In Vitro Phytotoxicity and Antioxidant Activity of Selected Flavonoids
Abstract
:1. Introduction
2. Results and Discussion
2.1. Phytotoxic Activity
2.2. Antioxidant Activity
3. Experimental Section
3.1. Flavonoids
3.2. Flavonoid Solutions
3.3. Phytotoxic Assay
3.4. Bleaching of the Free-Radical 1,1-Diphenyl-2-picrylhydrazyl (DPPH Test)
3.5. Statistical Analysis
4. Conclusions
References
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Raphanus sativus L. | Lepidium sativum L. | |||||
---|---|---|---|---|---|---|
Germinated seeds ± SD | Germinated seeds ± SD | |||||
10−6 M | 10−5 M | 10−4 M | 10−6 M | 10−5 M | 10−4 M | |
Control | 9.3 ± 0.8 | 9.3 ± 0.8 | 9.3 ± 0.8 | 9.5 ± 0.8 | 9.5 ± 0.8 | 9.5 ± 0.8 |
Flavone | 9.7 ± 0.6 | 8.0 ± 1.0 | 9.3 ± 0.6 | 9.8 ± 0.8 | 9.4 ± 0.8 | 9.4 ± 0.8 |
7-OH-Flavone | 9.3 ± 1.2 | 9.7 ± 0.6 | 8.7 ± 1.2 | 10.0 ± 0.0 | 10.0 ± 0.0 | 10.0 ± 0.0 |
7-OCH3-Flavone | 8.7 ± 0.7 | 9.0 ± 1.0 | 9.3 ± 1.2 | 8.8 ± 0.8 | 9.4 ± 0.8 | 8.8 ± 0.8 |
5,7-di-OH-Flavone (chrysin) | 9.3 ± 0.8 | 8.3 ± 1.5 | 8.7 ± 0.8 | 9.5 ± 0.8 | 9.1 ± 0.8 | 8.8 ± 1.3 |
5,7-di-OCH3-Flavone (chrysin dimethylether) | 9.0 ± 0.0 | 9.3 ± 1.5 | 9.7 ± 0.8 | 8.5 ± 1.5 | 9.5 ± 0.8 | 8.8 ± 1.3 |
3′,4′-di-OCH3-Flavone | 9.6 ± 0.9 | 9.6 ± 0.5 | 10.0 ± 0.6 | 10.0 ± 0.8 * | 10.3 ± 0.0 | 10.0 ± 0.8* |
5,7,3′,4′-tetra-OH-Flavone (luteolin) | 8.7 ± 0.8 | 8.3 ± 2.0 | 9.0 ± 1.3 | 8.5 ± 2.8 | 9.1 ± 1.5 | 9.5 ± 0.8 |
5,7,3′,4′-tetra-OCH3-Flavone (luteolin tetramethylether) | 9.3 ± 1.5 | 9.0 ± 1.3 | 9.0 ± 1.3 | 9.1 ± 0.8 | 9.8 ± 1.3 | 6.9 ± 4.8 |
3-OH-Flavone | 9.0 ± 1.7 | 9.0 ± 1.0 | 9.3 ± 0.6 | 10.0 ± 0.0 | 10.0 ± 0.0 | 8.8 ± 2.0 |
3-OCH3-Flavone | 9.7 ± 0.6 | 8.7 ± 1.5 | 8.0 ± 1.0 | 7.6 ± 0.9 * | 8.4 ± 1.5 | 9.8 ± 0.8 |
2′,3,4′,5,7-penta-OH-Flavone (morin) | 8.7 ± 1.2 | 8.4 ± 1.0 | 9.0 ± 0.6 | 7.9 ± 1.5 | 8.9 ± 1.2 | 8.9 ± 0.6 |
3,5,7,3′,4′-penta-OH-Flavone (quercetin) | 9.0 ± 0.6 | 8.7 ± 0.6 | 9.0 ± 0.6 | 8.2 ± 0.6* | 8.9 ± 0.6 | 9.5 ± 0.0 |
Quercetin-3-rutinoside (rutin) | 9.0 ± 1.3 | 9.3 ± 1.5 | 9.3 ± 1.5 | 8.9 ± 0.8 | 9.2 ± 0.0 | 8.9 ± 0.8 |
β-Naphtoflavone | 9.0 ± 0.8 | 7.4 ± 4.3 | 8.6 ± 1.3 | 10.0 ± 0.0 | 10.0 ± 0.0 | 9.9 ± 0.8 |
4′,5,7-tri-OH-Isoflavone | 9.0 ± 1.0 | 8.7 ± 0.6 | 9.0 ± 1.0 | 8.9 ± 0.8 | 9.2 ± 1.3 | 8.0 ± 0.8 * |
Flavanone | 9.3 ± 0.6 | 9.6 ± 0.0 | 8.2 ± 0.8 | 9.9 ± 0.8 | 10.0 ± 0.8 | 10.0 ± 0.8 |
7-OH-Flavanone | 9.3 ± 0.3 | 10.0 ± 0.3 | 9.3 ± 0.3 | 10.0 ± 0.8 | 10.0 ± 0.8 | 10.0 ± 0.8 * |
7-OCH3-Flavanone | 9.6 ± 0.9 | 9.6 ± 0.5 | 10.0 ± 0.3 | 10.0 ± 0.8 | 9.9 ± 2.0 | 10.0 ± 0.8 |
5,7-di-OH-Flavanone (pinocembrin) | 8.3 ± 1.5 | 8.0 ± 0.0 * | 9.7 ± 0.8 | 9.2 ± 1.3 | 8.9 ± 0.8 | 8.9 ± 0.8 |
5,7-di-OCH3-Flavanone | 9.3 ± 1.5 | 9.0 ± 1.3 | 9.0 ± 0.0 | 9.1 ± 0.8 | 9.8 ± 0.0 | 8.5 ± 0.8 |
(2S)-4′,5,7-tri-OH-Flavanone (naringenin) | 9.0 ± 1.3 | 9.3 ± 0.8 | 9.3 ± 1.5 | 8.6 ± 1.5 | 8.3 ± 0.0 | 8.6 ± 0.8 |
Naringin (naringenin 7-rhamnoglucoside) | 8.7 ± 2.0 | 8.3 ± 0.8 | 9.3 ± 0.8 | 8.3 ± 1.3 | 8.9 ± 0.8 | 8.3 ± 1.3 |
3′,5,7-tri-OH-4′-OCH3-Flavanone (hesperetin) | 8.6 ± 1.3 | 9.0 ± 1.5 | 8.6 ± 1.3 | 10.0 ± 0.0 | 10.0 ± 0.0 | 9.9 ± 0.8 |
Hesperidin (hesperetin 7-rutinoside) | 9.0 ± 0.8 | 8.3 ± 2.0 | 8.3 ± 0.8 | 9.7 ± 0.9 | 8.7 ± 2.8 | 10.0 ± 1.9 |
(+)-Catechin | 9.3 ± 0.8 | 9.3 ± 0.8 | 9.3 ± 0.8 | 9.9 ± 0.8 | 9.9 ± 0.8 | 8.2 ± 1.3 |
Catechol | 9.6 ± 0.0 | 9.6 ± 0.0 | 9.6 ± 0.0 | 9.2 ± 2.3 | 9.5 ± 1.5 | 8.2 ± 2.3 |
Phloridzin | 9.0 ± 0.6 | 9.0 ± 0.6 | 8.7 ± 0.6 | 8.9 ± 0.6 | 9.2 ± 0.6 | 9.2 ± 0.6 |
Raphanus sativus L. | Lepidium sativum L. | |||||
---|---|---|---|---|---|---|
Radical elongation ± SD | Radical elongation ± SD | |||||
10−6 M | 10−5 M | 10−4 M | 10−6 M | 10−5 M | 10−4 M | |
Control | 5.2 ± 2.8 | 5.2 ± 2.8 | 5.2 ± 2.8 | 3.6 ± 2.3 | 3.6 ± 2.3 | 3.6 ± 2.3 |
Flavone | 7.0 ± 4.7 | 4.5 ± 3.2 | 5.0 ± 2.4 | 3.7 ± 1.9 | 4.2 ± 2.3 | 2.3 ± 1.4** |
7-OH-Flavone | 7.1 ± 2.8* | 3.7 ± 2.1** | 5.8 ± 3.1 | 3.7 ± 2.6 | 3.2 ± 2.4 | 3.7 ± 2.3 |
7-OCH3-Flavone | 4.3 ± 3.5 | 4.1 ± 3.2 | 2.9 ± 1.9*** | 2.8 ± 2.0 | 2.6 ± 2.0 | 2.4 ± 1.6** |
5,7-di-OH-Flavone (chrysin) | 7.1 ± 2.4* | 4.9 ± 2.5 | 2.7 ± 1.5*** | 4.7 ± 2.2 | 4.9 ± 2.6 | 4.8 ± 2.7 |
5,7-di-OCH3-Flavone (chrysin dimethylether) | 3.9 ± 2.5 | 1.9 ± 1.7*** | 0.4 ± 0.2*** | 4.9 ± 2.8 | 2.1 ± 1.1** | 0.2 ± 0.1*** |
3′,4′-di-OCH3-Flavone | 3.1 ± 2.2** | 5.4 ± 2.5 | 3.2 ± 1.9** | 2.7 ± 1.5 | 2.3 ± 1.5* | 2.3 ± 1.5* |
5,7,3′,4′-tetra-OH-Flavone (luteolin) | 5.1 ± 2.0 | 6.8 ± 2.2* | 4.2 ± 2.7 | 4.0 ± 1.8 | 6.2 ± 2.3*** | 4.6 ± 2.7 |
5,7,3′,4′-tetra-OCH3-Flavone (luteolin tetramethylether) | 3.1 ± 1.8** | 4.7 ± 2.1 | 3.9 ± 2.4 | 4.4 ± 2.0 | 5.3 ± 2.6* | 3.0 ± 1.7 |
3-OH-Flavone | 4.3 ± 3.5 | 3.4 ± 2.6 | 4.6 ± 2.6 | 4.1 ± 1.7 | 3.5 ± 2.1 | 3.0 ± 1.5 |
3-OCH3-Flavone | 5.5 ± 2.3 | 3.6 ± 2.0 | 4.8 ± 2.4 | 2.2 ± 1.0* | 2.0 ± 1.3*** | 2.8 ± 1.3 |
2′,3,4′,5,7-penta-OHFlavone (morin) | 3.9 ± 2.1* | 4.7 ± 2.6 | 4.1 ± 2.2 | 3.5 ± 1.9 | 4.2 ± 3.0 | 2.5 ± 2.0* |
3,5,7,3′,4′-penta-OHFlavone (quercetin) | 5.0 ± 2.9 | 4.6 ± 2.4 | 5.8 ± 3.1 | 5.5 ± 2.9** | 4.6 ± 3.0 | 3.5 ± 2.1 |
Quercetin-3-rutinoside (rutin) | 5.1 ± 2.3 | 4.8 ± 3.0 | 5.3 ± 3.3 | 4.4 ± 2.5 | 4.3 ± 2.4 | 3.8 ± 2.6 |
β-Naphtoflavone | 6.0 ± 2.8 | 3.6 ± 2.5 | 5.1 ± 2.4 | 4.2 ± 2.2 | 5.4 ± 3.2** | 3.7 ± 2.5 |
4′,5,7-tri-OH-Isoflavone | 4.6 ± 2.2 | 5.8 ± 2.5 | 4.3 ± 2.5 | 4.1 ± 3.5 | 4.3 ± 2.4 | 4.2 ± 3.3 |
Flavanone | 5.2 ± 2.2 | 5.3 ± 2.3 | 4.7 ± 1.9 | 4.2 ± 2.0 | 3.2 ± 1.6 | 3.4 ± 1.4 |
7-OH-Flavanone | 4.9 ± 2.4 | 5.0 ± 2.3 | 5.1 ± 2.1 | 4.0 ± 1.9 | 4.2 ± 2.0 | 4.0 ± 2.4 |
7-OCH3-Flavanone | 3.7 ± 2.3* | 5.3 ± 2.6 | 5.0 ± 2.1 | 4.4 ± 2.1 | 3.5 ± 1.7 | 2.0 ± 1.2** |
5,7-di-OH-Flavanone (pinocembrin) | 4.5 ± 2.6 | 3.4 ± 2.7* | 5.1 ± 2.5 | 4.7 ± 3.3 | 4.1 ± 3.5 | 4.9 ± 3.7 |
5,7-di-OCH3-Flavanone | 5.2 ± 3.1 | 3.1 ± 1.5** | 1.0 ± 1.2*** | 5.0 ± 2.4* | 3.2 ± 1.4 | 1.1 ± 0.5*** |
(2S)-4′,5,7-tri-OH-Flavanone (naringenin) | 4.5 ± 3.9 | 4.9 ± 2.7 | 3.8 ± 2.8 | 4.3 ± 2.7 | 5.4 ± 3.1 | 5.0 ± 2.5 |
Naringin (naringenin 7-rhamnoglucoside) | 4.1 ± 3.1 | 5.5 ± 2.6 | 3.6 ± 3.0 | 4.0 ± 2.6 | 5.4 ± 4.4* | 3.2 ± 2.8 |
3′,5,7-tri-OH-4′-OCH3-Flavanone (hesperetin) | 6.1 ± 2.4 | 5.1 ± 2.6 | 6.3 ± 2.5 | 5.3 ± 3.1** | 5.1 ± 2.6** | 6.0 ± 3.6*** |
Hesperidin (hesperetin 7-rutinoside) | 7.5 ± 3.2* | 4.6 ± 1.9 | 5.8 ± 2.8 | 5.0 ± 3.3* | 4.9 ± 3.6 | 4.1 ± 3.7 |
(+)-Catechin | 4.8 ± 2.9 | 7.0 ± 3.8 | 6.9 ± 3.8 | 6.7 ± 3.4*** | 4.8 ± 3.5 | 4.0 ± 2.1 |
Catechol | 5.7 ± 3.1 | 6.4 ± 3.7 | 6.3 ± 3.4 | 5.2 ± 3.3* | 4.2 ± 3.8 | 4.7 ± 3.5 |
Phloridzin | 3.5 ± 2.2** | 4.7 ± 2.3 | 4.4 ± 2.6 | 5.0 ± 3.4* | 3.5 ± 2.6 | 2.6 ± 1.6 |
Compound | DPPH test [IC50 (μg of compound/mL)] |
---|---|
Flavone | >100 |
7-OH-Flavone | >100 |
7-OCH3-Flavone | >100 |
5,7-di-OH-Flavone (chrysin) | >100 |
5,7-di-OCH3-Flavone (chrysin dimethylether) | >100 |
3′,4′-di-OCH3-Flavone | >100 |
5,7,3′,4′-tetra-OH-Flavone (luteolin) | 2.051 ± 0.638 a |
5,7,3′,4′-tetra-OCH3-Flavone (luteolin tetramethylether) | >100 |
3-OH-Flavone | 93.721 ± 3.201 a |
3-OCH3-Flavone | >100 |
2′,3,4′,5,7-penta-OH-Flavone (morin) | 5.803 ± 1.375 a |
3,5,7,3′,4′-penta-OH-Flavone (quercetin) | 2.355 ± 0.847 a |
Quercetin-3-rutinoside (rutin) | 11.406 ± 1.302 a |
β-Naphtoflavone | >100 |
4′,5,7-tri-OH-Isoflavone | >100 |
Flavanone | >100 |
7-OH-Flavanone | >100 |
7-OCH3-Flavanone | >100 |
5,7-di-OH-Flavanone (pinocembrin) | >100 |
5,7-di-OCH3-Flavanone | >100 |
(2S)-4′,5,7-tri-OH-Flavanone (naringenin) | >100 |
Naringin (naringenin 7-rhamnoglucoside) | >100 |
3′,5,7-tri-OH-4′-OCH3-Flavanone (hesperetin) | 176.893 ± 2.428 a |
Hesperidin (hesperetin 7-rutinoside) | >100 |
(+)-Catechin | 15.819 ± 1.273 a |
Catechol | 2.774 ± 0.289 a |
Phloridzin | >100 |
α-Tocopherol b | 10.100 ± 1.300 a |
Vitamin C b | 5.851 ± 0.9206 a |
© 2012 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland. This article is an open-access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
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De Martino, L.; Mencherini, T.; Mancini, E.; Aquino, R.P.; De Almeida, L.F.R.; De Feo, V. In Vitro Phytotoxicity and Antioxidant Activity of Selected Flavonoids. Int. J. Mol. Sci. 2012, 13, 5406-5419. https://doi.org/10.3390/ijms13055406
De Martino L, Mencherini T, Mancini E, Aquino RP, De Almeida LFR, De Feo V. In Vitro Phytotoxicity and Antioxidant Activity of Selected Flavonoids. International Journal of Molecular Sciences. 2012; 13(5):5406-5419. https://doi.org/10.3390/ijms13055406
Chicago/Turabian StyleDe Martino, Laura, Teresa Mencherini, Emilia Mancini, Rita Patrizia Aquino, Luiz Fernando Rolim De Almeida, and Vincenzo De Feo. 2012. "In Vitro Phytotoxicity and Antioxidant Activity of Selected Flavonoids" International Journal of Molecular Sciences 13, no. 5: 5406-5419. https://doi.org/10.3390/ijms13055406