Kaempferol-3-O-β-D-glucopyranosid | 480-10-4

• 物质功能分类: 生物化工 - 提取物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: Kaempferol-3-O-β-D-glucopyranosid
• 英文别名: 3,4',5,7-tetrahydroxyflavone-3-glucoside；kaempferol 3‐O‐glucoside；kaempferol-3-O-β-D-glucoside；kaempferol-3-O-b-D-glucopyranoside；kaempferol 3-O-β-glucoside；kaempferol 3-O-glucoside；kaempferol 3-O-beta-L-glucopyranoside；5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• CAS: 480-10-4；23627-87-4；31159-41-8；69292-77-9；107163-34-8
• 化学式: C₂₁H₂₀O₁₁
• 分子量: 448.383
• InChiKey: JPUKWEQWGBDDQB-LQSBFMDOSA-N

物化性质

• 熔点：
  223-229°C
• 沸点：
  823.2±65.0 °C(Predicted)
• 密度：
  1.79±0.1 g/cm3(Predicted)
• 溶解度：
  DMF：30mg/mL； DMSO：30mg/mL； DMSO:PBS (pH 7.2) (1:6)：0.14 mg/mL
• LogP：
  1.950 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  186
• 氢给体数：
  7
• 氢受体数：
  11

安全信息

• WGK Germany：
  3
• RTECS号：
  DJ3080000
• 海关编码：
  29389090
• 安全说明：
  S22
• 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

根据您提供的信息，总结了紫云英苷的相关性质、提取与合成方法以及相关的参考资料。以下是对这些内容的详细概述：

化学性质和来源

• 化学性质：易溶于DMSO（二甲基亚砜）、甲醇和氯仿的混合溶剂，可溶于热甲醇，不溶于石油醚。
• 来源：主要来源于百蕊草。

提取方法

1. 超声波辅助提取荷叶紫云英苷的方法
   • 条件优化结果表明，在低频超声波（25.5 kHz）、20分钟的提取时间、55℃的温度下，使用体积分数70%乙醇作为提取溶剂时，能获得较好的提取效果。该条件下荷叶紫云英苷的提取率为1.67%。

合成方法

一种酶促合成紫云英苷的方法包括以下步骤：

1. 克隆、表达和纯化在合成途经中所需关键酶：糖原磷酸化酶GP、葡萄糖焦磷酸化酶GalU、黄烷酮-3-羟化酶F3H、黄烷酮合酶FLS1和类黄酮3-O-葡萄糖基转移酶UGT78K2。
2. 肌糖原Gn在GP作用下合成葡萄糖-1-磷酸G-1-P。
3. G-1-P在GalU作用下生成尿苷二磷酸葡萄糖UDPG。
4. 柚皮素NRN在F3H作用下合成二氢山奈酚DHK。
5. DHK在FLS1作用下转化成山奈酚KMF。
6. KMF和UDPG在UGT78K2的作用下最终生成紫云英苷。

药代动力学研究

• 在刘红菊等人的研究中，采用液相色谱-串联质谱（LC-MS）技术测定并研究了大鼠血浆中紫云英苷的浓度及其药代动力学特性。结果显示该方法在低浓度范围内线性关系良好且具有较高的准确性。

药理作用

• 紫云英苷具有调节体内血糖、增强肌体免疫力、促进生长和提高抗氧化能力等多种生物活性。

参考文献

1. 刘红菊等，“液相色谱-串联质谱测定大鼠血浆中紫云英苷的浓度及其药代动力学研究”，《南方医科大学学报》, 2013年第7期。
2. 杨豪伟等，“紫云英苷对小鼠成骨细胞MC3T3-E1增殖与分化的影响” ，《中医药大学报》，2013年第4期。
3. 纪晓花，“荷叶紫云英苷的超声辅助提取及其抑菌活性研究”，《食品工业》, 2014年第10期。
4. 刘洋等，“RP-HPLC 测定百蕊草中紫云英苷的含量” ，《中国中药杂志》，2006年第21期。
5. 张新跃等，“一种酶促合成紫云英苷的方法”，专利号：CN201610029307.3, 申请日2016年1月15日。

综上所述，紫云英苷是一种具有多种潜在生物活性的化合物，通过上述研究已经对其化学性质、提取与合成方法以及药理作用进行了深入探讨。

反应信息

• 作为反应物：
  描述：

  Kaempferol-3-O-β-D-glucopyranosid 在 water-d2 、 甲酸铵 作用下， 以 aq. buffer 为溶剂， 生成
  参考文献：
  名称：

  Regioselective solvent-phase deuteration of polyphenolic compounds informs their identification by mass spectrometry

  摘要：

  Liquid chromatography-mass spectrometry (LC-MS) is a highly sensitive tool for the analysis of polyphenolic compounds in complex food and beverage matrices. However, the high degree of isomerism among polyphenols in general often complicates this approach, especially for identification of novel compounds. Here, we explore the utility of mild acid-catalyzed deuterium (MACD) labeling via electrophilic aromatic substitution as a complementary method for informing polyphenolic compound structure elucidation. To prevent hydrolysis of acid-labile glycosidic linkages, optimal reaction conditions that maximize regioselective hydrogen/deuterium (HID) exchange of aromatic protons while preserving compound integrity were characterized (60 degrees C, pH 3.0, 72 h). Under these conditions, standard compounds varying in the number and position of hydroxyl, glycosyl, and methyl groups about their aromatic core structure produced distinguishable H/D exchange patterns. The applicability of this method for the analysis of complex mixtures was demonstrated in red wine where the extent of deuterium exchange, together with accurate mass information, led to the putative identification of an unknown compound. The identification was further supported by tandem MS (MS/MS) data, which matched conclusively to the same compound in the Metlin LC-MS/MS library. With the capacity to discriminate between select isomeric forms, MACD labeling provides structural information that complements accurate mass and tandem mass spectral measurements for informing the identification of polyphenolics by MS. (C) 2014 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.ab.2014.02.018

文献信息

• Regioselective solvent-phase deuteration of polyphenolic compounds informs their identification by mass spectrometry
  作者：Mikel R. Roe、Jerry D. Cohen、Adrian D. Hegeman

  DOI：10.1016/j.ab.2014.02.018

  日期：2014.5

  Liquid chromatography-mass spectrometry (LC-MS) is a highly sensitive tool for the analysis of polyphenolic compounds in complex food and beverage matrices. However, the high degree of isomerism among polyphenols in general often complicates this approach, especially for identification of novel compounds. Here, we explore the utility of mild acid-catalyzed deuterium (MACD) labeling via electrophilic aromatic substitution as a complementary method for informing polyphenolic compound structure elucidation. To prevent hydrolysis of acid-labile glycosidic linkages, optimal reaction conditions that maximize regioselective hydrogen/deuterium (HID) exchange of aromatic protons while preserving compound integrity were characterized (60 degrees C, pH 3.0, 72 h). Under these conditions, standard compounds varying in the number and position of hydroxyl, glycosyl, and methyl groups about their aromatic core structure produced distinguishable H/D exchange patterns. The applicability of this method for the analysis of complex mixtures was demonstrated in red wine where the extent of deuterium exchange, together with accurate mass information, led to the putative identification of an unknown compound. The identification was further supported by tandem MS (MS/MS) data, which matched conclusively to the same compound in the Metlin LC-MS/MS library. With the capacity to discriminate between select isomeric forms, MACD labeling provides structural information that complements accurate mass and tandem mass spectral measurements for informing the identification of polyphenolics by MS. (C) 2014 Elsevier Inc. All rights reserved.