Identification of caffeoylquinic acid derivatives as natural protein tyrosine phosphatase 1B inhibitors from Artemisia princeps
[Display omitted] •Caffeoylquinic acid derivatives are natural PTP1B inhibitors.•Chlorogenic acid showed potent PTP1B inhibitory activity.•Chlorogenic acid is a noncompetitive inhibitor.•Chlorogenic acid binds to the allosteric site of PTP1B. Considerable attention has been paid to protein tyrosine...
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| Published in | Bioorganic & medicinal chemistry letters Vol. 28; no. 7; pp. 1194 - 1197 |
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| Main Authors | , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
England
Elsevier Ltd
15.04.2018
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| Subjects | |
| Online Access | Get full text |
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| Abstract | [Display omitted]
•Caffeoylquinic acid derivatives are natural PTP1B inhibitors.•Chlorogenic acid showed potent PTP1B inhibitory activity.•Chlorogenic acid is a noncompetitive inhibitor.•Chlorogenic acid binds to the allosteric site of PTP1B.
Considerable attention has been paid to protein tyrosine phosphatase 1B (PTP1B) inhibitors as a potential therapy for diabetes, obesity, and cancer. Ten caffeoylquinic acid derivatives (1–10) from leaves of Artemisia princeps Pamp. (Asteraceae) were identified as natural PTP1B inhibitors. Among them, chlorogenic acid (3) showed the most potent inhibitory activity (IC50 11.1 μM). Compound 3 was demonstrated to be a noncompetitive inhibitor by a kinetic analysis. Molecular docking simulation suggested that compound 3 bound to the allosteric site of PTP1B. Furthermore, compound 3 showed remarkable selectivity against four homologous PTPs. According to these findings, compound 3 might be potentially valuable for further drug development. |
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| AbstractList | [Display omitted]
•Caffeoylquinic acid derivatives are natural PTP1B inhibitors.•Chlorogenic acid showed potent PTP1B inhibitory activity.•Chlorogenic acid is a noncompetitive inhibitor.•Chlorogenic acid binds to the allosteric site of PTP1B.
Considerable attention has been paid to protein tyrosine phosphatase 1B (PTP1B) inhibitors as a potential therapy for diabetes, obesity, and cancer. Ten caffeoylquinic acid derivatives (1–10) from leaves of Artemisia princeps Pamp. (Asteraceae) were identified as natural PTP1B inhibitors. Among them, chlorogenic acid (3) showed the most potent inhibitory activity (IC50 11.1 μM). Compound 3 was demonstrated to be a noncompetitive inhibitor by a kinetic analysis. Molecular docking simulation suggested that compound 3 bound to the allosteric site of PTP1B. Furthermore, compound 3 showed remarkable selectivity against four homologous PTPs. According to these findings, compound 3 might be potentially valuable for further drug development. Considerable attention has been paid to protein tyrosine phosphatase 1B (PTP1B) inhibitors as a potential therapy for diabetes, obesity, and cancer. Ten caffeoylquinic acid derivatives (1-10) from leaves of Artemisia princeps Pamp. (Asteraceae) were identified as natural PTP1B inhibitors. Among them, chlorogenic acid (3) showed the most potent inhibitory activity (IC 11.1 μM). Compound 3 was demonstrated to be a noncompetitive inhibitor by a kinetic analysis. Molecular docking simulation suggested that compound 3 bound to the allosteric site of PTP1B. Furthermore, compound 3 showed remarkable selectivity against four homologous PTPs. According to these findings, compound 3 might be potentially valuable for further drug development. Considerable attention has been paid to protein tyrosine phosphatase 1B (PTP1B) inhibitors as a potential therapy for diabetes, obesity, and cancer. Ten caffeoylquinic acid derivatives (1-10) from leaves of Artemisia princeps Pamp. (Asteraceae) were identified as natural PTP1B inhibitors. Among them, chlorogenic acid (3) showed the most potent inhibitory activity (IC50 11.1 μM). Compound 3 was demonstrated to be a noncompetitive inhibitor by a kinetic analysis. Molecular docking simulation suggested that compound 3 bound to the allosteric site of PTP1B. Furthermore, compound 3 showed remarkable selectivity against four homologous PTPs. According to these findings, compound 3 might be potentially valuable for further drug development.Considerable attention has been paid to protein tyrosine phosphatase 1B (PTP1B) inhibitors as a potential therapy for diabetes, obesity, and cancer. Ten caffeoylquinic acid derivatives (1-10) from leaves of Artemisia princeps Pamp. (Asteraceae) were identified as natural PTP1B inhibitors. Among them, chlorogenic acid (3) showed the most potent inhibitory activity (IC50 11.1 μM). Compound 3 was demonstrated to be a noncompetitive inhibitor by a kinetic analysis. Molecular docking simulation suggested that compound 3 bound to the allosteric site of PTP1B. Furthermore, compound 3 showed remarkable selectivity against four homologous PTPs. According to these findings, compound 3 might be potentially valuable for further drug development. |
| Author | Nagata, Kazuya Wang, Jian Higai, Koji Feng, Feng Li, Wei Sasaki, Tatsunori Koike, Kazuo Zhang, Jie Cheng, Maosheng |
| Author_xml | – sequence: 1 givenname: Jie surname: Zhang fullname: Zhang, Jie organization: Department of Natural Medicine Chemistry, China Pharmaceutical University, 24 Tongjiaxiang, Nanjing 210009, China – sequence: 2 givenname: Tatsunori surname: Sasaki fullname: Sasaki, Tatsunori organization: Faculty of Pharmaceutical Sciences, Toho University, Miyama 2-2-1, Funabashi, Chiba 274-8510, Japan – sequence: 3 givenname: Wei orcidid: 0000-0003-4143-8597 surname: Li fullname: Li, Wei email: liwei@phar.toho-u.ac.jp organization: Faculty of Pharmaceutical Sciences, Toho University, Miyama 2-2-1, Funabashi, Chiba 274-8510, Japan – sequence: 4 givenname: Kazuya surname: Nagata fullname: Nagata, Kazuya organization: Faculty of Pharmaceutical Sciences, Toho University, Miyama 2-2-1, Funabashi, Chiba 274-8510, Japan – sequence: 5 givenname: Koji orcidid: 0000-0003-3870-396X surname: Higai fullname: Higai, Koji organization: Faculty of Pharmaceutical Sciences, Toho University, Miyama 2-2-1, Funabashi, Chiba 274-8510, Japan – sequence: 6 givenname: Feng surname: Feng fullname: Feng, Feng organization: Department of Natural Medicine Chemistry, China Pharmaceutical University, 24 Tongjiaxiang, Nanjing 210009, China – sequence: 7 givenname: Jian surname: Wang fullname: Wang, Jian organization: Key Laboratory of Structure-Based Drug Design and Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, China – sequence: 8 givenname: Maosheng surname: Cheng fullname: Cheng, Maosheng organization: Key Laboratory of Structure-Based Drug Design and Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, China – sequence: 9 givenname: Kazuo surname: Koike fullname: Koike, Kazuo organization: Faculty of Pharmaceutical Sciences, Toho University, Miyama 2-2-1, Funabashi, Chiba 274-8510, Japan |
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| Keywords | Protein tyrosine phosphatase 1B Chlorogenic acid Artemisia princeps Caffeoylquinic acid CWVRJTMFETXNAD-JUHZACGLSA-N |
| Language | English |
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Fraction A4 (7.2 g) was passed through an ODS column, and eluted with a gradient of MeOH-H – reference: O (0:1→1:0) to afford four fractions, A4-1-A4-4. A portion (150 mg) of fraction A4–1 (2.9 g) was separated by RP-HPLC using MeCN-H – reference: (2.1 mg, – reference: 18.0 min). A portion (600 mg) of fraction A4–2 (2.8 g) was separated by RP-HPLC using MeCN-H – reference: (47.2 mg, – reference: 25.6 min), and – reference: 19.5 min), – volume: 186 start-page: 84 year: 2016 ident: b0065 publication-title: J Ethnopharmacol – volume: 23 start-page: 5836 year: 2013 ident: b0080 publication-title: Bioorg Med Chem Lett – reference: was crushed into powder. The pulverized sample was weighed (200 g), and extracted with MeOH (ultrasonication, 3 h, 3 times) to yield a MeOH extract (30.1 g). 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•Caffeoylquinic acid derivatives are natural PTP1B inhibitors.•Chlorogenic acid showed potent PTP1B inhibitory activity.•Chlorogenic acid is... Considerable attention has been paid to protein tyrosine phosphatase 1B (PTP1B) inhibitors as a potential therapy for diabetes, obesity, and cancer. Ten... |
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| SubjectTerms | Artemisia - chemistry Artemisia princeps Caffeoylquinic acid Chlorogenic acid Dose-Response Relationship, Drug Humans Molecular Docking Simulation Molecular Structure Protein tyrosine phosphatase 1B Protein Tyrosine Phosphatase, Non-Receptor Type 1 - antagonists & inhibitors Protein Tyrosine Phosphatase, Non-Receptor Type 1 - metabolism Quinic Acid - analogs & derivatives Quinic Acid - chemical synthesis Quinic Acid - chemistry Quinic Acid - pharmacology Structure-Activity Relationship |
| Title | Identification of caffeoylquinic acid derivatives as natural protein tyrosine phosphatase 1B inhibitors from Artemisia princeps |
| URI | https://dx.doi.org/10.1016/j.bmcl.2018.02.052 https://www.ncbi.nlm.nih.gov/pubmed/29525218 https://www.proquest.com/docview/2013102691 |
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