Thermodynamic, kinetic and docking studies of some unsaturated fatty acids-quercetin derivatives as inhibitors of mushroom tyrosinase

Vaezi, Morteza; Behbehani, G. Rezaei; Gheibi, Nematollah; Farasat, Alireza

doi:10.3934/biophy.2020027

Cited by 11 publications

(9 citation statements)

References 26 publications

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“…The inhibition constants of ligands represent that the esterification of unsaturated fatty acids confirms that these ligands are potential inhibitors for MT activity. As shown in previous studies, it was found that esters of quercetin‐ linoleic acid and quercetin‐oleic acid are stronger tyrosinase inhibitors with compared to some fatty acids (Vaezi et al., 2020; Guo et al., 2010; Watabe et al, 2004). Compared their K I values, it was found that quercetin ( K I = 0.064 mM) exhibited stronger inhibition than quercetin omega‐6 ( K I = 0.31 mM) and quercetin omega‐9 esters ( K I = 0.43 mM) (Fan et al., 2017; Vaezi et al., 2020).…”

Section: Resultsmentioning

confidence: 52%

“…As shown in previous studies, it was found that esters of quercetin‐ linoleic acid and quercetin‐oleic acid are stronger tyrosinase inhibitors with compared to some fatty acids (Vaezi et al., 2020; Guo et al., 2010; Watabe et al, 2004). Compared their K I values, it was found that quercetin ( K I = 0.064 mM) exhibited stronger inhibition than quercetin omega‐6 ( K I = 0.31 mM) and quercetin omega‐9 esters ( K I = 0.43 mM) (Fan et al., 2017; Vaezi et al., 2020). This may be due to large ligands reduce movement to access to enzyme binding sites.…”

Section: Resultsmentioning

confidence: 52%

“…It was found that the inhibitory potential of ligands depended on the concentration, number of double bonds and the length of chain unsaturated fatty acids (De Caterina et al., 2000; Guo et al., 2010; Oda et al., 2002). The ligands inhibition constants ( K I ) were obtained by the method previously described (Vaezi et al., 2020). The inhibition constants of ligands represent that the esterification of unsaturated fatty acids confirms that these ligands are potential inhibitors for MT activity.…”

Section: Resultsmentioning

confidence: 99%

“…Isopropyl alcohol was used to make all stock solutions for the inhibitors and substrates. Bioactive ligands A and B were synthetized using as previously described (Hu et al., 2016; Mainini et al., 2013; Vaezi et al., 2020). Distilled water was used, and all other reagents were of analytical grade.…”

Section: Methodsmentioning

confidence: 99%

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Evaluation of quercetin omega‐6 and ‐9 esters on activity and structure of mushroom tyrosinase: Spectroscopic and molecular docking studies

Vaezi

2021

J Food Biochem

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Quercetin is one of the most ubiquitous dietary flavonoids widely distributed in plants and foods of plant origin, and is a potent tyrosinase inhibitor. Quercetin fatty esters could lead to an improve in quercetin lipophilicity which could positively affect its pharmacological activity. In this study, the inhibitory effect of two novel esters of quercetin‐linoleic acid (ligand A) and quercetin‐oleic acid (ligand B) has been investigated on structure and diphenolase activity of mushroom tyrosinase (MT) by experimental and molecular docking techniques. The inhibitory kinetics study using UV‐visible spectrophotometry in the presence of its substrate 3,4‐dihydroxyphenylalanine (L‐dopa), revealed that both esters successfully inhibit the activity of tyrosinase and reduce the formation of dopaquinone. Results showed that the binding of ligands to MT induced rearrangement and conformational changes of the enzyme. Thermodynamic parameters of these interactions (Ka, ∆G°, ∆H° and ∆S°) were obtained at pH = 6.8 and temperatures of 298 and 310 K. Molecular docking studies further was applied to calculation of binding energies (ΔGbA = −21.84 kJ/mol, ΔGbB = −20.92 kJ/mol), inhibition constant values (KIA = 160 µM, KIB = 220 µM) and the special binding site. It can be deduced that ligands act as a potential tyrosinase inhibitor and it was found that the best possible interaction condition with binding modes visualize was achieved by ligand A and exhibited the potent tyrosinase inhibitory activity. These findings may be helpful to understand the inhibition mechanism of quercetin fatty acids esters on tyrosinase and provide a convenient screening method to differentiate phenolic tyrosinase inhibitors. Practical applications Bioavailability and antioxidant activity of conjugated fatty acids with their bioequivalence in several biological effects and metabolic processes such as beta‐oxidation from various forms has been reported to be highly variable and useful. Quercetin shows beneficial role in human health, but its biological effects in vivo is limited by poor bioavailability, low skin permeability and solubility. This study design new tyrosinase inhibitors which helpful to functional research of unsaturated fatty acid esters in the treatment of inflammatory diseases and hyperpigmentation disorders. In addition, undesirable enzymatic browning of plant derived‐foods by tyrosinase causes a decrease in market value and economic loss of food products. The results suggest that the conjugation of quercetin with linoleic and oleic acids resulted in novel stronger tyrosinase inhibitors which may have therapeutic applications and replacement of toxic tyrosinase inhibitors and contribute as anti‐ browning agents in food, cosmetic and pharmaceutical industry.

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Section: Resultsmentioning

confidence: 52%

Section: Resultsmentioning

confidence: 52%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Evaluation of quercetin omega‐6 and ‐9 esters on activity and structure of mushroom tyrosinase: Spectroscopic and molecular docking studies

Vaezi

2021

J Food Biochem

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“…The K I values could be different from those in previous studies because they are affected by the reaction time and substrate and enzyme concentrations. Previous studies have synthesized quercetin-7-oleate using quercetin and oleic acid, and their inhibition of tyrosinase was measured [ 18 ]. Quercetin-7-oleate is a competitive inhibitor of tyrosinase.…”

Section: Discussionmentioning

confidence: 99%

Novel Quercetin Derivative of 3,7-Dioleylquercetin Shows Less Toxicity and Highly Potent Tyrosinase Inhibition Activity

Choi

Yang

Kim

et al. 2021

IJMS

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Quercetin is a well-known plant flavonol and antioxidant; however, there has been some debate regarding the efficacy and safety of native quercetin as a skin-whitening agent via tyrosinase inhibition. Several researchers have synthesized quercetin derivatives as low-toxicity antioxidants and whitening agents. However, no suitable quercetin derivatives have been reported to date. In this study, a novel quercetin derivative was synthesized by the SN2 reaction using quercetin and oleyl bromide. The relationship between the structures and activities of quercetin derivatives as anti-melanogenic agents was assessed using in vitro enzyme kinetics, molecular docking, and quenching studies; cell line experiments; and in vivo zebrafish model studies. Novel 3,7-dioleylquercetin (OQ) exhibited a low cytotoxic concentration level at >100 µg/mL (125 µM), which is five times less toxic than native quercetin. The inhibition mechanism showed that OQ is a competitive inhibitor, similar to native quercetin. Expression of tyrosinase, tyrosinase-related protein 1 (TRP-1) and tyrosinase-related protein 2 (TRP-2), and microphthalmia-associated transcription factor was inhibited in B16F10 melanoma cell lines. mRNA transcription levels of tyrosinase, TRP-1, and TRP-2 decreased in a dose-dependent manner. Melanin formation was confirmed in the zebrafish model using quercetin derivatives. Therefore, OQ might be a valuable asset for the development of novel skin-whitening agents.

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Development of new sustainable pyridinium ionic liquids: From reactivity studies to mechanism-based activity predictions

Borikhonov,

Berdimurodov,

Kholikov

et al. 2024

J Mol Model

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Thermodynamic, kinetic and docking studies of some unsaturated fatty acids-quercetin derivatives as inhibitors of mushroom tyrosinase

Cited by 11 publications

References 26 publications

Evaluation of quercetin omega‐6 and ‐9 esters on activity and structure of mushroom tyrosinase: Spectroscopic and molecular docking studies

Evaluation of quercetin omega‐6 and ‐9 esters on activity and structure of mushroom tyrosinase: Spectroscopic and molecular docking studies

Novel Quercetin Derivative of 3,7-Dioleylquercetin Shows Less Toxicity and Highly Potent Tyrosinase Inhibition Activity

Development of new sustainable pyridinium ionic liquids: From reactivity studies to mechanism-based activity predictions

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