A new coumarin from pericarps of Zanthoxylum bungeanum Maxim

2021 ◽  
pp. 174751982110520
Author(s):  
Tian Chai ◽  
Wen-Han Zhang ◽  
Hui Jiao ◽  
Yin Qiang
Keyword(s):  
Cancer Cells ◽  
Inhibitory Activity ◽  
Spectroscopic Analysis ◽  
Tyrosine Phosphatase ◽  
Sirtuin 1 ◽  
Protein Tyrosine Phosphatase 1B ◽  
Acylation Reaction ◽  
Isolated Compound ◽  
Hepg2 Cell Lines ◽  
Zanthoxylum Bungeanum

A new coumarin, 7-oxo-7 H-furo-[3,2-g]chromen-9-yl dimethylcarbamate, is isolated from a methanol extract of Zanthoxylum bungeanum pericarps. The structure of this compound 1 is elucidated based on extensive spectroscopic analysis, including infrared, nuclear magnetic resonance, and mass spectrometry. This new compound is also synthesized by a simple acylation reaction with dimethylcarbamoyl chloride. The inhibitory activity of the isolated compound against HeLa and HepG2 cell lines is described. The protein tyrosine phosphatase 1B inhibitory activity against HeLa and HepG2 cancer cells and the sirtuin 1 inhibitory activity against HepG2 cancer cells are also evaluated.

Inhibition of Protein Tyrosine Phosphatase 1B by Lutein Derivatives isolated from Mexican Oregano (Lippia graveolens)

2018 ◽  
Vol 17 (3) ◽  
pp. 134-139
Author(s):  
R.M. Perez-Gutierrez
Keyword(s):  
Protein Tyrosine Phosphatase ◽  
Inhibitory Activity ◽  
Spectroscopic Data ◽  
Methanol Extract ◽  
Tyrosine Phosphatase ◽  
Positive Control ◽  
Protein Tyrosine Phosphatase 1B ◽  
Protein Tyrosine ◽  
Ic50 Value ◽  
Ic50 Values

Methanol extract from Lippia graveolens (Mexican oregano) was studied in order to identify inhibitory bioactives for protein tyrosine phosphatase 1B (PTP1B). Known flavone as lutein (1), and another flavone glycoside such as lutein-7-o-glucoside (2), 6-hydroxy-lutein-7-ohexoside (3) and lutein-7-o-ramnoide (4) were isolated from methanol extract of aerial parts of the Lippia graveolens. All isolates were identified based on extensive spectroscopic data analysis, including UV, IR, NMR, MS and compared with spectroscopic data previously reported. These flavones were evaluated for PTP1B inhibitory activity. Among them, compounds 1 and 3 displayed potential inhibitory activity against PTP1B with IC50 values of 7.01 ± 1.25 μg/ml and 18.4 μg/ml, respectively. In addition, compound 2 and 4 showed moderate inhibitory activity with an IC50 value of 23.8 ± 6.21 and 67.8 ± 5.80 μg/ml respectively. Among the four compounds, luteolin was found to be the most potent PTP1B inhibitor compared to the positive control ursolic acid, with an IC50 value of 8.12 ± 1.06 μg/ml. These results indicate that flavonoids constituents contained in Lippia graveolens can be considered as a natural source for the treatment of type 2 diabetes.

scholarly journals Inhibitory Effects of Secondary Metabolites from the Lichen Stereocaulon evolutum on Protein Tyrosine Phosphatase 1B

Planta Medica ◽  
2021 ◽  
Author(s):  
Birgit Waltenberger ◽  
Françoise Lohézic-Le Dévéhat ◽  
Thi Huyen Vu ◽  
Olivier Delalande ◽  
Claudia Lalli ◽  
...  
Keyword(s):  
Protein Tyrosine Phosphatase ◽  
Inhibitory Activity ◽  
Tyrosine Phosphatase ◽  
Inhibitory Effect ◽  
Positive Control ◽  
Protein Tyrosine Phosphatase 1B ◽  
Protein Tyrosine ◽  
Ic50 Values ◽  
A Cell

AbstractProtein tyrosine phosphatase 1B plays a significant role in type 2 diabetes mellitus and other diseases and is therefore considered a new drug target. Within this study, an acetone extract from the lichen Stereocaulon evolutum was identified to possess strong protein tyrosine phosphatase 1B inhibition in a cell-free assay (IC50 of 11.8 µg/mL). Fractionation of this bioactive extract led to the isolation of seven known molecules belonging to the depsidones and the related diphenylethers and one new natural product, i.e., 3-butyl-3,7-dihydroxy-5-methoxy-1(3H)-isobenzofurane. The isolated compounds were evaluated for their inhibition of protein tyrosine phosphatase 1B. Two depsidones, lobaric acid and norlobaric acid, and the diphenylether anhydrosakisacaulon A potently inhibited protein tyrosine phosphatase 1B with IC50 values of 12.9, 15.1, and 16.1 µM, respectively, which is in the range of the protein tyrosine phosphatase 1B inhibitory activity of the positive control ursolic acid (IC50 of 14.4 µM). Molecular simulations performed on the eight compounds showed that i) a contact between the molecule and the four main regions of the protein is required for inhibitory activity, ii) the relative rigidity of the depsidones lobaric acid and norlobaric acid and the reactivity related to hydrogen bond donors or acceptors, which interact with protein tyrosine phosphatase 1B key amino acids, are involved in the bioactivity on protein tyrosine phosphatase 1B, iii) the cycle opening observed for diphenylethers decreased the inhibition, except for anhydrosakisacaulon A where its double bond on C-8 offsets this loss of activity, iv) the function present at C-8 is a determinant for the inhibitory effect on protein tyrosine phosphatase 1B, and v) the more hydrogen bonds with Arg221 there are, the more anchorage is favored.

Protein Tyrosine Phosphatase 1B Inhibitory Activity of Lavandulyl Flavonoids from Roots of Sophora flavescens

Planta Medica ◽  
2014 ◽  
Vol 80 (07) ◽  
pp. 557-560 ◽  
Author(s):  
Tatsunori Sasaki ◽  
Wei Li ◽  
Koji Higai ◽  
Tran Quang ◽  
Young Kim ◽  
...  
Keyword(s):  
Protein Tyrosine Phosphatase ◽  
Inhibitory Activity ◽  
Tyrosine Phosphatase ◽  
Protein Tyrosine Phosphatase 1B ◽  
Sophora Flavescens ◽  
Protein Tyrosine

scholarly journals New Hippolide Derivatives with Protein Tyrosine Phosphatase 1B Inhibitory Activity from the Marine Sponge Hippospongia lachne

Marine Drugs ◽  
2014 ◽  
Vol 12 (7) ◽  
pp. 4096-4109 ◽  
Author(s):  
Shu-Juan Piao ◽  
Wei-Hua Jiao ◽  
Fan Yang ◽  
Yang-Hua Yi ◽  
Ying-Tong Di ◽  
...  
Keyword(s):  
Marine Sponge ◽  
Protein Tyrosine Phosphatase ◽  
Inhibitory Activity ◽  
Tyrosine Phosphatase ◽  
Protein Tyrosine Phosphatase 1B ◽  
Protein Tyrosine
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