Biotransformation of the Phenolic Constituents from Licorice and Cytotoxicity Evaluation of Their Metabolites

Abstract

Biotransformation of four bioactive phenolic constituents from licorice, namely licoisoflavanone (1), glycyrrhisoflavone (2), echinatin (3), and isobavachalcone (4), was performed by the selected fungal strain Aspergillus niger KCCM 60332, leading to the isolation of seventeen metabolites (5–21). Structures of the isolated compounds were determined on the basis of extensive spectroscopic methods, twelve of which (5–7, 10–17 and 19) have been previously undescribed. A series of reactions including hydroxylation, hydrogenation, epoxidation, hydrolysis, reduction, cyclization, and alkylation was observed in the biotransformation process. All compounds were tested for their cytotoxic activities against three different human cancer cell lines including A375P, MCF-7, and HT-29. Compounds 1 and 12 exhibited most considerable cytotoxic activities against all the cell lines investigated, while compounds 2 and 4 were moderately cytotoxic. These findings will contribute to expanding the chemical diversity of phenolic compounds, and compounds 1 and 12 may serve as leads for the development of potential cancer chemopreventive agents.

Advances on resources, biosynthesis pathway, bioavailability, bioactivity, and application of corylifolinin

“…The neuroprotection associated with corylifolinin (Y. Xiao et al, 2021). These findings underscore corylifolinin' multifaceted approach to preserving bone health.…”

“…These findings hold potential for expanding the chemical diversity of phenolic compounds and advancing the development of prospective cancer chemopreventive agents (Y. Xiao et al, 2021).…”

Microbial Transformation of Yakuchinone A and Cytotoxicity Evaluation of Its Metabolites

“…All preliminary screening experiments were performed by a standard two-stage procedure [ 37 , 38 ]. The actively growing microbial cultures were inoculated in 100 mL flasks containing 20 mL of media and incubated for 24 h in a temperature-controlled shaking incubator operating at 200 rpm and 25 °C.…”

Isobavachalcone: A comprehensive review of its plant sources, pharmacokinetics, toxicity, pharmacological activities and related molecular mechanisms

“…It is considered to be the second most common cancer worldwide. IBC significantly inhibited the proliferation and colony formation of human colorectal cancer SW480, HT29, and HCT116 cells in a dose‐dependent manner (Xiao, Han, & Lee, 2021), which can block the cell cycle in the G0/G1 phase by down‐regulating the expression of Cyclin D1 protein, up‐regulate the expression of cycle‐dependent kinase inhibitor P21 protein and up‐regulate the autophagy marker protein LC3B‐II in SW480 cells by ROS. In addition, the Wnt/β‐catenin signaling pathway was down‐regulated to inhibit cell proliferation and induce apoptosis (Li, 2020; Li et al, 2019).…”