Next Article in Journal
Bone Morphogenetic Protein-7 Ameliorates Cerebral Ischemia and Reperfusion Injury via Inhibiting Oxidative Stress and Neuronal Apoptosis
Previous Article in Journal
Role of Sam68 in Post-Transcriptional Gene Regulation
Int. J. Mol. Sci. 2013, 14(12), 23420-23440; doi:10.3390/ijms141223420
Article

Tyrosol and Its Analogues Inhibit Alpha-Melanocyte-Stimulating Hormone Induced Melanogenesis

1
, 2
, 1
, 1
, 1
, 1
 and 1,*
Received: 18 September 2013; in revised form: 11 November 2013 / Accepted: 18 November 2013 / Published: 28 November 2013
(This article belongs to the Section Bioactives and Nutraceuticals)
View Full-Text   |   Download PDF [1596 KB, uploaded 19 June 2014]   |   Browse Figures
Abstract: Melanin is responsible for skin color and plays a major role in defending against harmful external factors such as ultraviolet (UV) irradiation. Tyrosinase is responsible for the critical steps of melanogenesis, including the rate-limiting step of tyrosine hydroxylation. The mechanisms of action of skin hypopigmenting agents are thought to be based on the ability of a given agent to inhibit the activity of tyrosinase and, hence, down regulate melanin synthesis. Tyrosol and its glycoside, salidroside, are active components of Rhodiola rosea, and in our preliminary study we found that Rhodiola rosea extract inhibited melanogenesis. In this study, we examined the effects of tyrosol and its analogues on melanin synthesis. We found that treatment of B16F0 cells to tyrosol (1), 4-hydroxyphenylacetic acid (5), 3-hydroxyphenylacetic acid (6), 2-hydroxyphenylacetic acid (7), or salidroside (11) resulted in a reduction in melanin content and inhibition of tyrosinase activity as well as its expression. Tyrosol (1), 4-hydroxyphenylacetic acid (5) and 2-hydroxyphenylacetic acid (7) suppressed MC1R expression. Tyrosol (1), 4-hydroxyphenylacetic acid (5), 3-hydroxyphenylacetic acid (6), and 2-hydroxyphenylacetic acid (7) inhibited α-MSH induced TRP-1 expression, but salidroside (11) did not. All the compounds did not affect MITF and TRP-2 expression. Furthermore, we found that the cell viability of tyrosol (1), 4-hydroxyphenylacetic acid (5), 3-hydroxyphenylacetic acid (6), and 2-hydroxyphenylacetic acid (7) at concentrations below 4 mM and salidroside (11) at concentrations below 0.5 mM were higher than 90%. The compounds exhibited metal-coordinating interactions with copper ion in molecular docking with tyrosinase. Our results suggest that tyrosol, 4-hydroxyphenylacetic acid, 3-hydroxyphenylacetic acid, 2-hydroxyphenylacetic acid, and salidroside are potential hypopigmenting agents.
Keywords: melanogenesis; melanocortin 1 receptor; tyrosol; tyrosol analogues; tyrosinase-related protein melanogenesis; melanocortin 1 receptor; tyrosol; tyrosol analogues; tyrosinase-related protein
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Export to BibTeX |
EndNote


MDPI and ACS Style

Wen, K.-C.; Chang, C.-S.; Chien, Y.-C.; Wang, H.-W.; Wu, W.-C.; Wu, C.-S.; Chiang, H.-M. Tyrosol and Its Analogues Inhibit Alpha-Melanocyte-Stimulating Hormone Induced Melanogenesis. Int. J. Mol. Sci. 2013, 14, 23420-23440.

AMA Style

Wen K-C, Chang C-S, Chien Y-C, Wang H-W, Wu W-C, Wu C-S, Chiang H-M. Tyrosol and Its Analogues Inhibit Alpha-Melanocyte-Stimulating Hormone Induced Melanogenesis. International Journal of Molecular Sciences. 2013; 14(12):23420-23440.

Chicago/Turabian Style

Wen, Kuo-Ching; Chang, Chih-Shiang; Chien, Yin-Chih; Wang, Hsiao-Wen; Wu, Wan-Chen; Wu, Chin-Sheng; Chiang, Hsiu-Mei. 2013. "Tyrosol and Its Analogues Inhibit Alpha-Melanocyte-Stimulating Hormone Induced Melanogenesis." Int. J. Mol. Sci. 14, no. 12: 23420-23440.


Int. J. Mol. Sci. EISSN 1422-0067 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert