4,4'-((2S,3S,4S,5S)-2,3,4,5-tetrahydroxyhexane-1,1-diyl)bis(5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one) | 1215179-78-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 4,4'-((2S,3S,4S,5S)-2,3,4,5-tetrahydroxyhexane-1,1-diyl)bis(5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one)
• CAS: 1215179-78-4
• 化学式: C₂₆H₃₀N₄O₆
• 分子量: 494.547
• InChiKey: SYPQQTCKXUPZIU-CKOGPGJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.14
• 重原子数：
  36.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  146.26
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  L-鼠李糖 、 依达拉奉 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 0.5h， 生成 4,4'-((2S,3S,4S,5S)-2,3,4,5-tetrahydroxyhexane-1,1-diyl)bis(5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one)
  参考文献：
  名称：

  快速高效的CZE方法和校正因子的测定方法的建立和应用，用于测定麻黄中酸性杂多糖的单糖组成

  摘要：

  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。

  DOI：

  10.1002/pca.1235

文献信息

• Sugar Composition Analysis of Fuzi Polysaccharides by HPLC-MSn and Their Protective Effects on Schwann Cells Exposed to High Glucose
  作者：Bei-Bei Wang、Jia-Li Wang、Jiang Yuan、Qing-Hua Quan、Rui-Fang Ji、Peng Tan、Jing Han、Yong-Gang Liu

  DOI：10.3390/molecules21111496

  日期：——

  Fuzi has been used to treat diabetic complications for many years in china. In a previous study, we have shown that Fuzi aqueous extract can attenuate Diabetic peripheral neuropathy (DPN) in rats and protect Schwann cells from injury. Thus, the protective effect of Fuzi polysaccharides (FPS) on high glucose-induced SCs and the preliminary mechanism were investigated. Firstly, the FPS were obtained and their monose composition was analyzed by the combination of pre-column derivatization and high performance liquid chromatography coupled with electrospray ionization multi-tandem mass spectrometry (HPLC/ESI-MSn). The results witnessed the efficiency of this method and seven monosaccharides were tentatively identified, among which fucose was first reported. Simultaneously, m/z 215 can be considered as diagnostic ions to confirm the number of monosaccharides. Next, high glucose-induced SC model was applied and divided into model group, treated group of FPS, normal and osmotic control group. After treatment for 48 h, the data showed FPS could significantly decrease the intracellular ROS and apoptosis, which were determined by the corresponding fluorescent probes. Then, the expression of oxidative stress-related proteins in SCs were measured by Western blot. Furthermore, the protein tests found that FPS markedly up-regulated superoxide dismutase (SOD), catalase (CAT) and peroxisome proliferator-activated receptor gamma coactivator 1-alpha (PGC-1α) protein level, but down-regulated NADPH oxidase-1 (Nox1) protein level. Moreover, FPS could also increase AMP-activated protein kinase (AMPK) activation significantly. Hence, we preliminary deduced that AMPK-PGC-1α pathway may play an important role in the protective effect of FPS against high glucose-induced cell damage.

  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。
• 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.