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RESEARCH PRODUCT
Structure and cytotoxicity of steroidal glycosides from Allium schoenoprasum
Tomofumi MiyamotoMarie Aleth Lacaille-duboisJean François MirjoletChiaki TanakaAnne Claire Mitaine-offerGaoussou TimitéOlivier Duchampsubject
Magnetic Resonance SpectroscopySteroidal glycosidesCell SurvivalStereochemistryChivePharmaceutical SciencePlant ScienceHorticultureBiochemistryAnalytical ChemistryInhibitory Concentration 50foodDrug DiscoveryHumansGlycosidesCytotoxicityMolecular BiologyPharmacologychemistry.chemical_classificationMolecular StructureOrganic ChemistryGlycosideGeneral MedicineSaponinsHCT116 CellsAllium schoenoprasumfood.foodHuman colon cancerComplementary and alternative medicinePhytochemicalchemistryColonic NeoplasmsMolecular MedicinePlant StructuresHT29 CellsTwo-dimensional nuclear magnetic resonance spectroscopydescription
Abstract A phytochemical analysis of the whole plant of Allium schoenoprasum , has led to the isolation of four spirostane-type glycosides ( 1 – 4 ), and four known steroidal saponins. Their structures were elucidated mainly by 2D NMR spectroscopic analysis and mass spectrometry as (20 S ,25 S )-spirost-5-en-3β,12β,21-triol 3- O -α- l -rhamnopyranosyl-(1 → 2)-β- d -glucopyranoside ( 1 ), (20 S ,25 S )-spirost-5-en-3β,11α,21-triol 3- O -α- l -rhamnopyranosyl-(1 → 2)-β- d -glucopyranoside ( 2 ), laxogenin 3- O -α- l -rhamnopyranosyl-(1 → 2)-[β- d -glucopyranosyl-(1 → 4)]-β- d -glucopyranoside ( 3 ), and (25 R )-5α-spirostan-3β,11α-diol 3- O -β- d -glucopyranosyl-(1 → 3)-[β- d -glucopyranosyl-(1 → 4)]-β- d -galactopyranoside ( 4 ). Four of the isolated compounds were tested for cytotoxic activity against the HCT 116 and HT-29 human colon cancer cell lines.
year | journal | country | edition | language |
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2013-04-01 | Phytochemistry |