Anti-Inflammatory and Immunomodulating Properties of a Sterol Fraction from Sideritis foetens Clem.

Abstract

Interest in the phytochemical study of species of the Sideritis genus (Lamiaceae) has been stimulated by their pharmacological activity and their wide range of medicinal folk uses in Spain such as vulnerary, anti-infectious, anti-inflammatory, anti-rheumatic and anti-ulcerous applications. Various flavonoids and terpenoids have been isolated from this genus. 1,2) We have recently reported the anti-inflammatory properties of a lipid fraction obtained from Sideritis javalambrensis and those of the diterpenoid (ent-13(16),14-labdadiene-6a,8a,18triol-andalusol-) isolated from the acetone extract of Sideritis foetens, an endemic plant of Southern Spain. 3,4,5) Inflammation is normally a localized protective response which serves to destroy, dilute, or wall-off both the injurious agent and the injured tissue. The inflammatory response is coordinated by cells such as macrophages, lymphocytes, leukocytes and mast cells. A large number of mediators produced by these cells play a key role, for example, arachidonic acid metabolites such as prostaglandins and leukotrienes, reactive oxygen species, hydrolytic enzymes, histamine, nitric oxide, cytokines, etc. [6][7][8] Acute inflammation is associated with a rapid, early infiltration of polymorphonuclear leukocytes and increased vascular permeability at the site of injury.In this paper, we have evaluated the in vivo anti-inflammatory properties of a sterol fraction obtained from S. foetens on different inflammatory responses in mice. In addition, the interaction of this fraction with the functional properties of leukocytes and mast cells was analyzed in vitro. Immunomodulating activity through interaction with complement activation was also investigated. MATERIALS AND METHODS Plant MaterialThe aerial parts of Sideritis foetens were collected in Sierra de Gádor, Almería province (Spain). A voucher specimen has been deposited in the Department of Botany, Faculty of Pharmacy, Complutense University, Madrid (Spain). Extraction and IdentificationThe carrageenan-induced mouse paw oedema model was used for a bioassay guidedfractionation based on the anti-inflammatory activity.Dried aerial parts of Sideritis foetens (3 kg) were macerated with 99.5% acetone (12 l) at room temperature. The acetone extract was evaporated in vacuo to yield 84.8 g of residue. This extract (11.8 g) was fractionated by flash column chromatography over a silica gel (450 g, 230-400 mesh) column (6ϫ80 cm) using cyclohexane: acetone 70/30 to yield nine fractions. The most active fraction (subfraction B) (1.5 g) was chromatographed over a silica gel column (80 g, 230-400 mesh) using cyclohexane/ethyl acetate 70/30 as solvent, yielding the sterol fraction as white needles (800 mg).Sterol identification was performed by GC analysis [Perkin Elmer Sigma 3B equipped with a SE-30 Sobrechromosob WHP 3/100 column (lenght 2 m, i.d. 0.32 mm). Experimental conditions were: injector temp., 295°C; oven temp., 270°C (isotherm); detection temp., 285°C)]. The relative retention times were compared to standard samples. Campester...

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