Bioactive Sesquiterpene Lactones from Centaurea Species and their Cytotoxic/Cytostatic Activity Against Human Cell Lines in vitro

Abstract

Sesquiterpene lactones isolated from the aerial parts of various species of the genus Centaurea were examined for their in vitro cytotoxic/cytostatic activity against five human cell lines (i. e., DLD1, SF268, MCF7, H460 and OVCAR3). Compounds 1 - 4 were isolated from C. zuccariniana, 5 and 6 from C. achaia, 7 from C. thessala ssp. drakiensis and compounds 8 and 9 from C. deusta. Compound 1, 8alpha- O-(3,4-dihydroxy-2-methylenebutanoyloxy)dehydromelitensine was found to be the most active, exhibited a considerable growth inhibiting activity against three of the cell lines tested, while compound 5 8alpha- O-(3-hydroxy-2-methylenepropanoyl)dehydromelitensin exhibited a growth inhibiting effect against most of the tested cell lines. A new eudesmanolide (8alpha-hydroxysonchucarpolide, 4) was isolated from C. zuccariniana and its structure was elucidated by spectroscopic methods.

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

“…castellana Bruno et al (2002) Centaurea paui Cardona et al (1997), Gousiadou and Skaltsa (2003) Centaurea pelia Nowak et al (1984), Gousiadou and Skaltsa (2003) Centaurea pseudomaculosa Adekenov et al (1979Adekenov et al ( , 1986a Tarasov et al (1973), Gonzalez et al (1977a), Isamukhamedova et al (1977) Centaurea stoebe Suchy and Herout (1962), Rybalko et al (1975), Gonzalez et al (1977a), Huneck et al (1986a), Tešević et al (2007) Centaurea sulphurea Geppert et al (1983), Gonzalez et al (1984), Barrero et al (2000), Lakhal et al (2010) Centaurea thessala ssp. drakiensis Skaltsa et al (1999), Georgiadou et al (2000), Gousiadou and Skaltsa (2003) Centaurea transiens Nowak et al (1984), Gousiadou and Skaltsa (2003) Centaurea tymphaea Nowak et al (1984), Gousiadou and Skaltsa (2003) (continued on next page) M. Bruno et al / Phytochemistry xxx (2013) xxx-xxx 9 Geppert et al (1983), Landau et al (1994), Gousiadou and Skaltsa (2003) Centaurea zuccariniana Nowak et al (1984), Koukoulitsa et al (2002), Gousiadou and Skaltsa (2003) Cnicus benedictus Korte and Beckmann (1958), Suchy et al (1959a), Suchy et al (1959b), …”

“…DLD1, SF268, MCF-7, H460, OVCAR3). Compounds 75 and 80 were found to be the most active and exhibited a considerable growth-inhibiting activity against most of the cell lines tested (Koukoulitsa et al, 2002). Cnicin (19), salitenolide (4) and the elemanes 66, 70, 80, 83 were tested against nine cancer cell lines.…”

Medicinal Potentials and Toxicity Concerns of Bioactive Principles

“…The terpenoids encompasses other classes of bioactive principles in diverse collections of plants. Notable examples include: mono-and sesquiterpene volatile derivatives from Antirrhinum tortuosum [182], mono-and sesquiterpenes from Phlomis fruticosa [183], saponins and sapogenins from Asparagus aphyllus [184], sesquiterpene lactones from Palaeocyanus crassifolius [185] tetraterpene carotenoids from Arum italicum [186], triterpenoids from Olea europaea [187,188] and β-sitosterol; a triterpene-like compound from Acanthus mollis [189] that exhibits plasma cholesterol lowering properties.…”

The Phytochemical and In Vitro Pharmacological Testing of Maltese Medicinal Plants

“…Some plants exhibited the presence of terpenes and related compounds in all solvent systems. Typical examples included Acanthus mollis, which mainly contains -sitosterol as the triterpene-like compound (Loukis & Philianos, 1980), Antirrhinum tortuosum, with mono and sesquiterpene volatile derivatives (Nagegowda et al, 2008), Arum italicum, with the tetraterpene carotenoids (Bonora et al, 2000), Asparagus aphyllus with saponins and sapogenins (Shao et al, 1996), Olea europaea containing mainly triterpenoids (Caputo et al, 1974;Elamrani, 2011), Palaeocyanus crassifolius containing sesquiterpene lactones (Koukoulitsa et al, 2002) and Phlomis fruticosa, mainly containing mono-and sesquiterpenes (Amor et al, 2009). In the case of Fumaria capreolata the main constituents mentioned in previous studies were the alkaloids (Soušek et al, 1999;MaizaBenabdesselam et al, 2007).…”