Convenient Synthesis and Physiological Activities of Flavonoids in Coreopsis lanceolata L. Petals and Their Related Compounds

Abstract

Chalcones, flavanones, and flavonols, including 8-methoxybutin isolated from Coreopsis lanceolata L. petals, were successfully synthesized with total yields of 2–59% from O-methylpyrogallols using the Horner–Wadsworth–Emmons reaction as a key reaction. Aurones, including leptosidin, were also successfully synthesized with 5–36% total yields using the Aldol condensation reaction as a key reaction. Each chalcone, flavanone, flavonol, and aurone with the 3,4-dihydroxy groups in the B-ring showed high antioxidant activity. Additionally, each of the chalcones, flavanones, flavonols, and aurones with the 2,4-dihydroxy groups in the B-ring showed an excellent whitening ability.

Anti-Neuroinflammatory and Anti-Inflammatory Activities of Phenylheptatriyne Isolated from the Flowers of Coreopsis lanceolata L. via NF-κB Inhibition and HO-1 Expression in BV2 and RAW264.7 Cells

“…From the analysis of HMBC data, unlike compound 3 , this compound was found to have two hydroxy groups attached at positions 7′ and 3′, while the methoxy group at position 4′ was substituted with a hydroxy group. From the comparison with 1 H- and 13 C-NMR data from previous literature, the structure of compound 4 was determined to be 2-(3,4-dihydroxyphenyl)-7-hydroxy-8-methoxy-2,3-dihydrochromen-4-one (8-methoxybutin) [ 20 ].…”

“…4′,7-Dimethoxyflavanone ( 3 ) is a compound with a flavanone skeleton, reported to have anticancer effects [ 42 ], however there are no reports on its anti-inflammatory activity. 8-Methoxybutine ( 4 ) and leptosidin ( 5 ) are known to have whitening and antioxidant effects and have been reported to be isolated from C. lanceolata [ 20 ].…”

Constituents of Coreopsis lanceolata Flower and Their Dipeptidyl Peptidase IV Inhibitory Effects

“…Among chalcones isolated in this study, 3 – 5 showed less inhibitory activity than 2 , indicating that chalcones substituted with additional methoxy group and/or sugar are less effective. The most active compound, 2, has been reported as having various biological, activities such as antileukemic [ 11 ], antioxidant [ 4 ] and anti-cancer [ 5 ], however its DPP-IV potential has not been studied previously. Compounds 6 and 7, with the structures of aurone and flavanone, respectively, exhibited moderate DPP-IV inhibitory effects, while flavone ( 8 ), flavonol ( 9 ) and polyacetylenes ( 1 , 10 and 11 ) did not show their activities.…”

“…Coreopsis is a perennial plant belonging to the Compositae family [ 1 ]. It was planted for decoration on the roadsides in North America, Asia and Oceania regions [ 2 , 3 , 4 ]. Typically, C. lanceolata , C. tinctoria and C. drummondii are generally Coreopsis plants distributed all around Korea [ 5 ].…”

Evaluation and Optimization of the Anti-Melanogenic Activity of 1-(2-Cyclohexylmethoxy-6-hydroxy-phenyl)-3-(4-hydroxymethyl-phenyl)-propenone Derivatives

“…We previously reported the anti-melanogenic activity of chalcone 21 [13]. To obtain more potent anti-melanogenic agents, we synthesized a series of chalcone derivatives by aldol condensation reactions (Scheme 1) [8,14]. Detailed synthetic procedures and the 1 H-NMR and 13 C-NMR spectroscopic data are shown in the Materials and Methods.…”