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United States Department of Agriculture

Agricultural Research Service

Research Project: DIET AND IMMUNE FUNCTION RELATED TO INFECTIOUS AND ALLERGIC DISEASE

Location: Diet, Genomics and Immunology Lab

Title: Synthesis, biological activity, and bioavailability of moschamine, a safflomide-type phenylpropenoic acid amide found in Centaurea cyanus

Author
item Park, Jae

Submitted to: Natural Product Research
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: April 23, 2013
Publication Date: August 7, 2012
Citation: Park, J.B. 2012. Synthesis, biological activity, and bioavailability of moschamine, a safflomide-type phenylpropenoic acid amide found in Centaurea cyanus. Natural Product Research. 26(16):1465-72.

Interpretive Summary: Moschamine is one of the safflomide-type phenylpropanoid amides found in numerous plants such as coffee (Coffea canephora), coco (Theobroma cacao) and safflower (Carthamus tinctorius). Recent studies suggested that safflomide analogues have potent serotoninergic and antioxidant activities important in the development and progress of several human diseases such as inflammation, obesity, hypertension, behavior, and cognitive dysfunction. However, the bioavailability and biological activities of moschamine are currently unknown, making it difficult to accurately propose mechanisms of action and assess effects in vivo. In this study, the synthesis, biological activities, and bioavailability of moschamine were described. The outcomes of this study will provide researchers in nutrition, molecular biology, and medicine with new information on the potential pathways and applications of this substance in the diet.

Technical Abstract: Moschamine is a safflomide-type phenylpropenoic acid amide originally isolated from Centaurea cyanus. This paper describes the synthesis, detection of serotoninergic and COX inhibitory activities, and bioavailability of moschamine. Moschamine was chemically synthesized and identified using NMR spectroscopic methods. The synthesis was simple, and the yield was greater than 40%. Moschamine was able to inhibit forskolin-stimulated cAMP formation by 25 % via serotonin receptors in OK renal epithelial cells at a concentration of 10 µM. 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 on the cells. Also, moschamine was a very potent compound able to inhibit COX-I by 58 % and COX-II by 54 % at a concentration of 0.1 µM. The bioavailability of moschamine was also determined in mice administered 2 and 4 mg per 30 g body weight per os. These data suggest that moschamine is absorbed in the intestine and can act as a 5-HT1 agonist and COX inhibitor.

Last Modified: 8/22/2014
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