2-羟基柚皮素; 2,3-二氢-2,5,7-三羟基-2-(4-羟基苯基)-4H-1-苯并吡喃-4-酮 | 58124-18-8

• 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
• 中文名称: 2-羟基柚皮素; 2,3-二氢-2,5,7-三羟基-2-(4-羟基苯基)-4H-1-苯并吡喃-4-酮
• 中文别名: 2,3-二氢-2,5,7-三羟基-2-(4-羟基苯基)-4H-1-苯并吡喃-4-酮
• 英文名称: 2,4’,5,7-tetrahydroxyflavanone
• 英文别名: 2-hydroxynaringenin；2,5,7-trihydroxy-2-(4-hydroxyphenyl)-3H-chromen-4-one
• CAS: 58124-18-8
• 化学式: C₁₅H₁₂O₆
• 分子量: 288.257
• InChiKey: NFENYLPEYDNIMO-UHFFFAOYSA-N

物化性质

• 沸点：
  635.0±55.0 °C(Predicted)
• 密度：
  1.613±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

安全信息

• 海关编码：
  2932999099
• 储存条件：
  储存温度应控制在2-8℃之间，需保持干燥并密封保存。

制备方法与用途

2-羟基柚皮素是一种黄酮类化合物，可以从芍药中分离获得。

反应信息

• 作为反应物：
  描述：

  2-羟基柚皮素; 2,3-二氢-2,5,7-三羟基-2-(4-羟基苯基)-4H-1-苯并吡喃-4-酮 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 以100%的产率得到德国春黄菊油
  参考文献：
  名称：

  C-Glucosylflavonoid biosynthesis from 2-hydroxynaringenin by Desmodium uncinatum (Jacq.) (Fabaceae)

  摘要：

  [2',3',5',6'-H-2(4)]-2-Hydroxynaringenin is synthesised and incubated with commercially available UDP-glucose and the crude protein extract from Desmoduim uncinatum leaves. The organic extract produces isotopically labelled [2',3',5',6'-H-2(4)]-vitexin and [2',3',5',6'-H-2(4)]-isovitexin. Repeating the experiment with denatured protein or replacing the 2-hydroxynaringenin with [2',3',5',6'-H-2(4)]-apigenin or [2',3',5',6'-H-2(4)]- naringenin results in no observable incorporation. 2-Hydroxynaringenin is therefore the substrate for C-glucosylflavonoid biosynthesis in D. uncinatum. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.07.118
• 作为产物：
  描述：

  (Z)-3-hydroxy-1-[2-hydroxy-4,6-bis(phenylmethoxy)phenyl]-3-(4-phenylmethoxyphenyl)prop-2-en-1-one 以65的产率得到2-羟基柚皮素; 2,3-二氢-2,5,7-三羟基-2-(4-羟基苯基)-4H-1-苯并吡喃-4-酮
  参考文献：
  名称：

  Chirality, 2011, 23, 891-896

  摘要：

  DOI：

文献信息

• GENE ENCODING FLAVONE SYNTHASE
  申请人：SUNTORY LIMITED

  公开号：EP1067189A1

  公开（公告）日：2001-01-10

  DNA obtained, for example, from snapdragon or torenia, encoding an enzyme that can convert flavanones directly to flavones, and its uses; the DNA and amino acid sequences for enzymes encoded thereby are listed as SEQ.ID. No. 1 & 2 and 3 & 4, for example. Introduction of the genes into plants can, for example, alter the flower colors of the plants.

  例如，从龙须菜或香椿中获得的 DNA，编码可将黄酮直接转化为黄酮的酶及其用途；其编码的酶的 DNA 和氨基酸序列列于 SEQ.ID.1和2以及3和4。将这些基因导入植物可改变植物的花色等。
• Genes coding for flavone synthases
  申请人：SUNTORY LIMITED

  公开号：EP1726653A2

  公开（公告）日：2006-11-29

  DNA obtained, for example, from snapdragon or torenia, encoding an enzyme that can convert flavanones directly to flavones, and its uses; the DNA and amino acid sequences for enzymes encoded thereby are listed as SEQ.ID. No. 1 & 2 and 3 & 4, for example. Introduction of the genes into plants can, for example, alter the flower colors of the plants.

  例如，从龙须菜或香椿中获得的 DNA，编码可将黄酮直接转化为黄酮的酶及其用途；其编码的酶的 DNA 和氨基酸序列列于 SEQ.ID.1和2以及3和4。将这些基因导入植物可改变植物的花色等。
• BIFUNCTIONAL C-GLYCOSIDE GLYCOSYLTRANSFERASES AND APPLICATION THEREOF
  申请人：CAS Center for Excellence in Molecular Plant Sciences

  公开号：EP4108777A1

  公开（公告）日：2022-12-28

  The present disclosure provides a group of novel uridine diphosphate (UDP)-glycosyltransferases, which are bifunctional C-glycoside arabinosyltransferases and C-glycoside glucosyltransferases. The glycosyltransferases can specifically and efficiently catalyze C-glycoside arabinosylation and glucosylation of dihydrochalcone compounds or 2-hydroxyflavanone compounds, to generate C-glycoside dihydrochalcone or C-glycoside-2-hydroxyflavanone compounds; the C-glycoside-2-hydroxyflavanone compounds are further subjected to a dehydration reaction to form flavone-C-glycoside compounds. The present disclosure also provides an application of the novel UDP-glycosyltransferases to artificially constructed recombinant expression systems to generate C-glycoside dihydrochalcone and flavone-C-glycoside compounds by means of fermentation engineering.

  本公开提供了一组新型二磷酸尿苷（UDP）-糖基转移酶，它们是双功能 C-糖苷阿拉伯糖基转移酶和 C-糖苷葡萄糖基转移酶。糖基转移酶可以特异、高效地催化二氢查尔酮化合物或 2-羟基黄烷酮化合物的 C-糖苷阿拉伯化和葡萄糖基化，生成 C-糖苷二氢查尔酮或 C-糖苷-2-羟基黄烷酮化合物；C-糖苷-2-羟基黄烷酮化合物进一步经脱水反应生成黄酮-C-糖苷化合物。本公开还提供了新型 UDP-糖基转移酶在人工构建的重组表达系统中的应用，通过发酵工程生成 C-糖苷二氢查尔酮和黄酮-C-糖苷化合物。
• Glycosylation modification of bioactive compounds and drugs by plant glycosyltransferases (UGTs)
  申请人：UNIVERSITY OF NORTH TEXAS

  公开号：US11261477B2

  公开（公告）日：2022-03-01

  In alternative embodiments, provided are methods for the glycosylation modification of bioactive compounds and drugs using isolated, recombinant or genetically modified uridine diphosphate glycosyl-transferases (UGTs). In alternative embodiments, provided are methods for modifying UGTs to generate recombinant UGTs with altered donor and/or acceptor specificities. In alternative embodiments, provided are methods for screening for recombinantly engineered UGTs with new or altered properties, for example, for new or altered donor and/or acceptor specificities, where in alternative embodiments the screening comprise use of bacterial, yeast or baculovirus expression system.

  在另一个实施方案中，提供了使用分离的、重组的或遗传修饰的二磷酸尿苷糖基转移酶（UGTs）对生物活性化合物和药物进行糖基化修饰的方法。在另一些实施方案中，提供了对 UGTs 进行修饰以产生具有改变的供体和/或受体特异性的重组 UGTs 的方法。在另一个实施方案中，提供了筛选具有新的或改变的特性的重组工程UGT的方法，例如，筛选新的或改变的供体和/或受体特异性的方法，其中在另一个实施方案中，筛选包括使用细菌、酵母或杆状病毒表达系统。
• DNAs coding for flavone synthases, methods of using flavone synthase DNAs, and plants, flowers, and vectors containing flavone synthase DNAs
  申请人：Mizutani Masako

  公开号：US20060248609A1

  公开（公告）日：2006-11-02

  DNA obtained, for example, from snapdragon or torenia, encoding an enzyme that can convert flavanones directly to flavones, and its uses; the DNA and amino acid sequences for enzymes encoded thereby are listed as SEQ. ID. No. 1 & 2 and 3 & 4, for example. Introduction of the genes into plants can, for example, alter the flower colors of the plants.

  例如，从龙须菜或鸢尾属植物中获得的 DNA 黄酮 编码可将黄酮直接转化为黄酮的酶及其用途；其编码的酶的 DNA 和氨基酸序列列为 SEQ.ID.1和2以及3和4。将这些基因导入植物可改变植物的花色等。