Sesquiterpene Lactones from Centaurea achaia, a Greek Endemic Species: Antifungal Activity

Abstract

The aerial parts of Centaurea achaia afforded, in addition to several known sesquiterpene lactones and sesquiterpene hydroxyesters, a new germacranolide and a new elemanolide. Their structures were determined as the 8a-0-(4,5-dihydroxy-tigloyloxy) esters of salonitenolide and of 11,13-dihydromelitensin, respectively. The in vitro antifungal activity of most compounds was tested against nine fungal species using the micro-dilution method. All the tested compounds showed strong antifungal activity.

Elemanolide sesquiterpenes and eudesmane sesquiterpene glycosides from Centaurea hierapolitana

“…Elemane-type sesquiterpenes have also been isolated from C. chilensis (Negrete et al, 1993), C. paui (Cardona et al, 1997), C. cuneifolia (Aslan and Oksuz, 1999), C. achaia (Skaltsa et al, 2000b) and C. aspera (Marco et al, 2005). Our investigation demonstrated that elemane-type metabolites are the main sesquiterpenes in C. hierapolitana which is a member of Phalolepis section.…”

VolSurf analysis of pharmacokinetic properties for several antifungal sesquiterpene lactones isolated from Greek Centaurea sp.

“…However, it should be noted that low polarity is one of the molecular requirements suggested for the antifungal activity of sesquiterpene lactones [25,28,33]. As it is observed from the reported tables of MICs and MFCs values [16][17][18], among the studied compounds, germacranolides which have retention times on a RP-18 column higher than the other groups are the most active. This supports the hypothesis of an inverse relationship between polarity and antifungal activity for sesquiterpene lactones.…”

“…Continuing our study on sesquiterpene lactones, in a first step we attempted to predict the pharmacokinetic properties of an interesting data set of potent antifungal sesquiterpene lactones, isolated from Greek taxa of Centaurea sp., by projection on the pre-calculated ADME models developed in VolSurf [16][17][18]. In a second step, we tried to optimize the pharmacokinetic properties of data set's selected molecules by ADME in silico screening of a semi-synthetic derivatives virtual library.…”

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

“…All the compounds tested showed great antifungal activity comparable and sometimes better than miconazole used as control (Skaltsa et al, 2000a;.…”