Spectroscopic methods and in silico analyses using density functional theory to characterize and identify piperine alkaloid crystals isolated from pepper (<i>Piper Nigrum</i> L.)

Alves, Fabrine Silva; Rêgo, José de Arimatéia Rodrigues do; Costa, Marcondes Lima da; Silva, Luiz Fernando Lobato Da; Costa, Renato Araújo da; Cruz, Jorddy Neves; Brasil, Davi do Socorro Barros

doi:10.1080/07391102.2019.1639547

Cited by 21 publications

(12 citation statements)

References 7 publications

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“…The methanol solvent signal was observed around 3.31 ppm and 4.88 ppm. The 1 H-NMR piperine signal was similar to the previously reported NMR of the piperine compound (Alves et al, 2019).…”

Section: Nmr Analysissupporting

confidence: 86%

“…All 13 C-NMR values were similar to the previous studies (Alves et al, 2019). The use of different solvents in the NMR analysis in the previous studies (Alves et al, 2019) Peaks in the range 100-150 and 167.89 corresponded to carbon-carbon double bonds and carbon-oxygen double bonds, respectively The 1 H-NMR spectrum of the isolated piperine (Figure8) showed 19 protons with the following signals: δ 1.599 (2H, m, H-13), δ 1.708 (2H, m, H-14), δ 3.624 (2H, m, H-15), δ 5.966 ( 2H, s, H-12), δ 7.0956 (1H, m, H-7), δ 6.845 (1H, d, H-9), δ 6.617 (IH, d, H-2), δ 6.876 (1H, d, H-8), δ 6.806 (1H, d, H-5), δ 6.790 (1H, m, H-4), and δ 7.3215 (1H, ddd, H-3). The methanol solvent signal was observed around 3.31 ppm and 4.88 ppm.…”

Section: Nmr Analysissupporting

confidence: 86%

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Development of New Isolation and Quantification Method of Piperine from White Pepper Seeds (Piper Nigrum L) Using A Validated HPLC

et al. 2021

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Most of the active pharmaceutical ingredients in the pharmaceutical world are obtained from natural ingredients, one of which is white pepper. White pepper seeds (Piper nigrum L.) contain the main alkaloid compound piperine, which has a broad spectrum pharmacological effect. This research aimed to isolate the piperine compound from white pepper seeds to make piperine more economical, simple, and effective so that it can be applied to large scale production in the pharmaceutical industry. The method of extracting and purifying piperine compounds was carried out using n-hexane and cyclohexane. The results of the isolated piperine were tested for their purity with a set of melting point apparatus, bidimensional TLC, and HPLC. The structure compound was then analyzed using FTIR and NMR. Furthermore, the isolated piperine was tested for its antioxidant activities using DPPH, ABTS, and FRAP. Cyclohexane was successfully used to remove the resinous matter from the n-hexane extract of white pepper to produce isolated piperine with 97.24% of purity. The results of the melting point, FTIR, 1H-NMR, and 12C-NMR of the isolated piperine were similar to that of the piperine reference substance and the literature review. The isolated piperine has weak antioxidant activities in the ABTS and FRAP test with the results of 15.25 ± 0.004 mM and 10.53 mol TE/g of the sample, respectively.

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“…The methanol solvent signal was observed around 3.31 ppm and 4.88 ppm. The 1 H-NMR piperine signal was similar to the previously reported NMR of the piperine compound (Alves et al, 2019).…”

Section: Nmr Analysissupporting

confidence: 86%

Section: Nmr Analysissupporting

confidence: 86%

Development of New Isolation and Quantification Method of Piperine from White Pepper Seeds (Piper Nigrum L) Using A Validated HPLC

et al. 2021

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“…The initial structure for the system was obtained from molecular docking methods, as described in the previous section. The restrained electrostatic potential (RESP) protocol with the HF/6-31G* basis sets was applied to obtain the charges of the atoms of each ligand [ 106 , 107 , 108 ] Atomic charge calculated using Gaussian [ 81 , 109 , 110 ] The parameters of the ligand were constructed with the Antechamber module, available in the Amber16 package [ 111 , 112 , 113 ]. The protonation state of ionizable residues of protein structure was analyzed using the PROPKA [ 114 ] server in the neutral pH before performing the MD simulations.…”

Section: Methodsmentioning

confidence: 99%

Identification of New Rofecoxib-Based Cyclooxygenase-2 Inhibitors: A Bioinformatics Approach

et al. 2020

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The cyclooxygenase-2 receptor is a therapeutic target for planning potential drugs with anti-inflammatory activity. The selective cyclooxygenase-2 (COX-2) inhibitor rofecoxib was selected as a pivot molecule to perform virtual ligand-based screening from six commercial databases. We performed the search for similarly shaped Rapid Overlay of Chemical Structures (ROCS) and electrostatic (EON) compounds. After, we used pharmacokinetic and toxicological parameters to determine the best potential compounds, obtained through the softwares QikProp and Derek, respectively. Then, the compounds proceeded to the molecular anchorage study, which showed promising results of binding affinity with the hCOX-2 receptor: LMQC72 (∆G = −11.0 kcal/mol), LMQC36 (∆G = −10.6 kcal/mol), and LMQC50 (∆G = −10.2 kcal/mol). LMQC72 and LMQC36 showed higher binding affinity compared to rofecoxib (∆G = −10.4 kcal/mol). Finally, molecular dynamics (MD) simulations were used to evaluate the interaction of the compounds with the target hCOX-2 during 150 ns. In all MD simulation trajectories, the ligands remained interacting with the protein until the end of the simulation. The compounds were also complexing with hCOX-2 favorably. The compounds obtained the following affinity energy values: rofecoxib: ΔGbind = −45.31 kcal/mol; LMQC72: ΔGbind = −38.58 kcal/mol; LMQC36: ΔGbind = −36.10 kcal/mol; and LMQC50: ΔGbind = −39.40 kcal/mol. The selected LMQC72, LMQC50, and LMQC36 structures showed satisfactory pharmacokinetic results related to absorption and distribution. The toxicological predictions of these compounds did not display alerts for possible toxic groups and lower risk of cardiotoxicity compared to rofecoxib. Therefore, future in vitro and in vivo studies are needed to confirm the anti-inflammatory potential of the compounds selected here with bioinformatics approaches based on rofecoxib ligand.

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“…The initial structure for the system was obtained from molecular docking methods. The restrained electrostatic potential (RESP) protocol with the HF/6-31G* basis sets was applied to obtain the partial atomic charges of the atoms of each ligand [ 62 , 63 , 64 , 65 ]. The parameters of the ligand were constructed with the Antechamber module [ 66 ] using General Amber Force Field (GAFF) [ 67 ].…”

Section: Methodsmentioning

confidence: 99%

Identification of Potential COX-2 Inhibitors for the Treatment of Inflammatory Diseases Using Molecular Modeling Approaches

et al. 2020

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Non-steroidal anti-inflammatory drugs are inhibitors of cyclooxygenase-2 (COX-2) that were developed in order to avoid the side effects of non-selective inhibitors of COX-1. Thus, the present study aims to identify new selective chemical entities for the COX-2 enzyme via molecular modeling approaches. The best pharmacophore model was used to identify compounds within the ZINC database. The molecular properties were determined and selected with Pearson’s correlation for the construction of quantitative structure–activity relationship (QSAR) models to predict the biological activities of the compounds obtained with virtual screening. The pharmacokinetic/toxicological profiles of the compounds were determined, as well as the binding modes through molecular docking compared to commercial compounds (rofecoxib and celecoxib). The QSAR analysis showed a fit with R = 0.9617, R2 = 0.9250, standard error of estimate (SEE) = 0.2238, and F = 46.2739, with the tetra-parametric regression model. After the analysis, only three promising inhibitors were selected, Z-964, Z-627, and Z-814, with their predicted pIC50 (−log IC50) values, Z-814 = 7.9484, Z-627 = 9.3458, and Z-964 = 9.5272. All candidates inhibitors complied with Lipinski’s rule of five, which predicts a good oral availability and can be used in in vitro and in vivo tests in the zebrafish model in order to confirm the obtained in silico data.

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Spectroscopic methods and in silico analyses using density functional theory to characterize and identify piperine alkaloid crystals isolated from pepper (Piper Nigrum L.)

Cited by 21 publications

References 7 publications

Development of New Isolation and Quantification Method of Piperine from White Pepper Seeds (Piper Nigrum L) Using A Validated HPLC

Development of New Isolation and Quantification Method of Piperine from White Pepper Seeds (Piper Nigrum L) Using A Validated HPLC

Identification of New Rofecoxib-Based Cyclooxygenase-2 Inhibitors: A Bioinformatics Approach

Identification of Potential COX-2 Inhibitors for the Treatment of Inflammatory Diseases Using Molecular Modeling Approaches

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