RESUMEN
Objective: To study the chemical constituents from the fruits of Evodia rutaecarpa var. officinalis. Methods: The constituents were isolated and purified by chromatographic methods. The structures were elucidated by physicochemical properties and spectroscopic methods. The antifungal activities were tested with mycelium growth method. Results: Fifteen compounds were obtained from the 70% ethanol extract of E. rutaecarpa var. officinalis, and were identified as evodiamine (1), rutaecarpine (2), dehydroevodiamine (3), dihydroevocarpine (4), evocarpine (5), 1-methyl-2-undecyl-4 (1H)-quinolone (6), 1-methyl-2-[(4Z,7Z)- 4,7-tridecadienyl]-4 (1H)-quinolone (7), 1-methyl-2-[(6Z,9Z)-6,9-pentadecadienyl-4 (1H)-quinolone (8), limonin (9), shihulimonin A (10), isolimonexic acid (11), wuzhuyurutine B (12), stigmasterol (13), β-sitosterol (14), and β-daucosterin. (15). Conclusion: Compounds 5-8 and 11-13 are isolated from E. rutaecarpa var. officinalis for the first time. Different types of compounds show diverse antimicrobial activities against plant-pathogenic fungi.
RESUMEN
Objective: To develop a suitable method for the large-scale separation of quinolone alkaloids from the fruits of Evodia rutaecarpa by high-speed counter-current chromatography (HSCCC). Methods: Two solvent systems were developed for the separation method. The upper phase was used as the stationary phase, and the lower phase was used as the mobile phase at 35 °C with the flow rate of 2 mL/min and rotation speed of 855 r/min. Results Using the described method, 1-methyl-2-undecyl-4(1H)-quinolone (1), evocarpine (2), 1-methy-2-[(6Z,9Z)]-6,9-pentade-cadienyl-4-(1H)-quinolone (3), dihydroevocarpine (4), and the mixture (5) of 1-methyl-2-[(Z)-10-pentadecenyl]-4(1H)-quinolone (Va) and 1-methyl-2-[(Z)-6-pentadecenyl]-4(1H)-quinolone (Vb) could be isolated from a petroleum ether extract. They were identified by 1H-NMR, 13 C-NMR, and MS/MS, and the purities were 94.3%, 95.2%, 96.8%, 98.3%, and 96.8%, respectively. Conclusion: Five quinolone alkaloids from the fruits of E. rutaecarpa could be systematically isolated and purified using HSCCC. The presented method is simple and efficient with good potentials on the preparation of reference substances, especially on the quality control of Chinese materia medica. © 2014 Tianjin Press of Chinese Herbal Medicines.