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Updated: Jun 23, 2026

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Bioactive acylphloroglucinols from Hypericum densiflorum.

Geneive E Henry1, Matthew S Campbell, Ashlee A Zelinsky

  • 1Department of Chemistry, Susquehanna University, Selinsgrove, PA 17870, USA. henry@susqu.edu

Phytotherapy Research : PTR
|May 15, 2009
PubMed
Summary

Three acylphloroglucinol derivatives from Hypericum densiflorum showed significant antitumor, antibacterial, and antioxidant activities. These compounds also inhibited cyclooxygenase-2 (COX-2), highlighting their therapeutic potential.

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Area of Science:

  • Natural Product Chemistry
  • Pharmacology
  • Medicinal Chemistry

Background:

  • Phloroglucinol derivatives are known for diverse biological activities.
  • Hypericum species are a rich source of bioactive natural products.
  • Acylphloroglucinols from Hypericum densiflorum have not been extensively studied.

Purpose of the Study:

  • To isolate and characterize acylphloroglucinol derivatives from Hypericum densiflorum.
  • To evaluate the isolated compounds for antitumor, antibacterial, antioxidant, and enzyme inhibitory activities.

Main Methods:

  • Extraction and isolation of compounds using hexane and acetone.
  • Structure elucidation via Nuclear Magnetic Resonance (NMR) spectroscopy and mass spectrometry.
  • In vitro assays for cell proliferation inhibition, antibacterial activity, cyclooxygenase (COX) inhibition, and lipid peroxidation (LPO) assay.

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Main Results:

  • Three acylphloroglucinol derivatives were identified: 4-geranyloxy-2,6-dihydroxybenzophenone (1), 4-geranyloxy-1-(2-methylpropanoyl)-phloroglucinol (2), and 4-geranyloxy-1-(2-methylbutanoyl)-phloroglucinol (3).
  • Compounds 1-3 exhibited moderate to strong antitumor activity against various human cancer cell lines (MCF-7, NCI H460, SF-268, AGS, HCT-116).
  • All tested compounds demonstrated significant antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA), antioxidant properties in the LPO assay, and inhibition of COX-2.

Conclusions:

  • The isolated acylphloroglucinols possess broad-spectrum biological activities, including antitumor, antibacterial, and antioxidant effects.
  • The compounds are potent inhibitors of cyclooxygenase-2 (COX-2), suggesting anti-inflammatory potential.
  • This study reports the first occurrence of compound 3 within the Hypericum genus, expanding the known phytochemical profile of the plant.