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The Role of Plant-Based Natural Compounds in Inflammation
Published in Namrita Lall, Medicinal Plants for Cosmetics, Health and Diseases, 2022
Marcela Dvorakova, Premysl Landa, Lenka Langhansova
Three other compounds, tomentone, 3’-O-methyl-5’-methoxydiplacone and paulownione C, exerted selective inhibitory activity on 5-LOX (IC50 = 0.35 µM, 0.38 µM and 0.37 µM, respectively), which was comparable to Zileuton. Similarly, two compounds, 3’,4’-O-dimethyl-5’-hydroxydiplacone and mimulone, exhibited selective COXs inhibition with values comparable to Ibuprofen. From these results, it seems that especially the presence of ortho-hydroxyls on B-ring and their methylation pattern together with the presence of unmodified geranyl chain on A-ring are the most important structural features for the measured bioactivity (Hanakova et al., 2017). On the contrary, despite the lack of the vicinal phenolic hydroxyls, the previously reported prenylated flavonoids, kenusanone A and sophoraflavanone G, inhibited 5-LOX (IC50 = 0.7 and 0.15 µM, respectively), although with slightly lower potency than diplacone and 3’-O-methyl-5’-hydroxydiplacone (Chi et al., 2001). On the other hand, kenusanone A did not inhibit COXs and sophoraflavanone G inhibited only COX-1, though very efficiently (IC50 = 0.03 µM) (Chi et al., 2001).
Pharmacological actions of chemical constituents
Published in C. P. Khare, Evidence-based Ayurveda, 2019
A study demonstrated the inhibitory activity of quercetin, apigenin and 3,6,7,3′,4′-pentahydroxyflavone against Escherichia coli DNA gyrase. Naringenin and sophoraflavanone G have shown intensive antibacterial activity against methicilline resistant Staphylococcus aureus (MRSA) and streptococci. 5-hydroxyflavanones and 5-hydroxyisoflavanones inhibited the growth of S. mutans and Streptococcus sobrinus.
Acute and 13 weeks subchronic toxicological evaluation of the flavonoid-rich extract of Sophora flavescens
Published in Drug and Chemical Toxicology, 2023
Chaoqun Wu, Yun Huang, Huiqi Huang, Yuanren Ma, Qinxiong Lin, Xinzhou Yang, Kejian Pang
Using our previously published off-line semi-preparative HPLC and NMR, we characterized the main chemical constituents of SFEA as kushenol H (1), kushenol K (2), calycosin (3), (2S)-7,2′,4′-trihydroxy-5-methoxy-8-dimethylallyl flavanone (4), kurarinol (5), (2R)-3α,7,4′-trihydroxy-5-methoxy-8-dimethylallyl flavanone (6), isoxanthohumol (7), kushenol N (8), (−)-kurarinone (9), neokurarinol (10), kushenol C (11), sophoraflavanone G (12), leachianone A (13), kuraridine (14), and kushenol A (15) by comparing their MS, UV, and NMR spectra with published reference data (Yang et al.2015). All the obtained chromatographic peaks were integrated. The peak area percentages of individual peaks, representing 77.01% of SFEA, are presented in Figure 1. SFEA was found to be mainly comprised of kushenol H and kushenol K (4.66%), calycosin (2.88%), (2S)-7,2′,4′-trihydroxy-5-methoxy-8-dimethylallyl flavanone, and kurarinol (5.95%), (2 R)-3α,7,4′-trihydroxy-5-methoxy-8-dimethylallyl flavanone (3.90%), isoxanthohumol (7.42%), kushenol N (8.75%), (–)-kurarinone (18.00%), neokurarinol and kushenol C (10.01%), sophoraflavanone G (7.19%), leachianone A (4.08%), kuraridine (2.28%), and kushenol A (1.89%).
Liver metabolomic characterization of Sophora flavescens alcohol extract-induced hepatotoxicity in rats through UPLC/LTQ-Orbitrap mass spectrometry
Published in Xenobiotica, 2020
Peng Jiang, Yancai Sun, Nengneng Cheng
Sophora flavescens (Fabaceae) has been used as a traditional Chinese medicine (TCM) and functional food ingredient for thousands of years in Asian countries because of its potential health benefits. It is widely used to treat cancers, antimicrobial activities (Liu et al., 2018), anti-inflammatory activities (Ma et al., 2018), chronic osteomyelitis (Wang et al., 2018), viral hepatitis (Zhang et al., 2018), viral myocarditis and gastrointestinal hemorrhage (Yang et al., 2012). Many herbal products, including Kushen tablets, Xiaoyin tablets, Shiduqing capsules and Zhixue capsules, contain S. flavescens. However, S. flavescens was found to be the toxic ingredient of Zhixue capsules, which were removed from markets on account of severe hepatotoxic events (Tai et al., 2010). Unfortunately, the mechanisms of S. flavescens-induced hepatotoxicity remain unclear. In general, the preparation of S. flavescens used in clinics is an aqueous extract whose major components are matrine and oxymatrine, which are alkaloids that have hepatoprotective effects (Gao et al., 2018; Shi et al., 2013). However, S. flavescens alcohol extract (SFAE) mainly contains prenylflavanones, such as sophoraflavanone G and kurarinone, which are hepatotoxic constituents (Yu et al., 2013). Many herbal preparations contain SFAE, and the risks of its clinical use should be explored.
Kushenol A and 8-prenylkaempferol, tyrosinase inhibitors, derived from Sophora flavescens
Published in Journal of Enzyme Inhibition and Medicinal Chemistry, 2018
Jang Hoon Kim, In Sook Cho, Yang Kang So, Hyeong-Hwan Kim, Young Ho Kim
All of the compounds (1–5) were tested for inhibitory activity, as evidenced by a decrease in the amount of l-dihydroxyphenylalanine produced from l-tyrosine by tyrosinase using an ultraviolet-visible (UV-Vis) photometer at 475nm. Kojic acid was used as a positive control (IC50 value: 16.7±2.4μM). Among them, compounds 1–4, which exhibited over a 80% inhibitory rate at 100μM, were tested in vitro at a range of concentrations using a UV-Vis spectrophotometer to determine their IC50 values. As shown in Figure 2(A) and Table 1, compounds 1–4 displayed tyrosinase inhibitory activity in a dose-dependent manner, with IC50 values ranging from 1.1±0.7 μM to 24.1±2.3μM. According to these results, compounds 1 and 2 may act as potential inhibitors of tyrosinase, with IC50 values of 1.1±0.7 μM and 2.4±1.1μM, respectively. Previous report revealed that chalcone derivatives, kuraridinol and kuraridin, showed high inhibitory activity, with IC50 values of 0.8 and 0.6 μM12,13. Also, main components of prenylated flavonoids, sophoraflavanone G and kurarinone, possessed the inhibitory activity, with IC50 values of 6.6 and 6.2μM, respectively12,13. Although compounds 1 and 2 showed lower inhibitory activity on the catalytic reaction of tyrosinase than those of chalcone derivatives, they have worth having insight as a tyrosinase inhibitor because they regulate enzymes within a few micromole.