从吴茱萸 Evodia rutaecarpa 的果实中分离得到的新型细胞毒性喹诺酮生物碱。

New cytotoxic quinolone alkaloids from fruits of Evodia rutaecarpa.

机构信息

State Key Laboratory of Natural and Biomimetic Drugs, Department of Natural Medicines, School of Pharmaceutical Sciences, Peking University, Beijing 100191, PR China.

出版信息

Fitoterapia. 2012 Jun;83(4):709-14. doi: 10.1016/j.fitote.2012.02.009. Epub 2012 Mar 2.

DOI:10.1016/j.fitote.2012.02.009

PMID:22406451

Abstract

Three new quinolone alkaloids, 1-methyl-2-[7-hydroxy-(E)-9-tridecenyl]-4(1H)-quinolone (1), 1-methyl-2-[(Z)-4-nonenyl]-4(1H)-quinolone (2), 1-methyl-2-[(1E,5Z)-1,5-undecadienyl]-4(1H)-quinolone (3) and one new natural product, 1-methyl-2-[(E)-1-undecenyl]-4(1H)-quinolone (4), were isolated from the dried and nearly ripe fruits of Evodia rutaecarpa (Juss.) Benth., along with thirteen known compounds (5-17). In addition, one new artificial product, 1-methyl-2-[7-carbonyl-(E)-9-tridecenyl]-4(1H)-quinolone (1A) was also obtained. The structures of these compounds were determined by spectroscopic analyses. The cytotoxic activities of all of the compounds against the human cancer cell lines HL-60, N-87, H-460, and Hep G(2) cells were evaluated by MTT assay. The results showed that these alkaloids inhibited cell proliferation with IC(50) values between 14μM and 22μM.

摘要

从吴茱萸 Evodia rutaecarpa (Juss.) Benth. 的干燥近成熟果实中分离得到三个新的喹诺酮生物碱，1-甲基-2-[7-羟基-(E)-9-十三烯基]-4(1H)-喹诺酮（1）、1-甲基-2-[(Z)-4-壬烯基]-4(1H)-喹诺酮（2）、1-甲基-2-[(1E,5Z)-1,5-十一二烯基]-4(1H)-喹诺酮（3）和一个新的天然产物 1-甲基-2-[(E)-1-十一烯基]-4(1H)-喹诺酮（4），以及 13 个已知化合物（5-17）。此外，还得到了一个新的人工产物，1-甲基-2-[7-羰基-(E)-9-十三烯基]-4(1H)-喹诺酮（1A）。通过光谱分析确定了这些化合物的结构。通过 MTT 测定法评估了所有化合物对人癌细胞系 HL-60、N-87、H-460 和 Hep G(2)细胞的细胞毒性活性。结果表明，这些生物碱对细胞增殖具有抑制作用，IC(50)值在 14μM 和 22μM 之间。