Lignan and Phenylpropanoid Glycosides from Phillyrea latifolia and their In Vitro Anti-Inflammatory Activity

 

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Abstract

Three phenylpropanoid glycosides (salidroside, syringin and coniferin) and one lignan (phillyrin) isolated from the leaves of Phillyrea latifolia L. (Oleaceae) were tested for interactions with the cyclo-oxygenase and 5-lipoxygenase pathways of arachidonate metabolism in calcium-stimulated mouse peritoneal macrophages and human platelets, and for their effects on cell viability. These compounds are capable of exerting inhibitory actions on enzymes of the arachidonate cascade. Phillyrin, salidroside and syringin exert a preferential effect on the cyclo-oxygenase pathway, inhibiting release of the cyclo-oxygenase metabolites prostaglandin E₂ (IC₅₀ values 45.6 μM, 72.1 μM and 35.5 μM, respectively) and to a lesser extent reducing thromboxane B₂ levels (IC₅₀ values 168 μM, 154 μM and 29.3 μM, respectively). In contrast, coniferin can be classified as a ”dual inhibitor”, since it produces reduction in generation of both cyclo-oxygenase (IC₅₀ values 75.2 μM for prostaglandin E₂ and 619 μM for thromboxane B₂) and 5-lipoxygenase metabolites, but the effects are greater against leukotriene C₄ (IC₅₀ value 63.6 μM). Structure-activity relationships of the three phenylpropanoid glycosides are discussed. Thus, like some other compounds found in medicinal herbs, our molecules possess an array of potentially beneficial anti-eicosanoid properties which may, alongside other constituents, contribute to the claimed therapeutic properties of the plant from which they are derived.

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Dr. Paulina Bermejo Benito

Department of Pharmacology

Faculty of Pharmacy

University Complutense

28040 Madrid

Spain

Email: naber@eucmax.sim.ucm.es

Fax: +34-1-3941726