4,4'-((2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexane-1,1-diyl)bis(5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one) | 1215179-80-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,4'-((2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexane-1,1-diyl)bis(5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one)
• CAS: 1215179-80-8
• 化学式: C₂₆H₃₀N₄O₇
• 分子量: 510.547
• InChiKey: FZQSYMLVBWENGE-UFTZRREZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.12
• 重原子数：
  37.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  166.49
• 氢给体数：
  5.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  葡萄糖 、 依达拉奉 以 甲醇 为溶剂， 反应 0.5h， 生成 4,4'-((2S,3R,4R,5R)-2,3,4,5,6-pentahydroxyhexane-1,1-diyl)bis(5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one)
  参考文献：
  名称：

  Sugar Composition Analysis of Fuzi Polysaccharides by HPLC-MSn and Their Protective Effects on Schwann Cells Exposed to High Glucose

  摘要：

  符子在中国用于治疗糖尿病并发症已有多年。在之前的研究中，我们已经证明符子水提取物可以减轻大鼠的糖尿病周围神经病（DPN）并保护施旺细胞免受损伤。因此，本文研究了符子多糖（FPS）对高糖诱导的施旺细胞的保护作用及其初步机制。首先，提取了FPS，并通过前柱衍生化和高效液相色谱-电喷雾离子化多重串联质谱（HPLC/ESI-MSn）分析了其单糖成分。结果证明了该方法的有效性，并初步鉴定了七种单糖，其中来苏糖首次被报道。同时，m/z 215可以作为诊断离子确认单糖的数量。接下来，应用高糖诱导的施旺细胞模型，分为模型组、FPS处理组、正常对照组和渗透对照组。治疗48小时后，数据表明FPS显著降低了细胞内活性氧（ROS）和凋亡，这些是通过对应的荧光探针测定的。然后，通过西方印迹法测量了施旺细胞中与氧化应激相关蛋白的表达。此外，蛋白质检测发现FPS显著上调了超氧化物歧化酶（SOD）、催化酶（CAT）和过氧化物酶体增殖物激活受体γ协同激活因子1α（PGC-1α）蛋白水平，但下调了NADPH氧化酶-1（Nox1）蛋白水平。此外，FPS还显著增加了AMP激酶（AMPK）的活化。因此，我们初步推测AMPK-PGC-1α通路可能在FPS对高糖诱导的细胞损伤的保护作用中发挥重要作用。

  DOI：

  10.3390/molecules21111496

文献信息

• Development and application of a rapid and efficient CZE method coupled with correction factors for determination of monosaccharide composition of acidic hetero-polysaccharides from <i>Ephedra sinica</i>
  作者：Yong-gang Xia、Qiu-hong Wang、Jun Liang、Bing-you Yang、Guo-yu Li、Hai-xue Kuang

  DOI：10.1002/pca.1235

  日期：2011.3

  Introduction – Ephedrine alkaloids cannot account for all the effects of Ephedra sinica and the polysaccharides are also demonstrated to be one of the main bioactive constituents of E. sinica. However, no work has been reported on the analysis of monosaccharide composition of purified polysaccharides isolated from the stem of E. sinica.

  简介-麻黄碱不能解释所有的效果麻黄和多糖也被证明是主要的生物活性成分之一E.蛉。然而，尚未有关于从中华绒螯蟹茎中分离的纯化多糖的单糖组成分析的报道。
• A Novel Method for the Pre-Column Derivatization of Saccharides from Polygonatum cyrtonema Hua. by Integrating Lambert–Beer Law and Response Surface Methodology
  作者：Hui Liu、Yuanyuan Zhao、Leijing Chen、Jiao Du、Hongyan Guo、Bin Wang

  DOI：10.3390/molecules28052186

  日期：——

  Traditional Chinese medicine (TCM) safety and effectiveness can be ensured by establishing a suitable quality assessment system. This work aims to develop a pre-column derivatization HPLC method for Polygonatum cyrtonema Hua. quality control. In this study, 1-(4′-cyanophenyl)-3-methyl-5-pyrazolone (CPMP) was synthesized and reacted with monosaccharides derived from P. cyrtonema polysaccharides (PCPs), followed by HPLC separation. According to the Lambert–Beer law, CPMP has the highest molar extinction coefficient of all synthetic chemosensors. A satisfactory separation effect was obtained under a detection wavelength of 278 nm using a carbon-8 column and gradient elution over 14 min, with a flow rate of 1 mL per minute. Glucose (Glc), galactose (Gal), and mannose (Man) make up the majority of the monosaccharide components in PCPs, and their molar ratios are 1.73:0.58:1. The confirmed HPLC method has outstanding precision and accuracy, establishing a quality control method for PCPs. Additionally, the CPMP showed a visual improvement from colorless to orange after the detection of reducing sugars, allowing for further visual analysis.

  建立合适的质量评价体系可确保中药的安全性和有效性。本研究旨在建立一种柱前衍生高效液相色谱法，用于何首乌的质量控制。本研究合成了1-（4′-氰基苯基）-3-甲基-5-吡唑啉酮（CPMP），并将其与来源于华何首乌多糖（PCPs）的单糖反应，然后进行高效液相色谱分离。根据朗伯-比尔定律，CPMP 在所有合成化学传感器中具有最高的摩尔消光系数。在检测波长为 278 纳米的条件下，使用碳-8 色谱柱，以每分钟 1 毫升的流速进行梯度洗脱，历时 14 分钟，获得了令人满意的分离效果。在五氯苯酚的单糖成分中，葡萄糖（Glc）、半乳糖（Gal）和甘露糖（Man）占绝大多数，它们的摩尔比为 1.73:0.58:1。经确认的高效液相色谱法具有出色的精密度和准确度，可作为五氯苯酚的质量控制方法。此外，CPMP 在检测到还原糖后，视觉效果由无色变为橙色，可进一步进行视觉分析。

• Sugar compositional determination of polysaccharides from Dunaliella salina by modified RP-HPLC method of precolumn derivatization with 1-phenyl-3-methyl-5-pyrazolone
  作者：Jun Dai、Yan Wu、Shang-wei Chen、Song Zhu、Hong-ping Yin、Min Wang、Jian Tang

  DOI：10.1016/j.carbpol.2010.05.029

  日期：2010.10

  A modified high-performance liquid chromatography method of pre-column derivatization with 1-phenyl-3-methyl-5-pyrazolone (PMP) has been established for high resolution separation and high sensitivity determination of ten monosaccharides simultaneously, which frequently occur in algae polysaccharides. The effects of volume proportion of acetonitrile and pH value of mobile phase (0.1 M phosphate buffer acetonitrile) on retention and separation of the monosaccharide derivatives were investigated with Eclipse XPB-C18 column screened out. The hydrolyzation condition of polysaccharides and derivatization procedure of hydrolysates were also optimized. The modified analysis method was used for the determination of monosaccharide compositions in five polysaccharide fractions isolated from Duanaliella salina. The results showed that PD1 and PD4a were acidic heteropolysaccharide mainly containing glucose and galactose respectively, and PD4a contained sulfated groups; PD2 and PD3 all were a glucan; while PD4b was a complex of polysaccharide linked with nucleic acids by covalent bonds. (C) 2010 Elsevier Ltd. All rights reserved.
• Analysis of the monosaccharide composition of water-soluble polysaccharides from Sargassum fusiforme by high performance liquid chromatography/electrospray ionisation mass spectrometry
  作者：Xiaodan Wu、Wei Jiang、Jiajia Lu、Ying Yu、Bin Wu

  DOI：10.1016/j.foodchem.2013.09.019

  日期：2014.2

  Sargassum fusiforme (hijiki) is the well-known edible algae, whose polysaccharides have been proved to possess interesting bioactivities like antitumor, antioxidant, antimicrobial and immunomodulatory activities. A facile and sensitive method based on high-performance liquid chromatography method of pre-column derivatization with 1-phenyl-3-methyl-5-pyrazolone (PMP) coupled with electrospray ionisation mass spectrometry (HPLC/ESI-MS) has been established for the analysis of the monosaccharide composition of polysaccharides in S. fusiforme. Monosaccharides have been converted into PMP-labelled derivatives with aqueous ammonia as a catalyst at 70 degrees C for 30 min. The optimisation of the pre-column derivatization process was studied. The LODs of the monosaccharides were in the range from 0.01 to 0.02 nmol. PMP-labelled mixture of monosaccharides has been well separated by a reverse-phase HPLC and detected by on-line ESI-MS method under optimised conditions. The mobile phase of elution system was chosen as acetonitrile (solvent A) and 20 mM aqueous ammonium acetate (solvent B) (pH 3.0) with Zorbax XDB-C18 column at 30 degrees C for the separation of the monosaccharide derivatives. Identification of the monosaccharides composition was carried out by analysis with mass spectral behaviour and chromatography characteristics of 1-phenyl-3-methyl-5-pyrazolone (PMP) labelled monosaccharides. All PMP-labelled derivatives display high chemical stabilities, whose regular MS fragmentation is specific for reducing labelled sugars. The result showed that the S. fusiforme polysaccharide consisted of mannose, glucose, galactose, xylose, fucose and glucuronic acid or galacturonic acid, or both uronic acids. (C) 2013 Elsevier Ltd. All rights reserved.