Flavones from <i>Combretum quadrangulare</i> Growing in Vietnam and Their Alpha-Glucosidase Inhibitory Activity
<i>Combretum quadrangulare</i> Kurz is widely used in folk medicine in Eastern Asia and is associated with various ethnopharmacological properties including hepatoprotective, antipyretic, analgesic, antidysenteric, and anthelmintic activities. Previous phytochemical investigations report...
| Main Authors: | , , , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2021-04-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/26/9/2531 |
| _version_ | 1797536204420284416 |
|---|---|
| author | Thi-Bich-Ngoc Dao Truong-Minh-Tri Nguyen Van-Quy Nguyen Thi-Minh-Dinh Tran Nguyen-Minh-An Tran Chuong Hoang Nguyen Thi-Hoai-Thu Nguyen Huu-Hung Nguyen Jirapast Sichaem Cong-Luan Tran Thuc-Huy Duong |
| author_facet | Thi-Bich-Ngoc Dao Truong-Minh-Tri Nguyen Van-Quy Nguyen Thi-Minh-Dinh Tran Nguyen-Minh-An Tran Chuong Hoang Nguyen Thi-Hoai-Thu Nguyen Huu-Hung Nguyen Jirapast Sichaem Cong-Luan Tran Thuc-Huy Duong |
| author_sort | Thi-Bich-Ngoc Dao |
| collection | DOAJ |
| description | <i>Combretum quadrangulare</i> Kurz is widely used in folk medicine in Eastern Asia and is associated with various ethnopharmacological properties including hepatoprotective, antipyretic, analgesic, antidysenteric, and anthelmintic activities. Previous phytochemical investigations reported the presence of numerous triterpenes (mostly cycloartanes, ursanes, lupanes, and oleananes) along with dozens of flavonoids. However, the extracts of <i>C. quadrangulare</i> and isolated flavonoids have not been evaluated for their alpha-glucosidase inhibition. In the frame of our efforts dedicated to the chemical investigation of Vietnamese medicinal plants and their biological activities, a phytochemical study of the MeOH extract of the leaves of <i>C. quadrangulare</i> using bioactive guided isolation was undertaken. In this paper, the isolation and structure elucidation of twelve known compounds, 5-hydroxy-3,7,4′-trimethoxyflavone (<b>1</b>), ayanin (<b>2</b>), kumatakenin (<b>3</b>), rhamnocitrin (<b>4</b>), ombuin (<b>5</b>), myricetin-3,7,3′,5′-tetramethyl ether (<b>6</b>), gardenin D (<b>7</b>), luteolin (<b>12</b>), apigenin (<b>13</b>), mearnsetin (<b>14</b>), isoorientin (<b>15</b>), and vitexin (<b>16</b>) were reported. Bromination was applied to compounds <b>2</b> and <b>3</b> to provide four new synthetic analogues <b>8</b>–<b>11</b>. All isolated and synthesized compounds were evaluated for alpha-glucosidase inhibition and antibacterial activity. Compounds <b>4</b> and <b>5</b> showed moderate antibacterial activity against methicillin-resistant <i>Staphylococcus aureus</i> while others were inactive. All compounds failed to reveal any activity toward extended spectrum beta-lactamase-producing <i>Escherichia coli</i>. Compounds <b>2</b>, <b>4</b>, <b>6</b>–<b>9</b>, and <b>11</b>–<b>14</b> showed good alpha-glucosidase inhibition with IC<sub>50</sub> values in the range of 30.5–282.0 µM. The kinetic of enzyme inhibition showed that <b>8</b> and <b>11</b> were noncompetitive type inhibition against alpha-glucosidase. In silico molecular docking model indicated that compounds <b>8</b> and <b>11</b> were potential inhibitors against enzyme <i>α</i>-glucosidase. |
| first_indexed | 2024-03-10T11:56:18Z |
| format | Article |
| id | doaj.art-bf2ed77b10af42838ac49e8359e2ce0f |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T11:56:18Z |
| publishDate | 2021-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-bf2ed77b10af42838ac49e8359e2ce0f2023-11-21T17:16:37ZengMDPI AGMolecules1420-30492021-04-01269253110.3390/molecules26092531Flavones from <i>Combretum quadrangulare</i> Growing in Vietnam and Their Alpha-Glucosidase Inhibitory ActivityThi-Bich-Ngoc Dao0Truong-Minh-Tri Nguyen1Van-Quy Nguyen2Thi-Minh-Dinh Tran3Nguyen-Minh-An Tran4Chuong Hoang Nguyen5Thi-Hoai-Thu Nguyen6Huu-Hung Nguyen7Jirapast Sichaem8Cong-Luan Tran9Thuc-Huy Duong10Department of Chemistry, University of Education, 280 An Duong Vuong Street, District 5, Ho Chi Minh City 72711, VietnamDepartment of Chemistry, University of Education, 280 An Duong Vuong Street, District 5, Ho Chi Minh City 72711, VietnamDepartment of Chemistry, University of Education, 280 An Duong Vuong Street, District 5, Ho Chi Minh City 72711, VietnamDepartment of Biology, Ho Chi Minh City University of Education, 280 An Duong Vuong Street, District 5, Ho Chi Minh City 72711, VietnamIndustrial University of Ho Chi Minh City, Ho Chi Minh City 71420, VietnamUniversity of Science, Vietnam National University, Ho Chi Minh City 72711, VietnamFaculty of Basic Sciences, University of Medicine and Pharmacy at Ho Chi Minh City, 217 Hong Bang Street, District 5, Ho Chi Minh City 72714, VietnamFaculty of Technology, Van Lang University, 45 Nguyen Khac Nhu, District 1, Ho Chi Minh City 71013, VietnamResearch Unit in Natural Products Chemistry and Bioactivities, Faculty of Science and Technology, Thammasat University Lampang Campus, Lampang 52190, ThailandFaculty of Pharmacy and Nursery, Tay Do University, Can Tho 94000, VietnamDepartment of Chemistry, University of Education, 280 An Duong Vuong Street, District 5, Ho Chi Minh City 72711, Vietnam<i>Combretum quadrangulare</i> Kurz is widely used in folk medicine in Eastern Asia and is associated with various ethnopharmacological properties including hepatoprotective, antipyretic, analgesic, antidysenteric, and anthelmintic activities. Previous phytochemical investigations reported the presence of numerous triterpenes (mostly cycloartanes, ursanes, lupanes, and oleananes) along with dozens of flavonoids. However, the extracts of <i>C. quadrangulare</i> and isolated flavonoids have not been evaluated for their alpha-glucosidase inhibition. In the frame of our efforts dedicated to the chemical investigation of Vietnamese medicinal plants and their biological activities, a phytochemical study of the MeOH extract of the leaves of <i>C. quadrangulare</i> using bioactive guided isolation was undertaken. In this paper, the isolation and structure elucidation of twelve known compounds, 5-hydroxy-3,7,4′-trimethoxyflavone (<b>1</b>), ayanin (<b>2</b>), kumatakenin (<b>3</b>), rhamnocitrin (<b>4</b>), ombuin (<b>5</b>), myricetin-3,7,3′,5′-tetramethyl ether (<b>6</b>), gardenin D (<b>7</b>), luteolin (<b>12</b>), apigenin (<b>13</b>), mearnsetin (<b>14</b>), isoorientin (<b>15</b>), and vitexin (<b>16</b>) were reported. Bromination was applied to compounds <b>2</b> and <b>3</b> to provide four new synthetic analogues <b>8</b>–<b>11</b>. All isolated and synthesized compounds were evaluated for alpha-glucosidase inhibition and antibacterial activity. Compounds <b>4</b> and <b>5</b> showed moderate antibacterial activity against methicillin-resistant <i>Staphylococcus aureus</i> while others were inactive. All compounds failed to reveal any activity toward extended spectrum beta-lactamase-producing <i>Escherichia coli</i>. Compounds <b>2</b>, <b>4</b>, <b>6</b>–<b>9</b>, and <b>11</b>–<b>14</b> showed good alpha-glucosidase inhibition with IC<sub>50</sub> values in the range of 30.5–282.0 µM. The kinetic of enzyme inhibition showed that <b>8</b> and <b>11</b> were noncompetitive type inhibition against alpha-glucosidase. In silico molecular docking model indicated that compounds <b>8</b> and <b>11</b> were potential inhibitors against enzyme <i>α</i>-glucosidase.https://www.mdpi.com/1420-3049/26/9/2531<i>Combretum quadrangulare</i> Kurzflavonoidalpha-glucosidaseantibacterialmolecular docking |
| spellingShingle | Thi-Bich-Ngoc Dao Truong-Minh-Tri Nguyen Van-Quy Nguyen Thi-Minh-Dinh Tran Nguyen-Minh-An Tran Chuong Hoang Nguyen Thi-Hoai-Thu Nguyen Huu-Hung Nguyen Jirapast Sichaem Cong-Luan Tran Thuc-Huy Duong Flavones from <i>Combretum quadrangulare</i> Growing in Vietnam and Their Alpha-Glucosidase Inhibitory Activity Molecules <i>Combretum quadrangulare</i> Kurz flavonoid alpha-glucosidase antibacterial molecular docking |
| title | Flavones from <i>Combretum quadrangulare</i> Growing in Vietnam and Their Alpha-Glucosidase Inhibitory Activity |
| title_full | Flavones from <i>Combretum quadrangulare</i> Growing in Vietnam and Their Alpha-Glucosidase Inhibitory Activity |
| title_fullStr | Flavones from <i>Combretum quadrangulare</i> Growing in Vietnam and Their Alpha-Glucosidase Inhibitory Activity |
| title_full_unstemmed | Flavones from <i>Combretum quadrangulare</i> Growing in Vietnam and Their Alpha-Glucosidase Inhibitory Activity |
| title_short | Flavones from <i>Combretum quadrangulare</i> Growing in Vietnam and Their Alpha-Glucosidase Inhibitory Activity |
| title_sort | flavones from i combretum quadrangulare i growing in vietnam and their alpha glucosidase inhibitory activity |
| topic | <i>Combretum quadrangulare</i> Kurz flavonoid alpha-glucosidase antibacterial molecular docking |
| url | https://www.mdpi.com/1420-3049/26/9/2531 |
| work_keys_str_mv | AT thibichngocdao flavonesfromicombretumquadrangulareigrowinginvietnamandtheiralphaglucosidaseinhibitoryactivity AT truongminhtringuyen flavonesfromicombretumquadrangulareigrowinginvietnamandtheiralphaglucosidaseinhibitoryactivity AT vanquynguyen flavonesfromicombretumquadrangulareigrowinginvietnamandtheiralphaglucosidaseinhibitoryactivity AT thiminhdinhtran flavonesfromicombretumquadrangulareigrowinginvietnamandtheiralphaglucosidaseinhibitoryactivity AT nguyenminhantran flavonesfromicombretumquadrangulareigrowinginvietnamandtheiralphaglucosidaseinhibitoryactivity AT chuonghoangnguyen flavonesfromicombretumquadrangulareigrowinginvietnamandtheiralphaglucosidaseinhibitoryactivity AT thihoaithunguyen flavonesfromicombretumquadrangulareigrowinginvietnamandtheiralphaglucosidaseinhibitoryactivity AT huuhungnguyen flavonesfromicombretumquadrangulareigrowinginvietnamandtheiralphaglucosidaseinhibitoryactivity AT jirapastsichaem flavonesfromicombretumquadrangulareigrowinginvietnamandtheiralphaglucosidaseinhibitoryactivity AT congluantran flavonesfromicombretumquadrangulareigrowinginvietnamandtheiralphaglucosidaseinhibitoryactivity AT thuchuyduong flavonesfromicombretumquadrangulareigrowinginvietnamandtheiralphaglucosidaseinhibitoryactivity |