Salvigenin, a Trimethoxylated Flavone from Achillea Wilhelmsii C. Koch, Exerts Combined Lipid-Lowering and Mitochondrial Stimulatory Effects

Phytochemical analysis of the Iranian plant Achillea wilhelmsii led to the isolation of 17 pure secondary metabolites belonging to the classes of sesquiterpenoids and phenolics. Two of these compounds, named wilhemsin (7) and wilhelmsolide (9), are new sesquiterpenoids, and the first shows undescribed structural features. Their structures were elucidated through extensive spectroscopic analysis, mainly based on 1D and 2D NMR, and chemical derivatization. Starting from plant traditional use and previous reports on the activity of the plant extracts, all the pure compounds were evaluated on endpoints related to the treatment of metabolic syndrome. The sesquiterpene hanphyllin (8) showed a selective cholesterol-lowering activity (-12.7% at 30 mu M), santoflavone (13) stimulated glucose uptake via the GLUT transporter (+16.2% at 30 mu M), while the trimethoxylated flavone salvigenin (14) showed a dual activity in decreasing lipid levels (-22.5% palmitic acid biosynthesis at 30 mu M) and stimulating mitochondrial functionality (+15.4% at 30 mu M). This study further confirms that, in addition to the antioxidants vitexin, isovitexin, and isoschaftoside, A. wilhelmsii extracts contain molecules that can act at different levels on the metabolic syndrome symptoms.

Automated summary

Phytochemical analysis of Iranian plant Achillea wilhelmsii resulted in the isolation of 17 pure secondary metabolites belonging to sesquiterpenoids and phenolics classes. Two of these compounds are newly discovered sesquiterpenoids, with one showing previously undescribed structural features. Evaluation of these compounds revealed positive effects on endpoints related to the treatment of metabolic syndrome.