Flavonoids from the roots of Dioclea reflexa (Hook F.)

Oladimeji, Abdulkabir Oladele; Oladosu, I. A.; Ali, Mohammad; Ahmed, Zeeshan

doi:10.4314/bcse.v29i3.12

Cited by 14 publications

(5 citation statements)

References 11 publications

(23 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…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%

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: 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

“…While compounds 4 and 5 were isolated in low amounts and thus some signals were missing in their respective 1 H-NMR and 13 C-NMR spectra, the signal assignment for both compounds could be completed by using the respective spectra of the mixture of 4 and 5 . The known compounds were identified as 3’,4’,5,5’,7-pentahydroxyflavanone ( 6 ) [ 38 ] and mearnsetin ( 7 ) [ 39 ] by comparison of their NMR and MS data with those reported in the literature. A mixture of stigmasterol and β-sitosterol was also isolated and identified by comparison of the analytical TLC and IR spectra with a sample from our laboratory.…”

Section: Resultsmentioning

confidence: 99%

Prenylated Flavonoids and C-15 Isoprenoid Analogues with Antibacterial Properties from the Whole Plant of Imperata cylindrica (L.) Raeusch (Gramineae)

et al. 2021

View full text Add to dashboard Cite

The local botanical Imperata cylindrica in Cameroon was investigated for its antibacterial potency. The methanol extract afforded a total of seven compounds, including five hitherto unreported compounds comprising three flavonoids (1–3) and two C-15 isoprenoid analogues (4 and 5) together with known derivatives (6 and 7). The novelty of the flavonoids was related to the presence of both methyl and prenyl groups. The potential origin of the methyl in the flavonoids is discussed, as well as the chemophenetic significance of our findings. Isolation was performed over repeated silica gel and Sephadex LH-20 column chromatography and the structures were elucidated by (NMR and MS). The crude methanol extract and isolated compounds showed considerable antibacterial potency against a panel of multi-drug resistant (MDR) bacterial strains. The best MIC values were obtained with compound (2) against S. aureus ATCC 25923 (32 µg/mL) and MRSA1 (16 µg/mL).

show abstract

“…91-93°C; m/z 470) [31], 7-hydroxy-2-(4-hydroxyphenyl)-4 H -chromen-4-one, C 15 H 10 O 4 ( 3 ; m.p. 315°C; m/z 254) [32], and 6-hydroxy-2-(4-hydroxyphenyl)-4 H -chromen-4-one, C 15 H 10 O 4 ( 4 ; m.p. 325°C; m/z 254 ) [33] (Figure 1).…”

Section: Resultsmentioning

confidence: 99%

Cytotoxicity of Crude Extract and Isolated Constituents of theDichrostachys cinereaBark towards Multifactorial Drug-Resistant Cancer Cells

Mbaveng

Damen

Mpetga

et al. 2019

Evidence-Based Complementary and Alternative Medicine

View full text Add to dashboard Cite

The effectiveness of anticancer chemotherapy is greatly impeded by the resistance of malignant cells to cytotoxic drugs. In this study, the cytotoxicity of the crude extract (DCB) and compounds isolated from the bark of Dichrostachys cinerea, namely, betulinic acid (1), glyceryl-1-hexacosanoate (2), 7-hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one (3), and 6-hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one (4), was investigated. The study was extended to the assessment of the mode of induction of apoptosis by DCB and compound 1. The resazurin reduction assay was used for cytotoxicity studies. Assessments of cell cycle distribution, apoptosis, mitochondrial membrane potential (MMP), and reactive oxygen species (ROS) were performed by flow cytometry. Constituents of DCB were isolated by column chromatography. Triterpenoid 1 and flavone 4 had cytotoxic effects towards the 9 tested cancer cell lines with IC50 values below 50 μM. The recorded IC50 values varied from 7.65 μM (towards multidrug-resistant CEM-ADR5000 leukemia cells) to 44.17 μM (against HepG2 hepatocarcinoma cells) for 1, 18.90 μM (CCRF-CEM leukemia cells) to 88.86 μM (against HCT116p53+/+ colon adenocarcinoma cells) for 4, and 0.02 μM (against CCRF-CEM cells) to 122.96 μM (against CEM/ADR5000 cells) for doxorubicin. DCB induced apoptosis in CCRF-CEM cells mostly mediated by MMP alteration and enhanced ROS production; compound 1 induced apoptosis through caspases activation and MMP alteration and increased ROS production. Dichrostachys cinerea is an interesting cytotoxic plant and deserves more studies leading to new antineoplastic agents to fight cancer and mostly leukemia.

show abstract

Flavonoids from the roots of Dioclea reflexa (Hook F.)

Cited by 14 publications

References 11 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

Prenylated Flavonoids and C-15 Isoprenoid Analogues with Antibacterial Properties from the Whole Plant of Imperata cylindrica (L.) Raeusch (Gramineae)

Cytotoxicity of Crude Extract and Isolated Constituents of theDichrostachys cinereaBark towards Multifactorial Drug-Resistant Cancer Cells

Contact Info

Product

Resources

About