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Antioxidant capacity of the leaf extract obtained from Arrabidaea chica cultivated in Southern Brazil.

Siraichi JT, Felipe DF, Brambilla LZ, Gatto MJ, Terra VA, Cecchini AL, Cortez LE, Rodrigues-Filho E, Cortez DA - PLoS ONE (2013)

Bottom Line: The 2 main flavonoids, scutellarein and apigenin, were separated, and their antioxidant activity was found to be the same as that of the plant extract.These 2 flavonoids were quantified in the plant extract by using a validated HPLC-UV method.The results of these tests showed that the extract of A. chica had a significant antioxidant activity, which could be attributed to the presence of the mixture of flavonoids in the plant extract, with the main contribution of scutellarein and apigenin.

View Article: PubMed Central - PubMed

Affiliation: Pharmaceutical Sciences Postgraduate Program, Universidade Estadual de Maringá, Maringá, State of Paraná, Brazil.

ABSTRACT
Arrabidaea chica leaf extract has been used by people as an anti-inflammatory and astringent agent as well as a remedy for intestinal colic, diarrhea, leucorrhea, anemia, and leukemia. A. chica is known to be a good producer of phenolics. Therefore, in the present study, we investigated its antioxidant activity. The phenolic composition of A. chica leaves was studied by liquid chromatography coupled to diode array detection (LC-DAD) and liquid chromatography coupled to electrospray ionization-tandem mass spectrometry (LC-ESI-MS/MS), and isoscutellarein, 6-hydroxyluteolin, hispidulin, scutellarein, luteolin, and apigenin were identified. The extract from leaves of A. chica was tested for antioxidant activity using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) method, β-carotene bleaching test, and total reactive antioxidant potential (TRAP) method. The crude extract quenched DPPH free radicals in a dose-dependent manner, and the IC50 of the extract was 13.51 µg/mL. The β-carotene bleaching test showed that the addition of the A. chica extract in different concentrations (200 and 500 µg/mL) prevented the bleaching of β-carotene at different degrees (51.2% ±3.38% and 94% ±4.61%, respectively). The TRAP test showed dose-dependent correlation between the increasing concentrations of A. chica extract (0.1, 0.5, and 1.0 µg/mL) and the TRAP values obtained by trolox (hydro-soluble vitamin E) 0.4738±0.0466, 1.981±0.1603, and 6.877±1.445 µM, respectively. The 2 main flavonoids, scutellarein and apigenin, were separated, and their antioxidant activity was found to be the same as that of the plant extract. These 2 flavonoids were quantified in the plant extract by using a validated HPLC-UV method. The results of these tests showed that the extract of A. chica had a significant antioxidant activity, which could be attributed to the presence of the mixture of flavonoids in the plant extract, with the main contribution of scutellarein and apigenin.

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LC–DAD chromatogram at 335 nm of the hydroethanolic extract of Arrabidaea chica leaves.The peaks are labeled according to the compounds listed in Table 1.
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pone-0072733-g001: LC–DAD chromatogram at 335 nm of the hydroethanolic extract of Arrabidaea chica leaves.The peaks are labeled according to the compounds listed in Table 1.

Mentions: The crude extract was also analyzed by LC-UV-MS/MS. The LC-UV chromatogram (Figure 1) with diode array detection (DAD) shows the presence of other minor flavonoids such as compounds 3 (isoscutellarein), 5 (6-hydroxyluteolin), 6 (hispidulin), and 7 (luteolin) [28]–[31]. These compounds belong to the same flavone sub-class of flavonoids and produced UV-spectra with almost the same molar absorptivity at 335 nm. Therefore, the peaks at 9.8 (1) and 13.7 (2) min accounted majorly for the polyphenolic composition of the extract. The polyphenolic flavones could be identified by MS-MS ion scans. The collision of the precursor ions produced by ESI in the negative ion mode from the detected flavones yielded mass spectra for product ions; these spectra were used for their structural identification (Table 1). The most important product ions were produced by the retro-Diels-Alder type fragmentation at ring-C (dihydropyran ring), where the bond cleavage occurred at O(1)-C(2) and C(3)-C(4), resulting in anionic fragments containing ring A (m/z 151 and 167 respectively for di- and trihydroxylated ring A) and ring B (m/z 117 and 133 respectively for mono- and dihydroxylated ring B). Only compound 6 (hispidulin), which contains a methoxyl group at ring A, did not follow this fragmentation behavior. The first cleavage in this molecule is related to the loss of a radicalar methyl group; therefore, the path of fragmentation differed from the other flavones, and the retro-Diels-Alder fragmentation produced only minor fragments in its product ion spectrum.


Antioxidant capacity of the leaf extract obtained from Arrabidaea chica cultivated in Southern Brazil.

Siraichi JT, Felipe DF, Brambilla LZ, Gatto MJ, Terra VA, Cecchini AL, Cortez LE, Rodrigues-Filho E, Cortez DA - PLoS ONE (2013)

LC–DAD chromatogram at 335 nm of the hydroethanolic extract of Arrabidaea chica leaves.The peaks are labeled according to the compounds listed in Table 1.
© Copyright Policy
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC3757019&req=5

pone-0072733-g001: LC–DAD chromatogram at 335 nm of the hydroethanolic extract of Arrabidaea chica leaves.The peaks are labeled according to the compounds listed in Table 1.
Mentions: The crude extract was also analyzed by LC-UV-MS/MS. The LC-UV chromatogram (Figure 1) with diode array detection (DAD) shows the presence of other minor flavonoids such as compounds 3 (isoscutellarein), 5 (6-hydroxyluteolin), 6 (hispidulin), and 7 (luteolin) [28]–[31]. These compounds belong to the same flavone sub-class of flavonoids and produced UV-spectra with almost the same molar absorptivity at 335 nm. Therefore, the peaks at 9.8 (1) and 13.7 (2) min accounted majorly for the polyphenolic composition of the extract. The polyphenolic flavones could be identified by MS-MS ion scans. The collision of the precursor ions produced by ESI in the negative ion mode from the detected flavones yielded mass spectra for product ions; these spectra were used for their structural identification (Table 1). The most important product ions were produced by the retro-Diels-Alder type fragmentation at ring-C (dihydropyran ring), where the bond cleavage occurred at O(1)-C(2) and C(3)-C(4), resulting in anionic fragments containing ring A (m/z 151 and 167 respectively for di- and trihydroxylated ring A) and ring B (m/z 117 and 133 respectively for mono- and dihydroxylated ring B). Only compound 6 (hispidulin), which contains a methoxyl group at ring A, did not follow this fragmentation behavior. The first cleavage in this molecule is related to the loss of a radicalar methyl group; therefore, the path of fragmentation differed from the other flavones, and the retro-Diels-Alder fragmentation produced only minor fragments in its product ion spectrum.

Bottom Line: The 2 main flavonoids, scutellarein and apigenin, were separated, and their antioxidant activity was found to be the same as that of the plant extract.These 2 flavonoids were quantified in the plant extract by using a validated HPLC-UV method.The results of these tests showed that the extract of A. chica had a significant antioxidant activity, which could be attributed to the presence of the mixture of flavonoids in the plant extract, with the main contribution of scutellarein and apigenin.

View Article: PubMed Central - PubMed

Affiliation: Pharmaceutical Sciences Postgraduate Program, Universidade Estadual de Maringá, Maringá, State of Paraná, Brazil.

ABSTRACT
Arrabidaea chica leaf extract has been used by people as an anti-inflammatory and astringent agent as well as a remedy for intestinal colic, diarrhea, leucorrhea, anemia, and leukemia. A. chica is known to be a good producer of phenolics. Therefore, in the present study, we investigated its antioxidant activity. The phenolic composition of A. chica leaves was studied by liquid chromatography coupled to diode array detection (LC-DAD) and liquid chromatography coupled to electrospray ionization-tandem mass spectrometry (LC-ESI-MS/MS), and isoscutellarein, 6-hydroxyluteolin, hispidulin, scutellarein, luteolin, and apigenin were identified. The extract from leaves of A. chica was tested for antioxidant activity using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) method, β-carotene bleaching test, and total reactive antioxidant potential (TRAP) method. The crude extract quenched DPPH free radicals in a dose-dependent manner, and the IC50 of the extract was 13.51 µg/mL. The β-carotene bleaching test showed that the addition of the A. chica extract in different concentrations (200 and 500 µg/mL) prevented the bleaching of β-carotene at different degrees (51.2% ±3.38% and 94% ±4.61%, respectively). The TRAP test showed dose-dependent correlation between the increasing concentrations of A. chica extract (0.1, 0.5, and 1.0 µg/mL) and the TRAP values obtained by trolox (hydro-soluble vitamin E) 0.4738±0.0466, 1.981±0.1603, and 6.877±1.445 µM, respectively. The 2 main flavonoids, scutellarein and apigenin, were separated, and their antioxidant activity was found to be the same as that of the plant extract. These 2 flavonoids were quantified in the plant extract by using a validated HPLC-UV method. The results of these tests showed that the extract of A. chica had a significant antioxidant activity, which could be attributed to the presence of the mixture of flavonoids in the plant extract, with the main contribution of scutellarein and apigenin.

Show MeSH
Related in: MedlinePlus