Chemical Constituents of the Stem Bark of Bombax ceiba

Sichaem, Jirapast; Inthanon, Kewalin; Funnimid, Nutthapol; Phontree, Kiettipum; Phan, Hoang-Vinh-Truong; Tran, Thi-Minh-Dinh; Niamnont, Nakorn; Srikittiwanna, Kittiwat; Sedlak, Suttira; Duong, Thuc‐Huy

doi:10.1007/s10600-020-03183-z

Cited by 7 publications

(3 citation statements)

References 10 publications

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“…Signals due to two sp 2 aromatic quaternary species were observed at δ C 122.4 (C-1′) and 105.4(C-4a), along with five sp 2 methine carbons at δ C 122.4(C-2′), 115.0(C-3′), 111.5(C-6′), 97.6 (C-6), and 91.8 (C-8). The above spectral data, along with comparison with the literature report, suggest that compound 5 is a flavonoid named quercetin 3,3,4′-trimethyl ether . The structure of compound 5 was also confirmed by 2D NMR, including COSY and HMBC (Figure S20).…”

Section: Resultsmentioning

confidence: 97%

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Antibacterial and Cytotoxicity of Extracts and Isolated Compounds from Artemisia abyssinica: A Combined Experimental and Computational Study

Tesfaye,

Endale,

Ramachandran

et al. 2024

ACS Omega

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Artemisia abyssinica is a widely cultivated hedge plant in Ethiopia. Traditionally, they have been used to treat a variety of health conditions, including intestinal problems, infectious diseases, tonsillitis, and leishmaniasis. Silica gel chromatographic separation of the methanol and ethyl acetate extracts of the leaves, roots, and stem barks of A. abyssinica led to the isolation of 12 compounds, labeled as 1−12. Among these, compounds 1, 3, 4, 5, and 7−11 are reported as new to the genus Artemisia. The extracts and isolated compounds from A. abyssinica were evaluated for their in vitro antibacterial activity against four bacterial strains: Streptococcus pyogenes, Staphylococcus aureus, Pseudomonas aeruginosa, and Escherichia coli, using the disc diffusion assay. All of the extracts displayed weak antibacterial activity, with inhibition zone diameters (IZDs) ranging from 6.10 ± 0.3 to 9.30 ± 0.20 mm. The isolated compounds, on the other hand, exhibited weak to moderate antibacterial activity, with IZDs ranging from 6.00 ± 0.300 to 13.50 ± 0.50 mm. The most potent antibacterial activity was observed for compound 6, which showed an IZD of 13.30 ± 0.50 mm against E. coli and 13.50 ± 0.50 mm against P. aeruginosa. This activity was comparable to that of the positive control ceftriaxone, which had IZDs of 14.1 ± 0.3 and 13.8 ± 0.5 mm against E. coli and P. aeruginosa, respectively. The in silico molecular docking analysis against DNA gyrase B revealed that compound 5 showed a higher binding affinity (−6.9 kcal/mol), followed by compound 10 (−6.7 kcal/mol) and compound 12 (−6.3 kcal/mol), whereas ciprofloxacin showed −7.3 kcal/mol. The binding affinities of compounds 5, 11, 10, and 9 were found to be −5.0, −4.3, −4.2, and −4.0 kcal/mol against S. aureus Pyruvate kinase, respectively, whereas ciprofloxacin showed a binding affinity of −4.9 kcal/mol, suggesting that compound 5 had a better binding affinity compared with ciprofloxacin. The effect of extracts of A. abyssinica was evaluated for cytotoxic activity against the breast cancer cell line (MCF-7) by the MTT assay. The extracts induced a decrease in cell viability and exerted a cytotoxic effect at a concentration of 20 μg/mL. The highest percent cell viability was observed for the methanol extract of the stem (92.9%), whereas the least was observed for the methanol extract of the root (34.5%). The result of the latter was significant compared with the positive control. The binding affinities of the isolated compounds were also assessed against human topoisomerase inhibitors IIβ. Results showed that compound 5 showed a binding affinity of −6.0 kcal/mol, followed by 11 (−5.4 kcal/mol), 10 (−5.0 kcal/mol), and 11 (−4.9 kcal/mol). Similar to ciprofloxacin, compounds 4, 5, 6, 9, 10, and 12 comply with Lipinski's rule of five. Overall, the comprehensive investigation of the chemical constituents and their biological activities reinforces the traditional medicinal applications of A. abyssinica and warrants further exploration of this plant as a source of novel therapeut...

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Section: Resultsmentioning

confidence: 97%

“…The above spectral data, along with comparison with the literature report, suggest that compound 5 is a flavonoid named quercetin 3,3,4′-trimethyl ether. 32 The structure of compound 5 was also confirmed by 2D NMR, including COSY and HMBC (Figure S20).…”

Section: Resultsmentioning

confidence: 98%

Antibacterial and Cytotoxicity of Extracts and Isolated Compounds from Artemisia abyssinica: A Combined Experimental and Computational Study

Tesfaye,

Endale,

Ramachandran

et al. 2024

ACS Omega

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“…Lupeol was isolated from the Vietnamese plant Bombax ceiba, following our previously reported procedure [8]. Lupeol was transformed to products 2, 2a, and 2b using oxidation with Oxone ® , a potassium triple-salt (KHSO 5 •1/2KHSO 4 •1/2K 2 SO 4 ) [6,9].…”

Section: Synthesismentioning

confidence: 99%

New Derivatives of Lupeol and Their Biological Activity

Chau

Duong

et al. 2021

Molbank

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The natural product lupeol (1) was isolated from Bombax ceiba leaves, which were used as starting material in the semisynthetic approach. Three new derivatives (2a, 2b, and 3) were synthesized using oxidation and aldolization. Their chemical structures were elucidated by spectroscopic analyses (HRESIMS and NMR). Compounds 3 showed significant α-glucosidase inhibition with an IC50 value of 202 µM, whereas 2a and 2b were inactive.

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