RRC ID 38901
Author Kitai Y, Hayashi K, Otsuka M, Nishiwaki H, Senoo T, Ishii T, Sakane G, Sugiura M, Tamura H.
Title New Sesquiterpene Lactone Dimer, Uvedafolin, Extracted from Eight Yacon Leaf Varieties (Smallanthus sonchifolius): Cytotoxicity in HeLa, HL-60, and Murine B16-F10 Melanoma Cell Lines.
Journal J Agric Food Chem
Abstract 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 μM, against the three tumor cell lines when compared with monomers 3-6 (IC50 values 0.7-9.9 μM) and etoposide (IC50 values 0.8-114 μM). 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.
Volume 63(50)
Pages 10856-61
Published 2015-12-23
DOI 10.1021/acs.jafc.5b05229
PMID 26576855
MeSH Animals Antineoplastic Agents, Phytogenic / pharmacology* Asteraceae / chemistry* Chromatography, High Pressure Liquid Crystallography, X-Ray HL-60 Cells HeLa Cells Humans Lactones / chemistry* Lactones / pharmacology* Melanoma, Experimental Mice Models, Molecular Molecular Structure Plant Extracts / chemistry Plant Leaves / chemistry* Sesquiterpenes / chemistry* Sesquiterpenes / pharmacology* Spectrometry, Mass, Electrospray Ionization Structure-Activity Relationship
IF 4.192
Times Cited 11
WOS Category AGRICULTURE, MULTIDISCIPLINARY FOOD SCIENCE & TECHNOLOGY CHEMISTRY, APPLIED
Resource
Human and Animal Cells HL-60 HeLa