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Two types of O-methyltransferase are involved in biosynthesis of anticancer methoxylated 4'-deoxyflavones in Scutellaria baicalensis Georgi.

ABSTRACT: The medicinal plant Scutellaria baicalensis Georgi is rich in specialized 4'-deoxyflavones, which are reported to have many health-promoting properties. We assayed Scutellaria flavones with different methoxyl groups on human cancer cell lines and found that polymethoxylated 4'-deoxyflavones, like skullcapflavone I and tenaxin I have stronger ability to induce apoptosis compared to unmethylated baicalein, showing that methoxylation enhances bioactivity as well as the physical properties of specialized flavones, while having no side-effects on healthy cells. We investigated the formation of methoxylated flavones and found that two O-methyltransferase (OMT) families are active in the roots of S. baicalensis. The Type II OMTs, SbPFOMT2 and SbPFOMT5, decorate one of two adjacent hydroxyl groups on flavones and are responsible for methylation on the C6, 8 and 3'-hydroxyl positions, to form oroxylin A, tenaxin II and chrysoeriol respectively. The Type I OMTs, SbFOMT3, SbFOMT5 and SbFOMT6 account mainly for C7-methoxylation of flavones, but SbFOMT5 can also methylate baicalein on its C5 and C6-hydroxyl positions. The dimethoxylated flavone, skullcapflavone I (found naturally in roots of S. baicalensis) can be produced in yeast by co-expressing SbPFOMT5 plus SbFOMT6 when the appropriately hydroxylated 4'-deoxyflavone substrates are supplied in the medium. Co-expression of SbPFOMT5 plus SbFOMT5 in yeast produced tenaxin I, also found in Scutellaria roots. This work showed that both type I and type II OMT enzymes are involved in biosynthesis of methoxylated flavones in S. baicalensis.

SUBMITTER: Cui MY

PROVIDER: S-EPMC8710825 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Project description:BackgroundScutellaria baicalensis Georgi is a commonly used medicinal herb in several Asian countries like Korea, China and Japan for thousands of years. It has been reported to have various medicinal properties such as anti-microbial, anti-inflammatory and anti-cancer effects. However, the anti-inflammatory mechanism of S. baicalensis G at proteome level has not yet been reported. Hence, we performed a proteome analysis to study differentially expressed proteins and its anti-inflammatory role in lipopolysaccharide (LPS) stimulated L6 skeletal muscle cells response to flavonoids isolated from S. baicalensis G.MethodsFor that, 150 μg of proteins from the L6 cells of the control (Vehicle only), LPS treated and flavonoid treated groups were separated using 18 cm, pH 4-7 IPG strips in the first dimension and resolved by 12% linear gradient SDS-polyacrylamide gel electrophoresis (SDS-PAGE). The silver stained gels were analyzed by using progenesis SameSpots software and twenty six differentially expressed protein spots (≥ 2 fold, p < 0.05) were selected for matrix assisted laser desorption ionization- time of flight mass spectroscopy/mass spectrometry (MALDI-TOF/MS) analysis. Also, the expression of COX-2, iNOS and Annexin A2 proteins were analyzed by western blot.ResultsTotally, 12 differentially expressed proteins were successfully identified by MALDI-TOF/MS and database searching, that's involved in inflammatory responses such vimentin, T-box transcription factor TBX3, annexin A1, annexin A2 and annexin A5. In addition, flavonoids inhibited the expression of COX-2, iNOS and Annexin A2 proteins in LPS-stimulated L6 skeletal muscle cells.ConclusionsThe findings revealed that the flavonoids from S. baicalensis G. directly protect the LPS stimulated inflammation process in L6 cells and, would be helpful to study further the muscle cell inflammatory mechanism. This is the first proteome study provide the anti-inflammatory mechanism of flavonoids from S. baicalensis G. in LPS stimulated L6 skeletal muscle cells.

Project description:Scutellaria baicalensis Georgi is a valuable medicinal plant of the Lamiaceae family. The roots, Scutellariae baicalensis radix, are valued in the traditional medicine of East Asia and are also listed in several pharmacopeias, such as the Chinese and European versions. The roots contain a high amount of flavones, such as baicalein, wogonin and their glucuronides, baicalin and wogonoside, respectively, with rare structures of unsubstituted B-ring. These major constituents are responsible for its pharmacological activity, mainly anti-inflammatory, antiviral, and antitumor, as well as BDZ-receptor modulating. There is a fast-growing demand for both the crude drug and the individual flavonoids obtained from it. However, the variability of content and composition of flavonoids in the roots is significant and affects pharmaceutical use, and little is known about the influence of various factors on root quality. In our experiments, we use aeroponics to determine the effect of electroporation as an abiotic stressor on plant growth, development, and root mass, as well as on its metabolic profile.ResultsElectroporation significantly impacted plant growth and the content of flavonoids, especially baicalein and wogonin, depending on the treatment parameters. Concentrations of aglycones were increased in at least half of the treatment conditions. The greatest amounts (a 2.5-fold increase compared to controls) were recorded after applying an electrical field characterized by the following parameters: E = 3 kV/cm, t = 100 μs, and N = 10. In conclusion, electrostimulation is an innovative and efficient way to increase plant growth and yield in an aeroponic system, as well as modulate the profile and content of bioactive flavones in the roots. However, the fine-tuning of these parameters, such as the electrical field strength (E), length (t), and number (N) of impulses delivered, is of great importance. It was also shown that cultivation of the experimental plants in aeroponics had a positive impact on their survival and development while being a sustainable and efficient horticultural practice.

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Two types of O-methyltransferase are involved in biosynthesis of anticancer methoxylated 4'-deoxyflavones in Scutellaria baicalensis Georgi.

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