山柰酚-3,7-二-O-葡萄糖苷 | 25615-14-9

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 山柰酚-3,7-二-O-葡萄糖苷
• 英文名称: 3,7-Di-O-glucosylkaempferol
• 英文别名: kaempferol-3-O-β-D-glucopyranosyl-7-O-β-D-glucopyranoside；kaempferol 7-O-β-glucopyranosyl 3-O-β-glucopyranoside；kaempferol 3,7,-di-O-β-D-glucopyranoside；kaempferol 3,7-di-O-β-D-glucopyranoside；kaempferol-3,7-di-O-β-D-glucopyranoside；kaempferol 3,7-O-β-D-diglucopyranoside；Kaempferol 3,7-diglucoside；5-hydroxy-2-(4-hydroxyphenyl)-3,7-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]chromen-4-one
• CAS: 25615-14-9
• 化学式: C₂₇H₃₀O₁₆
• 分子量: 610.526
• InChiKey: XFFQVRFGLSBFON-DEFKTLOSSA-N

物化性质

• 熔点：
  180-183 °C
• 沸点：
  1007.4±65.0 °C(Predicted)
• 密度：
  1.82±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  43
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  266
• 氢给体数：
  10
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  山柰酚-3,7-二-O-葡萄糖苷 在 硫酸 作用下， 生成 山奈酚
  参考文献：
  名称：

  Kaempferol derivatives from the fruit of the Japanese pagoda tree

  摘要：

  DOI：

  10.1007/bf00579994
• 作为产物：
  描述：

  槲皮素 在 甲醇 、 4-二甲氨基吡啶 、 palladium 10% on activated carbon 、 四丁基溴化铵 、 氨 、 氢气 、 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 152.0h， 生成 山柰酚-3,7-二-O-葡萄糖苷
  参考文献：
  名称：

  캄페롤-3,7-β-D-비스글루코사이드의 화학적 대량 합성 방법 및 그 용도

  摘要：

  本发明涉及康普鲁-3,7-β-D-双葡萄糖苷的化学大规模合成方法及其用途。

  公开号：

  KR101549700B1

文献信息

• Functional Characterization and Protein Engineering of a Triterpene 3‐/6‐/2′‐ <i>O</i> ‐Glycosyltransferase Reveal a Conserved Residue Critical for the Regiospecificity
  作者：Meng Zhang、Yang Yi、Bai‐Han Gao、Hui‐Fei Su、Yang‐Oujie Bao、Xiao‐Meng Shi、Hai‐Dong Wang、Fu‐Dong Li、Min Ye、Xue Qiao

  DOI：10.1002/anie.202113587

  日期：2022.2.14

  We characterized the first plant cycloartane glycosyltransferase AmGT8 from A. membranaceus. Its mutants A394F, A394D, and T131V were discovered using semi-rational design, which showed specific 6-O, 3-O, and 2′-O glycosylation activities, respectively. This study uncovered a conserved residue critical for the regiospecificity of plant glycosyltransferases.

  我们对来自A. membranaceus的第一个植物环阿坦糖基转移酶 AmGT8 进行了表征。其突变体 A394F、A394D 和 T131V 是使用半理性设计发现的，它们分别显示出特定的 6- O、3 - O和 2' - O糖基化活性。这项研究发现了一个对植物糖基转移酶的区域特异性至关重要的保守残基。
• Flavonoid glycosides from the leaves of Allium victorialis var. platyphyllum and their anti-neuroinflammatory effects
  作者：Kyeong Wan Woo、Eunjung Moon、So Young Park、Sun Yeou Kim、Kang Ro Lee

  DOI：10.1016/j.bmcl.2012.10.043

  日期：2012.12

  Eight new flavonoid glycosides, named allivictoside A-H (1-8), together with twelve known flavonoids (9-20) were isolated from the leaves of Allium victorialis var. platyphyllum. The structures of 1-8 were determined by chemical and spectroscopic methods, including 1D, 2D NMR analyses and HR-MS. To evaluate the anti-neuroinflammatory activities of all isolates, we measured the secreted nitric oxide levels in murine microglia BV-2 cells stimulated by lipopolysaccharide. In this study, compounds 2, 6, 10, and 18 significantly inhibited nitric oxide production (IC50 values of 20.67, 20.42, 21.48 and 19.80 mu M, respectively) without cell toxicity. Therefore, we suggest that allivictoside B (2) and F (6), 3-O-beta-D-glucosyl-7-O-beta-D-(2-O-feruloyl) glucosylkaempferol (10) and quercetin 3-O-beta-D-glucopyranoside (18) may be considered as candidates for the treatment of diseases associated with neuroinflammation. (C) 2012 Elsevier Ltd. All rights reserved.
• Evolvosides C–E, flavonol-4-O-triglycosides from Evolvulus alsinoides and their anti-stress activity
  作者：Prasoon Gupta、Upasana Sharma、Praveen Gupta、Kiran Babu Siripurapu、Rakesh Maurya

  DOI：10.1016/j.bmc.2012.12.040

  日期：2013.3

  Phytochemical investigation of the n-butanol fraction of Evolvulus alsinoides (Linn.) led to the isolation of three new phenolic glycosides, evolvosides C, D and E (1-3) along with six known compounds (4-9). The structures of the compounds were elucidated on the basis of spectroscopic analysis, viz. 1D and 2D NMR experiments, chemical study, and comparison with literature data. Evolvoside C (1) was characterized as kaempferol 4'-O-beta-D-glucopyranosyl-(1 -> 2)-alpha-L-rhamnopyranosyl-(1 -> 6)-beta-D-glucopyranoside, whereas evolvosides D and E (2-3) were found to be mono and di-O-methyl derivatives of 1. The new compounds (1-3) represent rare triglycoside derivatives of flavonol at C-4'. The isolated compounds (1-6) were screened for acute stress-induced biochemical changes in male Sprague-Dawley rats at a dose of 40 mg/kg body weight. Compounds 1 and 2 displayed anti-stress effects by normalizing hyperglycemia, plasma corticosterone, plasma creatine kinase, and adrenal hypertrophy. Compounds 3 and 6 were also found to be effective in normalizing most of these stress parameters, whereas compounds 4 and 5 were ineffective in normalizing most of these effects. (C) 2013 Elsevier Ltd. All rights reserved.
• Identification and Characterization of CtUGT3 as the Key Player of Astragalin Biosynthesis in <i>Carthamus tinctorius</i> L.
  作者：Chaoxiang Ren、Ziqing Xi、Bin Xian、Chao Chen、Xulong Huang、Huajuan Jiang、Jiang Chen、Cheng Peng、Jin Pei

  DOI：10.1021/acs.jafc.3c05117

  日期：2023.11.1
• Kaempferol derivatives from the fruit of the Japanese pagoda tree
  作者：N. M. Akhmedkhodzhaeva、A. N. Svechnikova

  DOI：10.1007/bf00579994

  日期：——