(-)-epitaxifolin

• 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: (-)-epitaxifolin
• 英文别名: cis-dihydroquercetin；(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-2,3-dihydrochromen-4-one
• 化学式: C₁₅H₁₂O₇
• 分子量: 304.256
• InChiKey: CXQWRCVTCMQVQX-HUUCEWRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 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：
  127
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (-)-epitaxifolin 以 甲醇 为溶剂， 反应 1440.0h， 生成 (-)-二氢槲皮素
  参考文献：
  名称：

  来自樟子松针叶的顺式和反式二氢槲皮素糖苷

  摘要：

  摘要 (-)- 顺式 -2,3-二氢槲皮素（推测为 3'- O -β- d -吡喃葡萄糖苷）；(+)-反式-2,3-二氢槲皮素、二氢杨梅素和圣草酚的3'-O-d-吡喃葡萄糖苷；(+)-儿茶素和(+)-没食子儿茶素已从樟子松的针叶中分离出来。二氢槲皮素苷元在甲醇溶液中相互转化。根据其二氢槲皮素、二氢杨梅素和圣草酚的含量，可以区分樟子松的两种化学型。

  DOI：

  10.1016/0031-9422(88)84101-3
• 作为产物：
  描述：

  (-)-epitaxifolin 3-O-β-D-xylopyranoside 以 水 为溶剂， 生成 D-木糖 、 (-)-epitaxifolin
  参考文献：
  名称：

  Nonaka, Gen-Ichiro; Goto, Yuko; Kinjo, Jun-Ei, Chemical and pharmaceutical bulletin, 1987, vol. 35, # 3, p. 1105 - 1108

  摘要：

  DOI：

文献信息

• Unexpected different chemoselectivity in the aerobic oxidation of methylated planar catechin and bent epicatechin derivatives catalysed by the Trametes villosa laccase/1-hydroxybenzotriazole system
  作者：Roberta Bernini、Fernanda Crisante、Patrizia Gentili、Sergio Menta、Fabio Morana、Marco Pierini

  DOI：10.1039/c3ra47753c

  日期：——

  C ring and the newly formed cycle D. The oxidation of compounds 5 and 6 in the presence of the Trametes villosa laccase/1-hydroxybenzotriazole (HBT) system was investigated under aerobic conditions in both a biphasic system and a reverse micelle. The unexpected different chemoselective oxidation at the benzylic position of catechin and epicatechin derivatives 5 and 6 has been rationalized using a molecular

  未报道的甲基化儿茶素和表儿茶素衍生物5和6是通过oxa-Pictet-Spengler反应合成的。儿茶素5显示B和C环共面，因为在C环和新生成的六项周期D之间形成了反接，进而缩合到环B。相反，表儿茶素6由于弯曲而形成了弯曲的几何形状。在C环和新形成的环D之间建立一个顺式连接。在Trametes villosa存在下化合物5和6的氧化漆酶/ 1-羟基苯并三唑（HBT）系统在有氧条件下在双相系统和反胶束中进行了研究。儿茶素和表儿茶素衍生物5和6的苄基位置发生了意想不到的不同化学选择性氧化，已使用分子建模方法进行了合理化处理。这些结果表明，Trametes villosa漆酶/ HBT系统代表了一种有用的工具，可根据结构特征对酚类化合物的C-2或C-4位置进行功能化。
• Design, synthesis and characterization of novel inhibitors against mycobacterial β-ketoacyl CoA reductase FabG4
  作者：Deb Ranjan Banerjee、Debajyoti Dutta、Baisakhee Saha、Sudipta Bhattacharyya、Kalyan Senapati、Amit K. Das、Amit Basak

  DOI：10.1039/c3ob41676c

  日期：——

  We report the design and synthesis of triazole-polyphenol hybrid compounds 1 and 2 as inhibitors of the FabG4 (Rv0242c) enzyme of Mycobacterium tuberculosis for the first time. A major advance in this field occurred only a couple of years ago with the X-ray crystal structure of FabG4, which has helped us to design these inhibitors by the computational fragment-based drug design (FBDD) approach. Compound 1 has shown competitive inhibition with an inhibition constant (Ki) value of 3.97 ± 0.02 μM. On the other hand, compound 2 has been found to be a mixed type inhibitor with a Ki value of 0.88 ± 0.01 μM. Thermodynamic analysis using isothermal titration calorimetry (ITC) reveals that both inhibitors bind at the NADH co-factor binding domain. Their MIC values, as determined by resazurin assay against M. smegmatis, indicated their good anti-mycobacterial properties. A preliminary structure–activity relationship (SAR) study supports the design of these inhibitors. These compounds may be possible candidates as lead compounds for alternate anti-tubercular drugs. All of the reductase enzymes of the Mycobacterium family have a similar ketoacyl reductase (KAR) domain. Hence, this work may be extrapolated to find structure-based inhibitors of other reductase enzymes.

  我们首次报道了三唑-多酚混合化合物1和2的设计与合成，作为结核分枝杆菌FabG4（Rv0242c）酶的抑制剂。该领域的一项重大进展发生在几年前，FabG4的X射线晶体结构的公布帮助我们通过计算片段药物设计（FBDD）方法设计了这些抑制剂。化合物1表现出竞争抑制，其抑制常数（Ki）值为3.97 ± 0.02 μM。另一方面，化合物2被发现为混合型抑制剂，Ki值为0.88 ± 0.01 μM。使用等温滴定热量计（ITC）进行的热力学分析显示，这两种抑制剂都在NADH辅因子结合域结合。通过对M. smegmatis进行的罗丹明B实验确定的最小抑菌浓度（MIC）值表明它们具有良好的抗分枝杆菌特性。初步的结构-活性关系（SAR）研究支持了这些抑制剂的设计。这些化合物可能作为替代抗结核药物的先导化合物候选者。结核分枝杆菌家族的所有还原酶都有类似的酮酰还原酶（KAR）结构域。因此，这项工作可以外推以寻找其他还原酶的基于结构的抑制剂。
• Water Soluble and Activable Phenolics Derivatives with Dermocosmetic and Therapeutic Applications and Process for Preparing Said Derivatives
  申请人：Auriol Daniel

  公开号：US20090233876A1

  公开（公告）日：2009-09-17

  The invention relates to the preparation of phenolics derivatives by enzymatic condensation of phenolics selected among pyrocatechol or its derivatives with the glucose moiety of sucrose. The production of said phenolics derivatives is achieved with a glucosyltransferase (EC 2.4.1.5). These O-α-glucosides of selected phenolics are new, have a solubility in water higher than that of their parent polyphenol and have useful applications in cosmetic and pharmaceutical compositions, such as antioxidative, antiviral, antibacterial, immune-stimulating, antiallergic, antihypertensive, antiischemic, antiarrhythmic, antithrombotic, hypocholesterolemic, antilipoperoxidant, hepatoprotective, anti-inflammatory, anticarcinogenic antimutagenic, antineoplastic, anti-thrombotic, and vasodilatory formulations, or in any other field of application.

  该发明涉及通过酶催化将选择自间苯二酚或其衍生物的酚类与蔗糖的葡萄糖部分进行缩合来制备酚类衍生物。所述酚类衍生物的生产是通过葡萄糖转移酶（EC 2.4.1.5）实现的。所选酚类的这些O-α-葡糖苷是新的，其在水中的溶解度高于它们的原始多酚，并且在化妆品和药用组合物中具有有用的应用，如抗氧化、抗病毒、抗菌、免疫刺激、抗过敏、降压、抗缺血、抗心律失常、抗血栓形成、降胆固醇、抗脂质过氧化、肝脏保护、抗炎症、抗癌变突变、抗肿瘤、抗血栓形成和扩血管等配方，或者在任何其他应用领域中。
• Water soluble phenolics derivatives with dermocosmetic and therapeutic applications
  申请人：Libragen

  公开号：EP1867729A1

  公开（公告）日：2007-12-19

  The invention relates to the preparation of phenolics derivatives by enzymatic condensation of phenolics selected among pyrocatechol or its derivatives including (i) protocatechuic acid and its derivatives, (ii) 3,4-dihydroxycinnamic acid with its transisomer or caffeic acid and its derivatives, especially hydrocaffeic acid, rosmarinic acid, chlorogenic acid and caffeic acid phenethyl ester, and with its cis-isomer and its derivatives, especially esculin, (iii) dihydroxyphenylglycol, and (iv) members of the flavonoid familly such as taxifolin and fustin (dihydroflavonols), fisetin (a flavonol), eriodictyol (a flavanone), , with the glucose moiety of sucrose. The production of said phenolics derivatives is achieved with a glucosyltransferase (EC 2.4.1.5) obtained from a culture of Leuconostoc species, and more particularly from the culture of Leuconostoc mesenteroides NRRL B-512F. These O-glucosides of selected phenolics are new, have a solubility in water higher than that of their parent polyphenol and have useful applications in cosmetic and pharmaceutical compositions, such as antioxidative, antiviral, antibacterial, immune-stimulating, antiallergic, antihypertensive, antiischemic, antiarrhytmic, antithrombotic, hypocholesterolemic, antilipoperoxidant, hepatoprotective, anti-inflammatory, anticarcinogenic antimutagenic, antineoplastic, anti-thrombotic, and vasodilatory formulations, or in any other field of application. All the more, glucosylated phenolics derivatives objects of the invention can be hydrolyzed by the human natural microbiotes, thus releasing the active part of the phenolic compound upon time during their usage or by an α-glucosidase (EC 3.2.1.20).

  本发明涉及用酶缩合法制备酚类衍生物，所选酚类包括焦儿茶酚或其衍生物，包括(i) 原儿茶酸及其衍生物，(ii) 3,4-二羟基肉桂酸与其反式异构体或咖啡酸及其衍生物，特别是氢咖啡酸、(iii) 二羟基苯甘醇，以及 (iv) 黄酮家族成员，如 taxifolin 和 fustin（二氢黄酮醇）、fisetin（一种黄酮醇）、eriodictyol（一种黄酮），以及蔗糖的葡萄糖分子。上述酚类衍生物的生产是通过一种葡糖基转移酶（EC 2.4.1.5）实现的，该酶是从白色念珠菌（Leuconostoc spECies）的培养物中获得的，尤其是从中肠白色念珠菌（Leuconostoc mesenteroides NRRL B-512F）的培养物中获得的。抗高血压、抗缺血、抗心律失常、抗血栓、降胆固醇、抗脂过氧化、保肝、抗炎、抗癌、抗突变、抗肿瘤、抗血栓和血管扩张配方，或任何其他应用领域。此外，本发明的葡糖基化酚类衍生物可被人体天然微生物水解，从而在使用过程中或通过α-葡萄糖苷酶（EC 3.2.1.20）释放出酚类化合物的活性部分。
• Modulation of cellular DNA repair activity to intercept malignancy
  申请人：THE BOARD OF TRUSTEES OF THE LELAND STANFORD JUNIOR UNIVERSITY

  公开号：US10188617B2

  公开（公告）日：2019-01-29

  Disclosed herein are methods for identifying compounds that enhance base excision repair, as well as compounds identified thereby and methods of using such compounds in the interception of malignancy, i.e. the prevention of progression of a disease from a state of susceptibility to active disease. Exemplified compounds are acetohexamide and related compounds, as well as benserazide and analogs thereof. Exemplified malignancies are those of human breast cells carrying mutations, in particular, SUM149 cells and HCC1937 cells, which cells carry BRCA1 mutations.

  本文公开了用于鉴定可增强碱基切除修复的化合物的方法，以及由此鉴定出的化合物和将此类化合物用于阻断恶性肿瘤的方法，即防止疾病从易感状态发展为活动性疾病的方法。示例化合物是乙酰己酰胺和相关化合物，以及苄丝肼及其类似物。示例性恶性肿瘤是携带突变的人类乳腺细胞，特别是携带 BRCA1 突变的 SUM149 细胞和 HCC1937 细胞。