Bioactive acylphloroglucinols with adamantyl skeleton from Hypericum sampsonii

Area of Science:

• Natural Products Chemistry
• Medicinal Chemistry
• Virology

Background:

• The plant Hypericum sampsonii is a source of diverse chemical compounds.
• Natural products are crucial for discovering novel therapeutic agents, including antivirals.
• Identifying compounds with anti-HIV activity is a priority in pharmaceutical research.

Purpose of the Study:

• To isolate and characterize new chemical entities from Hypericum sampsonii.
• To investigate the anti-HIV potential of isolated compounds.
• To elucidate the structures and absolute configurations of novel compounds.

Main Methods:

• Isolation of compounds using chromatographic techniques.
• Structure elucidation via comprehensive spectroscopic methods (NMR, MS).
• Determination of absolute configuration using Electronic Circular Dichroism (ECD) calculations and single X-ray crystallography.

Main Results:

• Four new compounds, hyperisampsins A-D (1-4), with unique tetracyclo[6.3.1.1(3,10).0(3,7)]tridecane skeletons, were isolated.
• Seven known related congeners (5-11) were also identified.
• Hyperisampsins A and D exhibited potent anti-HIV activity with EC50 values of 2.97 μM and 0.97 μM, respectively, and favorable selectivity indices.

Conclusions:

• Hyperisampsins A-D represent novel chemical structures from Hypericum sampsonii.
• Hyperisampsins A and D show promising anti-HIV activity, warranting further investigation for drug development.
• Spectroscopic and crystallographic analyses confirmed the structures and absolute configurations of the isolated compounds.