5,5'-bis(2-hydroxyethyl)-[1,1'-biphenyl]-2,2',3,3'-tetraol | 1280572-17-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5,5'-bis(2-hydroxyethyl)-[1,1'-biphenyl]-2,2',3,3'-tetraol
• 英文别名: 3-[2,3-Dihydroxy-5-(2-hydroxyethyl)phenyl]-5-(2-hydroxyethyl)benzene-1,2-diol
• CAS: 1280572-17-9
• 化学式: C₁₆H₁₈O₆
• 分子量: 306.315
• InChiKey: KQHMQCWRPFEOBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  121
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  羟基酪醇 在 laccase from Trametes versicolor 、 氧气 作用下， 以 甲醇 、 aq. phosphate buffer 为溶剂， 生成 5,5'-bis(2-hydroxyethyl)-[1,1'-biphenyl]-2,2',3,3'-tetraol
  参考文献：
  名称：

  通过Trametes versicolor漆酶的氧化增强羟基酪醇的生物活性

  摘要：

  研究了漆酶催化的羟基酪醇（HT）氧化形成其生物活性低聚物衍生物的过程。生物催化低聚反应由水性或各种与水混溶的有机溶剂和低共熔溶剂 (DES) 基介质中的漆酶催化。使用质谱和核磁共振来表征产品。使用的溶剂系统显着影响HT低聚的程度。 50%甲醇的使用有利于HT二聚体的产生，而其他有机溶剂以及DES导致羟基酪醇三聚体和其他低聚物的形成。研究表明，与母体化合物相比，HT 二聚体对革兰氏阳性菌和革兰氏阴性菌的抗菌活性增强了 3 至 4 倍。此外，HT二聚体抑制大豆脂氧合酶和脂肪酶活性的能力比HT高1.5倍，分子对接支持了这些结果。此外，HT二聚体对 HEK293 细胞的细胞毒性降低，并表现出很强的抑制 ROS 形成的能力。 HT 二聚体增强的生物活性表明该化合物可考虑用于化妆品、护肤品和营养保健品。

  DOI：

  10.1016/j.jbiotec.2024.02.011

文献信息

• [EN] HYDROXYTYROSOL COMPOUNDS<br/>[FR] COMPOSÉS D'HYDROXYTYROSOL
  申请人：UNIV CAPE TOWN

  公开号：WO2011036537A1

  公开（公告）日：2011-03-31

  A hydroxytyrosol polymer formed by either C-C coupling or C-O-C coupling is provided. Preferred polymers are formed by C-C coupling and the dimer has the following structure:(Formula I) (I) Compounds of the invention have been found to have antioxidant properties and their use in antioxidant compositions forms a further aspect of the invention.

  提供了一种通过C-C偶联或C-O-C偶联形成的羟基酪醇聚合物。优选的聚合物是通过C-C偶联形成的，该二聚体具有以下结构：（式I）（I）已发现本发明的化合物具有抗氧化性能，并将它们用于抗氧化剂组合物中形成了本发明的另一个方面。
• Chemoenzymatic Synthesis and α-Glucosidase Inhibitory Activity of Dimeric Neolignans Inspired by Magnolol
  作者：Luana Pulvirenti、Vera Muccilli、Nunzio Cardullo、Carmela Spatafora、Corrado Tringali

  DOI：10.1021/acs.jnatprod.7b00250

  日期：2017.5.26

  A chemoenzymatic synthesis of a small library of dimeric neolignans inspired by magnolol (1) is reported. The 2-iodoxybenzoic acid (IBX)-mediated regioselective orthohydroxylation of magnolol is described, affording the bisphenols 6 and 7. Further magnolol analogues (12, 13, 15-17, 19-23) were obtained from eugenol (3), tyrosol (4), and homovanillic alcohol (5), through horseradish peroxidase (HRP)-mediated oxidative coupling and regioselective orthohydroxylation or ortho-demethylation in the presence of MX, followed by reductive treatment with Na2S2O4. A chemoselective protection/deprotection of the alcoholic group of 4 and 5 was carried out by lipase-mediated acetylation/deacetylation. The dimeric neolignans, together with 1 and honokiol (2), were evaluated as inhibitors of yeast a-glucosidase, in view of their possible utilization and optimization as antidiabetic drugs. The synthetic analogues of magnolol showed a strong inhibitory activity with IC50 values in the range 0.15-4.1 mu M, much lower than those of honokiol and the reference compounds quercetin and acarbose. In particular, a very potent inhibitory activity, with an IC50 of 0.15 mu M, was observed for 1,1'-dityrosol-8,8'-diacetate (15), and comparable inhibitory activities were also shown by bisphenols 6 (0.49 mu M), 13 (0.50 mu M), and 22 (0.86 mu M). A kinetic study showed that 15 acts as a competitive inhibitor, with a K-i value of 0.86 mu M.
• HYDROXYTYROSOL COMPOUNDS
  申请人：Burton Stephanie Gail

  公开号：US20120269745A1

  公开（公告）日：2012-10-25

  A hydroxytyrosol polymer formed by either C—C coupling or C—O—C coupling is provided. Preferred polymers are formed by C—C coupling and the dimer has the following structure: (Formula I) (I) Compounds of the invention have been found to have antioxidant properties and their use in antioxidant compositions forms a further aspect of the invention.
• US8663608B2
  申请人：——

  公开号：US8663608B2

  公开（公告）日：2014-03-04
• Enhancement of the biological activity of hydroxytyrosol through its oxidation by laccase from Trametes versicolor
  作者：Alexandra V. Chatzikonstantinou、Myrto G. Bellou、Stamatia Spyrou、Angelos Papanikolaou、Yannis V. Simos、Dimitrios Peschos、Haralambos Stamatis

  DOI：10.1016/j.jbiotec.2024.02.011

  日期：2024.4

  media. Mass Spectroscopy and Nuclear Magnetic Resonance were used for the characterization of the products. The solvent system used significantly affects the degree of HT oligomerization. The use of 50 % methanol favored the production of the HT dimer, while other organic solvents as well as DESs led to the formation of hydroxytyrosol trimer and other oligomers. studies showed that the HT dimer exhibits

  研究了漆酶催化的羟基酪醇（HT）氧化形成其生物活性低聚物衍生物的过程。生物催化低聚反应由水性或各种与水混溶的有机溶剂和低共熔溶剂 (DES) 基介质中的漆酶催化。使用质谱和核磁共振来表征产品。使用的溶剂系统显着影响HT低聚的程度。 50%甲醇的使用有利于HT二聚体的产生，而其他有机溶剂以及DES导致羟基酪醇三聚体和其他低聚物的形成。研究表明，与母体化合物相比，HT 二聚体对革兰氏阳性菌和革兰氏阴性菌的抗菌活性增强了 3 至 4 倍。此外，HT二聚体抑制大豆脂氧合酶和脂肪酶活性的能力比HT高1.5倍，分子对接支持了这些结果。此外，HT二聚体对 HEK293 细胞的细胞毒性降低，并表现出很强的抑制 ROS 形成的能力。 HT 二聚体增强的生物活性表明该化合物可考虑用于化妆品、护肤品和营养保健品。