Structural and Microbiological Characterization of 5-Hydroxy-3,7,4′-Trimethoxyflavone: A Flavonoid Isolated from <i>Vitex gardneriana</i> Schauer Leaves

Macedo, Iasminy; Silva, João Hermínio da; Silva, Priscila T. da; Cruz, Beatriz Gonçalves; Vale, Jean Parcelli Costa do; Santos, Hélcio Silva dos; Bandeira, Paulo Nogueira; Souza, Elnatan Bezerra de; Xavier, Maria Regivânia; Coutinho, Henrique Douglas Melo; Braz-Filho, Raimundo; Teixeira, Alexandre Magno Rodrigues

doi:10.1089/mdr.2018.0359

Cited by 22 publications

(16 citation statements)

References 22 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…From the Vietnamese plant C. quadrangulare, twelve alpha-glucosidase inhibitors were isolated and elucidated, including 5-hydroxy-3,7,4 -trimethoxyflavone (1), ayanin (2), kamatakenin (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). To the best of our knowledge, compounds 4-7 and 12-14 were reported for the first time from C. quadrangulare.…”

Section: Discussionmentioning

confidence: 99%

“…The crude extract were fractioned and purified using chromatographic techniques to furnish 5-hydroxy-3,7,4 -trimethoxyflavone (1) [14], ayanin (2) [15], kumatakenin (3) [16], rhamnocitrin (4) [17], ombuin (5) [18], myricetin-3,7,3 ,5 -tetramethyl ether (6) [19], gardenin D (7) [20], luteolin (12) [21], apigenin (13) [22], mearnsetin (14) [23], vitexin (15) [24], and isoorientin (16) [25] (Figure 1). These were identified by comparing their NMR spectra with published data (Tables S1 and S2).…”

Section: Phytochemical Study and Derivatization Of Compounds 2 Andmentioning

confidence: 99%

See 1 more Smart Citation

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

Dao¹,

Nguyen²,

Nguyen³

et al. 2021

Molecules

View full text Add to dashboard Cite

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 8–11. 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, 6–9, and 11–14 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.

show abstract

Section: Discussionmentioning

confidence: 99%

Section: Phytochemical Study and Derivatization Of Compounds 2 Andmentioning

confidence: 99%

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

Dao¹,

Nguyen²,

Nguyen³

et al. 2021

Molecules

View full text Add to dashboard Cite

show abstract

“…Nitric oxide (NO) participates in various responses of host resistance to various pathogens and joins to adjust various aspects of life such as vascular integrity, maintains hemostasis, or modulates neural activity [ 36 , 37 ]. The overproduction of NO induced pathological problems related to acute and chronic inflammatory, apoptosis and necrosis, or neurodegenerative diseases [ 38 , 39 ].…”

Section: Resultsmentioning

confidence: 99%

“…Compounds 1-5, 7-11, and 13-17 were isolated for the first time from E. japonicum (Figure 1). [36,37]. e overproduction of NO induced pathological problems related to acute and chronic inflammatory, apoptosis and necrosis, or neurodegenerative diseases [38,39].…”

Section: Isolation and Ms/nmr Elucidation Of Compounds 1-17mentioning

confidence: 99%

Chemical Constituents of Eupatorium japonicum and Anti-Inflammatory, Cytotoxic, and Apoptotic Activities of Eupatoriopicrin on Cancer Stem Cells

Giang

Thao

Nguyen

et al. 2021

Evidence-Based Complementary and Alternative Medicine

View full text Add to dashboard Cite

Eupatorium japonicum Thunb. of the plant family Asteraceae is a popular traditional herb in Vietnam. However, its chemical constituents as well as bioactive principles have not been investigated yet. We investigated the phytochemistry of E. japonicum in Vietnam and isolated seventeen compounds (1–17) including phytosterols, terpenoids, phenolic acids, flavonoids, fatty alcohols, and fatty acids. They were structurally determined by MS and NMR analysis. Except for compounds 6 and 12, all the other compounds were identified for the first time from E. japonicum. Since many sesquiterpene lactones with α-methylene γ-lactone ring are reported as anti-inflammatory and anticancer agents, eupatoriopicrin (10), 1-hydroxy-8-(4,5-dihydroxytigloyloxy)eudesma-4(15),11(13)-dien-6,12-olide (11) were selected among the isolates for biological assays. Compound 10 was identified as the main bioactive sesquiterpene lactone of E. japonicum showing its potent anti-inflammatory and cytotoxic activity through inhibiting NO production and the growth of HepG2 and MCF-7 human cancer cell lines. For the first time, eupatoriopicrin (10) was demonstrated to strongly inhibit NTERA-2 human cancer stem cell (CSC) line in vitro. It is noticeable that the cytotoxicity of eupatoriopicrin against NTERA-2 cells is mediated by its apoptosis-inducing capability of 10 as demonstrated by the results of Hoechst 33342 staining, flow cytometry apoptosis analysis, and caspase-3 activity assays. The biological activities of the main bioactive constituents 1–7, 10, 12, and 15 supported the reported anti-inflammatory and anticancer properties of extracts from E. japonicum.

show abstract

“…The literature review provides numerous reports indicating that flavonoids, including naringenin, may potentiate the antimicrobial effect of various groups of antibiotics [ 36 , 43 , 44 ]. Despite the apparent non-selectivity of flavonoids in the enhancing of antibiotic activity, a closer analysis indicates representatives of beta-lactam antibiotics, glycopeptides, fluoroquinolones, nitroimidazoles, aminoglycosides, tetracyclines, and macrolides [ 36 , 42 , 43 , 44 , 45 , 46 , 47 ]. Knowledge of their target site on a bacterial cell [ 48 ] allowed us to conclude that flavonoids enhance the activity of antibiotics acting on the cell wall, genetic material, or protein synthesis.…”

Section: Resultsmentioning

confidence: 99%

Antimicrobial O-Alkyl Derivatives of Naringenin and Their Oximes Against Multidrug-Resistant Bacteria

et al. 2020

View full text Add to dashboard Cite

New antimicrobial agents are needed to address infections caused by multidrug-resistant bacteria. Here, we are reporting novel O-alkyl derivatives of naringenin and their oximes, including novel compounds with a naringenin core and O-hexyl chains, showing activity against clinical strains of clarithromycin-resistant Helicobacter pylori, vancomycin-resistant Enterococcus faecalis, methicillin-resistant Staphylococcus aureus, and beta-lactam-resistant Acinetobacter baumannii and Klebsiella pneumoniae. The minimum inhibitory concentrations (MICs), which provide a quantitative measure of antimicrobial activity, were in the low microgram range for the selected compounds. Checkerboard assays for the most active compounds in combination with antibiotics revealed interactions that varied from synergistic to neutral.

show abstract

Structural and Microbiological Characterization of 5-Hydroxy-3,7,4′-Trimethoxyflavone: A Flavonoid Isolated from Vitex gardneriana Schauer Leaves

Cited by 22 publications

References 22 publications

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

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

Chemical Constituents of Eupatorium japonicum and Anti-Inflammatory, Cytotoxic, and Apoptotic Activities of Eupatoriopicrin on Cancer Stem Cells

Antimicrobial O-Alkyl Derivatives of Naringenin and Their Oximes Against Multidrug-Resistant Bacteria

Contact Info

Product

Resources

About