## 3 Results and Discussion
### Molecular Docking Studies
Based on our _in silico_ results regarding the CP450 enzyme, the formation of pi-pi interactions with Phe476 and/or Phe214 was observed for all of the examined compounds. In a recent publication, [PERSON] et al. [23] suggested that interactions with Phe100, Phe214 and Phe467 may be crucial for CP450 binding, confirming our findings. Among tested compounds, naringin presents the most interesting results because it exhibits the highest docking score but also interacts via hydrogen bonds with Phe100 and Thr301, like the co-crystallized ligand, and via pi-pi interaction with Phe114. Interestingly, its aromatic ring is found at a close proximity to the heme ring. From the results (Tables 4 and 5), it is obvious that several phenolic compounds could not bind to the lipoxygenase (LOX) enzyme. However, five compounds belonging to the phenolic acid group exhibited common interactions, including a pi-pi interaction with His518, an interaction crucial for the binding. The docked poses of the examined compounds at the MP binding sites indicated greater docking scores compared to the positive control (MEL) and also pointed out a variety of interactions, including direct hydrogen bonds. Notably, among the examined compounds, cafartic acid and kaempherd 3-glucose form five hydrogen bonds. The hydrogen bonds with Asn189, Val199 and Gln201 residues are common to MEL [23]. \begin{table}
\begin{tabular}{c c c c c c} \hline \hline \multirow{2}{*}{**Compounds**} & **NADPH Oxidase** & \multirow{2}{*}{
\begin{tabular}{c} **Cyochrome P450** \\ **(CP450)** \\ **(PDB: 10 GS)** \\ \end{tabular} } & **Lipoxygenase** & **Myeloperoxidase** & **Xanthine Oxidase** \\  & & **(CPB: 10 GS)** & **(PDB: 1 NSQ)** & **(PDB: 1 DNU)** & **(PDB: 3 NRZ)** \\ \hline \multicolumn{6}{c}{**Docking Score (kcal-mol\({}^{-1}\))**} \\ \hline Dextromethorphan (DEX) & \(-\)3.82 & NT \({}^{1}\) & NT & NT & NT \\
5-Fluorouracil (FLU) & NT & \(-\)6.13 & NT & NT & NT \\ Zileuton (ZIL) & NT & NT & \(-\)2.35 & NT & NT \\ Melatonin (MEL) & NT & NT & NT & \(-\)3.53 & NT \\ Feubroostat (FEB) & NT & NT & NT & NT & \(-\)6.70 \\ Caftaric acid & \(-\)6.97 & \(-\)5.41 & NB \({}^{2}\) & \(-\)4.30 & \(-\)6.39 \\ Caffeic acid & \(-\)5.76 & \(-\)6.84 & \(-\)5.21 & \(-\)4.69 & \(-\)5.55 \\ Catechin & \(-\)6.75 & \(-\)5.78 & NB & \(-\)5.19 & \(-\)7.83 \\ Chlorogenic acid & \(-\)5.97 & \(-\)5.88 & NB & \(-\)5.14 & \(-\)5.40 \\ Epicatechin & \(-\)6.67 & \(-\)8.73 & NB & \(-\)5.23 & \(-\)4.09 \\ Epicatechin gallate & \(-\)5.24 & \(-\)7.76 & NB & \(-\)4.03 & \(-\)4.00 \\ Epigallocatechin gallate & \(-\)5.24 & \(-\)7.76 & NB & \(-\)5.22 & NB \\ Gallic acid & \(-\)5.27 & \(-\)5.87 & \(-\)6.36 & \(-\)4.84 & \(-\)7.68 \\ Hesperetin & \(-\)6.11 & \(-\)6.08 & NB & \(-\)4.41 & \(-\)6.76 \\ Hesperidin & \(-\)4.88 & \(-\)6.83 & NB & \(-\)5.32 & NB \\ Kaempherd 3-glucoside & \(-\)6.01 & \(-\)6.60 & NB & \(-\)4.56 & NB \\ Myricetin & \(-\)6.56 & \(-\)6.18 & NB & \(-\)4.84 & \(-\)7.31 \\ Naringenin & \(-\)6.43 & \(-\)6.99 & NB & \(-\)5.10 & \(-\)5.44 \\ Naringen & \(-\)4.54 & \(-\)8.15 & NB & \(-\)4.29 & NB \\ Proxyandini B1 & \(-\)4.01 & \(-\)7.72 & NB & \(-\)4.13 & NB \\ Procyandini B2 & \(-\)4.84 & \(-\)7.90 & NB & \(-\)4.41 & NB \\ Pyrogallol & \(-\)4.63 & \(-\)5.75 & \(-\)6.45 & \(-\)4.61 & \(-\)6.37 \\ Quercitin 3-Glucoside & \(-\)6.57 & \(-\)5.84 & NB & \(-\)5.01 & NB \\ Resveratrol & \(-\)6.84 & \(-\)5.62 & NB & \(-\)4.86 & \(-\)8.23 \\ Rutin & \(-\)4.91 & \(-\)8.13 & NB & \(-\)5.18 & NB \\ Syringic acid & \(-\)5.96 & \(-\)5.39 & \(-\)5.49 & \(-\)4.70 & \(-\)5.94 \\ Vanillic acid & \(-\)5.77 & \(-\)5.78 & \(-\)6.08 & \(-\)4.67 & \(-\)6.54 \\ \hline \hline \end{tabular} \({}^{1}\) NT: Not tested, \({}^{2}\) NB: Not bound.  
\end{table} 
Table 4: The docking scores of the examined compounds at the binding sites of various molecular targets.