Secondary Metabolites from Satureja Species. New Triterpenoid from Satureja acinos

Abstract

The chemistry of the genus Satureja (syn. Calamintha) (Labiatae) has not been thoroughly studied. Previous reports (1)(2)(3)(4) indicate the presence of ursolic, epiursolic, and oleanolic acids, and two 3,4seco-tri terpenoids, calainthadiol and isocalaminthadiol (3,4). We report here the content of secondary metabolites of three species, Satureja acinos (L.) Scheele, Satureja montana L., and Satureja obovata Lag., collected in central Spain.Besides a new triterpene, of the ursene type, other known triterpenes, such as oleanolic, ursolic, or crataegolic acid, have been isolated from these species, ß-Sitosterol^-D-glucoside is common to the three species. Naringenin 7-0rutinoside and eriodictyol 7-0rutinoside has been isolated from S. acinos and S. montana, respectively. The presence of these flavanone glycosides was previously described in the peels of navel and valencia oranges (5) and lemons (6), respectively, and the structure of the naringenin glycoside (narirutin) confirmed by synthesis (7). RESULTS AND DISCUSSIONChromatography of the crude Me2CO extract obtained from S. acinos afforded compound 1 plus ursolic acid and the glucoside of ß-sitosterol. The two latter compounds were identified by compari-son of their physical constants and spectral data with those of authentic specimens and further confirmed by the preparation of derivatives.

Sterols from the fruit barks of Coelocaryon klainei Pierre ex Heckel (Myristicaceae)

“…This compound is having six methyl, eleven methylene and three quaternary carbons with a hydroxyl group. The above spectral features are in closed agreement to those observed for β-sitosterol according to (Escudero et al, 1985;Manoharan et al, 2005).…”

Chemical composition and antifungal effects of three species of Satureja (S. hortensis, S. spicigera, and S. khuzistanica) essential oils on the main pathogens of strawberry fruit

“…Some members of this genus are of economic importance since they have been used as culinary herbs, flavouring agents in perfumery and cosmetics. The positive effects of savory on human health have now been attributed to its various biologically active constituents such as essential oil, triterpenes (Escudero et al, 1985) and flavonoids (Tomás- Barberán et al, 1988). The essential oil of savory contains antioxidative compounds, namely carvacrol, thymol, b-caryophyllene, g-terpinene, p-cymene, together with linalool, which has been reported to possess strong antioxidant effects (Ruberto and Baratta, 2000) and also has dipentane, ursolic acid, etheral oil, phenolic substances, resins, tannins and mucilage (Lawrence, 2000).…”

Influence of pre-treatments on yield, chemical composition and antioxidant activity of Satureja montana extracts obtained by supercritical carbon dioxide

“…Beside traditional use in folk medicine, many scientific studies confirmed S. montana significant pharmacological activity (Table 1). S. montana contains various biologically active constituents including essential oil, triterpenes [22] and flavonoids [23]. Main components are aromatic monoterpens.…”