Gracilone, a new sesquiterpene lactone from Tanacetum gracile (Tansies)

Abstract

The methanolic extract of the Tanacetum gracile afforded the isolation of new sesquiterpene lactone, named gracilone (1) along with four known compounds as 14α-taraxeran-3-one (2), 14α-taraxeran-3-ol (3), apigenin (4) and β-sitosterol (5). The structure of compound 1 was elucidated on the basis of 1D, 2D NMR and MS spectroscopic analysis. Antimicrobial, antioxidant and anticancer activities of all compounds were evaluated, from which gracilone (1) showed a moderate antibacterial activity, while apigenin (4) showed comparatively more antibacterial activity against both gram-positive and gram-negative tested strains.

Antibacterial and Antifungal Sesquiterpenoids: Chemistry, Resource, and Activity

“…Gracilone ( 120 , Figure 9 ) was isolated from the methanol extract of Tanacetum gracile. Compound 120 showed moderate antibacterial activity against S. aureus , B. subtilis , E. coli , and P. aeruginosa , with diameters of the growth inhibition zones of 6.70, 14.3, 14.4, and 17.3 mm, respectively, determined by the agar disc diffusion method (50 μg/disk) [ 54 ].…”

“…The hydrophobicity of some sesquiterpenoids disturbs the cytoplasmic membrane or compounds in it, such as some classes of proteins, increasing the ionic permeability and causing cytoplasmic extravasation and, as consequence, cellular lysis, as well as interfering with the activity of the respiratory current and energy production. Terpenes isolated from essential oils, such as thymol and carvacrol, may act as permeabilizers of the cell membrane, increasing the entry of antibiotics [ 54 ]. Thus, α -bisabolol is possibly responsible for the antibacterial and synergic action when associated with antibiotics.…”