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
  • [1] Inhibitory Mechanism of Ferulic Acid on Xanthine Oxidase
    Zhang N.
    Jin Y.
    Chen Y.
    Zhou J.
    Zhao L.
    Zhang L.
    Wu W.
    Zhou F.
    Journal of Food Science and Technology (China), 2023, 41 (01): : 115 - 125
  • [2] Ferulic acid ameliorates hyperuricemia by regulating xanthine oxidase
    Lou, Ye
    Gao, Qiang
    Fan, Mingcong
    Waleed, AL-Ansi
    Wang, Li
    Li, Yan
    Qian, Haifeng
    INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, 2023, 253
  • [3] Inhibition Activity and Mechanism Studies of Sulfonate Derivatives of Chrysin on Xanthine Oxidase
    Wang, Xeuqin
    Cui, Zhenzhen
    Zhang, Yele
    Yang, Xinbin
    LATIN AMERICAN JOURNAL OF PHARMACY, 2022, 41 (06): : 1172 - 1179
  • [4] Insights from the interaction of ferulic acid with bovine xanthine oxidase
    Loredana, Dumitrascu
    Nicoleta, Stanciuc
    Iuliana, Aprodu
    Gabriela, Bahrim Elena
    JOURNAL OF BIOTECHNOLOGY, 2015, 208 : S68 - S68
  • [5] Insights into the binding of ferulic acid to the thermally treated xanthine oxidase
    Dumitrascu, Loredana
    Stanciuc, Nicoleta
    Bahrim, Gabriela Elena
    Aprodu, Iuliana
    LUMINESCENCE, 2016, 31 (06) : 1259 - 1266
  • [6] Antioxidant activity and xanthine oxidase inhibition activity of reductic acid: Ascorbic acid analogue
    Mashino, T
    Takigawa, Y
    Saito, N
    Wong, LQQ
    Mochizuki, M
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (24) : 2783 - 2785
  • [7] Xanthine oxidase inhibitory activity of caffeic, chlorogenic and ferulic acids
    Talla, SRR
    Halter, RC
    Dwivedi, C
    BIOCHEMICAL ARCHIVES, 1996, 12 (04) : 245 - 247
  • [8] INHIBITION OF XANTHINE OXIDASE BY ASCORBIC ACID
    FEIGELSON, P
    FEDERATION PROCEEDINGS, 1952, 11 (01) : 210 - 210
  • [9] Inhibition of xanthine oxidase by different pteridine derivatives
    Oettl, K
    Koppe, L
    Reibnegger, G
    CHEMISTRY AND BIOLOGY OF PTERIDINES AND FOLATES 1997, 1997, : 819 - 822
  • [10] HYDROXYLAMINE INHIBITION OF XANTHINE OXIDASE ACTIVITY
    DIETRICH, LS
    BORRIES, E
    JOURNAL OF BIOLOGICAL CHEMISTRY, 1956, 219 (01) : 375 - 382