Isolation of quinolone alkaloids from Tetradium ruticarpum via preparative high-speed counter-current chromatography and evaluation of their binding affinities for bovine serum albumin

By application of preparative high-speed counter-current chromatography (HSCCC) to the crude quinolone alkaloids (1.1 g) from the fruit of Tetradium ruticarpum, 1-methyl-2((6Z,9Z)-pentadecadienyl)-4(1H)-quinolone (1, 8.4 mg), dihydroevocarpine (2, 27.0 mg), and 1-methyl-2-pentadecyl-4(1H)-quinolone (3, 18.8 mg) were isolated in one step with sufficient purity using the solvent system composed of hexane–ethyl acetate–methanol–water (Hex–EtOAc–MeOH–H2O, 5:2:5:3). Further purification of the subfraction was performed by amending the solvent composition and achieved another three quinolone alkaloids, i.e., 1-methyl-2-undecylquinolin-4(1H)-one (4, 13.7 mg), (Z)-1-methyl-2-(tridec-5-en-1-yl) quinolin-4(1H)-one (5, 14.0 mg) from subfraction FR3-A3-85 using Hex–EtOAc–MeOH–H2O (5:3.5:8.75:8.25), and 1-methyl-2-nonylquinolin-4(1H)-one (6, 15.1 mg) from subfraction FR3-A3-36 using Hex–EtOAc–MeOH–H2O (5:3.8:5:4.8). The relationship between the structure of the six alkaloids and their affinities for bovine serum album...