Inhibitory effect on soybean lipoxygenase and docking studies of some secondary metabolites, isolated from Origanum vulgare L. ssp. hirtum

Abstract

In this study, five secondary metabolites (caffeic acid, rosmarinic acid, lithospermic acid B, 12-hydroxyjasmonic acid 12-O-β-glucoside and p-menth-3-ene-1,2-diol 1-O-β-glucopyranoside) isolated from the polar extracts of the plant Origanum vulgare L. ssp. hirtum, were tested in vitro for their ability to inhibit soybean lipoxygenase. Among the examined compounds, lithospermic acid B demonstrated the best inhibitory activity on soybean lipoxygenase with IC₅₀ = 0.1 mM. Docking studies have been undertaken as an attempt for better understanding the interactions of these compounds within the active site of soybean lipoxygenase. The predicted binding energy values correlated well with the observed biological data.

Keywords::

• docking
• GLUE
• origanum vulgare L. ssp. hirtum
• soybean lipoxygenase
• inhibition

Acknowledgements

We are grateful to Prof. Gabriele Cruciani (Laboratory for Chemometrics, School of Chemistry, University of Perugia, Italy) for providing us GRID package and VolSurf program. We also thank Dr Simone Sciabola for useful advices and Dr Paolo Benedetti and Dr Giuliano Berellini for technical assistance (same laboratory).