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.
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.
authors.affiliation: The United Graduate School of Agricultural Sciences, Ehime University , 3-5-7 Tarumi, Matsuyama, Ehime, 790-8566 Japan.
authors.forename: Yurika
authors.initials: Y
authors.lastname: Kitai
authors.affiliation: The Graduate School of Agriculture, Kagawa University , 2393 Ikenobe, Miki, Kagawa, 761-0795 Japan.
authors.forename: Kana
authors.initials: K
authors.lastname: Hayashi
authors.affiliation: The Graduate School of Agriculture, Kagawa University , 2393 Ikenobe, Miki, Kagawa, 761-0795 Japan.
authors.forename: Moe
authors.initials: M
authors.lastname: Otsuka
authors.affiliation: The United Graduate School of Agricultural Sciences, Ehime University , 3-5-7 Tarumi, Matsuyama, Ehime, 790-8566 Japan.
authors.forename: Hisashi
authors.initials: H
authors.lastname: Nishiwaki
authors.affiliation: Department of Advanced Materials Science, Faculty of Engineering, Kagawa University , 2217-20 Hayashicho, Takamatsu, Kagawa, 761-0396 Japan.
authors.forename: Tatsuya
authors.initials: T
authors.lastname: Senoo
authors.affiliation: Department of Advanced Materials Science, Faculty of Engineering, Kagawa University , 2217-20 Hayashicho, Takamatsu, Kagawa, 761-0396 Japan.
authors.forename: Tomohiko
authors.initials: T
authors.lastname: Ishii
authors.affiliation: Department of Chemistry, Okayama University of Science , 1-1 Ridai-cho, Kita-ku, Okayama, 700-0005 Japan.
authors.forename: Genta
authors.initials: G
authors.lastname: Sakane
authors.affiliation: Western Region Agricultural Research Center, National Agriculture and Food Research Organization , 1-3-1 Butsuyuucho, Zentsuji, Kagawa, 765-8508 Japan.
authors.forename: Makoto
authors.initials: M
authors.lastname: Sugiura
authors.affiliation: The United Graduate School of Agricultural Sciences, Ehime University , 3-5-7 Tarumi, Matsuyama, Ehime, 790-8566 Japan.|The Graduate School of Agriculture, Kagawa University , 2393 Ikenobe, Miki, Kagawa, 761-0795 Japan.
authors.forename: Hirotoshi
authors.initials: H
authors.lastname: Tamura
mesh_terms: D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000494:pharmacology*; D019659:Asteraceae / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D018360:Crystallography, X-Ray; D018922:HL-60 Cells; D006367:HeLa Cells; D006801:Humans; D007783:Lactones / Q000737:chemistry* / Q000494:pharmacology*; D008546:Melanoma, Experimental; D051379:Mice; D008958:Models, Molecular; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry; D018515:Plant Leaves / Q000737:chemistry*; D012717:Sesquiterpenes / Q000737:chemistry* / Q000494:pharmacology*; D021241:Spectrometry, Mass, Electrospray Ionization; D013329:Structure-Activity Relationship
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D007783:Lactones; D010936:Plant Extracts; D012717:Sesquiterpenes; C000609701:uvedafolin
keywords: Smallanthus sonchifolius; cytotoxicity; dimer sesquiterpene lactone; ‘Sarada otome’