Investigation on structural, spectroscopic, DFT, biological activity and molecular docking simulation of essential oil Gamma-Terpinene

Zochedh, Azar; Priya, M.; Athimoolam, S.; Kathiresan, Thandavarayan; Sultan, Asath Bahadur

doi:10.1016/j.molstruc.2022.133651

Cited by 57 publications

(15 citation statements)

References 58 publications

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“…The oxygen atom possesses negative charge and all carbon atoms except C2 (0.305805e), C6 (0.141043e), C7 (0.09688e), and C8 (0.363855e) have negative charges, whereas these carbon atoms C2, C6, and C8 were connected to CH 3 replacement. This reveals that allo‐ocimenol has a more amount of charge delocalization [66].…”

Section: Resultsmentioning

confidence: 99%

Quantum chemical calculation, topological analysis, biological evaluation and molecular docking of allo‐ocimenol against breast cancer

Chandran,

Zochedh,

Sukumaran

et al. 2023

Int J of Quantum Chemistry

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The main aim of this study is to identify the structural stability of allo‐ocimenol and its molecular reactivity against breast cancer‐associated proteins to confirm its anti‐cancer capability using density function theory and molecular docking analysis. The structural optimization was carried out via the DFT/B3LYP technique with a 6‐311++G (d,p) basis set. The molecular geometry and vibrational assignments of the Allo‐Ocimenol molecule were analyzed through density functional theory (DFT). Through optimized molecular structure, the vibrational frequencies (FT‐IR and FT‐Raman) were assigned and related with experimentally observed vibrational frequencies and the UV spectrum was computed and experimentally confirmed. The allo‐ocimenol's reactive activity was further analyzed through a computed molecular electrostatic potential surface. Utilizing the HOMO‐LUMO energies and molecular electrostatic potential energy gap, the reactivity and molecular stability of the allo‐ocimenol molecule was calculated. Mulliken and natural population analyses were used to determine the charge distribution across the allo‐ocimenol atoms. The natural bond orbitals were used to demonstrate the bioactivity of the titled molecule. RDG evaluation was used to examine the weak interactions of the allo‐ocimenol molecule. ELF and LOL analyses were utilized to investigate the topology of the allo‐ocimenol molecule. Thermodynamic evaluation has been utilized to acquire values and asses the thermodynamic parameters that reveal the thermal stability of the title molecule. Allo‐Ocimenol's anti‐microbial activity was assessed through an in‐vitro disc diffusion method, and its tumor inhibitory and pharmacokinetic properties were evaluated through an in‐silico approach using molecular docking and ADMET investigation. Zones of clearance were seen in anti‐microbial analyses at various concentrations, and the breast cancer target protein NAMPT established the greatest binding potential, with a docking value of −7.4 Kcal mol−1.

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Section: Resultsmentioning

confidence: 99%

Quantum chemical calculation, topological analysis, biological evaluation and molecular docking of allo‐ocimenol against breast cancer

Chandran,

Zochedh,

Sukumaran

et al. 2023

Int J of Quantum Chemistry

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“…Azar Zochedh et al found γ-Terpinene showed good anticancer activity with a high affinity for the breast cancer target protein ERα. [55] Thus, the appropriate increase of γ-Terpinene content in the EO compounds process is beneficial to enhance the therapeutic effect on human breast cancer. For single essential oils with specific bioactivities, compound EOs could be formed in appropriate proportions to provide a superimposed effect that takes into account multiple properties.…”

Section: Discussionmentioning

confidence: 99%

“…Azar Zochedh et al. found γ‐Terpinene showed good anticancer activity with a high affinity for the breast cancer target protein ERα [55] . Thus, the appropriate increase of γ‐Terpinene content in the EO compounds process is beneficial to enhance the therapeutic effect on human breast cancer.…”

Section: Discussionmentioning

confidence: 99%

Contribution of Constituents in Rosemary‐Magnolia Compound Essential Oil to Antibacterial, Antioxidant and Cytotoxicity Bioactivities Revealed by Grey Correlation Analysis

Song

Zhang

Jin³

et al. 2023

Chemistry & Biodiversity

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The compound of essential oils (EOs) is a key approach to achieving the superimposed efficacy of plant EOs. In this article, grey correlation analysis was applied for the first time to explore the compound ratios and contribution between constituents and the bioactivity of the compound EOs. There were 12 active constituents shared in rosemary and magnolia EOs prepared by negative pressure distillation. With different proportions, these two EOs were blended and analyzed for the antioxidant, bacteriostatic and antitumor effects. According to the results of the inhibition circle, minimum bactericidal and inhibitory concentration, the most obvious inhibition effect of the compound EOs on different strains of bacteria was shown in Staphylococcus aureus. The results of antioxidant test showed that single EO from rosemary had the best antioxidant effect, and its EO content was directly proportional to the antioxidant effect. The cytotoxicity results showed that, there was a significant difference in the lethality of the compound EOs between tumor cells Mcf-7 (human breast cancer cells) and SGC-7901 cells (human gastric cancer cells). Furthermore, single EO from magnolia had an obvious inhibitory effect on the growth of Mcf-7 cells and SGC-7901 cells, and the cell lethality rate was as high as 95.19 % and 97.96 %, respectively. As the results of grey correlation analysis, the constituents with the maximal correlation of inhibitory effects on bacteria were as follows: S. aureus -Terpinolene (0.893), E. coli -Eucalyptol (0.901), B. subtilis -α-Pinene (0.823), B. cereus -Terpinolene (0.913) and Salmonella -α-Phellandrene (0.855). For the ABTS and DPPH scavenging effects, the constituents with the maximal correlation were (À )-Camphor (0.860) and β-Pinene (0.780), respectively. In terms of the effects of the active constituents of compound EOs on the inhibitory activities of tumor cells Mcf-7 and SGC-7901, the three active constituents of γ-Terpinene, (R)-(+)-β-Citronellol and (À )-Camphor were in the top three, and their correlation were Mcf-7 (0.833, 0.820, 0.795) and SGC-7901 (0.797, 0.766, 0.740). Our study determined the contribution degree of active constituents in the antibacterial, antioxidant, and antitumor bioactivities of rosemarymagnolia compound EOs, and also provided new insights for the research of EOs combination formulations.

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“…Atomic charges are crucial for modifying a molecule's polarizability, electronic structure, dipole moment, and other properties as well as for applying quantum chemistry to the study of molecular systems. The atomic charge distribution advises the creation of acceptor and donor pairs involved in charge transfer in a molecule [50]. The Mulliken charge population through the B3LYP/6-311 G basis set in the gas phase was used to assess the charge distribution over the atoms for the gemcitabine-docetaxel complex, and the results are given in Table S2.…”

Section: Electrostatic Potential and Mulliken Charge Distribution Ana...mentioning

confidence: 99%

Exploring the co‐activity of FDA approved drug gemcitabine and docetaxel for enhanced anti‐breast cancer activity: DFT, docking, molecular dynamics simulation and pharmacophore studies

Sukumaran,

Zochedh,

Chandran

et al. 2024

Int J of Quantum Chemistry

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Combining FDA‐approved medications may increase biological activity by simultaneously targeting many protein mechanisms while being less toxic. Gemcitabine and docetaxel together might have a synergistic impact that kills cancer cells and makes them more effective against breast cancer. This study used the foundation set B3LYP/6–311 G to optimize the gemcitabine with the docetaxel structure that was created. Theoretical calculations were made for the ultraviolet to visible spectrum were studied in gas and liquid phase. The structural stability and reactivity of the combined structure were studied using the energy gap between HOMO and LUMO, and the computed energy gap (ΔE) was 4.219 eV. The electrostatic potential of complex structure was determined and the Mulliken charge population was evaluated. Through RDG analysis weak interactions of GEDT was evaluated and topology properties were studied through ELF and LOL analysis. Breast cancer target proteins were utilized in the molecular docking studies. The docking scores revealed a greater binding affinity for the complex molecule, confirming a superior combinatorial interaction between gemcitabine and docetaxel. Highest binding ability of the GEDT was against Caspase‐6 and the network analysis of Caspase‐6 was assessed through graph theory model. The stability of GEDT with Caspase‐6 was studied through molecular dynamic simulation for 100 ns. The adsorption, distribution, metabolism, excretion, and toxicity characteristics of the complex structure were investigated, and the findings revealed the complex lead compound's safety profile and its potential for use as a potent anticancer medication.

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Investigation on structural, spectroscopic, DFT, biological activity and molecular docking simulation of essential oil Gamma-Terpinene

Cited by 57 publications

References 58 publications

Quantum chemical calculation, topological analysis, biological evaluation and molecular docking of allo‐ocimenol against breast cancer

Quantum chemical calculation, topological analysis, biological evaluation and molecular docking of allo‐ocimenol against breast cancer

Contribution of Constituents in Rosemary‐Magnolia Compound Essential Oil to Antibacterial, Antioxidant and Cytotoxicity Bioactivities Revealed by Grey Correlation Analysis

Exploring the co‐activity of FDA approved drug gemcitabine and docetaxel for enhanced anti‐breast cancer activity: DFT, docking, molecular dynamics simulation and pharmacophore studies

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