Drying methods and structure–activity relationships of hydroxycinnamic acid derivatives in Idesia polycarpa Maxim. Leaves

Abstract

Idesia polycarpa Maxim. leaves are an excellent source of hydroxycinnamic acid derivatives and have drawn special attention due to their various biological activities. However, the effects of post-harvest treatment on the structure–activity relationships of hydroxycinnamic acid derivatives in leaves of I. polycarpa are still unknown. In the current study, we compared the contents of unstable compounds in leaves with four drying methods, namely sun-drying, freeze-drying, shade-drying, and oven-drying. We found that the four hydroxycinnamic acid derivative isomers of leaves were significantly affected after drying processing with four different drying methods. Consequently, the underlying mechanisms responsible for the variation of these compounds during the drying processes have been well elucidated: UV lighting induced the isomerization of 1-[(6′-O-(E)-p-coumaroyl)-β-D-glucopyranosyl]-oxy-2-phenol (1) and 1-[(4′-O-(E)-p-coumaroyl)-β-D-glucopyranosyl]-oxy-2-phenol (3) into 1-[(6′-O-(Z)-p-coumaroyl)-β-D-glucopyranosyl]-oxy-2-phenol (2) and 1-[(4′-O-(Z)-p-coumaroyl)-β-D-glucopyranosyl]-oxy-2-phenol (4). Also, heat (exceeding 20 °C) led to the rearrangement of the (E/Z)-p-coumaric acid moiety of compounds 3 and 4, of which the 4-O-acylglucoses changed into the 6-O-acylglucoses to generate compounds 1 and 2, respectively. Interestingly, the hepatocyte-free fatty acid accumulation in OA-induced steatosis-conditioned HepG2 cells decreased by 65.00%, 10.69%, and 47.00%, respectively, following treatment with compounds 2, 3 and 4, and compound 1 presented no lipid-lowering activity. In addition, the bioactivities of compounds 2 and 4 were substantially enhanced by 58.42% and 25.33% with the sun-drying method compared to the freeze-dying methods. Our study suggests that sun-drying processing is the best method among the four drying processing methods of I. polycarpa Maxim. leaves.