In the course of an investigation of human neutrophil elastase (HNE) associated with inflammation, the extract of the flower parts of Hypericum ascyron showed a significant influence to HNE. The responsible metabolites to HNE inhibition were found to be eight polyprenylated acylphloroglucinols, PPAPs (1-8) which showed IC ranges between 2.4 and 19.9 μM. This is the first report to demonstrate that PPAP skeleton exhibits potent HNE inhibition. The compounds 1-3 were characterized and newly named as ascyronone E (IC = 4.3 μM), ascyronone F (IC = 19.9 μM), ascyronone G (IC = 4.5 μM) based on 2D-NMR spectroscopic data. In the kinetic analysis of double reciprocal plots, all the compounds showed noncompetitive behaviors to HNE enzyme with the remaining of K and the increase of V. The binding affinity levels (K) by using fluorescence were sufficient to be able to prove that PPAPs (1-8) had compliant interaction with inhibitory potencies.
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