isorhamnetin 3-β-D-galactopyranoside | 5041-82-7

• 物质功能分类: 天然产物 - 黄酮类化合物
• 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: isorhamnetin 3-β-D-galactopyranoside
• 英文别名: 3,5,7,4'-tetrahydroxy-3'-methoxyflavone-3-O-β-D-galactopyranoside；3'-O-methylquercetin 3-O-β-D-galactopyranoside；isorhamnetin 3-O-β-D-galactopyranoside；isorhamnetin-3-O-β-D-galactopyranoside；isorhamnetin-3-O-β-D-galactoside；isorhamnetin 3-O-galactoside；Cacticin；5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• CAS: 5041-82-7；6743-92-6；50306-07-5
• 化学式: C₂₂H₂₂O₁₂
• 分子量: 478.409
• InChiKey: CQLRUIIRRZYHHS-UVHBULKNSA-N

物化性质

• 熔点：
  155-160°C
• 沸点：
  834.4±65.0 °C(Predicted)
• 密度：
  1.75±0.1 g/cm3(Predicted)
• 溶解度：
  DMSO：250 mg/mL（522.58 mM；需要超声波）

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  196
• 氢给体数：
  7
• 氢受体数：
  12

安全信息

• 海关编码：
  29389090

制备方法与用途

生物活性的isorhamnetin-3-O-glucoside 是一种广泛存在于蔬菜和水稻中的天然化合物，经消化后可在肠道菌群中代谢。其化学性质表现为黄色粉末，易溶于氯仿，较难溶于乙醇、丙酮和乙醚，而不溶于石油醚和水，该化合物来源于蒲黄。

用途方面，isorhamnetin-3-O-glucoside 可用于含量测定、鉴定以及药理实验等。此外，其具有显著的降血脂作用。

反应信息

• 作为反应物：
  描述：

  isorhamnetin 3-β-D-galactopyranoside 在 盐酸 、 水 作用下， 反应 1.0h， 生成 D-吡喃葡萄糖
  参考文献：
  名称：

  Phenolic constituents of the inflorescences of Sorbus torminalis (L.) Crantz

  摘要：

  Torminaloside, a new acylated flavonol glycoside (3,5,7,4'-tetrahydroxy-3'-methoxyflavone-3-O-[6 ''-O-(3'''-hydroxy-3'''-methylglutaroyl)]-beta-D-galactopyranoside, 6), together with five further methoxylated flavones 1-5, hyperoside (7), isoquercitrin (8), chlorogenic acid (9) and neochlorogenic acid (10), were isolated for the first time from Sorbus torminalis (L.) Crantz. The structures of the isolates were elucidated by extensive spectroscopic studies, including UV, IR, 1D- and 2D-NMR, LSI-MS and HR-LSI-MS experiments. In addition to torminaloside, three further flavonoids: 5,7,4'-trihydroxy-3'-methoxyflavone- 7-O-beta-D-glucopyranoside (1), 3,5,7,4'-tetrahydroxy-8,3'-dimethoxyflavone-3-O-beta-D-glucopyranoside (2), and 3,5,7,4'-tetrahydroxy-3'-methoxyflavone-3-O-beta-D-galactopyranoside (4) were found for the first time in the genus Sorbus. (C) 2011 Phytochemical Society of Europe. Published by Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.phytol.2011.02.005
• 作为产物：
  描述：

  3,5,7,4'-tetrahydroxy-3'-methoxyflavone-3-O-[6''-O-(3'''-hydroxy-3'''-methylglutaroyl)]-β-D-galactopyranoside 在 水 、 sodium hydroxide 作用下， 反应 0.5h， 生成 isorhamnetin 3-β-D-galactopyranoside
  参考文献：
  名称：

  Phenolic constituents of the inflorescences of Sorbus torminalis (L.) Crantz

  摘要：

  Torminaloside, a new acylated flavonol glycoside (3,5,7,4'-tetrahydroxy-3'-methoxyflavone-3-O-[6 ''-O-(3'''-hydroxy-3'''-methylglutaroyl)]-beta-D-galactopyranoside, 6), together with five further methoxylated flavones 1-5, hyperoside (7), isoquercitrin (8), chlorogenic acid (9) and neochlorogenic acid (10), were isolated for the first time from Sorbus torminalis (L.) Crantz. The structures of the isolates were elucidated by extensive spectroscopic studies, including UV, IR, 1D- and 2D-NMR, LSI-MS and HR-LSI-MS experiments. In addition to torminaloside, three further flavonoids: 5,7,4'-trihydroxy-3'-methoxyflavone- 7-O-beta-D-glucopyranoside (1), 3,5,7,4'-tetrahydroxy-8,3'-dimethoxyflavone-3-O-beta-D-glucopyranoside (2), and 3,5,7,4'-tetrahydroxy-3'-methoxyflavone-3-O-beta-D-galactopyranoside (4) were found for the first time in the genus Sorbus. (C) 2011 Phytochemical Society of Europe. Published by Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.phytol.2011.02.005

文献信息

• Highly Promiscuous Flavonoid 3-<i>O</i>-Glycosyltransferase from <i>Scutellaria baicalensis</i>
  作者：Zilong Wang、Shuang Wang、Zheng Xu、Mingwei Li、Kuan Chen、Yaqun Zhang、Zhimin Hu、Meng Zhang、Zhiyong Zhang、Xue Qiao、Min Ye

  DOI：10.1021/acs.orglett.9b00524

  日期：2019.4.5

  from Scutellaria baicalensis. Sb3GT1 could accept five sugar donors (UDP-Glc/-Gal/-GlcNAc/-Xyl/-Ara) to catalyze 3-O-glycosylation of 17 flavonols, and the conversion rates could be >98%. Five new glycosides were obtained by scaled-up enzymatic catalysis. Molecular modeling and site-directed mutagenesis revealed that G15 and P187 were critical catalytic residues for the donor promiscuity. Sb3GT1 could

  从黄cut中发现了一种高度区域特异性和供体混杂的3- O-糖基转移酶Sb3GT1（UGT78B4）。Sb3GT1可以接受五个糖供体（UDP-Glc / -Gal / -GlcNAc / -Xyl / -Ara）催化17种黄酮醇的3- O-糖基化，转化率可以> 98％。通过按比例放大的酶催化作用获得了五种新的糖苷。分子建模和定点诱变表明，G15和P187是供体滥交的关键催化残基。Sb3GT1可能是增加类黄酮3- O-糖苷结构多样性的有前途的催化剂。
• Effects of Functional Groups and Sugar Composition of Quercetin Derivatives on Their Radical Scavenging Properties
  作者：Komei Kato、Masayuki Ninomiya、Kaori Tanaka、Mamoru Koketsu

  DOI：10.1021/acs.jnatprod.6b00274

  日期：2016.7.22

  biological actions. The aim of this study was to investigate the structure–activity relationships of quercetin derivatives, with a focus on the influence of functional groups and sugar composition on their antioxidant capacity. A series of quercetin derivatives were therefore prepared and assessed for their DPPH radical scavenging properties. Isoquercetin O-gallates were more potent radical scavengers

  槲皮素衍生物广泛存在于植物界，并表现出各种生物学作用。这项研究的目的是研究槲皮素衍生物的结构-活性关系，重点是官能团和糖成分对其抗氧化能力的影响。因此，制备了一系列槲皮素衍生物，并评估了它们的DPPH自由基清除性能。异槲皮素O-加仑酸酯比槲皮素更有效的自由基清除剂。系统分析强调了异槲皮素O-没食子酸酯中羟基取代基的分布对其效能的重要性。