Prediction of Radical Scavenging Activities of Anthocyanins Applying Adaptive Neuro-Fuzzy Inference System (ANFIS) with Quantum Chemical Descriptors
Abstract
:1. Introduction
2. Results and Discussion
2.1. Correlation Analysis
Descriptors | PM6 | PM7 | ||||||||
---|---|---|---|---|---|---|---|---|---|---|
FC | QB4' | QB7 | CP | Ch | FC | QB4' | QB7 | CP | Ch | |
I | 0.554 ** | 0.343 | 0.674 ** | 0.233 | 0.121 | 0.504 * | 0.355 | 0.708 ** | 0.269 | 0.251 |
A | 0.673 ** | −0.166 | −0.256 | −0.473 * | −0.052 | 0.538 * | −0.206 | −0.037 | −0.289 | −0.199 |
η | 0.124 | 0.288 | 0.523 * | 0.530 * | 0.121 | 0.263 | 0.310 | 0.418 | 0.378 | 0.298 |
S | −0.153 | −0.171 | −0.503 * | −0.535 * | −0.138 | −0.238 | −0.132 | −0.398 | −0.411 | −0.284 |
ω | 0.328 | −0.127 | −0.305 | −0.470 * | −0.054 | 0.202 | −0.112 | −0.085 | −0.326 | −0.212 |
χ | 0.701 ** | 0.194 | 0.282 | −0.344 | 0.009 | 0.567 ** | 0.087 | 0.551 ** | −0.149 | 0.020 |
μ | −0.701 ** | −0.194 | −0.282 | 0.344 | −0.009 | −0.567 ** | −0.087 | −0.551 ** | 0.149 | −0.020 |
Compounds | Method | (1) BDE of FL | BDE of QB7 | ||||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
3 | 5 | 7 | 3' | 4' | 5' | 3 | 5 | 3' | 4' | 5' | |||||||||||||
cyanidin | PM6 | 80.98 | 84.8 | 90.2 | 82.06 | 83.34 | - | 67.08 | 75.5 | 76.04 | 72.44 | - | |||||||||||
PM7 | 81.77 | 81.77 | 91.41 | 83.43 | 84.78 | - | 68.98 | 75.72 | 75.54 | 75.16 | - | ||||||||||||
delphinidin | PM6 | 78.15 | 84.24 | 90.53 | 83.16 | 75.61 | 78.55 | 65.65 | 74.8 | 79.17 | 68.74 | 74.47 | |||||||||||
PM7 | 82.55 | 85.75 | 92.2 | 85.58 | 77.6 | 82.08 | 68.2 | 75.42 | 78.74 | 71.29 | 75.13 | ||||||||||||
malvidin | PM6 | 77.33 | 82.05 | 87.19 | - | 73.9 | - | 65.49 | 74.83 | - | 68.04 | - | |||||||||||
PM7 | 81.19 | 85.22 | 90.98 | - | 75.21 | - | 71.31 | 78.69 | - | 73.36 | - | ||||||||||||
pelargonidin | PM6 | 81.01 | 84.79 | 90.39 | - | 89.53 | - | 68.45 | 75.5 | - | 74.43 | - | |||||||||||
PM7 | 81.86 | 85.71 | 91.51 | - | 90.6 | - | 69.68 | 75.89 | - | 76.87 | - | ||||||||||||
peonidin | PM6 | 80.86 | 84.58 | 90.45 | - | 77.37 | - | 68.38 | 76.99 | - | 69.2 | - | |||||||||||
PM7 | 81.86 | 85.71 | 91.51 | - | 90.6 | - | 71.53 | 78.3 | - | 73.51 | - | ||||||||||||
cyanidin-3-coumaroyl-sambubioside-5-galactoside | PM6 | - | - | 88.15 | 80.05 | 82.17 | - | - | - | 74.12 | 75.16 | - | |||||||||||
PM7 | - | - | 86.57 | 77.29 | 78.88 | - | - | - | 76.74 | 77.52 | - | ||||||||||||
cyanidin-3-sambubioside-5-galactoside | PM6 | - | - | 89.15 | 80.07 | 82.15 | - | - | - | 74.12 | 75.23 | - | |||||||||||
PM7 | - | - | 98.43 | 88.66 | 90.97 | - | - | - | 76.74 | 78.07 | - | ||||||||||||
cyanidin-3,5-diglucoside | PM6 | - | - | 91.23 | 80.23 | 83.08 | - | - | - | 74.85 | 75.92 | - | |||||||||||
PM7 | - | 85.22 | - | 80.39 | 82.39 | - | - | - | 77.19 | 78.28 | - | ||||||||||||
cyanidin-3-arabinoside | PM6 | - | 86.49 | 91.25 | 80.53 | 82.61 | - | - | 77.32 | 76.27 | 73.99 | - | |||||||||||
PM7 | - | 88.14 | 92.69 | 82.63 | 85.54 | - | - | 77.87 | 77.09 | 77.48 | - | ||||||||||||
cyanidin-3-galactoside | PM6 | - | 93.17 | 93.58 | 81.03 | 83.71 | - | - | 76.74 | 74.76 | 75.55 | - | |||||||||||
PM7 | - | 96.62 | 96.76 | 84.86 | 85.8 | - | - | 81.26 | 80.34 | 79.3 | - | ||||||||||||
cyanidin-3-glucoside | PM6 | - | 86.87 | 92.58 | 81.78 | 84.4 | - | - | 76.07 | 74.91 | 75.63 | - | |||||||||||
PM7 | - | 87.79 | 82.92 | 82.92 | 85.51 | - | - | 77.07 | 77.52 | 77.99 | - | ||||||||||||
cyanidin-3-rutinoside | PM6 | - | 88.51 | 94.22 | 80.41 | 83.25 | - | - | 76.6 | 74.72 | 76.12 | - | |||||||||||
PM7 | - | 90.49 | 94.22 | 81.73 | 84.65 | - | - | 80.23 | 77.36 | 78.9 | - | ||||||||||||
delphinidin-3-glucoside | PM6 | - | 86.92 | 91.58 | 82.36 | 75.31 | 77.35 | - | 76.9 | 78.53 | 69.28 | 74.42 | |||||||||||
PM7 | - | 89.94 | 92.99 | 84.51 | 77.89 | 80.94 | - | 80.64 | 80.53 | 77.06 | 80.23 | ||||||||||||
delphinidin-3-rutinoside | PM6 | - | 88.23 | 91.05 | 82.52 | 75.93 | 75.74 | - | 75.22 | 77.2 | 70.95 | 72.55 | |||||||||||
PM7 | - | 84.54 | 92.68 | 84.59 | 77.79 | 76.34 | - | 72.62 | 80.15 | 73.79 | 73.62 | ||||||||||||
malvidin-3,5-diglucoside | PM6 | - | - | 86.32 | - | 73.67 | - | - | - | - | 71.07 | - | |||||||||||
PM7 | - | - | 91.84 | - | 76.05 | - | - | - | - | 72.45 | - | ||||||||||||
malvidin-3-galactoside | PM6 | - | 87.49 | 89.43 | - | 73.81 | - | - | 74.52 | - | 69.57 | - | |||||||||||
PM7 | - | 88.43 | 91.56 | - | 75.73 | - | - | 78.65 | - | 72.45 | - | ||||||||||||
malvidin-3-glucoside | PM6 | - | 85.75 | 89.51 | - | 73.89 | - | - | 76.84 | - | 68.59 | - | |||||||||||
PM7 | - | 88.63 | 94.26 | - | 78.17 | - | - | 73.52 | - | 71.67 | - | ||||||||||||
pelargonidin-3-glucoside | PM6 | - | 87.13 | 91.13 | - | 86.79 | - | - | 71.66 | - | 75.48 | - | |||||||||||
PM7 | - | 86.20 | 93.35 | - | 89.08 | - | - | 72.61 | - | 78.55 | - | ||||||||||||
peonidin-3-galactoside | PM6 | - | 88.79 | 98.46 | - | 76.39 | - | - | 79.56 | - | 68.31 | - | |||||||||||
PM7 | - | 88.94 | 92.01 | 78.78 | - | - | 77.10 | - | 72.78 | - | |||||||||||||
peonidin-3-glucoside | PM6 | - | 88.80 | 90.97 | - | 76.38 | - | - | 74.66 | - | 67.51 | - | |||||||||||
PM7 | - | 88.57 | 91.51 | - | 78.74 | - | - | 78.95 | - | 72.74 | - | ||||||||||||
petunidin-3-glucoside | PM6 | - | 86.34 | 90.85 | 82.33 | 74.17 | - | - | 76.79 | 79.31 | 68.40 | - | |||||||||||
PM7 | - | 88.62 | 94.78 | 87.69 | 78.51 | - | - | 73.73 | 80.33 | 71.51 | - |
2.2. Prediction of Radical Scavenging Activities of Anthocyanins
Compounds | (1) Experimental Radical Scavenging Activity | Predicted Radical Scavenging Activity | |
---|---|---|---|
PM6 | PM7 | ||
cyanidin | 33 | 35.3 | 33.2 |
delphinidin | 42 | 42.6 | 41.0 |
malvidin | 24 | 26.6 | 26.1 |
pelargonidin | 31 | 28.3 | 27.6 |
peonidin | 33 | 31.4 | 29.3 |
cyanidin-3-coumaroylsambubiose-5-galactoside | 26 | 22.4 | 25.2 |
cyanidin-3,5-diglucoside | 21 | 22.6 | 20.9 |
cyanidin-3-arabinoside | 26 | 28.5 | 27.3 |
cyanidin-3-sambubiose-5-galactoside | 22 | 22.1 | 21.5 |
cyanidin-3-galactoside | 25 | 30.3 | 30.2 |
cyanidin-3-glucoside | 32 | 31.1 | 28.8 |
cyanidin-3-rutinoside | 25 | 27.0 | 27.5 |
delphinidin-3-glucoside | 42 | 35.4 | 38.1 |
delphinidin-3-rutinoside | 32 | 33.4 | 30.4 |
malvidin-3,5-diglucoside | 14 | 16.6 | 14.9 |
malvidin-3-galactoside | 22 | 22.9 | 21.3 |
malvidin-3-glucoside | 26 | 22.6 | 21.2 |
pelargonidin-3-glucoside | 20 | 21.0 | 21.2 |
peonidin-3-galactoside | 20 | 22.2 | 21.1 |
peonidin-3-glucoside | 26 | 23.6 | 23.5 |
petunidin-3-glucoside | 23 | 28.0 | 25.7 |
(2) Mean absolute error | 2.43 ± 0.35 | 2.06 ± 0.32 | |
(2) Q-square | 0.82 ± 0.08 | 0.86 ± 0.08 |
3. Experimental Section
3.1. DPPH Radical Scavenging Activity
Family | Compounds | (1) nOH | R1 | R2 | (2) R3 | (2) R4 |
---|---|---|---|---|---|---|
anthocyanidin | cyanidin | 5 | OH | H | OH | OH |
delphinidin | 6 | OH | OH | OH | OH | |
malvidin | 4 | OCH3 | OCH3 | OH | OH | |
pelargonidin | 4 | H | H | OH | OH | |
peonidin | 4 | OCH3 | H | OH | OH | |
anthocyanin | cyanidin-3-coumaroyl-sambubioside-5-galactoside | 3 | OH | H | coumaroyl -sam | gal |
cyanidin-3-sambubioside-5-galactoside | 3 | OH | H | sam | gal | |
cyanidin-3-arabinoside | 4 | OH | H | ara | OH | |
cyanidin-3-galactoside | 4 | OH | H | gal | OH | |
cyanidin-3-glucoside | 4 | OH | H | glc | OH | |
cyanidin-3-rutinoside | 4 | OH | H | rut | OH | |
cyanidin-3,5-diglucoside | 3 | OH | H | glc | glc | |
delphinidin-3-glucoside | 5 | OH | OH | glc | OH | |
delphinidin-3-rutinoside | 5 | OH | OH | rut | OH | |
malvidin-3-galactoside | 3 | OCH3 | OCH3 | gal | OH | |
malvidin-3-glucoside | 3 | OCH3 | OCH3 | glc | OH | |
malvidin-3,5-diglucoside | 2 | OCH3 | OCH3 | glc | glc | |
pelargonidin-3-glucoside | 3 | H | H | glc | OH | |
peonidin-3-galactoside | 3 | OCH3 | H | gal | OH | |
peonidin-3-glucoside | 3 | OCH3 | H | glc | OH | |
petunidin-3-glucoside | 4 | OH | OCH3 | glc | OH |
3.2. Quantum Chemical Descriptors
3.2.1. Molecular Structure Preparation
3.2.2. Calculation of Quantum Chemical Descriptors
3.3. QSAR Model Development
3.3.1. Correlation Analysis
3.3.2. ANFIS
4. Conclusions
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Jhin, C.; Hwang, K.T. Prediction of Radical Scavenging Activities of Anthocyanins Applying Adaptive Neuro-Fuzzy Inference System (ANFIS) with Quantum Chemical Descriptors. Int. J. Mol. Sci. 2014, 15, 14715-14727. https://doi.org/10.3390/ijms150814715
Jhin C, Hwang KT. Prediction of Radical Scavenging Activities of Anthocyanins Applying Adaptive Neuro-Fuzzy Inference System (ANFIS) with Quantum Chemical Descriptors. International Journal of Molecular Sciences. 2014; 15(8):14715-14727. https://doi.org/10.3390/ijms150814715
Chicago/Turabian StyleJhin, Changho, and Keum Taek Hwang. 2014. "Prediction of Radical Scavenging Activities of Anthocyanins Applying Adaptive Neuro-Fuzzy Inference System (ANFIS) with Quantum Chemical Descriptors" International Journal of Molecular Sciences 15, no. 8: 14715-14727. https://doi.org/10.3390/ijms150814715