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United States Department of Agriculture

Agricultural Research Service

Title: N-Coumaroyltyramine Is a Potent Phytochemical to Arrest Meylocytic U937 and Lymphocytic Jurkat Cells at the S Phase of Cell Cycle

Authors
item Park, Jae
item Schoene, Norberta

Submitted to: Cancer Letters
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: March 21, 2002
Publication Date: April 12, 2002
Citation: Park, J.B., Schoene, N.W. 2003. N-coumaroyltyramine is a potent phytochemical to arrest meylocytic u937 and lymphocytic jurkat cells at the s phase of cell cycle. Cancer Letters. 202:161-171.

Interpretive Summary: Numerous phytochemicals in human diets are believed to contain the potential to improve general health and prevent certain chronic diseases. Finding beneficial biological effects of new phytochemicals is, therefore, the first step in understanding their potential impact on human health. N-coumaroyltyramine is found in various plants including banana, beans, nuts, and spinach. It has been speculated to act as an anti-prolif eration agent and as a neurotransmiter in humans, because of its structural similarity to experimental cancer drugs and prominent neurotransmitters (dopamine, epinephrine and norepinephrine). However, the study of this phytochemical has been hampered by its scarcity. This report describes the synthesis and chemical characterization of N- coumaroyl-tyramine and the anti-proliferation effect of N- coumaroyltyramine was demonstrated for the first time, particularly its ability to arrest tumor cells such as U937 and Jurkat cells at the S-phase of the cell cycle. Since N-coumaroyltyramine shares considerable structural resemblance to experimental cancer drugs and prominent neurotransmitters, the outcomes of current and future studies will provide researchers in nutrition, molecular biology, and medicinal fields novel in- formation regarding its suitability as a dietary factor for reducing risks of chronic diseases such as cancers and neurological abnormality.

Technical Abstract: Numerous phytochemicals are believed to have beneficial effects on human health. N-coumaroyltyramine accumulates in plants in response to wounding and pathogen attack. Due to the scarcity of N-coumaroyltyramine, its biological activities have not been studied in human cells. In this study, N-coumaroyltyramine was chemically synthesized and then purified by an HPLC equipped with a UV-visible absorbance detector. Retention times of major peaks were 14.3 and 20.7 min, and the peak at 20.7 min was confirmed by LC-MS as N-coumaroyltyramine with a mass/charge (m/z) unit of 284.1. The synthesis procedure was relatively easy and had an acceptable yield (approximately 55%). The compound exhibited a new activity, suppression of growth of human tumor cells such as U937 and Jurkat cells. The suppression was proportional to time and to concentrations of N- coumaroyltyramine. In addition, the suppressed growth of the cells was strongly associated with an increased percentage of cells in the S phase of the cell cycle progression. Furthermore, N-coumaroyltyramine was able to inhibit the protein tyrosine kinase of epidermal growth factor receptor (EGFR). This is the first report of the growth suppressing activity of N- coumaroyltyramine and its arrest of cells at the S phase of the cell cycle, possibly by inhibition of a protein tyrosine kinase (EGFR).

Last Modified: 7/22/2014
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