Cinnamoyl Sucrose Esters as Alpha Glucosidase Inhibitors for the Treatment of Diabetes
Cinnamoyl sucrose esters (CSEs) were evaluated as AGIs and their enzyme inhibition activity and potency were compared with gold standard acarbose. The inhibition activity of the CSEs against α-glucosidase and α-amylase depended on their structure including the number of the cinnamoyl moieties, their...
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MDPI AG
2021-01-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/2/469 |
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| author | Surabhi Devaraj Yew Mun Yip Parthasarathi Panda Li Lin Ong Pooi Wen Kathy Wong Dawei Zhang Zaher Judeh |
| author_facet | Surabhi Devaraj Yew Mun Yip Parthasarathi Panda Li Lin Ong Pooi Wen Kathy Wong Dawei Zhang Zaher Judeh |
| author_sort | Surabhi Devaraj |
| collection | DOAJ |
| description | Cinnamoyl sucrose esters (CSEs) were evaluated as AGIs and their enzyme inhibition activity and potency were compared with gold standard acarbose. The inhibition activity of the CSEs against α-glucosidase and α-amylase depended on their structure including the number of the cinnamoyl moieties, their position, and the presence or absence of the acetyl moieties. The inhibitory values of the CSEs <b>2</b>–<b>9</b> generally increases in the order of mono-cinnamoyl moieties < di-cinnamoyl ≤ tri-cinnamoyl < tetra-cinnamoyl. This trend was supported from both in vitro and in silico results. Both tetra-cinnamoyl CSEs <b>5</b> and <b>9</b> showed the highest α-glucosidase inhibitory activities of 77 ± 5%, 74 ± 9%, respectively, against acarbose at 27 ± 4%, and highest α-amylase inhibitory activities of 98 ± 2%, 99 ± 1%, respectively, against acarbose at 93 ± 2%. CSEs <b>3</b>, <b>4</b>, <b>6</b>, <b>7</b>, <b>8</b> showed desired higher inhibition of α-glucosidase than α-amylase suggesting potential for further development as AGIs with reduced side effects. Molecular docking studies on CSEs <b>5</b> and <b>9</b> attributed the high inhibition of these compounds to multiple π-π interactions and favorable projection of the cinnamoyl moieties (especially O-3 cinnamoyl) in the enzyme pockets. This work proposes CSEs as new AGIs with potentially reduced side effects. |
| first_indexed | 2024-03-09T04:28:58Z |
| format | Article |
| id | doaj.art-a8202d9f2b0f44808ad40604e45c7446 |
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| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T04:28:58Z |
| publishDate | 2021-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-a8202d9f2b0f44808ad40604e45c74462023-12-03T13:38:15ZengMDPI AGMolecules1420-30492021-01-0126246910.3390/molecules26020469Cinnamoyl Sucrose Esters as Alpha Glucosidase Inhibitors for the Treatment of DiabetesSurabhi Devaraj0Yew Mun Yip1Parthasarathi Panda2Li Lin Ong3Pooi Wen Kathy Wong4Dawei Zhang5Zaher Judeh6School of Chemical and Biomedical Engineering, Nanyang Technological University, 62 Nanyang Drive, N1.2–B1-14, Singapore 637459, SingaporeSchool of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371, SingaporeSchool of Chemical and Biomedical Engineering, Nanyang Technological University, 62 Nanyang Drive, N1.2–B1-14, Singapore 637459, SingaporeSchool of Chemical and Biomedical Engineering, Nanyang Technological University, 62 Nanyang Drive, N1.2–B1-14, Singapore 637459, SingaporeSchool of Chemical and Biomedical Engineering, Nanyang Technological University, 62 Nanyang Drive, N1.2–B1-14, Singapore 637459, SingaporeSchool of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371, SingaporeSchool of Chemical and Biomedical Engineering, Nanyang Technological University, 62 Nanyang Drive, N1.2–B1-14, Singapore 637459, SingaporeCinnamoyl sucrose esters (CSEs) were evaluated as AGIs and their enzyme inhibition activity and potency were compared with gold standard acarbose. The inhibition activity of the CSEs against α-glucosidase and α-amylase depended on their structure including the number of the cinnamoyl moieties, their position, and the presence or absence of the acetyl moieties. The inhibitory values of the CSEs <b>2</b>–<b>9</b> generally increases in the order of mono-cinnamoyl moieties < di-cinnamoyl ≤ tri-cinnamoyl < tetra-cinnamoyl. This trend was supported from both in vitro and in silico results. Both tetra-cinnamoyl CSEs <b>5</b> and <b>9</b> showed the highest α-glucosidase inhibitory activities of 77 ± 5%, 74 ± 9%, respectively, against acarbose at 27 ± 4%, and highest α-amylase inhibitory activities of 98 ± 2%, 99 ± 1%, respectively, against acarbose at 93 ± 2%. CSEs <b>3</b>, <b>4</b>, <b>6</b>, <b>7</b>, <b>8</b> showed desired higher inhibition of α-glucosidase than α-amylase suggesting potential for further development as AGIs with reduced side effects. Molecular docking studies on CSEs <b>5</b> and <b>9</b> attributed the high inhibition of these compounds to multiple π-π interactions and favorable projection of the cinnamoyl moieties (especially O-3 cinnamoyl) in the enzyme pockets. This work proposes CSEs as new AGIs with potentially reduced side effects.https://www.mdpi.com/1420-3049/26/2/469phenylpropanoid sucrose estersglycosidesnatural productsα-glucosidase inhibitionα-amylase inhibitionanti-diabetic |
| spellingShingle | Surabhi Devaraj Yew Mun Yip Parthasarathi Panda Li Lin Ong Pooi Wen Kathy Wong Dawei Zhang Zaher Judeh Cinnamoyl Sucrose Esters as Alpha Glucosidase Inhibitors for the Treatment of Diabetes Molecules phenylpropanoid sucrose esters glycosides natural products α-glucosidase inhibition α-amylase inhibition anti-diabetic |
| title | Cinnamoyl Sucrose Esters as Alpha Glucosidase Inhibitors for the Treatment of Diabetes |
| title_full | Cinnamoyl Sucrose Esters as Alpha Glucosidase Inhibitors for the Treatment of Diabetes |
| title_fullStr | Cinnamoyl Sucrose Esters as Alpha Glucosidase Inhibitors for the Treatment of Diabetes |
| title_full_unstemmed | Cinnamoyl Sucrose Esters as Alpha Glucosidase Inhibitors for the Treatment of Diabetes |
| title_short | Cinnamoyl Sucrose Esters as Alpha Glucosidase Inhibitors for the Treatment of Diabetes |
| title_sort | cinnamoyl sucrose esters as alpha glucosidase inhibitors for the treatment of diabetes |
| topic | phenylpropanoid sucrose esters glycosides natural products α-glucosidase inhibition α-amylase inhibition anti-diabetic |
| url | https://www.mdpi.com/1420-3049/26/2/469 |
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