Abstract
Sophora flavescens is a regularly used traditional Chinese medicine. In an attempt to discover adequate active agents, the isoprenoid flavonoids from S. flavescens were further investigated. In this work, two new compounds (1–2, kurarinol A-B) together with 26 known ones (3–28) were isolated and elucidated on the basis of extensive NMR, UV and MS analyses. Furthermore, the antioxidant activity of all constituents was assessed through ABTS, PTIO and DPPH methodologies and also were evaluated for cytotoxic activity by three tumor cell lines (HepG2, A549 and MCF7) and one human normal cell line (LO2 cells). As a result, a multitude of components revealed significant inhibitory activity. In particular, compound 1–2 (kurarinol A-B), two new flavanonols derivatives, exhibited the most potent ABTS inhibitory activity with IC50 of 1.21 µg/mL and 1.81 µg/mL, respectively. Meanwhile, the new compound 1 demonstrated remarkable cytotoxicity against three cancer cells lines with IC50 values ranging from 7.50–10.55 μM but showed little effect on the normal cell. The two new isoprenoid flavonoids could be promising antioxidant and anti-tumor nature agents.
Highlights
Sophora flavescens (Ku-Shen in Chinese), derived from the Fabaceae family, is widely distributed in China as a herb or shrub, and has a strong bitter taste ([1], pp. 202–203)
Three human cancer cell lines (HepG2, A549 and MCF7 cells) were obtained from American Type Culture Collection (ATCC, Manassas, MD, USA) and human normal cells were acquired from The Key Laboratory of Optimal Utilization of Natural Medicine Resources (Guiyang, China)
The positive control irinotecan was obtained from Shanghai Hongye were observed for compounds 2, 3, and 4 (10.3%, 4.5% and 0.7% inhibition against MCF7 cells) and their isoprenylated derivative, 1 (85.0% against MCF7 cells)
Summary
Sophora flavescens (Ku-Shen in Chinese), derived from the Fabaceae family, is widely distributed in China as a herb or shrub, and has a strong bitter taste ([1], pp. 202–203). The structures of flavonoids with a lavanduly, prenyl or Molecules 2021, 26, 7228 herba ephedrae, salvia miltiorrhiza and astragali radix have drawn worldwide attention for their potential health benefits [8]. 1D and 2D NMR spectra (Figure 3) revealed a lavandulyl group (δH 4.88, 1H, t), (δH 4.44, br s, δH 4.52, br s), (δH 1,91, 2H, m), (δH 1.45, 3H, s), (δH 1.52, 6H, s), a methoxy moiety (δH 3.58, δC 55.3) and three hydroxyl groups (δH 11.8, 9.47, 9.35), these data are similar to those of kushenol X [14] Their slight changes were that the positions of the groups at C-6 and C-8 were interchangeable and C-8 from H turned into a methoxy group on ring A of 2, as evidenced by the HMBC correlations from 7-OH (δH 9.35) to C-8 1 2 3 4 5 6 7 8 9 10 1 2 3 4 5 6 1 2 3 4 5 6 7 8 9 10 1 2 3 4 5 6 7 8 9 10 OCH3 OH OH OH OCH2O
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