The Inhibitory Effect of Flavonoid Aglycones on the Metabolic Activity of CYP3A4 Enzyme
Abstract
:1. Introduction
2. Results and Discussion
3. Materials and Methods
3.1. Materials
3.2. CYP3A4 Inhibition Assays
3.3. Determination of the Inhibition Type
3.4. HPLC-DAD Analysis
3.5. Statistical Analysis
4. Conclusions
Author Contributions
Funding
Conflicts of Interest
References
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Sample Availability: Samples of the compounds are available from the authors and commercially. |
Basic Skeleton of Flavonoids | |||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
Flavonoid | R1 | R2 | R3 | R4 | R5 | R6 | R7 | R8 | Residual Activity (%) | p | |
Flavanones | |||||||||||
1 | Acacetin | H | OH | H | OH | H | H | OCH3 | H | 5 ± 4 | 0.007 |
2 | Flavanone | H | H | H | H | H | H | H | H | 86 ± 46 | 0.361 |
3 | Hesperetin | H | OH | H | OH | H | H | OCH3 | OH | 49 ± 19 | 0.065 |
4 | Pinocembrin-7-methylether | H | OH | H | OCH3 | H | H | H | H | 83 ± 2 | 0.147 |
5 | Pinocembrin | H | OH | H | OH | H | H | H | H | 50 ± 15 | 0.003 |
6 | Sakuranetin | H | OH | H | OCH3 | H | H | OH | H | 94 ± 45 | 0.439 |
Flavones | |||||||||||
7 | 6-hydroxyflavone | H | H | OH | H | H | H | H | H | 83 ± 14 | 0.220 |
8 | 7-hydroxyflavone | H | H | H | OH | H | H | H | H | 78 ± 14 | 0.172 |
9 | Apigenin | H | OH | H | OH | H | H | OH | H | 24 ± 3 | 0.013 |
10 | Chrysin | H | OH | H | OH | H | H | H | H | 17 ± 3 | 0.010 |
11 | Chrysin-dimethylether | H | OCH3 | H | OCH3 | H | H | H | H | 61 ± 21 | 0.049 |
12 | Diosmetin | H | OH | H | OH | H | OH | OCH3 | H | 172 ± 82 | 0.169 |
13 | Flavone | H | H | H | H | H | H | H | H | 81 ± 16 | 0.087 |
14 | Luteolin | H | OH | H | OH | H | OH | OH | H | 112 ± 31 | 0.356 |
15 | Naringenin | H | OH | H | OH | H | H | OH | H | 65 ± 24 | 0.155 |
16 | Tangeretin 1 | H | OCH3 | OCH3 | OCH3 | H | H | OCH3 | H | 42 ± 3 | 0.027 |
17 | Techtocrysin | H | OH | H | OCH3 | H | H | H | H | 102 ± 15 | 0.449 |
Flavonoles | |||||||||||
18 | 3,6-dihydroxyflav. | OH | H | OH | H | H | H | H | H | 100 ± 14 | 0.220 |
19 | 3,7-dihydroxyflav. | OH | H | H | OH | H | H | H | H | 91 ± 27 | 0.375 |
20 | Galangin | OH | OH | H | OH | H | H | H | H | 48 ± 24 | 0.093 |
21 | Isohramnetin | OH | OH | H | OH | H | OCH3 | OH | H | 73 ± 6 | 0.048 |
22 | Kaempferol | OH | OH | H | OH | H | H | OH | H | 101 ± 14 | 0.449 |
23 | Morin | OH | OH | H | OH | OH | H | OH | H | 122 ± 8 | 0.061 |
24 | Myricetin | OH | OH | H | OH | H | OH | OH | OH | 133 ± 35 | 0.195 |
25 | Quercetin | OH | OH | H | OH | H | OH | OH | H | 126 ± 10 | 0.152 |
26 | Rhamnetin | OH | OH | H | OCH3 | H | OH | OH | H | 117 ± 84 | 0.386 |
27 | Tamarixetin | OH | OH | H | OH | H | OH | OCH3 | H | 195 ± 29 | 0.023 |
Isoflavones | |||||||||||
28 | Genistein | H | OH | H | OH | H | H | OH | H | 72 ± 24 | 0.179 |
29 | Prunetin | H | OH | H | OCH3 | H | H | OH | H | 74 ± 14 | 0.149 |
Catechins2 | |||||||||||
30 | Catechin | OH | OH | H | OH | H | H | OH | OH | 98 ± 10 | 0.441 |
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Šarić Mustapić, D.; Debeljak, Ž.; Maleš, Ž.; Bojić, M. The Inhibitory Effect of Flavonoid Aglycones on the Metabolic Activity of CYP3A4 Enzyme. Molecules 2018, 23, 2553. https://doi.org/10.3390/molecules23102553
Šarić Mustapić D, Debeljak Ž, Maleš Ž, Bojić M. The Inhibitory Effect of Flavonoid Aglycones on the Metabolic Activity of CYP3A4 Enzyme. Molecules. 2018; 23(10):2553. https://doi.org/10.3390/molecules23102553
Chicago/Turabian StyleŠarić Mustapić, Darija, Željko Debeljak, Željan Maleš, and Mirza Bojić. 2018. "The Inhibitory Effect of Flavonoid Aglycones on the Metabolic Activity of CYP3A4 Enzyme" Molecules 23, no. 10: 2553. https://doi.org/10.3390/molecules23102553