Two new sesquiterpene lactones, rhizantholide A (1) and rhizantholide B (2), together with five known compounds (3-7) have been isolated from the aerial parts of Centaurea rhizantha (Asteraceae). Sesquiterpene lactones belong to guaianolide class, and rhizantholide B is a rare guaianolide characterized by a free primary alcoholic function at C-10 along with a 3β,10β-epoxy function. Their structures have been established on the basis of 1D and 2D NMR experiments, as well as HR-ESIMS. The antimicrobial activity of compounds 1-7 has been evaluated against Gram-positive and Gram-negative strains. Only deacylcynaropicrin 8-O-[3′-hydroxy-2′-methylpropionate] (5) showed moderate antibacterial activity against Staphylococcus aureus with a MIC/MBC value of 500 μg/mL. All isolated compounds have been also evaluated for their cytotoxic activities against cancer cells. Among them, compound 5 showed the highest cytotoxic activity with IC50 values in the range 5.02–16.76 μg/mL.

Sesquiterpene lactones from Centaurea rhizantha C.A. Meyer

Masullo, Milena;Bottone, Alfredo;Piacente, Sonia;
2018-01-01

Abstract

Two new sesquiterpene lactones, rhizantholide A (1) and rhizantholide B (2), together with five known compounds (3-7) have been isolated from the aerial parts of Centaurea rhizantha (Asteraceae). Sesquiterpene lactones belong to guaianolide class, and rhizantholide B is a rare guaianolide characterized by a free primary alcoholic function at C-10 along with a 3β,10β-epoxy function. Their structures have been established on the basis of 1D and 2D NMR experiments, as well as HR-ESIMS. The antimicrobial activity of compounds 1-7 has been evaluated against Gram-positive and Gram-negative strains. Only deacylcynaropicrin 8-O-[3′-hydroxy-2′-methylpropionate] (5) showed moderate antibacterial activity against Staphylococcus aureus with a MIC/MBC value of 500 μg/mL. All isolated compounds have been also evaluated for their cytotoxic activities against cancer cells. Among them, compound 5 showed the highest cytotoxic activity with IC50 values in the range 5.02–16.76 μg/mL.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11386/4722519
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