Polycyclic phloroglucinols as PTP1B inhibitors from Hypericum longistylum: Structures, PTP1B inhibitory activities, and interactions with PTP1B

被引:25
作者
Cao, Xiangrong [1 ,2 ]
Yang, Xueyuan [1 ,2 ]
Wang, Peixia [1 ,2 ]
Liang, Yue [1 ,2 ]
Liu, Feng [1 ,2 ]
Tuerhong, Muhetaer [3 ]
Jin, Da-Qing [4 ]
Xu, Jing [1 ,2 ]
Lee, Dongho [5 ]
Ohizumi, Yasushi [6 ]
Guo, Yuanqiang [1 ,2 ]
机构
[1] Nankai Univ, State Key Lab Med Chem Biol, Coll Pharm, Tianjin 300071, Peoples R China
[2] Nankai Univ, Tianjin Key Lab Mol Drug Res, Tianjin 300071, Peoples R China
[3] Kashgar Univ, Coll Chem & Environm Sci, Lab Xinjiang Native Med & Edible Plant Resources, Kashgar 844000, Peoples R China
[4] Nankai Univ, Sch Med, Tianjin 300071, Peoples R China
[5] Korea Univ, Coll Life Sci & Biotechnol, Dept Biosyst & Biotechnol, Seoul 02841, South Korea
[6] Univ Shizuoka, Sch Pharmaceut Sci, Dept Med Biochem, Shizuoka, Japan
基金
中国国家自然科学基金;
关键词
PTP1B inhibitors; Hypericum longistylum; Polycyclic phloroglucinol; Molecular docking; ECD; PROTEIN-TYROSINE-PHOSPHATASE; POLYPRENYLATED ACYLPHLOROGLUCINOL CONGENERS; ST JOHNS WORT; BIOLOGICAL EVALUATION; INSULIN SENSITIVITY; DERIVATIVES; CONSTITUENTS;
D O I
10.1016/j.bioorg.2017.09.001
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Protein tyrosine phosphatase 1B (PTP1B) has been regarded as a target for the research and development of new drugs to treat type II diabetes and PTP1B inhibitors are potential lead compounds for this type of new drugs. A phytochemical investigation to obtain new PTP1B inhibitors resulted in the isolation of four new phloroglucinols, longistyliones A-D (1-4) from the aerial parts of Hypericum longistylum. The structures of 1-4 were elucidated on the basis of extensive 1D and 2D NMR spectroscopic data analysis, and the absolute configurations of these compounds were established by comparing their experimental electronic circular dichroism (ECD) spectra with those calculated by the time-dependent density functional theory method. Compounds 1-4 possess a rare polycyclic phloroglucinol skeleton. The following biological evaluation revealed that all of the compounds showed PTP1B inhibitory effects. The further molecular docking studies indicated the strong interactions between these bioactive compounds with the PTP1B protein, which revealed the possible mechanism of PTP1B inhibition of bioactive compounds. All of the results implied that these compounds are potentially useful for the treatment of type II diabetes. (C) 2017 Elsevier Inc. All rights reserved.
引用
收藏
页码:139 / 148
页数:10
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