Anticancer diarylheptanoid glycosides from the inner bark of Betula papyrifera.
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.
Mshvildadze
Vakhtang
V
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.
Legault
Jean
J
Lavoie
Serge
S
Gauthier
Charles
C
Pichette
André
A
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
D000972:Antineoplastic Agents, Phytogenic; D036381:Diarylheptanoids; D006027:Glycosides