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Diarylalkanoids as Potent Tyrosinase Inhibitors from the Stems of Semecarpus caudata.

ABSTRACT: From a CHCl₃-soluble extract of the stems of Semecarpus caudata (Anacardiaceae), two new diarylalkanoids, semedienone (1) and semetrienone (2), were isolated. Their structures were elucidated based on NMR spectroscopic data interpretation. These compounds possess strong tyrosinase inhibitory activity with the IC₅₀ values of 0.033 and 0.11??M, respectively. Docking studies of 1 and 2 with oxy-tyrosinase were carried out to analyze their interactions. Accordingly, semedienone (1) showed good interactions with the peroxide group and amino acid residues. The biosynthesis of the isolated diarylalkanoids was proposed.

SUBMITTER: Dang PH

PROVIDER: S-EPMC7801053 | biostudies-literature | 2021

REPOSITORIES: biostudies-literature

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Diarylalkanoids as Potent Tyrosinase Inhibitors from the Stems of Semecarpus caudata.

Dang Phu H PH Le Tho H TH Do Truong N V TNV Nguyen Hai X HX Nguyen Mai T T MTT Nguyen Nhan T NT

Evidence-based complementary and alternative medicine : eCAM 20210104

From a CHCl3-soluble extract of the stems of Semecarpus caudata (Anacardiaceae), two new diarylalkanoids, semedienone (1) and semetrienone (2), were isolated. Their structures were elucidated based on NMR spectroscopic data interpretation. These compounds possess strong tyrosinase inhibitory activity with the IC50 values of 0.033 and 0.11 μM, respectively. Docking studies of 1 and 2 with oxy-tyrosinase were carried out to ana ...[more]

PMID: 33488760

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Project description:Background and purposeTyrosinase enzyme has a key role in melanin biosynthesis by converting tyrosine into dopaquinone. It also participates in the enzymatic browning of vegetables by polyphenol oxidation. Therefore, tyrosinase inhibitors are useful in the fields of medicine, cosmetics, and agriculture. Many tyrosinase inhibitors having drawbacks have been reported to date; so, finding new inhibitors is a great need.Experimental approachA variety of 6-hydroxy-3,4-dihydronaphthalenone chalcone-like analogs (C1-C10) have been synthesized by aldol condensation of 6-hydroxy tetralone and differently substituted benzaldehydes. The compounds were evaluated for their inhibitory effect on mushroom tyrosinase by a spectrophotometric method. Moreover, the inhibition manner of the most active compound was determined by Lineweaver-Burk plots. Docking study was done using AutoDock 4.2. The drug-likeness scores and ADME features of the active derivatives were also predicted.Results/findingsMost of the compounds showed remarkable inhibitory activity against the tyrosinase enzyme. 6-Hydroxy-2-(3,4,5-trimethoxybenzylidene)-3,4-dihydronaphthalen-1(2H)-one (C2) was the most potent derivative amongst the series with an IC50 value of 8.8 μM which was slightly more favorable to that of the reference kojic acid (IC50 = 9.7 μM). Inhibitory kinetic studies revealed that C2 behaves as a competitive inhibitor. According to the docking results, compound C2 formed the most stable enzyme-inhibitor complex, mainly via establishing interactions with the two copper ions in the active site. In silico drug-likeness and pharmacokinetics predictions for the proposed tyrosinase inhibitors revealed that most of the compounds including C2 have proper drug-likeness scores and pharmacokinetic properties.Conclusion and implicationsTherefore, C2 could be suggested as a promising tyrosinase inhibitor that might be a good lead compound in medicine, cosmetics, and the food industry, and further drug development of this compound might be of great interest.

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Diarylalkanoids as Potent Tyrosinase Inhibitors from the Stems of Semecarpus caudata.

Publications

Diarylalkanoids as Potent Tyrosinase Inhibitors from the Stems of <i>Semecarpus caudata</i>.

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