Chenopodium bonus-henricus L. - A source of hepatoprotective flavonoids

- The aerial parts of Chenopodium bonus-henricus (wild spinach) were investigated.
- Novel acylated glycosides of patuletin, spinacetin and 6-methoxykaempferol were isolated.
- The structures were identified by extensive 1D- and 2D-NMR experiments.
- Hepatoprotective activity in in vitro/in vivo CCl4 models was tested.
- The cytotoxicity of the flavonoids on HepG2 cells was evaluated.

Three new flavonoid glycosides (7-9) named patuletin-3-O-(5″′-О-Е-feruloyl)-β-d-apiofuranosyl(1 → 2)[β-d-glucopyranosyl (1 → 6)]-β-d-glucopyranoside (7), spinacetin-3-O-(5″′-О-Е-feruloyl)-β-d-apiofuranosyl (1 → 2)[β-d-glucopyranosyl(1 → 6)]-β-d-glucopyranoside (8) and 6-methoxykaempferol-3-O-(5″′-О-Е-feruloyl)-β-d-apiofuranosyl(1 → 2)[β-d-glucopyranosyl (1 → 6)]-β-d-glucopyranoside (9) together with six known flavonoid glycosides of patuletin, spinacetin and 6-methoxykaempferol (1-6) were isolated from the aerial parts of C. bonus-henricus and identified with spectroscopic methods (1D and 2D NMR, UV, IR, HRESIMS). The MeOH extract exerts hepatoprotective and antioxidant activities comparable to those of flavonoid complex silymarin in in vitro (60 μg/mL) and in vivo (100 mg/kg/daily for 7 days) models of hepatotoxicity, induced by CCl4. Flavonoids (1-9) (100 μM), compared to silybin, significantly reduced the cellular damage caused by CCl4 in rat hepatocytes, preserved cell viability and GSH level, decreased LDH leakage and reduced lipid damage. High concentrations of compounds (1-9) showed marginal or no cytotoxicity on HepG2 cell line. The experiment data suggest that the glycosides of 6-methoxykaempferol, spinacetin and patuletin are a promising and safe class of hepatoprotective agents.

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