Journal
JOURNAL OF SEPARATION SCIENCE
Volume 42, Issue 6, Pages 1133-1143Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/jssc.201800986
Keywords
cyclooxygenase-2; enzyme-immobilized magnetic beads; high-speed countercurrent chromatography; semi-preparative high-performance liquid chromatography; Trifolium pratense L.
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Funding
- National Natural Science Foundation of China [31670358, 31870336]
- Natural Science Foundation of Jilin Province [20180414028GH, 201807414028GH]
- Jilin Provincial Education Department program [JJKH20181171KJ]
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Nonsteroidal anti-inflammatory drugs reportedly reduce the risk of developing cancer. One mechanism by which they reduce carcinogenesis involves the inhibition of the activity of cyclooxygenase-2, an enzyme that is overexpressed in various cancer tissues. Its overexpression increases cell proliferation and inhibits apoptosis. However, selected cyclooxygenase-2 inhibitors can also act through cyclooxygenase-independent mechanisms. In this study, using ultrafiltration, enzyme-immobilized magnetic beads, high-performance liquid chromatography, and electrospray-ionization mass spectrometry, several isoflavonoids in Trifolium pratense L. extracts were screened and identified. Semi-preparative high-performance liquid chromatography and high-speed counter-current chromatography were then applied to separate the active constituents. Using these methods, seven major compounds were identified in Trifolium pratense L. As cyclooxygenase-2 inhibitors: rothindin, ononin, daidzein, trifoside, pseudobaptigenin, formononetin, and biochanin A, which were then isolated with > 92% purity. This is the first report of the presence of potent cyclooxygenase-2 inhibitors in Trifolium pratense L. extracts. The results of this study demonstrate that the systematic isolation of bioactive components from Trifolium pratense L., by using ultrafiltration, enzyme-immobilized magnetic beads, semi-preparative high-performance liquid chromatography, and high-speed countercurrent chromatography, represents a feasible and efficient technique that could be extended for the identification and isolation of other enzyme inhibitors.
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