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A new simple phloroglucinol derivative characterized as 1-(6-hydroxy-2,4-dimethoxyphenyl)-2-methyl-1-propanone ( 1 ) was isolated from  Hypericum cistifolium  (Hypericaceae) as a major constituent of the non-polar plant extract. Minor amounts of this new compound, in addition to two known structurally related phloroglucinol derivatives ( 2  and  3 ), and two new terpenoid derivatives characterized, respectively, as 2-benzoyl-3,3-dimethyl-4 R ,6 S -bis-(3-methylbut-2-enyl)-cyclohexanone  (4a)  and 2-benzoyl-3,3-dimethyl-4 S ,6 R -bis-(3-methylbut-2-enyl)-cyclohexanone  (4b) , were isolated from a related species,  H. galioides  Lam. The chemical structures were established using 2D-NMR spectroscopy and mass spectrometry. These compounds were evaluated  in vitro  for antimicrobial activity against a panel of pathogenic microorganisms and anti-inflammatory activity through inhibition of COX-1, COX-2, and 5-LOX catalyzed LTB 4  formation.

Phloroglucinol and Terpenoid Derivatives from Hypericum cistifolium and H. galioides (Hypericaceae)