title: Antitumor agents. 261. 20(S)-protopanaxadiol and 20(s)-protopanaxatriol as antiangiogenic agents and total assignment of (1)H NMR spectra.
abstract: Angiogenesis is a critical step in tumor progression and involves several steps including endothelial cell (EC) proliferation, migration, and matrix remodeling. We investigated the antiangiogenic effects of 20( S)-protopanaxadiol ( 1) and 20( S)-protopanaxatriol ( 2), the sapogenins of two major ginseng saponins, in an angiogenesis model of human umbilical vein endothelial cells (HUVECs). These compounds inhibited the proliferative activity of HUVECs in a dose-dependent manner and have potential as anticancer drug candidates. In addition, we report the complete and unambiguous assignment of (1)H NMR spectra of 1 and 2, based on analyses of 2D NMR spectra including COSY, NOESY, HSQC, and HMBC. This report is the first to completely assign the (1)H NMR signals of 2, together with correction of data for 1 from prior reports.
authors.affiliation: School of Pharmacy, University of North Carolina, Chapel Hill, North Carolina 27599-7360, USA.
authors.forename: Yoshihide
authors.initials: Y
authors.lastname: Usami
authors.forename: Yi-Nan
authors.initials: YN
authors.lastname: Liu
authors.forename: An-Shen
authors.initials: AS
authors.lastname: Lin
authors.forename: Makio
authors.initials: M
authors.lastname: Shibano
authors.forename: Toshiyuki
authors.initials: T
authors.lastname: Akiyama
authors.forename: Hideji
authors.initials: H
authors.lastname: Itokawa
authors.forename: Susan L
authors.initials: SL
authors.lastname: Morris-Natschke
authors.forename: Kenneth
authors.initials: K
authors.lastname: Bastow
authors.forename: Ryoji
authors.initials: R
authors.lastname: Kasai
authors.forename: Kuo-Hsiung
authors.initials: KH
authors.lastname: Lee
mesh_terms: D020533:Angiogenesis Inhibitors / Q000737:chemistry* / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D006801:Humans; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D012502:Sapogenins / Q000737:chemistry* / Q000494:pharmacology*; D013237:Stereoisomerism; D014315:Triterpenes / Q000737:chemistry* / Q000494:pharmacology*; D014471:Umbilical Veins / Q000166:cytology / Q000187:drug effects
chemical_list: D020533:Angiogenesis Inhibitors; D012502:Sapogenins; D014315:Triterpenes; C081552:protopanaxatriol; C062916:protopanaxadiol