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. 2018 Feb 4:2018:6354972.
doi: 10.1155/2018/6354972. eCollection 2018.

36H: A Novel Potent Inhibitor for Antimelanogenesis

Li-Ching Lin  1 , Chung-Yi Chen  2 , Chia-Hung Kuo  3 , Yun-Sheng Lin  4 , Byeong Hee Hwang  5 , Tina Kaiting Wang  6   7 , Yueh-Hsiung Kuo  8   9 , Hui-Min David Wang  10   11   12
Affiliations

36H: A Novel Potent Inhibitor for Antimelanogenesis

Li-Ching Lin et al. Oxid Med Cell Longev. .

Abstract

N-Hydroxycinnamoylphenalkylamides (36H) exhibited both antioxidation and antityrosinase abilities. The compound was studied for its antioxidative properties, using a 1,1-diphenyl-2-picrylhydrazul- (DPPH-) scavenging test, a ferric ion-reducing antioxidant power assay (FRAP) assessment, and a metal-chelating power assay. The results showed that 36H had antioxidative capabilities in the DPPH-scavenging and ferric-reducing power examinations but the chelating power assay did not demonstrate antioxidative capability. 36H was also measured for tyrosinase inhibitory activity applying various species platforms, including in vitro mushroom, B16F10 mouse melanoma, and human melanocyte cells. In terms of in vitro mushroom tyrosinase suppression, 36H restrained the melanogenesis processes. It is assumed that 36H blocked the tyrosinase active site as a competitive inhibitor for mushroom tyrosinase, hence not decreasing the human normal melanocyte cellular viability. A quantitative real-time polymerase chain reaction (qRT-PCR) and western blot discovered that 36H downregulated melanogenesis-related RNA and proteins, including pigment production (MITF, tyrosinase, TRP-1, and TRP-2), melanosome maturation (Rab27a), and melanosome transportation (Myo5a, MLPH and Mreg). Overall, 36H displayed the biofunctions of antioxidation and melanin suppression, so there was a possibility for its application as a food additive or a skin-whitening agent.

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Figures

Figure 1
Figure 1
The chemical structure of N-hydroxycinnamoylphenalkylamides (36H).
Figure 2
Figure 2
Inhibitory enzyme kinetic effects of 36H on mushroom tyrosinase. (a) 36H at different concentrations (1, 5, and 10 mM) affects mushroom tyrosinase activity. The concentration of positive control, Kojic acid, is 10 mM. Data are representative of 3 experiments. (b) The inhibition of mushroom tyrosinase enzyme activity of 10 mM. (c) Inhibition effects of 36H at different concentrations (1, 5, and 10 mM) on the activity of mushroom tyrosinase for the oxidation of L-tyrosine. (d) Inhibitory effect of 36H at different concentrations (10, 50, and 100 mM) on mushroom tyrosinase. The data for Lineweaver-Burk plots were obtained as mean values of three independent assays with various concentrations of L-tyrosine (0.125, 0.25, 0.5, 1, and 2 mM) as the substrate.
Figure 3
Figure 3
The inhibitory effect of 36H in HMC. (a) The impact of 36H at different concentrations (1, 5, 10, and 25 μM) to human melanocyte cell viabilities. (b) The tyrosinase activity of the human melanocyte cell treated with various concentrations of 36H. (c) The melanin content of the human melanocyte cell treated with various concentrations of 36H. Data are shown as mean ± SD; n = 3; ∗P < 0.005, compared with the control groups.
Figure 4
Figure 4
The RNA and protein expressions associated with melanin biosynthesis of human melanocyte cell treated with various concentrations (0, 10, and 25 μM) of 36H. Data are representative of 3 experiments. ∗P < 0.05 as compared with the control.
Figure 5
Figure 5
The RNA and protein expressions associated with melanosome maturation of human melanocyte cell treated with various concentrations (0, 10, and 25 μM) of 36H. Data are representative of 3 experiments. ∗P < 0.05 as compared with the control.
Figure 6
Figure 6
The RNA and protein expressions associated with the melanosome transport of human melanocyte cell treated with various concentrations (0, 10, and 25 μM) of 36H. Data are representative of 3 experiments. ∗P < 0.05 as compared with the control.
Figure 7
Figure 7
Proposed schematic diagram of compound 36H biofunctions.
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