3',4',5,7-tetrahydroxy-6-C-glucopyranosylflavone | 4261-42-1

• 物质功能分类: 生物化工 - 提取物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 3',4',5,7-tetrahydroxy-6-C-glucopyranosylflavone
• 英文别名: luteolin 6-C-glucoside；luteolin-6-C-glucoside；Homoorientien；3',4',5,7-Tetrahydroxy-6-c-glucopyranosyl flavone；2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-[(3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
• CAS: 4261-42-1
• 化学式: C₂₁H₂₀O₁₁
• 分子量: 448.383
• InChiKey: ODBRNZZJSYPIDI-JWFOYSBNSA-N

物化性质

• 熔点：
  245-246°C
• 沸点：
  856.7±65.0 °C(Predicted)
• 密度：
  1.759±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于甲醇：5mg/mL，澄清，无色至黄色
• LogP：
  1.580 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  197
• 氢给体数：
  8
• 氢受体数：
  11

安全信息

• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

制备方法与用途

生物活性

Isoorientin是一种有效的COX-2抑制剂，IC50值为39 μM。

靶点

• COX-2: 39 μM (IC50)

体外研究

Isoorientin是从葛根中提取的选择性COX-2抑制剂。在PANC-1和PATU-8988细胞中，Isoorientin（浓度分别为0、20、40、80、160 μM）处理24小时后，细胞活力显著下降，尤其是当浓度达到20、40、80和160 μM时。此外，在PANC-1细胞中使用0、20、40、80、160 μM浓度，在PATU-8988细胞中使用0、20、40、80、160、320 μM浓度处理24小时后，通过Western blotting检测p-AMPK和AMPK的表达。Isoorientin处理后，p-AMPK表达增加。在shRNA组中，使用80 μM浓度检测Isoorientin的效果。与野生型PC细胞（WT）及转染负控 lentivirus (NC) 组相比，shRNA组的AMPK和p-AMPK表达水平显著降低。

体内研究

给动物腹腔注射Isoorientin，剂量分别为10 mg/kg和20 mg/kg体重后，可显著减少足肿胀，平均峰值厚度为1.19±0.05 mm和1.08±0.04 mm。这表明与对照组相比，Isoorientin显著减轻了足部肿胀。

化学性质

黄色粉末状物质，易溶于甲醇、乙醇及DMSO等有机溶剂。主要来源于竹叶、夏枯草和石竹。

用途

• 异荭草素具有抗心肌缺血的作用。
• 主要用作含量测定、鉴定及药理实验。

药理作用包括：

• 保肝作用
• 抗病毒活性
• 抗过氧化作用
• 解焦虑作用

反应信息

• 作为反应物：
  描述：

  3',4',5,7-tetrahydroxy-6-C-glucopyranosylflavone 在 盐酸 作用下， 反应 6.0h， 生成 荭草苷
  参考文献：
  名称：

  Dombris; Raynaud, Pharmazie, 1981, vol. 36, # 5, p. 384 - 384

  摘要：

  DOI：
• 作为产物：
  描述：

  荭草苷 在 盐酸 作用下， 反应 6.0h， 生成 3',4',5,7-tetrahydroxy-6-C-glucopyranosylflavone
  参考文献：
  名称：

  Dombris; Raynaud, Pharmazie, 1981, vol. 36, # 5, p. 384 - 384

  摘要：

  DOI：

文献信息

• ANTIHYPERTENSIVE POLYOL COMPOUND AND DERIVATIVE THEREOF
  申请人：East China University of Science and Technology

  公开号：EP3906969A1

  公开（公告）日：2021-11-10

  The present invention provides a compound as represented by formula I, or a pharmaceutically acceptable salt or ester, a prodrug, an optical isomer, a stereoisomer, or a solvate thereof. The compound provided by the present invention can be used for preparing drugs for preventing or treating hypertension, or hypertension-related diseases, or pulmonary hypertension, or pulmonary hypertension-related diseases. The compound provided by the present invention has a different mechanism from existing drugs for treating hypertension and pulmonary hypertension, thereby laying a new material foundation for the development of drugs for treating hypertension and pulmonary hypertension.

  本发明提供了一种由式I代表的化合物，或其药用可接受的盐或酯，前药，光学异构体，立体异构体或其溶剂合物。本发明提供的化合物可用于制备用于预防或治疗高血压或与高血压相关疾病，或肺动脉高压或与肺动脉高压相关疾病的药物。本发明提供的化合物与现有用于治疗高血压和肺动脉高压的药物具有不同的机制，从而为开发用于治疗高血压和肺动脉高压的药物奠定了新的物质基础。
• Extracts of Cyclanthera pedata and formulations and uses thereof
  申请人：Díaz Rebolledo Alejandro Mario

  公开号：US10220067B2

  公开（公告）日：2019-03-05

  The invention provides a method for extracting active therapeutic components from plant materials of the Cyclanthera pedata plant which comprises immersing said plant material containing active components and selected from the group consisting of fruits, flowers, leaves, stems, twigs, bark, wood, buds, seeds, roots, and pods in a solvent for a period of time of about 30 minutes to about 10 hours to achieve transfer of active components from the plant material to the solvent, separating the solvent containing active components from the plant material, and evaporating or distilling the solvent to produce a concentrated fraction containing active components. The invention further includes compositions and therapeutic formulations of such extracts to treat hypercholesterolemia and other high lipid related diseases.

  本发明提供了一种从 Cyclanthera pedata 植物材料中提取活性治疗成分的方法，该方法包括将所述含有活性成分且选自果实、花、叶、茎、小枝、树皮、木材、芽、种子、根和豆荚的植物材料浸泡在溶剂中约 30 分钟至约 10 小时，以实现活性成分从植物材料转移到溶剂中、和荚果在溶剂中浸泡约 30 分钟至约 10 小时，以实现活性成分从植物材料转移到溶剂中，将含有活性成分的溶剂从植物材料中分离出来，蒸发或蒸馏溶剂以产生含有活性成分的浓缩部分。本发明还包括此类提取物的组合物和治疗制剂，用于治疗高胆固醇血症和其他高血脂相关疾病。
• [EN] ANTIHYPERTENSIVE POLYOL COMPOUND AND DERIVATIVE THEREOF<br/>[FR] COMPOSÉ POLYOL ANTIHYPERTENSEUR ET DÉRIVÉ DE CELUI-CI<br/>[ZH] 抗高血压的多元醇化合物及其衍生物
  申请人：UNIV EAST CHINA SCIENCE & TECH

  公开号：WO2020249117A1

  公开（公告）日：2020-12-17

  本发明提供式I所示化合物、或其药学上可接受的盐或酯、前药、光学异构体、立体异构体或溶剂合物。本发明的化合物能够用于制备预防或治疗高血压或高血压相关疾病或肺动脉高压或肺动脉高压相关疾病的药物。本发明的化合物与现有的治疗高血压和肺动脉高压的药物具备不同的机理，从而为开发高血压和肺动脉高压治疗药物奠定了全新的物质基础。
• A New Flavone <i>C</i>-Glycoside and Antiplatelet and Vasorelaxing Flavones from <i>Gentiana arisanensis</i>
  作者：Chun-Nan Lin、Shih-Hsien Kuo、Mei-Ing Chung、Feng-Nien Ko、Che-Ming Teng

  DOI：10.1021/np970011e

  日期：1997.8.1

  A new flavone C-glycoside, isovitexin 6''-O-glucoside (1), and three known flavonoids. quercetin, isovitexin, and luteolin-7-O-beta-D-glucoside, have been further isolated from the whole plant of Gentiana arisanensis Hayata. The new compound was characterized by spectral methods and chemical reactions. The antiplatelet effects of isovitexin 6''-O-glucoside (1), isoorientin (2), 2 peracetate (3), isovitexin (4), luteolin 7-O-beta-D-glucoside (5), luteolin (6), isoorientin 6''-O-glucoside (7), and 7 peracetate (8) were studied using washed rabbit platelets. Of the compounds tested, 6 showed potent antiplatelet effects on arachidonic acid (AA)-induced platelet aggregation (IC50 = 43.5 mu M). The effect of 2, 5, and 6 on the contraction of rat thoracic aorta was also studied. Compound 6 depressed markedly the contraction induced by Ca2+ (1.9 mM) in high-K+ (80 mM) medium, with an IC50 of about 156 mu M and also inhibited noradrenaline (3 mu M)-induced phasic and tonic contractions, with an IC50 of about 68 and 72 mu M, respectively.
• EXTRACTS OF CYCLANTHERA PEDATA AND FORMULATIONS AND USES THEREOF
  申请人：Díaz Rebolledo Alejandro Mario

  公开号：US20170071995A1

  公开（公告）日：2017-03-16

  The invention provides a method for extracting active therapeutic components from plant materials of the cyclanthera pedata plant which comprises immersing said plant material containing active components and selected from the group consisting of fruits, flowers, leaves, stems, twigs, bark, wood, buds, seeds, roots, and pods in a solvent for a period of time of about 30 minutes to about 10 hours to achieve transfer of active components from the plant material to the solvent, separating the solvent containing active components from the plant material, and evaporating or distilling the solvent to produce a concentrated fraction containing active components. The invention further includes compositions and therapeutic formulations of such extracts to treat hypercholesterolemia and other high lipid related diseases.