title: Synthesis, biological activities and bioavailability of moschamine, a safflomide-type phenylpropenoic acid amide found in Centaurea cyanus.
abstract: Moschamine is a phenylpropenoic acid amide found in plants. In this article, the synthesis and two biological activities (serotoninergic and cyclooxygenase (COX) inhibitory activities) and bioavailability of moschamine were described. Moschamine was synthesised and confirmed using NMR spectroscopic methods. Using the moschamine synthesised, serotoninergic and COX inhibitory activities were investigated. At the concentration of 10 µmol L⁻¹, moschamine was able to inhibit forskolin-stimulated cAMP formation by 25% (p < 0.015), via inhibiting serotonin receptors in the OK cells. The inhibition was repressed by two 5-HT1 antagonists (Nan-190 and spiperone), suggesting that moschamine may suppress cAMP formation via binding to 5-HT1 receptors in the cells. Also, moschamine was a very potent compound that is able to inhibit COX-I by 58% (p < 0.012) and COX-II by 54% (p < 0.014), at the concentration of 0.1 µmol L⁻¹. The oral bioavailability of moschamine was also determined in mice.
authors: Diet, Genomics, and Immunology Laboratory, Beltsville Human Nutrition Research Center, Agricultural Research Service, US Department of Agriculture, Room 131, Building 307C, Beltsville, MD 20705, USA. jae.park@ars.usda.gov
authors: Jae B
authors: JB
authors: Park
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry / Q000493:pharmacokinetics / Q000494:pharmacology*; D000818:Animals; D002460:Cell Line; D031179:Centaurea / Q000737:chemistry*; D051545:Cyclooxygenase 1 / Q000378:metabolism*; D051546:Cyclooxygenase 2 / Q000378:metabolism*; D004789:Enzyme Activation / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D015394:Molecular Structure; D044263:Receptors, Serotonin, 5-HT1 / Q000187:drug effects; D012701:Serotonin / Q000031:analogs & derivatives
chemical_list: D000577:Amides; D044263:Receptors, Serotonin, 5-HT1; C512561:N-feruloylserotonin; D012701:Serotonin; D051545:Cyclooxygenase 1; D051546:Cyclooxygenase 2