Identification of caffeoylquinic acid derivatives as natural protein tyrosine phosphatase 1B inhibitors from Artemisia princeps

被引:21
|
作者
Zhang, Jie [1 ,2 ]
Sasaki, Tatsunori [2 ]
Li, Wei [2 ,3 ]
Nagata, Kazuya [2 ]
Higai, Koji [2 ]
Feng, Feng [1 ]
Wang, Jian [3 ]
Cheng, Maosheng [3 ]
Koike, Kazuo [2 ]
机构
[1] China Pharmaceut Univ, Dept Nat Med Chem, 24 Tongjiaxiang, Nanjing 210009, Jiangsu, Peoples R China
[2] Toho Univ, Fac Pharmaceut Sci, Miyama 2-2-1, Funabashi, Chiba 2748510, Japan
[3] Shenyang Pharmaceut Univ, Minist Educ, Key Lab Struct Based Drug Design & Discovery, Shenyang 110016, Liaoning, Peoples R China
基金
中国国家自然科学基金;
关键词
Protein tyrosine phosphatase 1B; Caffeoylquinic acid; Chlorogenic acid; Artemisia princeps; LIQUID-CHROMATOGRAPHY; PHENOLIC-COMPOUNDS; AERIAL PARTS; PTP1B; FLAVONOIDS; DISCOVERY; EUPATILIN; OBESITY; AGENT; MICE;
D O I
10.1016/j.bmcl.2018.02.052
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Considerable attention has been paid to protein tyrosine phosphatase 1B (PTP1B) inhibitors as a potential therapy for diabetes, obesity, and cancer. Ten caffeoylquinic acid derivatives (1-10) from leaves of Artemisia princeps Pamp. (Asteraceae) were identified as natural PTP1B inhibitors. Among them, chlorogenic acid (3) showed the most potent inhibitory activity (IC50 11.1 mu M). Compound 3 was demonstrated to be a noncompetitive inhibitor by a kinetic analysis. Molecular docking simulation suggested that compound 3 bound to the allosteric site of PTP1B. Furthermore, compound 3 showed remarkable selectivity against four homologous PTPs. According to these findings, compound 3 might be potentially valuable for further drug development. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1194 / 1197
页数:4
相关论文
共 50 条
  • [21] Discovery of novel and potent heterocyclic carboxylic acid derivatives as protein tyrosine phosphatase 1B inhibitors
    Basu, Sujay
    Prasad, Uppuleti Viplava
    Barawkar, Dinesh A.
    De, Siddhartha
    Palle, Venkata P.
    Menon, Suraj
    Patel, Meena
    Thorat, Sachin
    Singh, Umesh P.
    Das Sarma, Koushik
    Waman, Yogesh
    Niranjan, Sanjay
    Pathade, Vishal
    Gaur, Ashwani
    Reddy, Satyanarayana
    Ansari, Shariq
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2012, 22 (08) : 2843 - 2849
  • [22] Structural Insight into the Design on Oleanolic Acid Derivatives as Potent Protein Tyrosine Phosphatase 1B Inhibitors
    施建成
    涂文通
    罗敏
    黄初升
    Chinese Journal of Structural Chemistry, 2017, 36 (07) : 1063 - 1076
  • [23] Protein Tyrosine Phosphatase 1B Inhibitors from Plantago asiatica
    LEE Hyun-sun
    AHN Jong-seog
    Chinese Herbal Medicines, 2011, 3 (02) : 136 - 139
  • [24] Vanillic acid derivatives from the green algae Cladophora socialis as potent protein tyrosine phosphatase 1B inhibitors
    Feng, Yunjiang
    Carroll, Anthony R.
    Addepalli, Rama
    Fechner, Gregory A.
    Avery, Vicky M.
    Quinn, Ronald J.
    JOURNAL OF NATURAL PRODUCTS, 2007, 70 (11): : 1790 - 1792
  • [25] In vitro effects of cinnamic acid derivatives on protein tyrosine phosphatase 1B
    Adisakwattana, Sirichai
    Pongsuwan, Jirawan
    Wungcharoen, Chompunut
    Yibchok-anun, Sirintorn
    JOURNAL OF ENZYME INHIBITION AND MEDICINAL CHEMISTRY, 2013, 28 (05) : 1067 - 1072
  • [26] Thiazolidinone Derivatives as Competitive Inhibitors of Protein Tyrosine Phosphatase 1B (PTP1B)
    Aher, Nilkanth G.
    Kafle, Bhooshan
    Cho, Hyeongjin
    BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2013, 34 (04) : 1275 - 1277
  • [27] Virtual Screening of Protein Tyrosine Phosphatase 1B Inhibitors Based on Natural Products
    Zhang Qian
    Gan Qiang
    Liu Xia
    Chen Xi
    Feng Chang-Gen
    PROGRESS IN BIOCHEMISTRY AND BIOPHYSICS, 2018, 45 (04) : 442 - 452
  • [28] Identification of 2-substituted ethenesulfonic acid ester derivatives as novel, potent and selective inhibitors of protein tyrosine phosphatase 1B
    Deng, Xinxian
    Liu, Jingbao
    Jin, Yan
    Zhang, Yong
    He, Wan
    Bao, Jian
    Liu, Wenlu
    Jiang, Faqin
    Fu, Lei
    PHARMAZIE, 2015, 70 (12): : 777 - 783
  • [29] Binding mechanisms of varic acid inhibitors on protein tyrosine phosphatase 1B and in silico design of the novel derivatives
    Zhao, Dan
    Zhong, Shijun
    MOLECULAR SIMULATION, 2021, 47 (09) : 771 - 784
  • [30] Molecular modeling of protein tyrosine phosphatase 1B (PTP 1B) inhibitors
    Murthy, VS
    Kulkarni, VM
    BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (04) : 897 - 906