eriodictyol chalcone | 73692-51-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: eriodictyol chalcone
• 英文别名: 3,4,2',4',6'-pentahydroxychalcone；2a(2),4a(2),6a(2),3,4-Pentahydroxychalcone；3-(3,4-dihydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one
• CAS: 73692-51-0
• 化学式: C₁₅H₁₂O₆
• 分子量: 288.257
• InChiKey: CRBYNQCDRNZCNX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  118
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  eriodictyol chalcone 在 peroxidase from onion solid waste 、 双氧水 、 N,N-二甲基甲酰胺 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以95%的产率得到金色草素
  参考文献：
  名称：

  来自洋葱固体废物的粗过氧化物酶可作为有机合成的工具。第一部分：2'，3,4,4'，6'-五羟基查尔酮环化成金黄色葡萄球菌素

  摘要：

  描述了来自洋葱固体废物的粗过氧化物酶（POD）作为生物催化剂合成天然存在的金黄色素的潜力。粗酶制剂有效地促进了2'，3,4,4'，6'-五羟基查尔酮（不是洋葱POD的天然底物）的环化成金黄色素。

  DOI：

  10.1016/j.tetlet.2010.05.125
• 作为产物：
  描述：

  3,4-二羟基苯甲醛 在 盐酸 、 水 、 potassium carbonate 、 sodium hydroxide 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 48.0h， 生成 eriodictyol chalcone
  参考文献：
  名称：

  Design, synthesis and bioactivity of chalcones and its analogues

  摘要：

  The Vernohia anthelmintica L's extract is one of the most popular Uygur medicines used for vitiligo. It is believed that the chalcone compounds of the plant play an important role in the treatment since they may activate tyrosinase and improve melanin production. In this study, twenty-one chalcones and nine analogues were synthesized in view of three different components of chalcone (A, B ring and a, beta-unsaturated carbonyl). After biological evaluation of their activity on tyrosinase in cell-free systems, the result showed that most compounds (except polyhydroxy chalcones) possess activator effect on the tyrosinase, especially for 13a-15a, 20a and 1 b, which bearing a comparable activity to the positive control 8-MOP. SAR of these tyrosinase activator was summed up for the first time as well. Finally, compound 13a was found to increase melanin contents and tyrosinase activity 1.75 and 1.3 fold, respectively, compared with that of untreated murine B16 cells at the concentration of 40 mu g/mL (C) 2017 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2017.03.018

文献信息

• 一种天然活性产物二氢槲皮素的合成工艺
  申请人：张家港威胜生物医药有限公司

  公开号：CN103864743B

  公开（公告）日：2016-04-20

  本发明是公开了（2R，3R）-二氢槲皮素合成工艺，具体以咖啡酸酰氯和间苯三酚为原料，经过付克酰化，双键过氧化成环氧键，再酸性条件开环与酚羟基成醚，反应结束进行分离、纯化、结晶得到高含量和高纯度的产品。在反应使用试剂、原辅料方面均考虑以绿色环保、效率。本方法有高原子经济型、设备简单、生产程序绿色环保，有非常大的经济和社会效益。
• Discovery of Novel Bacterial Chalcone Isomerases by a Sequence‐Structure‐Function‐Evolution Strategy for Enzymatic Synthesis of ( <i>S</i> )‐Flavanones
  作者：Hannes Meinert、Dong Yi、Bastian Zirpel、Eva Schuiten、Torsten Geißler、Egon Gross、Stephan I. Brückner、Beate Hartmann、Carsten Röttger、Jakob P. Ley、Uwe T. Bornscheuer

  DOI：10.1002/anie.202107182

  日期：2021.7.26

  strategy. These novel bacterial CHIs show diversity in substrate specificity towards various hydroxylated and methoxylated chalcones. The mutagenesis of CHIera according to the substrate binding models of these novel bacterial CHIs resulted in several variants with greatly improved activity towards these chalcones. Furthermore, the preparative scale conversion catalyzed by bacterial CHIs has been performed

  查尔酮异构酶 (CHI) 是植物中类黄酮生物合成的关键酶。第一个细菌CHI（CHI时代）是从枝枝真杆菌中鉴定出来的，但其分布、进化来源、底物范围和立体选择性仍不清楚。在这里，我们描述了使用新型序列-结构-功能-进化 (SSFE) 策略从 Genbank 鉴定 66 种新型细菌 CHI。这些新型细菌 CHI 显示出对各种羟基化和甲氧基化查耳酮的底物特异性的多样性。CHI时代的诱变根据这些新型细菌 CHI 的底物结合模型，产生了几种变体，对这些查耳酮的活性大大提高。此外，已经对五种查耳酮进行了由细菌 CHIs 催化的制备规模转化，并显示出 ( S )-选择性高达 96% ee，这为高产率合成 ( S )-黄烷酮提供了一种替代生物催化途径。
• Anti-ulcer agent comprising chalcone derivative
  申请人：Tsumura Juntendo, Inc.

  公开号：US05234951A1

  公开（公告）日：1993-08-10

  The present invention relates to an anti-ulcer agent comprising a compound represented by the following general formula I as the effective ingredient, and a novel chalcone derivative included in the compound represented by this general formula I: ##STR1## wherein X and Y independently stand for a hydrogen atom or together form a single bond, R.sub.1 stands for a hydroxyl group, an acetoxy group, a carboxymethoxy group or a methoxycarbonylmethoxy group, R.sub.2 stands for a hydrogen atom, an isoprenyl group, isopentyl group or a propyl group, R.sub.3 stands for a hydroxyl group or a methoxy group, R.sub.4 stands for a hydrogen atom, a hydroxyl group or a methoxy group, R.sub.5 stands for a hydrogen atom, a hydroxyl group, a methoxy group or an isopentyl group, R.sub.6 stands for a hydroxyl group, a methoxy group or a carboxymethoxy group, and R.sub.7 stands for a hydrogen atom or a methoxy group.

  本发明涉及一种抗溃疡剂，其包括以下通式I所表示的化合物作为有效成分，以及包含在该通式I所表示的化合物中的一种新的查尔酮衍生物： 其中，X和Y独立地代表氢原子或共同形成单键，R1代表羟基、乙酰氧基、羧甲氧基或甲氧羰基甲氧基，R2代表氢原子、异戊烯基、异戊基或丙基，R3代表羟基或甲氧基，R4代表氢原子、羟基或甲氧基，R5代表氢原子、羟基、甲氧基或异戊基，R6代表羟基、甲氧基或羧甲氧基，R7代表氢原子或甲氧基。
• Anti-ulcer agent comprising chalcone derivative as effective ingredient
  申请人：Tsumura & Co.

  公开号：US05106871A1

  公开（公告）日：1992-04-21

  The present invention relates to an anti-ulcer agent comprising a compound represented by the following general formula I as the effective ingredient, and a novel chalcone derivative included in the compound represented by this general formula I: ##STR1## wherein X and Y independently stand for a hydrogen atom or together form a single bond, R.sub.1 stands for a hydroxyl group, an acetoxy group, a carboxymethoxy group or a methoxycarbonylmethoxy group, R.sub.2 stands for a hydrogen atom, an isoprenyl group, isopentyl group or a propyl group, R.sub.3 stands for hydroxyl group or a methoxy group, R.sub.4 stands for a hydrogen atom, a hydroxyl group or a methoxy group, R.sub.5 stands for a hydrogen atom, a hydroxyl group, a methoxy group or an isopentyl group, R.sub.6 stands for a hydroxyl group, a methoxy group or a carboxymethoxy group, and R.sub.7 stands for a hydrogen atom or a methoxy group.

  本发明涉及一种抗溃疡剂，其包括以下通式I所表示的化合物作为有效成分，以及包含在该通式I所表示的化合物中的一种新的查尔酮衍生物： ##STR1## 其中，X和Y独立地代表氢原子或形成单键，R1代表羟基、乙酰氧基、羧甲氧基或甲氧羰基甲氧基，R2代表氢原子、异戊烯基、异戊基或丙基，R3代表羟基或甲氧基，R4代表氢原子、羟基或甲氧基，R5代表氢原子、羟基、甲氧基或异戊基，R6代表羟基、甲氧基或羧甲氧基，R7代表氢原子或甲氧基。
• Synthesis and studies on antidepressant activity of 2′,4′,6′-trihydroxychalcone derivatives
  作者：Xin Sui、Ying-Chun Quan、Yue Chang、Rui-Peng Zhang、Yin-Feng Xu、Li-Ping Guan

  DOI：10.1007/s00044-011-9640-2

  日期：2012.7

  In this study, we synthesized a series of 2',4',6'-trihydroxychalcone derivatives and evaluated their antidepressant activities. The results of the nine compounds showed significantly reduced times during the forced swimming test at a dose of 10 mg/kg, indicative of antidepressant activity. Among the compounds, 2-bromo-2',4',6'-trihydroxychalcone (3h) was found to be the most potent, and it was observed that compound 3h at dose of 10, 20, and 40 mg/kg significantly reduced the duration of immobility times in the FST and TST in mice 30 min after treatment.