NO₂
• mdl: MFCD00801129
• 分子量: 175.187
• InChiKey: DFNZYFAJQPLJFI-UHFFFAOYSA-N

物化性质

• 熔点：
  84-86℃
• 沸点：
  386.5±42.0 °C(Predicted)
• 密度：
  1.225
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

制备方法与用途

生物活性方面，Gentianine 是一种有效的 Swertiamarin 代谢产物，展现出显著的抗糖尿病和抗炎作用。

反应信息

• 作为反应物：
  描述：

  秦艽甲素 在 potassium permanganate 、 过氧化苯甲酰 作用下， 以 丙酮 为溶剂， 生成 1-oxo-3,4-dihydro-1H-pyrano[3,4-c]pyridine-5-carboxylic acid
  参考文献：
  名称：

  Alkaloids of Gentiana olivieri

  摘要：

  DOI：

  10.1007/bf00563746
• 作为产物：
  描述：

  1-oxo-5-vinyl-1H-pyrano[3,4-c]pyridine-3-carboxylic acid ethyl ester 在 水 、 N,N-二甲基甲酰胺 、 sodium chloride 作用下， 生成 秦艽甲素
  参考文献：
  名称：

  Studies on the syntheses of heterocyclic compounds. 657. Total synthesis of angustine, nauclefine, and gentianine

  摘要：

  DOI：

  10.1021/jo00877a007

文献信息

• [EN] NOVEL PYRIDINE DERIVATIVES, A PROCESS FOR THEIR PREPARATION AND A PHARMACEUTICAL COMPOSITION CONTAINING THE SAME<br/>[FR] NOUVEAUX DERIVES DE PYRIDINE, LEUR PROCEDE DE PREPARATION ET COMPOSITION PHARMACEUTIQUE EN CONTENANT
  申请人：SK CHEMICALS CO LTD

  公开号：WO2005063768A1

  公开（公告）日：2005-07-14

  This invention relates to novel pyridine derivatives having an inhibitory effect on production of cytokines, which are involved in inflammatory responses, thus suggesting its usefulness as therapeutic agents for treating diseases related to inflammation, immune, chronic inflammation as well as an agent having an anti-inflammatory and analgesic effect. Further, this invention relates to a method of manufacturing the same and a pharmaceutical composition containing the same.

  这项发明涉及具有抑制细胞因子产生作用的新型吡啶衍生物，这些细胞因子参与炎症反应，因此表明其可用作治疗与炎症、免疫、慢性炎症相关疾病的治疗剂，同时具有抗炎和镇痛作用的药剂。此外，这项发明涉及制造该化合物的方法和含有该化合物的药物组合物。
• Effects of Gentianine on the Production of Pro-inflammatory Cytokines in Male Sprague-Dawley Rats Treated with Lipopolysaccharide (LPS)
  作者：Wie-Jong Kwak、Joo-Hyon Kim、Keun-Ho Ryu、Yong-Baik Cho、Sun-Duck Jeon、Chang-Kiu Moon

  DOI：10.1248/bpb.28.750

  日期：——

  This study was undertaken to elucidate the mechanism of anti-inflammatory action of gentianine, a constituent of Gentiana Macrophylla. The effects of gentianine on lipopolysacharide (LPS)-induced production of pro-inflammatory cytokines were investigated in male Sprague-Dawley rats. For the first time, we found that oral administration of gentianine (10—100 mg/kg) suppressed the increases in tumor necrosis factor-α (TNF-α) (ED50, 37.7 mg/kg) and interleukin (IL)-6 (ED50, 38.5 mg/kg) in the sera from the rats challenged with bacterial LPS (100 μg/kg; i.p.). However, LPS induced production of other interleukins, such as IL-α, was not significantly altered by gentianine. These results suggest that the potential anti-inflammatory action of gentianine might be at least partly based on the suppressed production of TNF-α and IL-6.

  本研究旨在阐明龙胆碱（龙胆的一种成分）的抗炎作用机制。在雄性 Sprague-Dawley 大鼠中研究了龙胆碱对脂多糖 (LPS) 诱导的促炎细胞因子产生的影响。我们首次发现口服龙胆碱（10-100 mg/kg）可抑制肿瘤坏死因子-α（TNF-α）（ED50，37.7 mg/kg）和白细胞介素（IL）-6（用细菌 LPS（100 μg/kg；腹腔注射）攻击的大鼠血清中的 ED50，38.5 mg/kg）。然而，LPS 诱导的其他白细胞介素（例如 IL-α）的产生并没有被龙胆碱显着改变。这些结果表明，龙胆碱的潜在抗炎作用可能至少部分是基于抑制 TNF-α 和 IL-6 的产生。
• Novel Pyridine Derivatives, a Process for Their Preparation and a Pharmaceutical Composition Containing the Same
  申请人：Kim Ook Hyung

  公开号：US20070254909A1

  公开（公告）日：2007-11-01

  The invention relates to novel pyridine derivatives having an inhibitory effect on production of cytokines, which are involved in inflammatory responses, thus suggesting its usefulness as therapeutic agents for treating diseases related to inflammation, immune, chronic inflammation as well as an agent having an anti-inflammatory and analgesic effect. Further, this invention relates to a method of manufacturing the same and a pharmaceutical composition containing the same.

  本发明涉及一种新型吡啶衍生物，具有抑制细胞因子产生的作用，这些细胞因子参与炎症反应，从而表明它们在治疗与炎症、免疫、慢性炎症相关的疾病中具有治疗作用，同时具有抗炎和镇痛作用的药剂。此外，本发明还涉及制造该药物的方法和含有该药物的药物组合物。
• Lithographic printing process
  申请人：FUJI PHOTO FILM CO., LTD.

  公开号：EP1147886A2

  公开（公告）日：2001-10-24

  A hydrophilic layer and an overcoat layer are provided in this order on a heat-sensitive layer having an ink receiving surface, so as to form an original (plate) for a lithographic printing plate. The overcoat layer can be removed during printing. A system capable of forming an inorganic hydrophilic matrix by sol-gel conversion is provided in the hydrophilic layer. Adhesion between the heat-sensitive layer and the hydrophilic layer decreases in a heated region through image processing. Emulsion ink is supplied to the plate surface during printing, whereby the overcoat layer and the hydrophilic layer at an image portion are removed with a hydrophilic component of the emulsion ink. Thus, with a heat-sensitive original that can be subjected to heat-mode prepress using laser exposure, good printed matter can be stably obtained, irrespective of balance between image and non-image portions, without using wetting water.

  在具有受墨表面的热敏层上依次设置亲水层和覆膜层，以形成平版印刷版的原版（印版）。覆盖层可在印刷过程中去除。亲水层中有一个能通过溶胶-凝胶转换形成无机亲水基质的系统。通过图像处理，热敏层和亲水层之间的粘合力会在加热区域减弱。在印刷过程中向印版表面提供乳剂墨水，从而用乳剂墨水中的亲水成分去除图像部分的覆膜层和亲水层。因此，对于可以使用激光曝光进行热模式印前处理的热敏原稿，无论图像部分和非图像部分之间的平衡如何，都可以稳定地获得良好的印刷品，而无需使用润湿水。
• RECOMBINANT MICROORGANISM FOR PREPARING TERPENOID AND METHOD FOR CONSTRUCTING RECOMBINANT MICROORGANISM
  申请人：Tianjin Institute Of Industrial Biotechnology, Chinese Academy of Sciences

  公开号：EP2952576A1

  公开（公告）日：2015-12-09

  Provided are a recombinant strain for preparing a terpenoid, and method for constructing the recombinant strain. Also provided is a recombinant bacterium 1, the recombinant bacterium 1 being a recombinant bacterium obtained in order to improve the enzymatic activity of α-ketoglutarate dehydrogenase in escherichia coli or the mutant thereof. The method for improving the enzymatic activity of α-ketoglutarate dehydrogenase in escherichia coli or the mutant thereof is replacing the original regulating element of the ketoglutarate dehydrogenase gene (sucAB) in escherichia coli or the mutant thereof with any of the following regulating elements: artificial regulating element M1-46, M1-37, and M1-93. Also provided are a plurality of recombinant bacteria. By improving the enzymatic activity of α-ketoglutarate dehydrogenase, succinic acid dehydrogenase and transaldolase therein and improving the ability of a cell to synthesize NADPH and ATP, the efficiency of the MEP pathway and the production capacity of terpenoid are improved.

  本发明提供了一种用于制备萜类化合物的重组菌株，以及构建该重组菌株的方法。还提供了一种重组菌 1，该重组菌 1 是为了提高大肠杆菌中 α-酮戊二酸脱氢酶或其突变体的酶活性而获得的重组菌。提高大肠杆菌或其突变体中α-酮戊二酸脱氢酶酶活性的方法是将大肠杆菌或其突变体中酮戊二酸脱氢酶基因（sucAB）的原始调控元件替换为以下任一调控元件：人工调控元件M1-46、M1-37和M1-93。还提供了多种重组细菌。通过提高其中α-酮戊二酸脱氢酶、琥珀酸脱氢酶和反式脱氢酶的酶活性，提高细胞合成 NADPH 和 ATP 的能力，从而提高 MEP 途径的效率和萜类化合物的生产能力。

表征谱图