title: Anticancer diarylheptanoid glycosides from the inner bark of Betula papyrifera.
abstract: Phytochemical investigations of the MeOH extract of Betula papyrifera inner bark led to the isolation of ten phenolic compounds of the following types: diarylheptanoid glycosides (1-4), a diarylheptanoid (5), a lignan (6), flavonoids (7-8) and chavicol glycosides (9-10). Among them, the diarylheptanoid glycoside, (S)-1,7-bis-(4-hydroxyphenyl)-heptan-3-one-5-O-alpha-L-arabinofuranosyl-(1-->6)-beta-D-glucopyranoside, papyriferoside A (1), was isolated and its structure was determined on the basis of 1D and 2D NMR, HPLC-MS, as well as high resolution mass spectroscopic data. Platyphylloside (4) exerted the strongest cytotoxic activity of all isolated compounds with IC(50) values ranging from 10.3 to 13.8 microM.
authors.affiliation: Laboratoire d'Analyse et de Séparation des Essences Végétales, Département des Sciences Fondamentales, Université du Québec à Chicoutimi, 555 boul. Université, Chicoutimi, Québec, Canada G7H 2B1.
authors.forename: Vakhtang
authors.initials: V
authors.lastname: Mshvildadze
authors.forename: Jean
authors.initials: J
authors.lastname: Legault
authors.forename: Serge
authors.initials: S
authors.lastname: Lavoie
authors.forename: Charles
authors.initials: C
authors.lastname: Gauthier
authors.forename: André
authors.initials: A
authors.lastname: Pichette
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D029662:Betula / Q000737:chemistry*; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D036381:Diarylheptanoids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D005347:Fibroblasts / Q000187:drug effects; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D006801:Humans; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D024301:Plant Bark / Q000737:chemistry
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D036381:Diarylheptanoids; D006027:Glycosides