Chemical and biological studies on Cichorium intybus L.

Cichorium intybus L. (Asteraceae family) is a world-wide grown plant known as chicory. In traditional medicine, this plant is used as diuretic, anti-inflammatory, digestive, cardiotonic and liver tonic. Chromatographic purification of the supercritical fluid extract of aerial parts of C. intybus on silica gel column led to isolation of three compounds: new compound, 28ß-hydroxytaraxasterol (I), and two known compounds usnic acid (II) and ß-sitosterol (III). Purification of the ethanolic extract of aerial parts of this plant on silica gel column chromatography yielded four compounds: 1,3-dioleylglycerate (IV), sitoindoside II (V), 11ß-13-dihydrolactucin (VI) and ß-sitosterol-3-O-glucoside (VII). The structures of the isolated compounds were determined by their 1D, 2D NMR and MS spectral data. All the fractions and isolated compounds were tested for cannabinoid and opioid receptor binding, as well as antibacterial, antifungal and antimalarial activities. Compound I showed moderate activity (60.5% displacement) towards CB1 receptor.

Isolation and Biological Evaluation of Prenylated Flavonoids from Maclura pomifera.

Phytochemical analysis of the ethanolic extract of Maclura pomifera fruits yielded four new compounds (I-IV) along with eleven known compounds (V-XV). The crude extract exhibited significant activity towards cannabinoid receptors (CB1: 103.4% displacement; CB2: 68.8% displacement) and possibly allosteric interaction with δ and µ opioid receptors (-49.7 and -53.8% displacement, resp.). Compound I was found to be possibly allosteric for κ and µ opioid receptors (-88.4 and -27.2% displacement, resp.) and showed moderate activity (60.5% displacement) towards CB1 receptor. Compound II exhibited moderate activity towards cannabinoid receptors CB1 and CB2 (47.9 and 42.3% displacement, resp.). The known compounds (V-VIII) exhibited prominent activity towards cannabinoid receptors: pomiferin (V) (IC50 of 2.110 and 1.318 µM for CB1 and CB2, resp.), auriculasin (VI) (IC50 of 8.923 µM for CB1), warangalone (VII) (IC50 of 1.670 and 4.438 µM for CB1 and CB2, resp.), and osajin (VIII) (IC50 of 3.859 and 7.646 µM for CB1 and CB2, resp.). The isolated compounds were also tested for inhibition of human monoamine oxidase-A and monoamine oxidase-B enzymes activities, where all the tested compounds showed fewer inhibitory effects on MAO-A compared to MAO-B activities: auriculasin (VI) (IC50 of 1.91 and 45.98 µM for MAO-B and MAO-A, resp.).