Tyrosinase Inhibitor Activity of Coumarin-Resveratrol Hybrids

Abstract

In the present work we report on the contribution of the coumarin moiety to tyrosinase inhibition. Coumarin-resveratrol hybrids 1-8 have been resynthesized to investigate the structure-activity relationships and the IC50 values of these compounds were measured. The results showed that these compounds exhibited tyrosinase inhibitory activity. Compound 3-(3’,4’,5’-trihydroxyphenyl)-6,8-dihydroxycoumarin (8) is the most potent compound (0.27 mM), more so than umbelliferone (0.42 mM), used as reference compound. The kinetic studies revealed that compound 8 caused non-competitive tyrosinase inhibition.

Tyrosinase inhibition and antioxidant properties of Asphodelus microcarpus extracts

“…Phytochemical studies on A. microcarpus revealed the presence of lipids, carbohydrates, sterols, anthraquinones and arylcoumarins [13, 14]. It is well known that the last two compounds have tyrosinase inhibitory activity [15–17] and plant extracts with antimelanogenic activity typically possess polyphenols such as flavonoids, which are usually the factors responsible for the activities in plant extracts [18]. The aim of this study was to investigate the inhibitory activity of three different extracts of A. microcarpus on tyrosinase activity and on melanogenesis in B16F10 melanoma cells.…”

2.14 Other Condensation Reactions (Knoevenagel, Perkin, Darzens)

“…85 The substitutional effect in the selective synthesis of cis, trans stilbenes and 3-arylcoumarine was investigated (Scheme 45). 86 The regio-and geometrical selectivity for synthesis of stilbene derivatives under the Perkin strategy strongly depends on the presence and absence of hydroxyl group as well as their positions in the phenyl ring.…”

Synthesis of a tyrosinase inhibitor by consecutive ethenolysis and cross-metathesis of crude cashew nutshell liquid

“…Furthermore, it is linked to several neurodegenerative diseases [30]. Therefore, the study and development of tyrosinase inhibitors from renewable resources is of particular interest for research and industry [31–32]. Fu et al investigated naturally occurring ginkgolic acids which they selectively synthesized from 2,6-dihydroxybenzoic acid ( 4 ), and found that the tridecanyl substituted derivative ginkgolic acid (13:0, 3 ) exhibits the most promising inhibitory activity.…”