6-Methoxyflavonol glycosides with in vitro hepatoprotective activity from Chenopodium bonus-henricus roots

Abstract

In Bulgarian folk medicine the roots of Chenopodium bonus-henricus L. are known as "chuven" and have been applied externally to treat skin iflammations, wounds and boils. The infusion of the drug has been also used as a mild laxative. In Bulgarian food industry the aqueous extract of the roots has been employed in production of "halva". One new, namely 6-methoxykaempferol 3-O-[β-apiofuranosyl(1→2)]-β-glucopyranosyl(1→6)-β-glucopyranoside 2, and two known flavonoid glycosides, spinacetin 3-O-[β-apiofuranosyl(1→2)]-β-glucopyranosyl(1→6)-β-glucopyranoside 1 and spinacetin 3-O-gentiobioside 3, were isolated from the roots of Chenopodium bonus-henricus L. Their structures were determined by means of spectroscopic methods (1D, 2D NMR, UV, IR, and HR-ESI-MS). Additionally, 1 and 3 significantly reduced the cellular damage caused by the hepatotoxic agent CCl4 in rat hepatocytes and preserved cell viability and GSH level, decreased LDH leakage and reduced lipid damage. Effects were similar to those of the positive control silymarin. Control of self-toxic effects were done in a MTT based assay using HepG2 cells and revealed a statistically significant cytotoxic effects only in very high concentrations exceeding mM concentrations and an incubation time of 72h, making flavonoid glycosides with a 6-methoxykaempferol skeleton a promising and save class of hepatoprotective compounds.