Preparation of ferulic acid derivatives and evaluation of their xanthine oxidase inhibition activity

被引:14
|
作者
Wang, Feng
Yang, Leixiang
Huang, Kexin
Li, Xiaokun
Hao, Xiaojiang
Stoeckigt, Joachim
Zhao, Yu
机构
[1] Zhejiang Univ, Dept Tradit Chinese Med & Nat Drug Res, Coll Pharmaceut Sci, Hangzhou 310031, Peoples R China
[2] Wenzhou Coll Med, Sch Pharm, Wenzhou 325035, Peoples R China
[3] Key Lab Chem Nat Prod Guizhou Prov, Guiyang 550022, Peoples R China
[4] Chinese Acad Sci, Guiyang 550022, Peoples R China
[5] Univ Mainz, Inst Pharm, Lehrstuhl Pharmazeut Biol, D-55099 Mainz, Germany
关键词
ferulic acid derivatives; xanthine oxidase inhibitor; gout;
D O I
10.1080/14786410601129648
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Several ferulic acid ethyl esters (3a-h) were synthesized under the Knoevengel reaction condition and they were further reduced to afford the respective allylic alcohol derivatives (4a-g). Some of them were evaluated for the xanthine oxidase (XO) inhibitory activity. Among them, 3h exhibited a significant inhibitory activity with an IC50 value of 1.35x10(-5) M, while the IC50 value of allopurinol used as the positive control was 1.49x10(-5) M. The study suggested that the higher acidity of the phenolic OH group in the ferulic acid derivatives might result in improved XO inhibitory activity.
引用
收藏
页码:196 / 202
页数:7
相关论文
共 50 条
  • [31] Screening of ferulic acid related compounds as inhibitors of xanthine oxidase and cyclooxygenase-2 with anti-inflammatory activity
    Shivraj Hariram Nile
    Eun Young Ko
    Doo Hwan Kim
    Young-Soo Keum
    Revista Brasileira de Farmacognosia, 2016, 26 : 50 - 55
  • [32] Synthesis and antimicrobial evaluation of ferulic acid derivatives
    Anurag Khatkar
    Arun Nanda
    Pradeep Kumar
    Balasubramanian Narasimhan
    Research on Chemical Intermediates, 2015, 41 : 299 - 309
  • [33] Synthesis and antimicrobial evaluation of ferulic acid derivatives
    Khatkar, Anurag
    Nanda, Arun
    Kumar, Pradeep
    Narasimhan, Balasubramanian
    RESEARCH ON CHEMICAL INTERMEDIATES, 2015, 41 (01) : 299 - 309
  • [35] Potential cow milk xanthine oxidase inhibitory and antioxidant activity of selected phenolic acid derivatives
    Nile, Shivraj Hariram
    Keum, Young Soo
    Nile, Arti Shivraj
    Kwon, Young Deuk
    Kim, Doo Hwan
    JOURNAL OF BIOCHEMICAL AND MOLECULAR TOXICOLOGY, 2018, 32 (01)
  • [36] QSAR study of the DPPH• radical scavenging activity of coumarin derivatives and xanthine oxidase inhibition by molecular docking
    Razo-Hernandez, Rodrigo S.
    Pineda-Urbina, Kayim
    Velazco-Medel, Marlene A.
    Villanueva-Garcia, Manuel
    Teresa Sumaya-Martinez, M.
    Martinez-Martinez, Francisco J.
    Gomez-Sandoval, Zeferino
    CENTRAL EUROPEAN JOURNAL OF CHEMISTRY, 2014, 12 (10): : 1067 - 1080
  • [37] Synthesis and biological evaluation of caffeic acid phenethyl ester (CAPE) derivatives as xanthine oxidase inhibitors
    Onate, Sandra
    Istre, Hannah
    Heppler, Ben
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 255
  • [38] THE HAEMOPOIETIC ACTIVITY OF FOLIC ACID TREATED WITH XANTHINE OXIDASE
    JACOBSON, W
    GOOD, PM
    QUARTERLY JOURNAL OF MEDICINE, 1952, 21 (81): : 1 - 18
  • [39] Inhibition of xanthine oxidase by phytic acid and its antioxidative action
    Muraoka, S
    Miura, T
    LIFE SCIENCES, 2004, 74 (13) : 1691 - 1700
  • [40] Inhibition of xanthine oxidase by phenolic conjugates of methylated quinic acid
    Góngora, L
    Méñez, S
    Giner, RM
    Recio, MD
    Schinella, G
    Ríos, JL
    PLANTA MEDICA, 2003, 69 (05) : 396 - 401