Convergent Synthesis of Moslosooflavone, Isowogonin and Norwogonin from Chrysin

Jing, Lin-Lin; Fan, Xiaofei; Jia, Zhengping; Fan, Pengcheng; Ma, Hui‐Ping

doi:10.1177/1934578x1501000303

Cited by 4 publications

(5 citation statements)

References 12 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…To further identify the methyl catalytic site of SbarFOMT-4, the product was purified and analyzed by NMR (nuclear magnetic resonance). The NMR results demonstrated that SbarFOMT-4 could transfer a methyl group to the C7 position of norwogonin (Figure S10), which was consistent with isowogonin synthesized by chemical methods . Therefore, SbarFOMT-4 was renamed as SbarF7OMT.…”

Section: Resultssupporting

confidence: 67%

De Novo Biosynthesis of Multiple Pinocembrin Derivatives in Saccharomyces cerevisiae

et al. 2020

View full text Add to dashboard Cite

Pinocembrin derived flavones are the major bioactive compounds presented in the Lamiaceae plants that have long been of interest due to their great pharmaceutical and economical significance. Modifications on the central skeleton of the flavone moiety have a huge impact on their biological activities. However, the enzymes responsible for structure modification of most flavones are either inefficient or remain unidentified. By integrating omics analysis of Scutellaria barbata and synthetic biology tools in yeast chassis, we characterized a novel gene encoding flavone 7-O-methyltransferase (F7OMT) and discovered a new flavone 8-hydroxylase (F8H) with increased activity. We also identified a series of flavone 6-hydroxylases (F6Hs) and flavone 8-O-methyltransferases (F8OMTs) in this study. Subsequently, we constructed the biosynthetic pathway for chrysin production by assembling catalytic elements from different species and improved the titer to 10.06 mg/L. Using the established chrysin production platform, we achieved the de novo biosynthesis of baicalein, baicalin, norwogonin, wogonin, isowogonin, and moslosooflavone in yeast. Our results indicated that the combination of omics and synthetic biology can greatly speed up the efficiency of gene mining in plants and the engineered yeasts established an alternative way for the production of pinocembrin derivatives.

show abstract

Section: Resultssupporting

confidence: 67%

De Novo Biosynthesis of Multiple Pinocembrin Derivatives in Saccharomyces cerevisiae

et al. 2020

View full text Add to dashboard Cite

show abstract

“…Norwogonin (purity≥98%) was synthesized according to our previous reported method [ 24 ]. Rutin (purity≥96%) was purchased from Ci Yuan Biotechology Co., Ltd. (Xian, Shannxi, China).…”

Section: Methodsmentioning

confidence: 99%

“…In order to address this problem, several synthesis methods of norwogonin are reported [ 22 , 23 ]. Our previous study also established a simple method for obtaining norwogonin from chrysin in four steps [ 24 ]. These researches have positively influenced the further evaluation of norwogonin′s biological activities.…”

Section: Introductionmentioning

confidence: 99%

Norwogonin attenuates hypoxia-induced oxidative stress and apoptosis in PC12 cells

Jing

Gao

Zhang

et al. 2021

BMC Complement Med Ther

View full text Add to dashboard Cite

Background Norwogonin is a natural flavone with three phenolic hydroxyl groups in skeletal structure and has excellent antioxidant activity. However, the neuroprotective effect of norwogonin remains unclear. Here, we investigated the protective capacity of norwogonin against oxidative damage elicited by hypoxia in PC12 cells. Methods The cell viability and apoptosis were examined by MTT assay and Annexin V-FITC/PI staining, respectively. Reactive oxygen species (ROS) content was measured using DCFH-DA assay. Lactate dehydrogenase (LDH), malondialdehyde (MDA) and antioxidant enzyme levels were determined using commercial kits. The expression of related genes and proteins was measured by real-time quantitative PCR and Western blotting, respectively. Results We found that norwogonin alleviated hypoxia-induced injury in PC12 cells by increasing the cell viability, reducing LDH release, and ameliorating the changes of cell morphology. Norwogonin also acted as an antioxidant by scavenging ROS, reducing MDA production, maintaining the activities of superoxide dismutase (SOD), catalase (CAT) and glutathione peroxidase (GPx), and decreasing the expression levels of HIF-1α and VEGF. In addition, norwogonin prevented cell apoptosis via inhibiting the expression levels of caspase-3, cytochrome c and Bax, while increasing the expression levels of Bcl-2 and the ratio of Bcl-2/Bax. Conclusions Norwogonin attenuates hypoxia-induced injury in PC12 cells by quenching ROS, maintaining the activities of antioxidant enzymes, and inhibiting mitochondrial apoptosis pathway.

show abstract

“…Due to its profound pharmacological function, conversion of plant metabolites has been widely explored via chemical, biological and photochemical routes. For instance, demethylation (enzymatic route) of lignin into polyphenol 49 and chrysin into moslosooflavone, isowogonin and norwogonin 50 has been performed and they were structurally elucidated using chromatography, NMR spectroscopy and mass spectroscopy. The electrochemical mode of WG → norwogonin analysis is comparatively a user-friendly process for rapid analysis of active herbaceuticals.…”

Section: Resultsmentioning

confidence: 99%

Buteinylated-hafnium oxide bionanoparticles for electrochemical sensing of wogonin

Krishnan,

Parandhaman,

Kanagaraj

et al. 2023

Nanoscale

View full text Add to dashboard Cite

show abstract

Convergent Synthesis of Moslosooflavone, Isowogonin and Norwogonin from Chrysin

Cited by 4 publications

References 12 publications

De Novo Biosynthesis of Multiple Pinocembrin Derivatives in Saccharomyces cerevisiae

De Novo Biosynthesis of Multiple Pinocembrin Derivatives in Saccharomyces cerevisiae

Norwogonin attenuates hypoxia-induced oxidative stress and apoptosis in PC12 cells

Buteinylated-hafnium oxide bionanoparticles for electrochemical sensing of wogonin

Contact Info

Product

Resources

About