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Flavones from Combretum quadrangulare Growing in Vietnam and Their Alpha-Glucosidase Inhibitory Activity

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Department of Chemistry, University of Education, 280 An Duong Vuong Street, District 5, Ho Chi Minh City 72711, Vietnam
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Department of Biology, Ho Chi Minh City University of Education, 280 An Duong Vuong Street, District 5, Ho Chi Minh City 72711, Vietnam
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Industrial University of Ho Chi Minh City, Ho Chi Minh City 71420, Vietnam
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University of Science, Vietnam National University, Ho Chi Minh City 72711, Vietnam
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Faculty of Basic Sciences, University of Medicine and Pharmacy at Ho Chi Minh City, 217 Hong Bang Street, District 5, Ho Chi Minh City 72714, Vietnam
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Faculty of Technology, Van Lang University, 45 Nguyen Khac Nhu, District 1, Ho Chi Minh City 71013, Vietnam
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Research Unit in Natural Products Chemistry and Bioactivities, Faculty of Science and Technology, Thammasat University Lampang Campus, Lampang 52190, Thailand
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Faculty of Pharmacy and Nursery, Tay Do University, Can Tho 94000, Vietnam
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Authors to whom correspondence should be addressed.
Academic Editor: Raffaele Capasso
Molecules 2021, 26(9), 2531; https://doi.org/10.3390/molecules26092531
Received: 11 April 2021 / Revised: 20 April 2021 / Accepted: 23 April 2021 / Published: 26 April 2021
(This article belongs to the Section Natural Products Chemistry)
Combretum quadrangulare 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 C. quadrangulare 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 C. quadrangulare using bioactive guided isolation was undertaken. In this paper, the isolation and structure elucidation of twelve known compounds, 5-hydroxy-3,7,4′-trimethoxyflavone (1), ayanin (2), kumatakenin (3), rhamnocitrin (4), ombuin (5), myricetin-3,7,3′,5′-tetramethyl ether (6), gardenin D (7), luteolin (12), apigenin (13), mearnsetin (14), isoorientin (15), and vitexin (16) were reported. Bromination was applied to compounds 2 and 3 to provide four new synthetic analogues 811. All isolated and synthesized compounds were evaluated for alpha-glucosidase inhibition and antibacterial activity. Compounds 4 and 5 showed moderate antibacterial activity against methicillin-resistant Staphylococcus aureus while others were inactive. All compounds failed to reveal any activity toward extended spectrum beta-lactamase-producing Escherichia coli. Compounds 2, 4, 69, and 1114 showed good alpha-glucosidase inhibition with IC50 values in the range of 30.5–282.0 µM. The kinetic of enzyme inhibition showed that 8 and 11 were noncompetitive type inhibition against alpha-glucosidase. In silico molecular docking model indicated that compounds 8 and 11 were potential inhibitors against enzyme α-glucosidase. View Full-Text
Keywords: Combretum quadrangulare Kurz; flavonoid; alpha-glucosidase; antibacterial; molecular docking Combretum quadrangulare Kurz; flavonoid; alpha-glucosidase; antibacterial; molecular docking
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MDPI and ACS Style

Dao, T.-B.-N.; Nguyen, T.-M.-T.; Nguyen, V.-Q.; Tran, T.-M.-D.; Tran, N.-M.-A.; Nguyen, C.H.; Nguyen, T.-H.-T.; Nguyen, H.-H.; Sichaem, J.; Tran, C.-L.; Duong, T.-H. Flavones from Combretum quadrangulare Growing in Vietnam and Their Alpha-Glucosidase Inhibitory Activity. Molecules 2021, 26, 2531. https://doi.org/10.3390/molecules26092531

AMA Style

Dao T-B-N, Nguyen T-M-T, Nguyen V-Q, Tran T-M-D, Tran N-M-A, Nguyen CH, Nguyen T-H-T, Nguyen H-H, Sichaem J, Tran C-L, Duong T-H. Flavones from Combretum quadrangulare Growing in Vietnam and Their Alpha-Glucosidase Inhibitory Activity. Molecules. 2021; 26(9):2531. https://doi.org/10.3390/molecules26092531

Chicago/Turabian Style

Dao, Thi-Bich-Ngoc; Nguyen, Truong-Minh-Tri; Nguyen, Van-Quy; Tran, Thi-Minh-Dinh; Tran, Nguyen-Minh-An; Nguyen, Chuong H.; Nguyen, Thi-Hoai-Thu; Nguyen, Huu-Hung; Sichaem, Jirapast; Tran, Cong-Luan; Duong, Thuc-Huy. 2021. "Flavones from Combretum quadrangulare Growing in Vietnam and Their Alpha-Glucosidase Inhibitory Activity" Molecules 26, no. 9: 2531. https://doi.org/10.3390/molecules26092531

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