Abstract
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-4R,6S-bis-(3-methylbut-2-enyl)-cyclohexanone (4a) and 2-benzoyl-3,3-dimethyl-4S,6R-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 LTB4 formation.
Highlights
As part of our continuing phytochemical investigation of the genus Hypericum, and in particular, the identification and elucidation of chemotaxonomic markers in species of section Myriandra, the non-polar extracts of H. cistifolium and H. galioides were targeted on basis of interesting TLC, UV, and HPLC characteristics
We had observed that simple phloroglucinols and filicinic acid derivatives generally display red to orange colors during TLC analysis upon spraying and heating, while more complex structures display blue to purple colors (Crockett, pers. obs.)
These characteristics aided the chromatographic fractionation and purification of phloroglucinol and terpenoid derivatives, namely, three new (1, 4a, and 4b) and two known compounds (2 and 3), which were subsequently identified from these two Hypericum species (Figure 1)
Summary
Considering the known bioactivities of reported phloroglucinol derivatives, the anti-inflammatory potentials of extracts and isolated compounds from H. cistifolium and H. galiodes were determined using in vitro assays that measured the inhibition of COX and 5-LOX product formation. As part of our continuing phytochemical investigation of the genus Hypericum, and in particular, the identification and elucidation of chemotaxonomic markers in species of section Myriandra, the non-polar extracts of H. cistifolium and H. galioides were targeted on basis of interesting TLC, UV, and HPLC characteristics.
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