Alkaloids from Chelidonium majus and their inhibitory effects on LPS-induced NO production in RAW264.7 cells.
A new alkaloid, methyl 2'-(7,8-dihydrosanguinarine-8-yl)acetate (1), together with six known alkaloids, stylopine (2), protopine (3), norchelidonine (4), chelidonine (5), berberine (6), and 8-hydroxydihydrosanguinarine (7), were isolated from Chelidonium majus. Their chemical structures were primarily established using 1D and 2D NMR techniques and mass spectrometry. The anti-inflammatory activity of the isolates was examined for their inhibitory effects on LPS-induced NO production in macrophage RAW264.7 cells. Among them, compounds 5 and 7 showed strong inhibitory activities toward the LPS-induced NO production in macrophage RAW264.7 cells with IC(50) values of 7.3 and 4.5 μM, respectively. In addition, compounds 5 and 7 inhibited the inductions of COX-2 and iNOS mRNA in dose-dependent manners, indicating that these compounds attenuated the syntheses of these transcripts at the transcriptional level.
College of Pharmacy, Catholic University of Daegu, Gyeongbuk, Republic of Korea.
Ji Eun
JE
Park
To Dao
TD
Cuong
Tran Manh
TM
Hung
IkSoo
I
Lee
MinKyun
M
Na
Jin Cheol
JC
Kim
SungWoo
S
Ryoo
Jeong Hyung
JH
Lee
Jae Sue
JS
Choi
Mi Hee
MH
Woo
Byung Sun
BS
Min
D000470:Alkaloids / Q000737:chemistry* / Q000494:pharmacology*; D000818:Animals; D053119:Benzophenanthridines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002460:Cell Line; D028281:Chelidonium / Q000737:chemistry*; D051546:Cyclooxygenase 2 / Q000378:metabolism; D020128:Inhibitory Concentration 50; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008070:Lipopolysaccharides / Q000494:pharmacology; D008264:Macrophages / Q000187:drug effects* / Q000378:metabolism; D051379:Mice; D015394:Molecular Structure; D009569:Nitric Oxide / Q000037:antagonists & inhibitors / Q000378:metabolism*; D010936:Plant Extracts / Q000494:pharmacology
D000470:Alkaloids; D053119:Benzophenanthridines; D007546:Isoquinolines; D008070:Lipopolysaccharides; D010936:Plant Extracts; C571273:methyl 2'-(7,8-dihydrosanguinarine-8-yl)acetate; D009569:Nitric Oxide; D051546:Cyclooxygenase 2