“…1 ). The optimized structures of the aforementioned compounds give rise to an average C–C bond distance of 1.398 within the six-membered rings corresponding to a delocalized π-electrons system as reported earlier [ 80 – 88 ] and reproduce the geometrical parameters found in an earlier work with an alternation between single and double bond of 1.336 and 1.522 Å, respectively, within the –CH 2 –CH‒CH 2 allylic group encountered in Eug 1 and Cur 9 [ 89 , 90 ]. Fig.…”
Density functional theory (DFT) calculations and molecular docking have been carried out on natural products containing eugenol, gingerol, ascorbic acid, oleurpoein, piperine, hesperidin, quercetin, Luteolin, and curcumin in order to predict their biological activities and to analyze their pancreatic lipase inhibition. The biological activity predictions are based on the global and local chemical descriptors, namely, HOMO–LUMO gaps, chemical hardness, chemical potential, electrophilicity, dipole moment, and Fukui functions. Our findings show that the studied compounds can be divided into two groups based on the chemical descriptors; the first group is composed of eugenol, gingerol, ascorbic acid, and oleuropein and the second one is composed of piperine, hesperidin, quercetin, Luteolin, and curcumin depending on the HOMO–LUMO gaps and electrophilicity values predicting best reactivity for the second group than the first one. The frontier orbitals offer a deeper insight concerning the electron donor and electron acceptor capabilities, whereas the local descriptors resulting from Fukui functions put emphasis on the active sites of different candidate ligands. The molecular docking was performed in order to compare and identify the inhibition activity of the natural candidate ligands against pancreatic lipase which were compared to that of synthesized ones. The molecular docking results revealed that the Luteolin compound has the best binding affinity of −8.56 kcal/mol due to their unique molecular structure and the position of -OH aromatic substituents.
Supplementary Information
The online version contains supplementary material available at 10.1007/s11224-023-02176-2.
“…1 ). The optimized structures of the aforementioned compounds give rise to an average C–C bond distance of 1.398 within the six-membered rings corresponding to a delocalized π-electrons system as reported earlier [ 80 – 88 ] and reproduce the geometrical parameters found in an earlier work with an alternation between single and double bond of 1.336 and 1.522 Å, respectively, within the –CH 2 –CH‒CH 2 allylic group encountered in Eug 1 and Cur 9 [ 89 , 90 ]. Fig.…”
Density functional theory (DFT) calculations and molecular docking have been carried out on natural products containing eugenol, gingerol, ascorbic acid, oleurpoein, piperine, hesperidin, quercetin, Luteolin, and curcumin in order to predict their biological activities and to analyze their pancreatic lipase inhibition. The biological activity predictions are based on the global and local chemical descriptors, namely, HOMO–LUMO gaps, chemical hardness, chemical potential, electrophilicity, dipole moment, and Fukui functions. Our findings show that the studied compounds can be divided into two groups based on the chemical descriptors; the first group is composed of eugenol, gingerol, ascorbic acid, and oleuropein and the second one is composed of piperine, hesperidin, quercetin, Luteolin, and curcumin depending on the HOMO–LUMO gaps and electrophilicity values predicting best reactivity for the second group than the first one. The frontier orbitals offer a deeper insight concerning the electron donor and electron acceptor capabilities, whereas the local descriptors resulting from Fukui functions put emphasis on the active sites of different candidate ligands. The molecular docking was performed in order to compare and identify the inhibition activity of the natural candidate ligands against pancreatic lipase which were compared to that of synthesized ones. The molecular docking results revealed that the Luteolin compound has the best binding affinity of −8.56 kcal/mol due to their unique molecular structure and the position of -OH aromatic substituents.
Supplementary Information
The online version contains supplementary material available at 10.1007/s11224-023-02176-2.
“…Male, Sutapa, Maahury, Jamal, & Male, (2022) Male et al (2022) telah meneliti potensi eugenol dan turunannya sebagai material aktif tabir menggunakan DFT/ B3LYP [4]. Kurniawan et al (2017) telah melakukan perhitungan reaksi konversi eugenol menjadi metil eugenol menggunakan teori DFT/B3LYP dan diperoleh nilai hasil teoritis mendekati hasil eksperimen [5]. Perhitungan secara komputasi terhadap eugenol, metil eugenol, dan asetil eugenol untuk mengetahui struktur teroptimasi (stabil) dan sifat elektroniknya seperti sebaran muatan atom, HOMO-LUMO, belum pernah dilakukan.…”
Eugenol is the active molecule naturally found in clove oil. The calculations have been done for the eugenol and its derivatives computationally. This computational calculation aims to obtain a stable structure and electronic properties of eugenol, methyl eugenol, and acetyl eugenol. The computational calculation used DFT for geometry optimization in the gas phase using B3LYP functional and 6-31G(d) as the basis set. The optimized structure of eugenol and its derivatives is not planar. The presence of methoxy replacing hydroxy increases the bond length and decreases the bond angle and the dihedral. The electronic properties such as atomic charge and density of HOMO-LUMO show the difference between the three molecules.
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