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Bioactive polycyclic polyprenylated acylphloroglucinols from Hypericum perforatum.

Yi Guo1, Na Zhang, Weiguang Sun

  • 1Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030, Hubei Province, People's Republic of China. yongboxue@mail.hust.edu.cn zhangyh@mails.tjmu.edu.cn.

Organic & Biomolecular Chemistry
|October 19, 2018
PubMed
Summary

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Fifteen new compounds from Hypericum perforatum were identified, with compound 5 showing dual activity against acetylcholinesterase (AChE) and BACE1, suggesting potential for Alzheimer's disease treatment.

Area of Science:

  • Natural Products Chemistry
  • Pharmacology
  • Medicinal Chemistry

Background:

  • Hypericum perforatum is a source of bioactive compounds.
  • Polycyclic polyprenylated acylphloroglucinols (PPAPs) are a class of natural products with diverse biological activities.
  • Alzheimer's disease pathogenesis involves acetylcholinesterase (AChE) and BACE1.

Purpose of the Study:

  • To isolate and characterize new PPAPs from Hypericum perforatum.
  • To evaluate the inhibitory activities of these compounds against AChE and BACE1.
  • To identify potential dual-targeted agents for Alzheimer's disease therapy.

Main Methods:

  • Isolation and structural elucidation of 18 compounds (15 new PPAPs) using NMR, ECD, X-ray crystallography, and QCP.
  • In vitro screening for AChE and BACE1 inhibitory activities.

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  • Molecular docking studies to predict binding interactions.

    • Main Results:

    • Fifteen new PPAPs, hyperforatones A-O (1-15), were isolated along with 3 analogues.
    • Compound 5 features a unique pentamethyltetrahydrofuran-3-yl)methanol moiety and an oxepane ring.
    • Compounds 5, 10, 11, and 15 exhibited significant AChE inhibition (IC50 6.9-9.2 μM).
    • Compounds 5, 10, 11, and 15 also inhibited BACE1.
    • Compound 5 demonstrated the most balanced dual inhibitory activity against AChE and BACE1.

    Conclusions:

    • The study identified novel PPAPs from Hypericum perforatum.
    • Compound 5 is a promising dual-targeted inhibitor of AChE and BACE1.
    • Compound 5 represents a potential lead compound for the development of Alzheimer's disease therapeutics.