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.
Highlights
Coreopsis lanceolata L. is a plant native to North America with a yellow flower that blooms from May to June in Japan
We report the synthesis of the several kinds of flavonoids including C. lanceolata L. petals and their analogs, and the relationship between structure and physiological activities
The process used to synthesize the chalcones, flavanones, and flavonols is shown in Scheme 1
Summary
Coreopsis lanceolata L. is a plant native to North America with a yellow flower that blooms from May to June in Japan. We previously reported the isolation and physiological activities of lanceolin (3,4,20 ,40 tetrahydroxy-30 -methoxychalcone-40 -glucoside), 8-methoxybutin (7,30 ,40 -trihydroxy-8-methoxyflavanone), and leptosidin (6,30 ,40 -trihydroxy-7-methoxyaurone) from C. lanceolata L. petals as shown in Figure 1 [1,2]. Koketsu et al reported the isolation of lanceoletin (3,4,20 ,40 -tetrahydroxy-30 -methoxychalcone), okanin (3,4,20 ,30 ,40 -pentahydroxychalcone), 4-methoxylanceoletin (3,20 ,40 -trihydroxy-4,30 -dimethoxychalcone), 8-methoxybutin, leptosidin, and leptosin (6,30 ,40 -trihydroxy-7-methoxyaurone-6-glucoside) from. C. lanceolata L., and the antileukemic activity of 4-methoxylanceoletin [3]. We report the synthesis of the several kinds of flavonoids including C. lanceolata L. petals and their analogs, and the relationship between structure and physiological activities.
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