Journal
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
Volume 63, Issue 50, Pages 10856-10861Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.jafc.5b05229
Keywords
dimer sesquiterpene lactone; cytotoxicity; Smallanthus sonchifolius; 'Sarada otome'
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Uvedafolin, 1, a new sesquiterpene lactone dimer, was isolated from the leaves of Smallanthus sonchifolius with five related compounds, 2-6, and their cytotoxicity was assessed against three tumor cell lines (HeLa, HL-60, B16-F10 melanoma). The stereostructure of 1 was newly elucidated by ESI-TOF-MS, 1D/2D NMR, and single-crystal X-ray diffraction. Dimers 1 and 2 had the most effective IC50 values, 0.2-1.9 mu M, against the three tumor cell lines when compared with monomers 3-6 (IC50 values 0.7-9.9 mu M) and etoposide (IC50 values 0.8-114 mu M). The ester linkages of two sets of monomers, uvedalin, 5, and sonchifolin, 6, for 1, and enhydrin, 4, and sonchifolin, 6, for 2, as well as the acetyl group at the C-9 position, were essential for the high cytotoxicity. Dimers 1 and 2 would have potential as anticancer agents.
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