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

Xiangrong Cao, Xueyuan Yang, Peixia Wang, Yue Liang, Feng Liu, Muhetaer Tuerhong, Da Qing Jin, Jing Xu, Dongho Lee, Yasushi Ohizumi, Yuanqiang Guo

    Research output: Contribution to journalArticlepeer-review

    27 Citations (Scopus)

    Abstract

    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.

    Original languageEnglish
    Pages (from-to)139-148
    Number of pages10
    JournalBioorganic Chemistry
    Volume75
    DOIs
    Publication statusPublished - 2017 Dec

    Bibliographical note

    Publisher Copyright:
    © 2017 Elsevier Inc.

    Keywords

    • ECD
    • Hypericum longistylum
    • Molecular docking
    • PTP1B inhibitors
    • Polycyclic phloroglucinol

    ASJC Scopus subject areas

    • Biochemistry
    • Molecular Biology
    • Drug Discovery
    • Organic Chemistry

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