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. 2018 Jan 22;23(1):232.
doi: 10.3390/molecules23010232.

Chemical Constituents from Apios americana and Their Inhibitory Activity on Tyrosinase

Jang Hoon Kim  1 , Hyo Young Kim  2 , Si Yong Kang  3 , Jin-Baek Kim  4 , Young Ho Kim  5 , Chang Hyun Jin  6
Affiliations

Chemical Constituents from Apios americana and Their Inhibitory Activity on Tyrosinase

Jang Hoon Kim et al. Molecules. .

Abstract

The goal of this study was to identify phytochemicals with inhibitory activity against tyrosinase. Nine compounds 1-9 were isolated from the tubers of Apios americana. This is the first report of aromadendrin 5-methyl ether (1) being isolated from the Apios species. Among them, compounds 2 and 8 showed inhibitory activity toward tyrosinase. Based on a Dixon plot, the potential Ki values of competitive inhibitors 2 and 8 were calculated as 10.3 ± 0.8 µM and 44.2 ± 1.7 µM, respectively. An IC50 value of 13.2 ± 1.0 µM was calculated for the slow-binding inhibitor 2 after preincubation with tyrosinase. Additionally, the predicted binding sites between the receptor and ligand, as well as secondary structure changes, in the presence of 2 were examined by molecular simulation.

Keywords: Apios americana; Leguminosae; molecular simulation; slow binding inhibitor; tyrosinase.

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Conflict of interest statement

The authors declared no conflict of interest.

Figures

Figure 1
Figure 1
Structure of compounds 1–9 isolated from A. americana.
Figure 2
Figure 2
Inhibitory activity of compounds 1–9 (A) on tyrosinase and compounds 2 and 8 (B); Lineweaver-burk plot and Dixon plot of respective compounds 2 (C,E) and 8 (D,F).
Figure 3
Figure 3
(A) Progress curves for slow-binding inhibition of tyrosinase by 2; (B) Dependence of the values of kobs on the concentration of 2; (C) Scheme for a slow-binding inhibition process.
Figure 4
Figure 4
Predicted docking poses of 2 (yellow) and 8 (green) with enzyme (A); The green arrow represented hydrogen bond (B,C) and hydrophobic (D,E) interactions between respective ligands (2 and 8) and receptor.
Figure 5
Figure 5
The potential energy (A); RMSD (B); Hydrogen bonding number (C); and RMSF (D) of tyrosinase without ligand and tyrosinase with 2, respectively.
Figure 6
Figure 6
The superpositions of apo-receptor (A) and receptor with ligand (B) for the simulation time (red: 0, orange: 1, yellow: 2, green: 3, forestgreen: 4, cyan: 5, blue: 6, purple: 7, hot pink: 8, magenta: 9, and, black:10 during 10 ns). The distance of copper with ligand (C).
See this image and copyright information in PMC

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