New crinine-type alkaloids with inhibitory effect on induction of inducible nitric oxide synthase from Crinum yemense.
The 80% aqueous methanolic extract from the bulbs of Crinum yemense showed a potent inhibitory effect on nitric oxide production in lipopolysaccharide-activated macrophages. Three new crinine-type alkaloids, yemenines A (1), B (2), and C (3), were isolated from the herbal extract together with six known alkaloids. The absolute configurations of 1-3 were determined on the basis of chemical and physicochemical evidence. The effects of the isolated alkaloids on nitric oxide production in lipopolysaccharide-activated macrophages were examined, and several alkaloids, e.g. 1, (+)-bulbispermine (6), (+)-crinamine (7), (+)-6-hydroxycrinamine (8), and (-)-lycorine (9), showed inhibitory effects on nitric oxide production and induction of inducible nitric oxide synthase.
Abdel-Halim
Osama Bashir
OB
Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt.
Morikawa
Toshio
T
Ando
Shin
S
Matsuda
Hisashi
H
Yoshikawa
Masayuki
M
D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D047151:Amaryllidaceae Alkaloids; D031407:Crinum / Q000737:chemistry*; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D007212:Indolizines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008070:Lipopolysaccharides / Q000378:metabolism; D017737:Macrophages, Peritoneal / Q000187:drug effects*; D015394:Molecular Structure; D009569:Nitric Oxide / Q000378:metabolism*; D019001:Nitric Oxide Synthase / Q000037:antagonists & inhibitors*; D052247:Nitric Oxide Synthase Type II; D010617:Phenanthridines / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D010946:Plants, Medicinal / Q000737:chemistry*; D015006:Yemen
D000470:Alkaloids; D047151:Amaryllidaceae Alkaloids; D004791:Enzyme Inhibitors; D007212:Indolizines; D008070:Lipopolysaccharides; D010617:Phenanthridines; C488649:yemenine A; C488651:yemenine B; C488650:yemenine C; D009569:Nitric Oxide; C411129:crinamine; D019001:Nitric Oxide Synthase; D052247:Nitric Oxide Synthase Type II; C015330:lycorine