Structural Design, Synthesis and Antioxidant, Antileishmania, Anti-Inflammatory and Anticancer Activities of a Novel Quercetin Acetylated Derivative
Quercetin (Q) is a bioflavonoid with biological potential; however, poor solubility in water, extensive enzymatic metabolism and a reduced bioavailability limit its biopharmacological use. The aim of this study was to perform structural modification in Q by acetylation, thus, obtaining the quercetin...
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MDPI AG
2021-11-01
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| Online Access: | https://www.mdpi.com/1420-3049/26/22/6923 |
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| author | Saul Vislei Simões da Silva Orlando Maia Barboza Jéssica Teles Souza Érica Novaes Soares Cleonice Creusa dos Santos Luciano Vasconcellos Pacheco Ivanilson Pimenta Santos Tatiana Barbosa dos Santos Magalhães Milena Botelho Pereira Soares Elisalva Teixeira Guimarães Cássio Santana Meira Silvia Lima Costa Victor Diógenes Amaral da Silva Lourenço Luís Botelho de Santana Aníbal de Freitas Santos Júnior |
| author_facet | Saul Vislei Simões da Silva Orlando Maia Barboza Jéssica Teles Souza Érica Novaes Soares Cleonice Creusa dos Santos Luciano Vasconcellos Pacheco Ivanilson Pimenta Santos Tatiana Barbosa dos Santos Magalhães Milena Botelho Pereira Soares Elisalva Teixeira Guimarães Cássio Santana Meira Silvia Lima Costa Victor Diógenes Amaral da Silva Lourenço Luís Botelho de Santana Aníbal de Freitas Santos Júnior |
| author_sort | Saul Vislei Simões da Silva |
| collection | DOAJ |
| description | Quercetin (Q) is a bioflavonoid with biological potential; however, poor solubility in water, extensive enzymatic metabolism and a reduced bioavailability limit its biopharmacological use. The aim of this study was to perform structural modification in Q by acetylation, thus, obtaining the quercetin pentaacetate (Q5) analogue, in order to investigate the biological potentials (antioxidant, antileishmania, anti-inflammatory and cytotoxicity activities) in cell cultures. Q5 was characterized by FTIR, <sup>1</sup>H and <sup>13</sup>C NMR spectra. The antioxidant potential was evaluated against the radical ABTS<sup>•+</sup>. The anti-inflammatory potential was evaluated by measuring the pro-inflammatory cytokine tumor necrosis factor (TNF) and the production of nitric oxide (NO) in peritoneal macrophages from BALB/c mice. Cytotoxicity tests were performed using the AlamarBlue method in cancer cells HepG2 (human hepatocarcinoma), HL-60 (promyelocytic leukemia) and MCR-5 (healthy human lung fibroblasts) as well as the MTT method for C6 cell cultures (rat glioma). Q and Q5 showed antioxidant activity of 29% and 18%, respectively, which is justified by the replacement of hydroxyls by acetyl groups. Q and Q5 showed concentration-dependent reductions in NO and TNF production (<i>p</i> < 0.05); Q and Q5 showed higher activity at concentrations > 40µM when compared to dexamethasone (20 µM). For the HL-60 lineage, Q5 demonstrated selectivity, inducing death in cancer cells, when compared to the healthy cell line MRC-5 (IC<sub>50</sub> > 80 µM). Finally, the cytotoxic superiority of Q5 was verified (IC<sub>50</sub> = 11 µM), which, at 50 µM for 24 h, induced changes in the morphology of C6 glioma cells characterized by a round body shape (not yet reported in the literature). The analogue Q5 had potential biological effects and may be promising for further investigations against other cell cultures, particularly neural ones. |
| first_indexed | 2024-03-10T05:13:54Z |
| format | Article |
| id | doaj.art-00138d6cee3c4b6e81565a22ed606e54 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T05:13:54Z |
| publishDate | 2021-11-01 |
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| series | Molecules |
| spelling | doaj.art-00138d6cee3c4b6e81565a22ed606e542023-11-23T00:35:49ZengMDPI AGMolecules1420-30492021-11-012622692310.3390/molecules26226923Structural Design, Synthesis and Antioxidant, Antileishmania, Anti-Inflammatory and Anticancer Activities of a Novel Quercetin Acetylated DerivativeSaul Vislei Simões da Silva0Orlando Maia Barboza1Jéssica Teles Souza2Érica Novaes Soares3Cleonice Creusa dos Santos4Luciano Vasconcellos Pacheco5Ivanilson Pimenta Santos6Tatiana Barbosa dos Santos Magalhães7Milena Botelho Pereira Soares8Elisalva Teixeira Guimarães9Cássio Santana Meira10Silvia Lima Costa11Victor Diógenes Amaral da Silva12Lourenço Luís Botelho de Santana13Aníbal de Freitas Santos Júnior14Department of Life Sciences, State University of Bahia (UNEB), Salvador 41150-000, BA, BrazilDepartment of Life Sciences, State University of Bahia (UNEB), Salvador 41150-000, BA, BrazilLaboratory of Neurochemistry and Cell Biology, Department of Biochemistry and Biophysics, Federal University of Bahia, Salvador 40231-300, BA, BrazilLaboratory of Neurochemistry and Cell Biology, Department of Biochemistry and Biophysics, Federal University of Bahia, Salvador 40231-300, BA, BrazilLaboratory of Neurochemistry and Cell Biology, Department of Biochemistry and Biophysics, Federal University of Bahia, Salvador 40231-300, BA, BrazilDepartment of Life Sciences, State University of Bahia (UNEB), Salvador 41150-000, BA, BrazilGonçalo Moniz Institute, FIOCRUZ, Salvador 40296-710, BA, BrazilDepartment of Life Sciences, State University of Bahia (UNEB), Salvador 41150-000, BA, BrazilGonçalo Moniz Institute, FIOCRUZ, Salvador 40296-710, BA, BrazilDepartment of Life Sciences, State University of Bahia (UNEB), Salvador 41150-000, BA, BrazilDepartment of Life Sciences, State University of Bahia (UNEB), Salvador 41150-000, BA, BrazilLaboratory of Neurochemistry and Cell Biology, Department of Biochemistry and Biophysics, Federal University of Bahia, Salvador 40231-300, BA, BrazilLaboratory of Neurochemistry and Cell Biology, Department of Biochemistry and Biophysics, Federal University of Bahia, Salvador 40231-300, BA, BrazilDepartment of Life Sciences, State University of Bahia (UNEB), Salvador 41150-000, BA, BrazilDepartment of Life Sciences, State University of Bahia (UNEB), Salvador 41150-000, BA, BrazilQuercetin (Q) is a bioflavonoid with biological potential; however, poor solubility in water, extensive enzymatic metabolism and a reduced bioavailability limit its biopharmacological use. The aim of this study was to perform structural modification in Q by acetylation, thus, obtaining the quercetin pentaacetate (Q5) analogue, in order to investigate the biological potentials (antioxidant, antileishmania, anti-inflammatory and cytotoxicity activities) in cell cultures. Q5 was characterized by FTIR, <sup>1</sup>H and <sup>13</sup>C NMR spectra. The antioxidant potential was evaluated against the radical ABTS<sup>•+</sup>. The anti-inflammatory potential was evaluated by measuring the pro-inflammatory cytokine tumor necrosis factor (TNF) and the production of nitric oxide (NO) in peritoneal macrophages from BALB/c mice. Cytotoxicity tests were performed using the AlamarBlue method in cancer cells HepG2 (human hepatocarcinoma), HL-60 (promyelocytic leukemia) and MCR-5 (healthy human lung fibroblasts) as well as the MTT method for C6 cell cultures (rat glioma). Q and Q5 showed antioxidant activity of 29% and 18%, respectively, which is justified by the replacement of hydroxyls by acetyl groups. Q and Q5 showed concentration-dependent reductions in NO and TNF production (<i>p</i> < 0.05); Q and Q5 showed higher activity at concentrations > 40µM when compared to dexamethasone (20 µM). For the HL-60 lineage, Q5 demonstrated selectivity, inducing death in cancer cells, when compared to the healthy cell line MRC-5 (IC<sub>50</sub> > 80 µM). Finally, the cytotoxic superiority of Q5 was verified (IC<sub>50</sub> = 11 µM), which, at 50 µM for 24 h, induced changes in the morphology of C6 glioma cells characterized by a round body shape (not yet reported in the literature). The analogue Q5 had potential biological effects and may be promising for further investigations against other cell cultures, particularly neural ones.https://www.mdpi.com/1420-3049/26/22/6923quercetinsynthesisquercetin pentaacetateantioxidantantileishmaniaanti-inflammatory |
| spellingShingle | Saul Vislei Simões da Silva Orlando Maia Barboza Jéssica Teles Souza Érica Novaes Soares Cleonice Creusa dos Santos Luciano Vasconcellos Pacheco Ivanilson Pimenta Santos Tatiana Barbosa dos Santos Magalhães Milena Botelho Pereira Soares Elisalva Teixeira Guimarães Cássio Santana Meira Silvia Lima Costa Victor Diógenes Amaral da Silva Lourenço Luís Botelho de Santana Aníbal de Freitas Santos Júnior Structural Design, Synthesis and Antioxidant, Antileishmania, Anti-Inflammatory and Anticancer Activities of a Novel Quercetin Acetylated Derivative Molecules quercetin synthesis quercetin pentaacetate antioxidant antileishmania anti-inflammatory |
| title | Structural Design, Synthesis and Antioxidant, Antileishmania, Anti-Inflammatory and Anticancer Activities of a Novel Quercetin Acetylated Derivative |
| title_full | Structural Design, Synthesis and Antioxidant, Antileishmania, Anti-Inflammatory and Anticancer Activities of a Novel Quercetin Acetylated Derivative |
| title_fullStr | Structural Design, Synthesis and Antioxidant, Antileishmania, Anti-Inflammatory and Anticancer Activities of a Novel Quercetin Acetylated Derivative |
| title_full_unstemmed | Structural Design, Synthesis and Antioxidant, Antileishmania, Anti-Inflammatory and Anticancer Activities of a Novel Quercetin Acetylated Derivative |
| title_short | Structural Design, Synthesis and Antioxidant, Antileishmania, Anti-Inflammatory and Anticancer Activities of a Novel Quercetin Acetylated Derivative |
| title_sort | structural design synthesis and antioxidant antileishmania anti inflammatory and anticancer activities of a novel quercetin acetylated derivative |
| topic | quercetin synthesis quercetin pentaacetate antioxidant antileishmania anti-inflammatory |
| url | https://www.mdpi.com/1420-3049/26/22/6923 |
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