Bio-guided Isolation of Antioxidant Compounds from Chrysophyllum perpulchrum, a Plant Used in the Ivory Coast Pharmacopeia

Chrysophyllum perpulchrum (Sapotaceae) is used in the traditional Ivory Coast pharmacopeia to cure fevers. The extract of C. perpulchrum used for this study was the powdered form obtained from the maceration of the dried plant bark in 96% methanol, followed by evaporation to dryness. In the present study, the antioxidative and radical-scavenging activities of the methanolic extract were studied with three standard biological tests: DPPH reduction, ferric thiocyanate (FTC) lipidic peroxidation inhibition and thiobarbituric acid reacting substances (TBARS). Gallic acid and quercetin were used as references. The total amount of phenolic compounds in the extract was determined by ultraviolet (UV) spectrometry and calculated as gallic acid equivalents. Catechin and two dimeric procyanidins were found to be the compounds responsible for the activities. They were chemically dereplicated in the extract by LC-MS. For quantitation purposes, they were isolated by successive chromatographic methods and characterized by mass spectrometry (MS) and nuclear magnetic resonance (NMR) spectrometry. The quantities of these compounds in C. perpulchrum were 5.4% for catechin (P1), and 5.6 and 9.2% for dimers (compounds 2 (P2) and 3 (P3)), respectively. They displayed antioxidant activity with IC50 values of 2.50 ± 0.15 μg/mL (P1), 2.10 ± 0.2 μg/mL (P2) and 2.10 ± 0.1 μg/mL (P3). The total extract, the active fractions and the pure compounds inhibited the lipid peroxidation by the FTC method and the TBARS method in the range of 60%. These values were comparable to those seen for quercetin.