Chelidonium majus is the only species in the genus Chelidonium, belongs to family Papaveraceae. The aerial parts of this plant are used as a traditional medicine for anti-bacterial, anti-inflammatory, anti-cancer activities to treat gastric ulcer, gastric cancer, many types of skin diseases and liver disorders. In the previous reports, the main constitutes of C. majus were confirmed as isoquinoline alkaloids, flavonoids and phenolic acids. On continuing research of the bioactive compounds from natural sources, we isolated two new isoquinoline alkaloids: cis-tetrahydrocoptisine N-oxide (1), trans-tetrahydrocoptisine N-oxide (2); three known isoquinoline alkaloids: impatien B (3)[1] spallidamine (4), oxychelerythrine (5); a phenolic acid: 3,4-methylenedioxy phthalic acid (6) and three known amides: noroxyhydrastinine (7), trans-N-coumaroyltyramine (8)[2], cis-N-coumaroyltyramine (9)[3] from the dried aerial parts of C. majus. Their structures were elucidated on the spectroscopic methods including 1D-NMR (1H, 13C-NMR), 2D-NMR (HSQC, HMBC, NOESY), mass (HR-ESI, ESI). Compounds 3, 5, 6, 8 and 9 were isolated for first time from C. majus. Additionally, all of the isolates were tested for their inhibitory effect on LPS-induced NO production in RAW 264.7 cells. Among them, compounds 2 and 5 showed inhibitory effect with IC50 values of 26.3 and 70.1 µM, while aminoguanidine, a positive control, showed an IC50 value of 15.9 µM.
References:
[1] Li JC. et al. Asian Journal of Chemistry 2013; 25(1): 585-586
[2] Holzbach JC and Lopes LMX. Molecules 2010; 15:9462-9472
[3] Kim DK, Lim JP, Kim JW, Park HW, Eun JS. Arch Pharm Res 2005; 28(1): 39-43