Kushenol O

Analysis of the mechanism of Sophorae Flavescentis Radix in the treatment of intractable itching based on network pharmacology and molecular docking.[Pubmed:38164832]

Eur Rev Med Pharmacol Sci. 2023 Dec;27(24):11691-11700.

OBJECTIVE: Sophorae Flavescentis Radix (Kuh-seng, SFR), a Traditional Chinese Medicine (TCM), is widely used alone or within a TCM formula to treat pruritus, especially histamine-independent intractable itching. In the previous study, potential antipruritic active components of the SFR were screened based on cell membrane immobilized chromatography (CMIC), revealing oxymatrine (OMT) as an antipruritic agent. However, the low oral bioavailability (OB) of OMT cannot explain the antipruritic effect of SFR when administered orally in clinic. In this study, we investigated the antipruritic effects and underlying mechanisms of orally administered SFR. MATERIALS AND METHODS: A network pharmacology and molecular docking were employed to screen the active components of SFR and predict their binding to disease-related target proteins, while the potential mechanisms were explored with Gene Ontology (GO) and Kyoto Encyclopedia of Genes and Genomes (KEGG) analysis. The binding energy between components and target proteins was calculated by molecular docking. RESULTS: The SFR-components-targets-intractable itching Protein-Protein Interactions (PPI) network was established, and 22 active components and 42 targets were screened. The GO enrichment analysis showed that the key target genes of SFR were related to nuclear receptors, transcription factors, and steroid hormone receptors. The results of the KEGG enrichment pathway analysis include Hepatitis B, epidermal growth factor receptor (EGFR) tyrosine kinase inhibitor resistance, advanced glycation end product (AGE)-receptor for AGE (RAGE) signaling pathway in diabetic complications, etc. Molecular docking showed that three key target proteins in the network, the vascular endothelial growth factor A (VEGFA), epidermal growth factor receptor (EGFR) and caspase-3 (CASP3), have higher binding activities with inermine, phaseolin and Kushenol O, respectively; the binding energy of each pair is stronger than that of the target protein-corresponding inhibitors. CONCLUSIONS: The complexity of the SFR-components-targets-intractable itching network demonstrated the holistic treatment effect of SFR on intractable itching. The partial coherence between results screened by CMIC in the previous study and network pharmacology demonstrated the potential of network pharmacology in active component screening. Inermine screened from both CMIC and network pharmacology is a VEGFA inhibitor, which possibly accounts for the antipruritic effect of orally administered SFR.

[Non-alkaloid components from Sophora flavescens].[Pubmed:24490565]

Zhongguo Zhong Yao Za Zhi. 2013 Oct;38(20):3520-4.

Five compounds were obtained from the stems and leaves of Sophora flavescens Ait. and ten compounds were obtained from the roots of S. flavescens by various chromatography methods including silica gel column chromatography and preparative HPLC. Their structures were identified on the basis of spectroscopic methods including 1H-NMR, 13C-NMR and ESI-MS, as corchionoside C (1), syringing (2), 2'-deoxythymidin (3), coniferin (4), benzyl O-beta-D-glucopyranoside (5), piscidic acid (6), trifolirhizin (7), kurarinone (8), trifolirhizin-6'-monoacetate (9), sophoraflavanone G (10), isoxanthohumol (11), noranhydroicaritin (12), 4'-methoxyisoflavone-7-O-beta-D-apiofuranosyl-(1 --> 6)-beta-D-glucopyranoside (13), Kushenol O (14) and 6"-beta-D-xylopyranosylgenistin (15). Compounds 1-6 were isolated from the Sophora genus for the first time.

[Isoflavone glycosides from the bark of Maackia amurensis].[Pubmed:19350824]

Yao Xue Xue Bao. 2009 Jan;44(1):63-8.

To study the chemical constituents of the Maackia amurensis, the constituents were isolated by various chromatographies and the structures were elucidated on the basis of chemical and spectroscopic data (ESI-MS, 1D and 2D NMR). Thirteen isoflavone glycosides were isolated from the n-BuOH-soluble fraction of the 70% ethanol extract and identified as 7-hydroxy-4',6-dimethoxyisoflavone-7-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside (1), dalsympathetin (2), ononin (3), glycitin (4), genestin (5), saikoisoflavonoside A (6), afrormosin-7-O-beta-D-glucopyranoside (7), gehuain (8), Kushenol O (9), 7-hydroxy-4',6-dimethoxyisoflavone-7-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (10), tectoridin (11), biochanin A 7-O-beta-D-gentiobioside (12) and 7-hydroxy-4'-methoxyisoflavone-7-O-beta-D-apiofuranosy l-(1-->6)-beta-D-glucopyranoside (13). Compound 1 is a new isoflavone glycoside, named as maackiaisoflavonoside, compounds 2, 8, 9, 10, 12 and 13 were isolated from this genus for the first time.

Characterization of flavonoids in the extract of Sophora flavescens Ait. by high-performance liquid chromatography coupled with diode-array detector and electrospray ionization mass spectrometry.[Pubmed:17658714]

J Pharm Biomed Anal. 2007 Sep 3;44(5):1019-28.

A method coupling high-performance liquid chromatography (HPLC) with diode-array detector (DAD) and electrospray ionization mass spectrometry (ESI) was established for the separation and characterization of flavonoids in Sophora flavescens Ait. Based on the chromatographic separation of most flavonoids present in S. flavescens Ait., a total of 24 flavonoids were identified. Fourteen compounds were unambiguously identified comparing experimental data for retention time (t(R)), UV and MS spectra with those of the authentic compounds: 3',7-dihydroxy-4'-methoxy-isoflavone (13), trifolirhizin (14), kurarinol (18), formononetin (19), 7,4'-dihydroxy-5-methoxy-8-(gamma,gamma-dimethylallyl)-flavanone (22), maackiain (21), isoxanthohumol (23), kuraridine (26), kuraridinol (27), sophoraflavanone G (30), xanthohumol (31), isokurarinone (33), kurarinone (35) and kushenol D (38), and additional 10 compounds were tentatively identified as Kushenol O (10), trifolirhizin-6''-malonate (15), sophoraisoflavanone A (20), norkurarinol/kosamol Q (24), kushenol I/N (25), kushenol C (28), 2'-methoxykurarinone (29), kosamol R (32), kushecarpin A (34) and kushenol A (37) by comparing experimental data for UV and MS spectra with those of literature. Furthermore, fragmentation pathways in positive ions mode of 24 flavonoid compounds of types of flavanone, flavanonol, flavonol, chalcone, isoflavone, isoflavanone and ptercocarpane were summarized. Some common features, such as CH(3)., H(2)O, CO, CO(2), C(3)O(2) and C(2)H(2)O losses, together with Retro-Diels-Alder fragmentations were observed in the prenylated flavonoids in S. flavescens Ait. The loss of the lanandulyl chain was their characteristic fragmentation, which might help deducing the structure of unknown flavonoid compounds. The present study provided an approach to rapidly characterize bioactive constituents in S. flavescens Ait.