Synthesis Of The Chemical Constituents Of Evodia And Quinolone Alkaloids

The fruit of Evodia rutaecarpa Bentham, a Chinese traditional drug (Wu-Chu-Yu), has been used in the treatment of headache, abdominal pain, migrains, chill limbs, postpartam hemorrhage, amenorrhage, dysentery, nausea and hyperbaropathy. Pharmacological studies reveal that Evodia rutaecarpa have analgesic, sedative, antiseptic, antianxia and antihypertensive actions. In order to search the biological active principles from the drug, further studies on the fruit has been undertaken.Thirty-one compounds were isolated from the fruit of Evodia rutaecarpa by CC, VLC, AgNO₃ silica gel CC, PTLC, RP C8 MPLC. The structures of twenty-four compounds were elucidated by spectral analysis and chemical methods. Six of them are new compounds whose structures are showed as following: 2-tridecyl-4(lH)-quinolone (18), 1-methyl-2-dodecyl-4QH)-quinolone (19), 1-methyl-2-[(Z)-5-undecenyl]-4(1H)-quinolone (17), 1-methyl-2-[(Z)-7-tridecenyl]-4(1H)-quinolone (15), 1-methyl-2-[(Z)-9-pentadecenyl]-4(1H)-quinolone (22) and 1-methyl-2-[(Z)-8-tetradecenyl]-4(lH)-quinolone (26). One is a new natural product, which is deduced as 1, 2, 3, 4-tetrahydro-1-oxo-β-carboline (8). The rest were known compounds including rutaecarpine (1), evodiamine (2), hydroxyevodiamine (3), formyldihydrorutaecarpine (4), goshuyuamide-I (5) evodiamide (6), β-carboline (7), dehydroevodiamine (9). N-methylanthranylamide (10), 1-methyl-2-nonyl-4(lH)-quinolone (11), l-methyl-2-undecyl-4(lH)-quinolone (12), dihydroevocarpine (13), evocarpine (14), 1-methyl-2-[(Z)-6-undecenyl-4(lH)-quinolone (16), 1-methyl-2-pentadecyl-4(1H)-quinolone (20), 1-methyl-2-[(Z)-10-pentadecenyl]-4(1H)-quinolone (21), β-sitosterol (23).Six quinolone alkaloids including three new compounds (17,...