Effects of scopoletin and aflatoxin B&lt;sub&gt;1&lt;/sub&gt; on bovine erythrocyte membrane Na-K-ATPase

Ezeokonkwo, C. A.; Obidoa, Onyechi; Eze, L. C.

doi:10.4314/wajpdr.v14i1.53411

Cited by 2 publications

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“…Three selected homologues bind tighter with shortening of the side chain at the 7-position. The binding modes of scopoletin with TcPMCA1 in the current study were different from our previous reports [ 32 ], which may be attributed to our use of different software to find the active binding site interactions of TcPMCA1 .…”

Section: Resultscontrasting

confidence: 99%

“…Studies have shown that scopoletin has a wide spectrum of biological activities, such as pronounced acaricidal [ 23 , 24 ], anti-inflammatory [ 25 , 26 ], antitumoral [ 27 ], antioxidative [ 20 ], hepatoprotective [ 28 ], insecticidal [ 29 ], antifungal [ 30 ], and alleopathic properties [ 31 ]. Based on its pronounced acaricidal activities, our research group further investigated the mechanism of action and found that Ca 2+ -ATPase, which is vital in nervous signal conduction [ 32 , 33 , 34 ], was inhibited [ 35 ] and TcPMCA1 from Ca 2+ -ATPase was significantly upregulated after T. cinnabarlnus was exposed to scopoletin, and molecular docking also showed that scopoletin inserts into the binding cavity and interacts with TcPMCA1 protein through the driving forces of hydrogen bonds [ 36 ]. However, its acaricidal activity remain lower than that of some registered synthetic chemical acaricides, such as pyridaben.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Acaricidal Activities of Scopoletin Phenolic Ether Derivatives: QSAR, Molecular Docking Study and in Silico ADME Predictions

et al. 2018

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Thirty phenolic ether derivatives of scopoletin modified at the 7-hydroxy position were synthesized, and their structures were confirmed by IR, 1H-NMR, 13C-NMR, MS and elemental analysis. Preliminary acaricidal activities of these compounds against female adults of Tetranychus cinnabarinus (Boisduval) were evaluated using the slide-dip method. The results indicated that some of these compounds exhibit more pronounced acaricidal activity than scopoletin, especially compounds 32, 20, 28, 27 and 8 which exhibited about 8.41-, 7.32-, 7.23-, 6.76-, and 6.65-fold higher acaricidal potency. Compound 32 possessed the the most promising acaricidal activity and exhibited about 1.45-fold higher acaricidal potency against T. cinnabarinus than propargite. Statistically significant 2D-QSAR model supports the observed acaricidal activities and reveals that polarizability (HATS5p) was the most important parameter controlling bioactivity. 3D-QSAR (CoMFA: q2 = 0.802, r2 = 0.993; CoMSIA: q2 = 0.735, r2 = 0.965) results show that bulky substituents at R4, R1, R2 and R5 (C6, C3, C4, and C7) positions, electron positive groups at R5 (C7) position, hydrophobic groups at R1 (C3) and R2 (C4), H-bond donors groups at R1 (C3) and R4 (C6) will increase their acaricidal activity, which provide a good insight into the molecular features relevant to the acaricidal activity for further designing novel acaricidal agents. Molecular docking demonstrates that these selected derivatives display different bide modes with TcPMCA1 from lead compound and they interact with more key amino acid residues than scopoletin. In silico ADME properties of scopoletin and its phenolic ether derivatives were also analyzed and showed potential to develop as good acaricidal candidates.

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Section: Resultscontrasting

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis and Acaricidal Activities of Scopoletin Phenolic Ether Derivatives: QSAR, Molecular Docking Study and in Silico ADME Predictions

et al. 2018

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“…The reported pharmacological effects of scopoletin presuppose some interactions with membrane-bound enzymes, such as Ca 2+ -ATPase, which is vital in nervous signal conduction [ 33 , 34 , 35 ]. Oliveira [ 36 ] reported that in rats, scopoletin inhibits Ca 2+ -ATPase activity by inhibiting the mobilization of intracellular calcium from noradrenaline-sensitive Ca stores.…”

Section: Discussionmentioning

confidence: 99%

3D-QSAR and Molecular Docking Studies on the TcPMCA1-Mediated Detoxification of Scopoletin and Coumarin Derivatives

Hou

Luo

Zhang

et al. 2017

IJMS

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The carmine spider mite, Tetranychus cinnabarinus (Boisduval), is an economically important agricultural pest that is difficult to prevent and control. Scopoletin is a botanical coumarin derivative that targets Ca2+-ATPase to exert a strong acaricidal effect on carmine spider mites. In this study, the full-length cDNA sequence of a plasma membrane Ca2+-ATPase 1 gene (TcPMCA1) was cloned. The sequence contains an open reading frame of 3750 bp and encodes a putative protein of 1249 amino acids. The effects of scopoletin on TcPMCA1 expression were investigated. TcPMCA1 was significantly upregulated after it was exposed to 10%, 30%, and 50% of the lethal concentration of scopoletin. Homology modeling, molecular docking, and three-dimensional quantitative structure-activity relationships were then studied to explore the relationship between scopoletin structure and TcPMCA1-inhibiting activity of scopoletin and other 30 coumarin derivatives. Results showed that scopoletin inserts into the binding cavity and interacts with amino acid residues at the binding site of the TcPMCA1 protein through the driving forces of hydrogen bonds. Furthermore, CoMFA (comparative molecular field analysis)- and CoMSIA (comparative molecular similarity index analysis)-derived models showed that the steric and H-bond fields of these compounds exert important influences on the activities of the coumarin compounds.Notably, the C3, C6, and C7 positions in the skeletal structure of the coumarins are the most suitable active sites. This work provides insights into the mechanism underlying the interaction of scopoletin with TcPMCA1. The present results can improve the understanding on plasma membrane Ca2+-ATPase-mediated (PMCA-mediated) detoxification of scopoletin and coumarin derivatives in T. cinnabarinus, as well as provide valuable information for the design of novel PMCA-inhibiting acaricides.

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Effects of scopoletin and aflatoxin B<sub>1</sub> on bovine erythrocyte membrane Na-K-ATPase

Cited by 2 publications

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Synthesis and Acaricidal Activities of Scopoletin Phenolic Ether Derivatives: QSAR, Molecular Docking Study and in Silico ADME Predictions

Synthesis and Acaricidal Activities of Scopoletin Phenolic Ether Derivatives: QSAR, Molecular Docking Study and in Silico ADME Predictions

3D-QSAR and Molecular Docking Studies on the TcPMCA1-Mediated Detoxification of Scopoletin and Coumarin Derivatives

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