title: Steroidal saponins from the roots of Smilax sp.: structure and bioactivity.
abstract: Phytochemical characterization of a commercial herb sample supplied as Smilax ornata Lem. (sarsaparilla) led to the isolation of five steroidal saponins, including two new furostanol saponins sarsaparilloside B (1) and sarsaparilloside C (2), whose structures were elucidated via a combination of multistage mass spectrometry (MS(n)), 1D and 2D NMR experiments, and chemical degradation. The previously unreported spectroscopic characterization of sarsaparilloside (3), Δ(20(22))-sarsaparilloside (4), and parillin (5) is also provided. The antiproliferative activity of the isolated saponins was compared in six human cell lines derived from different tumor types and one of the structures (2) was particularly active against the HT29 colon tumor cell line.
authors.affiliation: School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane QLD 4072, Australia.
authors.forename: Victoria L
authors.initials: VL
authors.lastname: Challinor
authors.forename: Peter G
authors.initials: PG
authors.lastname: Parsons
authors.forename: Sonet
authors.initials: S
authors.lastname: Chap
authors.forename: Eve F
authors.initials: EF
authors.lastname: White
authors.forename: Joanne T
authors.initials: JT
authors.lastname: Blanchfield
authors.forename: Reginald P
authors.initials: RP
authors.lastname: Lehmann
authors.forename: James J
authors.initials: JJ
authors.lastname: De Voss
mesh_terms: D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D005347:Fibroblasts / Q000166:cytology / Q000187:drug effects; D019073:HT29 Cells; D006367:HeLa Cells; D006801:Humans; D020014:K562 Cells; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D010840:Phytosterols / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D018517:Plant Roots / Q000737:chemistry*; D012503:Saponins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D032281:Smilax / Q000737:chemistry*
chemical_list: D010840:Phytosterols; D012503:Saponins; C574239:sarsaparilloside B; C574240:sarsaparilloside C