scholarly journals Coumarin and Moracin Derivatives from Mulberry Leaves (Morus alba L.) with Soluble Epoxide Hydrolase Inhibitory Activity

Molecules ◽  
2020 ◽  
Vol 25 (17) ◽  
pp. 3967
Author(s):  
Hong Xu Li ◽  
Myungsook Heo ◽  
Younghoon Go ◽  
Young Soo Kim ◽  
Young Ho Kim ◽  
...  
Keyword(s):  
Inhibitory Activity ◽  
Epoxide Hydrolase ◽  
2D Nmr ◽  
Soluble Epoxide Hydrolase ◽  
Inhibitory Effect ◽  
Mulberry Leaves ◽  
Ic50 Values ◽  
Nmr Methods ◽  
Reported Data ◽  
Mixed Types

This study identified three coumarins (1–3), and six moracin derivatives (4–9). The structures of these natural compounds were determined by the spectroscopic methods, including 1D and 2D NMR methods, and comparison with previous reported data. All of the isolated compounds were assessed for the effects on the soluble epoxide hydrolase (sEH) inhibitory activity. Among them, compounds 1–7 exhibited significant inhibitory effect with 100% inhibitory, with IC50 values of 6.9, 0.2, 15.9, 1.1, 1.2, 9.9, and 7.7 µM, respectively. A kinetic study revealed that compounds 1–4, and 6 were competitive types of inhibitors, compounds 5 and 7 were mixed types of inhibitors. These results suggest that moracin and coumarin derivatives from mulberry leaves are significant sEH inhibitors.

scholarly journals Isolation of Two New Compounds and Other Constituents from Leaves of Piper crocatum and Study of Their Soluble Epoxide Hydrolase Activities

Molecules ◽  
2019 ◽  
Vol 24 (3) ◽  
pp. 489 ◽  
Author(s):  
Hong Li ◽  
Seo Yang ◽  
Young Kim ◽  
Wei Li
Keyword(s):  
Inhibitory Activity ◽  
Epoxide Hydrolase ◽  
2D Nmr ◽  
Soluble Epoxide Hydrolase ◽  
Chemical Structures ◽  
Phenolic Glucosides ◽  
Spectroscopic Analyses ◽  
Ic50 Value ◽  
Reported Data ◽  
New Compounds

Two new phenolic glucosides, pipercroside A and B (1 and 2), along with 10 known compounds were isolated from the leaves of Piper crocatum Ruiz & Pav. Their chemical structures were elucidated through extensive spectroscopic analyses, including 1D and 2D NMR experiments and HR-ESI-MS analysis and comparison with previously reported data. All the isolated compounds were assessed for soluble epoxide hydrolase (sEH) inhibitory activity. Among them, erigeside II (5) showed inhibitory activity with an IC50 value of 58.5 µM.

scholarly journals Unusual Bicyclo[3.2.1]Octanoid Neolignans from Leaves of Piper crocatum and Their Effect on Pyruvate Dehydrogenase Activity

Plants ◽  
2021 ◽  
Vol 10 (9) ◽  
pp. 1855
Author(s):  
Yu Juan Chai ◽  
Younghoon Go ◽  
Hai Qi Zhou ◽  
Hong Xu Li ◽  
Sun Joo Lee ◽  
...  
Keyword(s):  
Pyruvate Dehydrogenase ◽  
2D Nmr ◽  
Inhibitory Effect ◽  
Positive Control ◽  
Inhibition Effect ◽  
Chemical Structures ◽  
Spectroscopic Analyses ◽  
Fluorescent Image ◽  
Ic50 Values ◽  
Reported Data

Three undescribed bicyclo[3.2.1]octanoid neolignan glucosides, along with a known neolignan, were isolated from the leaves of Piper crocatum Ruiz & Pav. Their chemical structures were elucidated using extensive spectroscopic analyses including 1D and 2D NMR experiments and HR-ESI-MS analysis, as well as through comparison with previously reported data. Two compounds were assessed for their inhibitory effect against pyruvate dehydrogenase E1α S300 phosphorylation. The fluorescent image suggested that both compounds (60 µM) revealed a stronger inhibition effect than the positive control (dichloroacetate, DCA 5 mM), with IC50 values of 99.82 µM and 80.25 µM, respectively.

scholarly journals In Vitro and In Silico Studies of Soluble Epoxide Hydrolase Inhibitors from the Roots of Lycopus lucidus

Plants ◽  
2021 ◽  
Vol 10 (2) ◽  
pp. 356
Author(s):  
Yoo Kyong Han ◽  
Ji Sun Lee ◽  
Seo Young Yang ◽  
Ki Yong Lee ◽  
Young Ho Kim
Keyword(s):  
Inhibitory Activity ◽  
Epoxide Hydrolase ◽  
Soluble Epoxide Hydrolase ◽  
In Silico Studies ◽  
Allosteric Sites ◽  
Soluble Epoxide Hydrolase Inhibitors ◽  
Ic50 Values ◽  
Dimethyl Lithospermate ◽  
Lycopus Lucidus

Soluble epoxide hydrolase (sEH) is an enzyme that is considered a potential therapeutic target in human cardiovascular disease. Triterpenes (1–4) and phenylpropanoids (5–10) were isolated from Lycopus lucidus to obtain sEH inhibitors through various chromatographic purificationtechniques. The isolated compounds were evaluated for their inhibitory activity against sEH, and methyl rosmarinate (7), martynoside (8), dimethyl lithospermate (9) and 9″ methyl lithospermate (10) showed remarkable inhibitory activity, with the IC50 values ranging from 10.6 ± 3.2 to 35.7 ± 2.1 µM. Kinetic analysis of these compounds revealed that 7, 9 and 10 were competitive inhibitors bound to the active site, and 8 was the preferred mixed type inhibitor for allosteric sites. Additionally, molecular modeling has identified interacting catalytic residues and bindings between sEH and inhibitors. The results suggest that these compounds are potential candidates that can be used for further development in the prevention and treatment for cardiovascular risk.

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.

scholarly journals IN VITRO SOLUBLE EPOXIDE HYDROLASE ENZYME INHIBITORY ACTIVITY OF SOME NOVEL CHALCONE DERIVATIVES

2012 ◽  
Vol 2 (4) ◽  
Author(s):  
Kuppusamy Asokkumar ◽  
Lokeswari Prathyusha Tangella ◽  
Muthusamy Umamaheshwari ◽  
Thirumalaisamy Shivashanmugam ◽  
Varadharajan Subhadradevi ◽  
...  
Keyword(s):  
Inhibitory Activity ◽  
Epoxide Hydrolase ◽  
Soluble Epoxide Hydrolase ◽  
Chalcone Derivatives

scholarly journals Inhibitory Activity of Quercetin 3-O-Arabinofuranoside and 2-Oxopomolic Acid Derived from Malus domestica on Soluble Epoxide Hydrolase

Molecules ◽  
2020 ◽  
Vol 25 (18) ◽  
pp. 4352
Author(s):  
In Sook Cho ◽  
Jang Hoon Kim ◽  
Yunjia Lin ◽  
Xiang Dong Su ◽  
Jong Seong Kang ◽  
...  
Keyword(s):  
Malus Domestica ◽  
Epoxide Hydrolase ◽  
Soluble Epoxide Hydrolase ◽  
Corosolic Acid ◽  
Allosteric Sites ◽  
Ic50 Values ◽  
Cardiovascular Tests ◽  
Potential Inhibitors ◽  
Molecular Docking And Dynamics

Flavonoids and triterpenoids were revealed to be the potential inhibitors on soluble epoxide hydrolase (sEH). The aim of this study is to reveal sEH inhibitors from Fuji apples. A flavonoid and three triterpenoids derived from the fruit of Malus domestica were identified as quercetin-3-O-arabinoside (1), ursolic acid (2), corosolic acid (3), and 2-oxopomolic acid (4). They had half-maximal inhibitory concentration of the inhibitors (IC50) values of 39.3 ± 3.4, 84.5 ± 9.5, 51.3 ± 4.9, and 11.4 ± 2.7 μM, respectively, on sEH. The inhibitors bound to allosteric sites of enzymes in mixed (1) and noncompetitive modes (2–4). Molecular simulations were carried out for inhibitors 1 and 4 to calculate the binding force of ligands to receptors. The inhibitors bound to the left (1) and right (4) pockets next to the enzyme’s active site. Based on analyses of their molecular docking and dynamics, it was shown that inhibitors 1 and 4 can stably bind sEH at 1 bar and 300 K. Finally, inhibitors 1 and 4 are promising candidates for further studies using cell-based assays and in vivo cardiovascular tests.

Soluble epoxide hydrolase inhibitory activity of anthraquinone components from Aloe

2015 ◽  
Vol 23 (20) ◽  
pp. 6659-6665 ◽  
Author(s):  
Ya Nan Sun ◽  
Jang Hoon Kim ◽  
Wei Li ◽  
A. Reum Jo ◽  
Xi Tao Yan ◽  
...  
Keyword(s):  
Inhibitory Activity ◽  
Epoxide Hydrolase ◽  
Soluble Epoxide Hydrolase

scholarly journals Structure Revision and Protein Tyrosine Phosphatase Inhibitory Activity of Drazepinone

Marine Drugs ◽  
2021 ◽  
Vol 19 (12) ◽  
pp. 714
Author(s):  
Fei Cao ◽  
Li Pan ◽  
Wen-Bin Gao ◽  
Yun-Feng Liu ◽  
Cai-Juan Zheng ◽  
...  
Keyword(s):  
Detailed Analysis ◽  
Protein Tyrosine Phosphatase ◽  
Inhibitory Activity ◽  
Chemical Shifts ◽  
Tyrosine Phosphatase ◽  
2D Nmr ◽  
Nmr Data ◽  
Structure Revision ◽  
Ic50 Values

From the marine-derived fungus Penicillium sumatrense (Trichocomaceae), a pair of enantiomers [(+)-1 and (−)-1] were isolated with identical 1D NMR data to drazepinone, which was originally reported to have a trisubstituted naphthofuroazepinone skeleton. In this study, we confirmed the structures of the two enantiomers as drazepinone and revised their structures by detailed analysis of extensive 2D NMR data and a comparison of the calculated 13C chemical shifts, ECD, VCD, and ORD spectra with those of the experiment ones. (+)-1 and (−)-1 were evaluated for their PTP inhibitory activity in vitro. (−)-1 showed selective PTP inhibitory activity against PTP1B and TCPTP with IC50 values of 1.56 and 12.5 μg/mL, respectively.

Soluble epoxide hydrolase inhibitory activity of anthraquinone components from Aloe

Planta Medica ◽  
2016 ◽  
Vol 81 (S 01) ◽  
pp. S1-S381
Author(s):  
YN Sun ◽  
AR Jo ◽  
JH Kim ◽  
JS Kang ◽  
YH Kim
Keyword(s):  
Inhibitory Activity ◽  
Epoxide Hydrolase ◽  
Soluble Epoxide Hydrolase

scholarly journals Ballodiolic Acid A and B: Two New ROS, (•OH), (ONOO−) Scavenging and Potent Antimicrobial Constituents Isolated from Ballota pseudodictamnus (L.) Benth.

Pharmaceutics ◽  
2021 ◽  
Vol 13 (3) ◽  
pp. 402
Author(s):  
Fozia ◽  
Asmat Shaheen ◽  
Ijaz Ahmad ◽  
Syed Badar Amin ◽  
Nisar Ahmad ◽  
...  
Keyword(s):  
Inhibitory Activity ◽  
Inhibition Zone ◽  
2D Nmr ◽  
Scavenging Activity ◽  
Bacterial Strains ◽  
Activity Test ◽  
Ic50 Values ◽  
Chemical Studies ◽  
Antibacterial And Antifungal ◽  
Total Ros

Bioassays guided phytochemical investigations on the ethyl acetate-soluble fraction of the root material of Ballota pseudodictamnus (L.) Benth. led to the isolation of two new compounds, ballodiolic acid A (1) and ballodiolic acid B (2), along with three known compounds ballodiolic acid (3), ballotenic acid (4), and β-amyrin (5), which were also isolated for the first time from this species by using multiple chromatographic techniques. The structures of the compounds (1–5) were determined by modern spectroscopic analysis including 1D and 2D NMR techniques and chemical studies. In three separate experiments, the isolated compounds (1–5) demonstrated potent antioxidant scavenging activity, with IC50 values ranging from 07.22–34.10 μM in the hydroxyl radical (•OH) inhibitory activity test, 58.10–148.55 μM in the total ROS (reactive oxygen species) inhibitory activity test, and 6.23–69.01 μM in the peroxynitrite (ONOO-) scavenging activity test. With IC50 values of (07.22 ± 0.03, 58.10 ± 0.07, 6.23 ± 0.04 μM) for •OH, total ROS, and scavenge ONOO-, respectively, ballodiolic acid B (2) showed the highest scavenging ability. Antibacterial and antifungal behaviors were also exposed to the pure compounds 1–5. In contrast to compound 5 and 4, compounds 1, 2, and 3 were active against all bacterial strains studied, with a good zone of inhibition proving these as a potent antibacterial agent. Similarly, compared to compounds 3–5, compounds 2 and 1 with a 47 percent and 45 percent respective inhibition zone were found to be more active against tested fungal strains.

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