Antioxidant and Tyrosinase Inhibitory Effects of Neolignan Glycosides from Crataegus pinnatifida Seeds

Abstract

In our efforts to find an inhibitor of melanin formation and develop potential depigmenting agents for skin-protecting cosmetics and medicinal products from natural resources, we focused on the seeds of Crataegus pinnatifida which showed antioxidant and tyrosinase-inhibiting activities. By activity-guided fractionation of an extract of C. pinnatifida seeds, four new neolignan glycosides, pinnatifidaninsides A-D (1-4), along with two known compounds (5-6), were isolated. Their structures were elucidated by spectroscopic analyses, especially 1D, 2D NMR and CD spectra. The antioxidant and tyrosinase-inhibiting activities of all isolates were assayed. Compound 6 showed good activity against 2,2-diphenyl-1-pikrylhydrazyl, while compounds 1, 2, 5, and 6 exhibited strong 2,2'-azino-bis (3-ethylbenzothiazoline-6-sulphonic acid) free radical scavenging activity, being as effective as, or even more effective than the positive control Trolox. Moreover, compounds 5 and 6 displayed a moderate mushroom tyrosinase inhibitory activity.

Untargeted metabolomic profiling of three Crataegus species (hawthorn) and their in vitro biological activities

“…All the extracts of the three Crataegus species have shown important inhibitory activity against tyrosinase, with the highest activity recorded for the methanolic extracts ( C. orientalis : 126.2 mg KAE g −1 for twig and 110.9 mg KAE g −1 for leaves; C. szovitsii : 128.1 mg KAE g −1 for twig and 117.1 mg KAE g −1 for leaves; and C. tanacetifolia : 128.7 mg KAE g −1 for twig and 110.6 mg KAE g −1 for leaves), followed by the decocted extracts. Huang et al . have reported on the tyrosinase inhibitory activity of neo‐lignan glycosides isolated from C. pinnatifida seeds.…”

Chemical composition and enzyme inhibition of Phytolacca dioica L. seeds extracts

“…The EC 50 values were strongly correlated with total phenolic contents, suggesting the contribution of these compounds to the antioxidant properties of the extracts. Moreover, most of the polyphenolics identified were lignans with well-known antioxidant activity 38 .…”

A comprehensive review on tyrosinase inhibitors

“…Lignans are complex and diverse structures, which are formed from three primary precursors. So far, lignans and lignan glycosides isolated from exocarp of Castanea henryi 342 , Marrubium velutinum and Marrubium cylleneum 343 , Pinellia ternate 344 and Crataegus pinnatifida 345 have been evaluated for their tyrosinase inhibitory potentials. However, these compounds mostly displayed a moderate mushroom tyrosinase inhibitory activity.…”