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Amphotericin B is a broad-spectrum antifungal agent that exploits structural differences between fungal and mammalian cell membranes. Its amphipathic structure—featuring a hydrophobic polyene-lactone ring and a hydrophilic region containing mycosamine and carboxylic acid groups—enables selective binding to ergosterol, a sterol predominantly found in fungal plasma membranes. This selective interaction underlies the drug’s antifungal activity, although weak binding to...
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Microbial membranes exhibit remarkable diversity in lipid composition, reflecting evolutionary adaptations to various environmental conditions. The three domains of life—Bacteria, Archaea, and Eukarya—synthesize membrane lipids through distinct biosynthetic pathways, leading to fundamental structural differences that impact membrane stability, function, and adaptability.Fatty Acid-Based Lipids in Bacteria and EukaryaBacteria and eukaryotes share a common fatty acid biosynthesis...
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Updated: Mar 19, 2026

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Polycyclic Polyprenylated Acylphloroglucinol Congeners from Hypericum scabrum.

Wan Gao1, Wei-Zhen Hou1, Jun Zhao2

  • 1State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College , Beijing 100050, People's Republic of China.

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|June 10, 2016
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Researchers isolated twenty polycyclic polyprenylated acylphloroglucinols (PPAPs) from Hypericum scabrum, discovering nine new compounds. Several PPAPs demonstrated significant neuroprotective and moderate hepatoprotective effects in cell-based assays.

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Area of Science:

  • Natural Product Chemistry
  • Pharmacology
  • Medicinal Chemistry

Background:

  • Hypericum scabrum is a plant species known for its diverse secondary metabolites.
  • Polycyclic polyprenylated acylphloroglucinols (PPAPs) are a class of natural products with various reported biological activities.
  • Investigating novel compounds from medicinal plants can lead to the discovery of new therapeutic agents.

Purpose of the Study:

  • To isolate and characterize compounds from Hypericum scabrum.
  • To evaluate the neuroprotective effects of isolated compounds against glutamate-induced toxicity.
  • To assess the hepatoprotective potential of isolated compounds against paracetamol-induced liver damage.

Main Methods:

  • Isolation of compounds using chromatographic techniques.
  • Structure elucidation utilizing Nuclear Magnetic Resonance (NMR) spectroscopy.
  • Determination of absolute configurations via experimental and calculated Electronic Circular Dichroism (ECD) spectra.
  • In vitro assays to evaluate neuroprotection in SK-N-SH cells and hepatoprotection in HepG2 cells.

Main Results:

  • Twenty PPAPs, including nine novel hyperscabrones A-I (1-9), were isolated.
  • Compounds 4-7 exhibited significant neuroprotective activity at 10 μM.
  • Compounds 3, 4, 7, and 9 displayed moderate hepatoprotective activity at 10 μM.
  • The isolated compounds represented seven distinct structural types.

Conclusions:

  • The study successfully identified and characterized new PPAPs from Hypericum scabrum.
  • Several isolated PPAPs possess promising neuroprotective and hepatoprotective properties.
  • These findings suggest potential therapeutic applications for Hypericum scabrum-derived compounds in neurological and liver diseases.