apigenin-4'-O-β-D-glucopyranoside | 20486-34-4

• 物质功能分类: 生物化工 - 核苷类药物
• 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: apigenin-4'-O-β-D-glucopyranoside
• 英文别名: apigenin-4′ -O-glucoside；apigenin 4'-O-β-D-glucoside；Apigenin-4'-glucoside；5,7-dihydroxy-2-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one
• CAS: 20486-34-4
• 化学式: C₂₁H₂₀O₁₀
• 分子量: 432.384
• InChiKey: ICLVCWSZHUZEFT-QNDFHXLGSA-N

物化性质

• 熔点：
  173-174 °C(Solv: ethanol (64-17-5))
• 沸点：
  763.3±60.0 °C(Predicted)
• 密度：
  1.642±0.06 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  31
• 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：
  166
• 氢给体数：
  6
• 氢受体数：
  10

制备方法与用途

芹菜素4′-O-β-D-吡喃葡萄糖苷是一种黄酮类化合物，可以在加里东圭亚那绒毛中找到。

反应信息

• 作为反应物：
  描述：

  apigenin-4'-O-β-D-glucopyranoside 在 硫酸 作用下， 以 乙醇 为溶剂， 生成 德国春黄菊油
  参考文献：
  名称：

  Chauhan; Vidyapati, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1996, vol. 35, # 9, p. 992 - 994

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3,4,6-四-O-乙酰基-α-D-吡喃葡萄糖酰氟 在 2,6-二叔丁基-4-甲基吡啶 、 三氟化硼乙醚 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 氯苯 为溶剂， 反应 16.0h， 生成 apigenin-4'-O-β-D-glucopyranoside
  参考文献：
  名称：

  Total synthesis of apigenin 7,4′-di-O-β-glucopyranoside, a component of blue flower pigment of Salvia patens, and seven chiral analogues

  摘要：

  We have succeeded in the first total synthesis of apigenin 7,4'-di-O-beta-D-glucopyranoside (1a), a component of blue pigment, protodelphin, from naringenin (2). Glycosylation of 2 according to Koenigs-Knorr reaction provided a monoglucoside 4a in 80% yield, and this was followed by DDQ oxidation to give apigenin 7-O-glucoside (12a). Further glycosylation of 4'-OH of 12a with 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl fluoride (5a) was achieved using a Lewis acid-and-base promotion system (BF3.Et2O, 2,6-di-tert-butyl-4-methylpyridine, and 1,1,3,3-tetramethylguanidine) in 70% yield, and subsequent deprotection produced 1a. Synthesis of three other chiral isomers of 1a, with replacement Of D-glucose at 7 and/or 4'-OH by L-glucose (1b-d), and four chiral isomers of apigenin 7-O-beta-glucosides (6a,b) and 4'-O-beta-glucosides (7a,b) also proved possible. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.01.001

文献信息

• Exploring the aglycon promiscuity of a new glycosyltransferase from Pueraria lobata
  作者：Lili Sun、Dawei Chen、Ridao Chen、Kebo Xie、Jimei Liu、Lin Yang、Jungui Dai

  DOI：10.1016/j.tetlet.2016.02.088

  日期：2016.3

  Enzymatic glycosylation catalyzed by glycosyltransferases has great potential for creating bioactive glycosylated small-molecule compounds. Here, we highlight the aglycon promiscuity of a new glycosyltransferase (PlGT7) from Pueraria lobata. PlGT7 exhibited the capability to glycosylate 26 structurally diverse drug-like scaffolds and simple phenolics with UDP-glucose to form O-, S-, and N-glycosides

  由糖基转移酶催化的酶促糖基化具有产生生物活性糖基化小分子化合物的巨大潜力。在这里，我们着重介绍了葛根中一种新的糖基转移酶（PlGT7）的糖苷配基混杂。PlGT7表现出用UDP-葡萄糖糖基化26种结构多样的药物样支架和简单酚类化合物以形成O-，S-和N-糖苷的能力。还利用PlGT7的可逆性及其底物​​柔性来利用简单的糖供体产生生物活性的糖苷。这些研究表明在药物开发中酶促方法对具有生物活性的天然和非天然产物进行糖基化的巨大潜力。
• 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。
• Extract of the aerial parts of Lawsonia inermis and its preparation method
  申请人：PIERRE FABRE DERMO-COSMETIQUE

  公开号：US11207265B2

  公开（公告）日：2021-12-28

  The invention relates to an extract of the aerial parts of Lawsonia inermis, as well as its preparation method and the extract that can be obtained by said method. The invention also relates to a cosmetic dye composition comprising such an extract. The invention finally concerns a cosmetic method for dying keratin fibers comprising the application of such a composition.

  本发明涉及光亮鼠李(Lawsonia inermis)地上部分的一种提取物，及其制备方法以及通过所述方法能够获得的提取物。本发明还涉及一种含有这种提取物的化妆品染料组合物。最后，本发明涉及一种用于使角蛋白纤维染色的化妆品方法，其包括应用这种组合物。
• Chiral Molecular Recognition on Formation of a Metalloanthocyanin: A Supramolecular Metal Complex Pigment from Blue Flowers ofSalvia patens
  作者：Tadao Kondo、Kin-ichi Oyama、Kumi Yoshida

  DOI：10.1002/1521-3773(20010302)40:5<894::aid-anie894>3.0.co;2-8

  日期：2001.3.2

  The chirality of the sugar moiety is responsible for the chiral molecular recognition on formation of a metalloanthocyanin from Salvia patens. This mechanism was revealed by using the synthetic apigenin 7,4'-diglucosides derived from D- or L-glucose. The supermolecule consists of six malonylawobanin molecules (blue) coordinated to two Mg2+ ions (red) with an M-helical arrangement of six 7,4'-diglucoside molecules (yellow) intercalated.
• LITVINENKO, V. I.;BUBENCHIKOVA, V. N., XIMIYA PRIROD. SOED.,(1988) N, S. 792-795
  作者：LITVINENKO, V. I.、BUBENCHIKOVA, V. N.

  DOI：——

  日期：——