Abstract
Phytochemical investigation of the methanol (MeOH) extract of Pueraria lobata roots, known as “kudzu”, combined with liquid chromatography/mass spectrometry (LC/MS)-based analysis, resulted in the identification of four norlignans (1–4), including three new norlignans, lobatamunsolides A–C (1–3), and five known isoflavonoids (5–9). The structures of the new compounds were elucidated by a combination of spectroscopic methods, including 1D and 2D nuclear magnetic resonance (NMR) and high resolution (HR)-electrospray ionization mass spectrometry (ESIMS), and their absolute configurations were determined by chemical reaction and quantum chemical electronic circular dichroism (ECD) calculations. The isolated compounds (1–9) were evaluated for their inhibitory effects on nitric oxide (NO) production in lipopolysaccharide (LPS)-stimulated RAW 264.7 macrophages. Compound 9 displayed the strongest NO inhibitory effect and compound 2 showed a weak effect. The potential mechanism of the effect of compound 9 was investigated by analysis of its molecular docking on the active site of inducible nitric oxide synthase (iNOS), which showed the potential interactions of compound 9 with key amino acid residues and the heme cofactor of iNOS. The mechanism as the inhibition of transcriptional iNOS protein expression was confirmed by western blotting experiments.
Highlights
Pueraria lobata (Willd.) Ohwi is a creeping, climbing, and trailing perennial vine belonging to the plant family Leguminosae, and is distributed in Southeast Asia, the Pacific, East Asia (Korea, China, Japan, and Russian far east), and the United States [1,2]
As part of ongoing projects to identify structurally and/or biologically novel compounds from natural sources [13,14,15,16,17], we investigated the active compounds from P. lobata root that have both estrogen-like and anti-breast cancer cell proliferative activities
We used the bioactivity-guided isolation approach employed in a recent report that demonstrated that genistein from P. lobata root has estrogen-like effects dependent on estrogen receptor (ER) pathway activation, and anti-proliferative effects mediated by the apoptosis pathway in MCF-7 breast cancer cells [18]
Summary
Pueraria lobata (Willd.) Ohwi is a creeping, climbing, and trailing perennial vine belonging to the plant family Leguminosae, and is distributed in Southeast Asia, the Pacific, East Asia (Korea, China, Japan, and Russian far east), and the United States [1,2]. Previous phytochemical studies on the roots of P. lobata have revealed that its major bioactive compounds are isoflavones such as daidzein, daidzin, puerarin, and genistein [8] These isoflavones exhibit diverse pharmacological effects, such as anti-inflammatory, antimicrobial, antioxidant, and antidipsotropic effects [9,10]. We used the bioactivity-guided isolation approach employed in a recent report that demonstrated that genistein from P. lobata root has estrogen-like effects dependent on estrogen receptor (ER) pathway activation, and anti-proliferative effects mediated by the apoptosis pathway in MCF-7 breast cancer cells [18]. These findings prompted us to investigate other potential bioactive components from P. lobata roots. We elucidated the inhibitory effects of compounds 1–9 on nitric oxide (NO) production in lipopolysaccharide (LPS)-activated RAW 264.7 macrophages
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