Studies on an alkylhydroquinone from Rhus succedanea as an inhibitor of tyrosinase and melanogenesis
Date Issued
2009
Date
2009
Author(s)
Chen, Yun-Ru
Abstract
The development of effective skin whitening agents has become an increasing important research area. Human have approximately the same number of melanocytes in the skin. Differences in skin color are primarily due to the ratio of eumelanin to pheomelanin, their distribution in keratinocytes, degree of tyrosinase activity in melanocyte, and environmental factors. Tyrosinase is a copper-containing oxidase that catalyses the oxidation of phenol like compounds (such as tyrosine) and is widespread in plants and animals. Tyrosinase catalyzes the production of melanin in mammals and other pigments from tyrosine by oxidation. Modulation of melanogenesis in the melanocytes can be achieved using chemicals that share structural homologies with the substrate tyrosine and as thus competitively inhibit the catalytic function of tyrosinase. In this study, alkylhydroquinone, 10''(Z)-heptadecenylhydroquinone [HQ17(1)], isolated from the sap of the lacquer tree Rhus succedanea, was found to inhibit the activity of tyrosinase and to suppress melanin production in animal cells. The IC50 of HQ17(1) as a tyrosinase inhibitor was 37 µM versus 70 µM for hydroquinone (HQ), a known inhibitor of tyrosinase and melanogenesis. For the inhibition of melanin production in mouse B16 melanoma cells, the EC50 of HQ17(1) was 40 µM versus 124 µM for HQ. HQ17(1) induced much less cellular reactive oxygen species (ROS) than did HQ. The effectiveness in inhibiting melanin production could be mimicked by intermittent exposure of cells to HQ17(1). The potent inhibitory effects of HQ17(1) on tyrosinase activity and melanin production are likely due to its heptadecenyl chain, which facilitates retention of the compound in cell membrane compartments and may impedes the oxidation of the hydroquinone ring. As tyrosinase activity accounts for the melanogenesis in animal skin, HQ17(1) could be useful in skin whitening cosmetics. In this study, we had also demonstrated that HQ17(1) can suppress the mRNA expression of melanogenesisi related genes and the cellular protein level of tyrosinase. This decreasing effect may due to the activation of ERK pathway by HQ17(1) induction. Taken together, HQ17(1) can inhibit the synthesis of melanin via a dual-action mechanism suggesting that HQ17(1) had the potential to become a useful tyrosinase inhibitor or anti-melanogensis agent in cosmetics and medicine.
Subjects
Rhus succedanea
alkylhydroquinone
tyrosinase inhibitor
anti-melanogenesis
skin whitening
SDGs
File(s)![Thumbnail Image]()
Loading...
Name
ntu-98-F90424003-1.pdf
Size
23.32 KB
Format
Adobe PDF
Checksum
(MD5):ebd7ca43317b49c623abaf1fda337f99