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RESEARCH PRODUCT

Steroidal saponins from Dioscorea preussii.

Turibio Kuiate TabopdaTuribio Kuiate TabopdaJean François MirjoletMarie Aleth Lacaille-duboisChiaki TanakaTomofumi MiyamotoOlivier DuchampAnne Claire Mitaine-offerBonaventure T. Ngadjui

subject

PharmacologyDioscorea preussiiMolecular StructureStereochemistryChemistryDioscoreaPhytosterolsGeneral MedicineSaponinsMass spectrometryHCT116 CellsRhizomeDihydroxylationCarcinoma CellDrug DiscoveryHumansDrug Screening Assays AntitumorCytotoxicityTwo-dimensional nuclear magnetic resonance spectroscopyHT29 CellsHuman colon

description

Abstract Three new steroidal saponins, named diospreussinosides A–C (1–3), along with two known ones (4, 5) were isolated from rhizomes of Dioscorea preussii. Their structures were elucidated mainly by 1D and 2D NMR spectroscopic analysis and mass spectrometry as (25S)-17α,25-dihydroxyspirost-5-en-3β-yl-O-α- l -rhamnopyranosyl-(1 → 4)-α- l -rhamnopyranosyl-(1 → 4)-β- d -glucopyranoside (1), (25S)-17α,25-dihydroxyspirost-5-en-3β-yl-O-α- l -rhamnopyranosyl-(1 → 4)-α- l -rhamnopyranosyl-(1 → 4)-[α- l -rhamnopyranosyl-(1 → 2)]-β- d -glucopyranoside (2), and (24S,25R)-17α,24,25-trihydroxyspirost-5-en-3β-yl-O-α- l -rhamnopyranosyl-(1 → 4)-α- l -rhamnopyranosyl-(1 → 4)-[α- l -rhamnopyranosyl-(1 → 2)]-β- d -glucopyranoside (3). The spirostane-type skeleton of compound 3 possessing an unusual dihydroxylation pattern on the F-ring is reported for the first time. Cytotoxicity of compounds 2–5 was evaluated against two human colon carcinoma cell lines (HT-29 and HCT 116).

10.1016/j.fitote.2014.06.006https://pubmed.ncbi.nlm.nih.gov/24928475