Alpha-Glucosidase Inhibition and Molecular Docking of Isolated Compounds from Traditional Thai Medicinal Plant, <i>Neuropeltis racemosa</i> Wall.
<i>Neuropeltis racemosa</i> Wall. (Convolvulaceae) is wildly distributed in Asia. Its stem is used as the component in traditional Thai recipes for treatments of muscle rigidity, skin disorder, dysentery, and hypoglycemia. However, the chemical constituents and biological activities of &...
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MDPI AG
2022-01-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/3/639 |
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| author | Oraphan Sakulkeo Chatchai Wattanapiromsakul Thanet Pitakbut Sukanya Dej-adisai |
| author_facet | Oraphan Sakulkeo Chatchai Wattanapiromsakul Thanet Pitakbut Sukanya Dej-adisai |
| author_sort | Oraphan Sakulkeo |
| collection | DOAJ |
| description | <i>Neuropeltis racemosa</i> Wall. (Convolvulaceae) is wildly distributed in Asia. Its stem is used as the component in traditional Thai recipes for treatments of muscle rigidity, skin disorder, dysentery, and hypoglycemia. However, the chemical constituents and biological activities of <i>N. racemosa</i> have not been reported. From a screening assay, <i>N. racemosa</i> stem crude extract showed the potent effect on alpha-glucosidase inhibition at 2 mg/mL as 96.09%. The bioassay-guiding isolation led to 5 compounds that were identified by spectroscopic techniques as scopoletin (<b>1</b>), syringic acid (<b>2</b>), methyl 3-methyl-2-butenoate (<b>3</b>), <i>N-trans-</i>feruloyltyramine (<b>4</b>), and <i>N-trans-</i> coumaroyltyramine (<b>5</b>). Compounds <b>1</b>, <b>4</b>, and <b>5</b> exhibited an IC<sub>50</sub> of 110.97, 29.87, and 0.92 µg/mL, respectively, while the IC<sub>50</sub> of positive standard, acarbose was 272.72 µg/mL. Kinetic study showed that compound <b>1</b> performed as the mixed-type inhibition mechanism, whereas compounds <b>4</b> and <b>5</b> displayed the uncompetitive inhibition mechanism. The docking study provided the molecular understanding of isolated aromatic compounds (<b>1</b>, <b>2</b>, <b>4</b> and <b>5</b>) to alpha-glucosidase. Hence, this study would be the first report of isolated compounds and their anti-alpha-glucosidase activity with the mechanism of action from <i>N. racemosa</i>. Thus, these active compounds will be further studied to be the lead compounds among natural antidiabetic drugs. |
| first_indexed | 2024-03-09T23:30:04Z |
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| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T23:30:04Z |
| publishDate | 2022-01-01 |
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| spelling | doaj.art-461bd88ade054f50ab23a2e7313f113f2023-11-23T17:10:00ZengMDPI AGMolecules1420-30492022-01-0127363910.3390/molecules27030639Alpha-Glucosidase Inhibition and Molecular Docking of Isolated Compounds from Traditional Thai Medicinal Plant, <i>Neuropeltis racemosa</i> Wall.Oraphan Sakulkeo0Chatchai Wattanapiromsakul1Thanet Pitakbut2Sukanya Dej-adisai3Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmaceutical Sciences, Prince of Songkla University, Hat Yai 90112, Songkhla, ThailandDepartment of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmaceutical Sciences, Prince of Songkla University, Hat Yai 90112, Songkhla, ThailandDepartment of Biochemical and Chemical Engineering, Technical University of Dortmund, 44227 Dortmund, GermanyDepartment of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmaceutical Sciences, Prince of Songkla University, Hat Yai 90112, Songkhla, Thailand<i>Neuropeltis racemosa</i> Wall. (Convolvulaceae) is wildly distributed in Asia. Its stem is used as the component in traditional Thai recipes for treatments of muscle rigidity, skin disorder, dysentery, and hypoglycemia. However, the chemical constituents and biological activities of <i>N. racemosa</i> have not been reported. From a screening assay, <i>N. racemosa</i> stem crude extract showed the potent effect on alpha-glucosidase inhibition at 2 mg/mL as 96.09%. The bioassay-guiding isolation led to 5 compounds that were identified by spectroscopic techniques as scopoletin (<b>1</b>), syringic acid (<b>2</b>), methyl 3-methyl-2-butenoate (<b>3</b>), <i>N-trans-</i>feruloyltyramine (<b>4</b>), and <i>N-trans-</i> coumaroyltyramine (<b>5</b>). Compounds <b>1</b>, <b>4</b>, and <b>5</b> exhibited an IC<sub>50</sub> of 110.97, 29.87, and 0.92 µg/mL, respectively, while the IC<sub>50</sub> of positive standard, acarbose was 272.72 µg/mL. Kinetic study showed that compound <b>1</b> performed as the mixed-type inhibition mechanism, whereas compounds <b>4</b> and <b>5</b> displayed the uncompetitive inhibition mechanism. The docking study provided the molecular understanding of isolated aromatic compounds (<b>1</b>, <b>2</b>, <b>4</b> and <b>5</b>) to alpha-glucosidase. Hence, this study would be the first report of isolated compounds and their anti-alpha-glucosidase activity with the mechanism of action from <i>N. racemosa</i>. Thus, these active compounds will be further studied to be the lead compounds among natural antidiabetic drugs.https://www.mdpi.com/1420-3049/27/3/639<i>Neuropeltis racemosa</i>alpha-glucosidase inhibitionanti-diabetesphytochemistrymolecular docking |
| spellingShingle | Oraphan Sakulkeo Chatchai Wattanapiromsakul Thanet Pitakbut Sukanya Dej-adisai Alpha-Glucosidase Inhibition and Molecular Docking of Isolated Compounds from Traditional Thai Medicinal Plant, <i>Neuropeltis racemosa</i> Wall. Molecules <i>Neuropeltis racemosa</i> alpha-glucosidase inhibition anti-diabetes phytochemistry molecular docking |
| title | Alpha-Glucosidase Inhibition and Molecular Docking of Isolated Compounds from Traditional Thai Medicinal Plant, <i>Neuropeltis racemosa</i> Wall. |
| title_full | Alpha-Glucosidase Inhibition and Molecular Docking of Isolated Compounds from Traditional Thai Medicinal Plant, <i>Neuropeltis racemosa</i> Wall. |
| title_fullStr | Alpha-Glucosidase Inhibition and Molecular Docking of Isolated Compounds from Traditional Thai Medicinal Plant, <i>Neuropeltis racemosa</i> Wall. |
| title_full_unstemmed | Alpha-Glucosidase Inhibition and Molecular Docking of Isolated Compounds from Traditional Thai Medicinal Plant, <i>Neuropeltis racemosa</i> Wall. |
| title_short | Alpha-Glucosidase Inhibition and Molecular Docking of Isolated Compounds from Traditional Thai Medicinal Plant, <i>Neuropeltis racemosa</i> Wall. |
| title_sort | alpha glucosidase inhibition and molecular docking of isolated compounds from traditional thai medicinal plant i neuropeltis racemosa i wall |
| topic | <i>Neuropeltis racemosa</i> alpha-glucosidase inhibition anti-diabetes phytochemistry molecular docking |
| url | https://www.mdpi.com/1420-3049/27/3/639 |
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