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Cited by 48Heterocyclic Compound Synthesis and BioactivityBioactive natural compoundsPlant chemical constituents analysis

Synthesis and Characterization of N-Coumaroyltyramine as a Potent Phytochemical Which Arrests Human Transformed Cells via Inhibiting Protein Tyrosine Kinases

Park, Jae B., Schoene, Norberta·2002·Biochemical and Biophysical Research Communications
DOI 10.1006/bbrc.2002.6752
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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 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. 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 kinases including 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 protein tyrosine kinases.

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Authors
Park, J. B., & Schoene, N.
Affiliations
Agricultural Research Service (US)
Corresponding author
Park, Jae B.
ORCID
Park, Jae B.
Venue
Biochemical and Biophysical Research Communications
Publisher
Elsevier BV
Published
2002-04
Volume
292
Issue
4
Pages
1104-1110
ISSN
0006-291X (ISSN-L)
DOI
10.1006/bbrc.2002.6752
OpenAlex
W1986828938
Cited by
48
References
42
Citations by year
2025: 3 · 2024: 3 · 2023: 2 · 2022: 1 · 2021: 3 · 2020: 3 · 2018: 1 · 2017: 1 · 2016: 1 · 2015: 1 · 2014: 1
FWCI
1.97
Type
journal article
Language
en
Open access
closed
Licence
www.elsevier.com/tdm/userlicense/1.0/ (tdm)
Locations
  • Biochemical and Biophysical Research Communications (publishedVersion)
  • PubMed (publishedVersion)
Funders
Mead Johnson Nutrition
Topics
  • Physical Sciences › Chemistry › Organic Chemistry › Heterocyclic Compound Synthesis and Bioactivity
  • Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Drug Discovery › Bioactive natural compounds
  • Life Sciences › Agricultural and Biological Sciences › Plant Science › Plant chemical constituents analysis
Keywords
phytochemicals, protein tyrosine kinase inhibition, epidermal growth factor receptor, cell cycle arrest, S phase, antiproliferative activity, U937 cells, Jurkat cells, plant defense compounds, chemical synthesis, tumor cell growth inhibition
MeSH terms
Antineoplastic Agents, Phytogenic, Cell Division, Cell Line, Transformed, Chromatography, High Pressure Liquid, Coumaric Acids, Drug Evaluation, Preclinical, Enzyme Inhibitors, Humans, Protein-Tyrosine Kinases, Mass Spectrometry, Tyramine, S Phase, Jurkat Cells, U937 Cells, ErbB Receptors

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