New flavonoids from the flowers of Coreopsis lanceolata and their pharmacological activities

The Coreopsis (Asteraceae) genus is one of the most common phanerogams that blossom in summer. C. lanceolata is a herbaceous perennial plant originated in America, South Africa and Eastern Asia, reported to have antioxidant [1], antiallergic, antibacterial, antileukemic [2], and nematicidal [3] effects. Despite several reported pharmacological activities of C. lanceolata, there is only one paper to isolate flavonoids in C. lanceolata flowers [1]. Therefore, the present study focused on the isolation and identification of active materials from the flowers of this plant, as well as evalutaion of various pharmacological activities.

Seven new chalcones, lanceolein A−G (5 and 7-12), five new flavanones, flavanolanceotin A−E (14 and 16-19), five known chalcones, two known flavanones, two known aurones, and two known flavonols were isolated from the methanolic extract of C. lanceolata flowers. All isolated flavonoids showed radical scavenging activities in DPPH and ABTS radical experiments and inhibited NO production in LPS-stimulated RAW264.7 macrophages. Some chalcones prevented the growth of human colon cancer cells via the induction of cellular cytotoxicity and apoptosis. Some flavanones protected against oxidative stress in PC-12 neuronal, Caco-2 colon epithelial, and RAW 264.7 macrophage cells. Moreover, two aurones and two flavonols recovered the damage of the pancreatic islets caused by alloxan treatment in zebrafish (Danio rerio) larvae. These results suggested that C. lanceolata flowers can be used as multi-metabolic diseases agents.

Fig. 1 Chemical structures of flavonoids 1−23 from the flowers of Coreopsis lanceolata. Glc: O-β-D-glucopyranosyl, 6-RG: O-α-L-rhamnopyranosyl-(1→6)-O-β-D-glucopyranosyl.

• References

• 1 Shang YF, Oidovsambuu S, Jeon JS, Nho CW, Um BH. Chalcones from the flowers of Coreopsis lanceolata and their in vitro antioxidative activity. Planta Med 2013; 79: 295-300
• 2 Pardede A, Mashita K, Ninomiya M, Tanaka K, Koketsu M. Flavonoid profile and antileukemic activity of Coreopsis lanceolata flowers. Bioorg Med Chem Lett 2016; 26: 2784-2787
• 3 Kimura Y, Hiraoka K, Kawano T, Fujioka S, Shimada A. Nematicidal activities of acetylene compounds from Coreopsis lanceolata L. J Biosci 2008; 63: 843-847