Sesquiterpene Lactones from Centaurea spinosa and Their Antibacterial and Cytotoxic Activities

Abstract

Ten sesquiterpene lactones, 8alpha-O-(3,4-dihydroxy-2-methylenebutanoyloxy)sonchucarpolide (4-epi-malacitanolide) (1), 8alpha-O-(4-acetoxy-2-hydroxymethylbuten-2-oyloxy)-4-epi-sonchucarpolide (2), malacitanolide (3), its 4'-acetyl derivative (4), 8alpha-O-(3,4-dihydroxy-2-methylenebutanoyloxy)dehydromelitensine (5), 8alpha-O-(3,4-dihydroxy-2-methylenebutanoyloxy)-15-oxo-5,7alphaH,6betaH-eleman-1,3,11(13)-trien-6,12-olide (6), the germacranolides 8alpha-O-(4-acetoxy-2-hydroxymethylbuten-2-oyloxy)salonitenolide (7), cnicin (8), and 4'-acetylcnicin (9), and the sesquiterpene methyl 8alpha-O-(3,4-dihydroxy-2-methylenebutanoyloxy)-6alpha,15-dihydroxyelema-1,3,11(13)-trien-12-oate (10), were isolated from the aerial parts of Centaurea spinosa. Nine known flavonoids were also isolated. The structures and the stereochemistry of the new compounds 1 and 2 were deduced by spectroscopic methods. The in vitro activity of 1-10 against three Gram-positive and three Gram-negative bacteria was evaluated using a microdilution method, and their in vitro cytotoxic activity was determined against a panel of human tumor cell lines.

Sesquiterpenoids in subtribe Centaureinae (Cass.) Dumort (tribe Cardueae, Asteraceae): Distribution, 13C NMR spectral data and biological properties

“…A moderate cytotoxic activity of compound 83 was also shown against SF268 and OVCAR3 tumor cell lines (Saroglou et al, 2005).…”

“…Compounds 19,21,23,80,83,95,109,110,111 and 113 isolated from Centaurea spinosa, were tested in vitro against three Gram+ and three GramÀ bacteria. They were all inactive against tested GramÀ bacteria whereas compounds 83, 110 and 113 showed an activity against Micrococcus flavus from four to six times higher than streptomycin (MIC = 0.6, 0.6 and 0.4 lg/mL, respectively) and compounds 19,21,23,80 and 83 showed a moderate activity against B. cereus (Saroglou et al, 2005). Also compound 32 exhibited moderate antibacterial activity only toward Gram+ bacteria (Suleimenov et al, 2005b Barrero et al, 1997b.…”

Anatomical characteristics and antioxidant ability of Centaurea sadleriana reveals an adaptation towards drought tolerance

“…Several species from the genus Centaurea are interesting from medicinal and pharmacological perspective, and thus recently the subject of intensive research [3][4][5][6][7][8][9][10][11][12][13][14]. Since structural and phytochemical characteristics of C. sadleriana were previously unknown, our work highlights this information.…”

“…As Centaurea species were generally classified as essential oil-poor plants, the investigations of these and antioxidant properties are rather scarse. However, antiinflammatory, antimicrobial, antifungal and cytotoxic activities had been found for extracts or natural products of some of the Centaurea species [3,[5][6][7][8][9][10][11][12][13][14].…”

Fitotoxicidad De Aceites Esenciales Y Extractos Acuosos De Plantas Mediterráneas Para El Control De Arvenses

“…Poseen gran variedad de actividades biológicas, entre ellas, insecticida (Datta y Saxena, 2001), antibacteriana (Saroglou et al, 2005), antifúngica (Ahmed y Abdelgaleil, 2005) y alelopática (Pandey et al, 1993;Macías et al, 1999), en cualquier caso, con un alto grado de actividad Batish et al, 2001). Abundan especialmente en la familia Compuestas (Fraga, 2005).…”