AUTHOR=Crockett Sara L. , Kunert Olaf , Pferschy-Wenzig Eva-Maria , Jacob Melissa , Schuehly Wolfgang , Bauer Rudolf 

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

JOURNAL=Frontiers in Plant Science

VOLUME=7

YEAR=2016

URL=https://www.frontiersin.org/journals/plant-science/articles/10.3389/fpls.2016.00961

DOI=10.3389/fpls.2016.00961

ISSN=1664-462X

ABSTRACT=<p>A new simple phloroglucinol derivative characterized as 1-(6-hydroxy-2,4-dimethoxyphenyl)-2-methyl-1-propanone (<bold>1</bold>) was isolated from <italic>Hypericum cistifolium</italic> (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 (<bold>2</bold> and <bold>3</bold>), and two new terpenoid derivatives characterized, respectively, as 2-benzoyl-3,3-dimethyl-4<italic>R</italic>,6<italic>S</italic>-bis-(3-methylbut-2-enyl)-cyclohexanone <bold>(4a)</bold> and 2-benzoyl-3,3-dimethyl-4<italic>S</italic>,6<italic>R</italic>-bis-(3-methylbut-2-enyl)-cyclohexanone <bold>(4b)</bold>, were isolated from a related species, <italic>H. galioides</italic> Lam. The chemical structures were established using 2D-NMR spectroscopy and mass spectrometry. These compounds were evaluated <italic>in vitro</italic> 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<sub>4</sub> formation.</p>