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Tyrosinase‐catalyzed oxidation of rhododendrol produces 2‐methylchromane‐6,7‐dione, the putative ultimate toxic metabolite: implications for melanocyte toxicity

Overview of attention for article published in Pigment Cell & Melanoma Research, June 2014
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Title
Tyrosinase‐catalyzed oxidation of rhododendrol produces 2‐methylchromane‐6,7‐dione, the putative ultimate toxic metabolite: implications for melanocyte toxicity
Published in
Pigment Cell & Melanoma Research, June 2014
DOI 10.1111/pcmr.12275
Pubmed ID
Authors

Shosuke Ito, Makoto Ojika, Toshiharu Yamashita, Kazumasa Wakamatsu

Abstract

RS-4-(4-Hydroxyphenyl)-2-butanol (rhododendrol, RD) was used as a skin-whitening agent until it was reported to induce leukoderma in July 2013. To explore the mechanism underlying its melanocyte toxicity, we characterized the tyrosinase-catalyzed oxidation of RD using spectrophotometry and HPLC. Oxidation of RD with mushroom tyrosinase rapidly produced RD-quinone, which was quickly converted to 2-methylchromane-6,7-dione (RD-cyclic quinone) and RD-hydroxy-p-quinone through cyclization and addition of water molecule, respectively. RD-quinone and RD-cyclic quinone were identified as RD-catechol and RD-cyclic catechol after NaBH4 reduction. Autoxidation of RD-cyclic catechol produced superoxide radical. RD-quinone and RD-cyclic quinone quantitatively bound to thiols such as cysteine and GSH. These results suggest that the melanocyte toxicity of RD is caused by its tyrosinase-catalyzed oxidation through production of RD-cyclic quinone which depletes cytosolic GSH and then binds to essential cellular proteins through their sulfhydryl groups. The production of ROS through autoxidation of RD-cyclic catechol may augment the toxicity.

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X Demographics

The data shown below were collected from the profiles of 4 X users who shared this research output. Click here to find out more about how the information was compiled.
Mendeley readers

Mendeley readers

The data shown below were compiled from readership statistics for 23 Mendeley readers of this research output. Click here to see the associated Mendeley record.

Geographical breakdown

Country Count As %
Japan 1 4%
Unknown 22 96%

Demographic breakdown

Readers by professional status Count As %
Student > Ph. D. Student 6 26%
Researcher 3 13%
Student > Doctoral Student 2 9%
Other 2 9%
Professor > Associate Professor 2 9%
Other 5 22%
Unknown 3 13%
Readers by discipline Count As %
Medicine and Dentistry 5 22%
Chemistry 5 22%
Biochemistry, Genetics and Molecular Biology 4 17%
Agricultural and Biological Sciences 3 13%
Pharmacology, Toxicology and Pharmaceutical Science 1 4%
Other 1 4%
Unknown 4 17%
Attention Score in Context

Attention Score in Context

This research output has an Altmetric Attention Score of 3. This is our high-level measure of the quality and quantity of online attention that it has received. This Attention Score, as well as the ranking and number of research outputs shown below, was calculated when the research output was last mentioned on 07 July 2014.
All research outputs
#15,208,162
of 25,554,853 outputs
Outputs from Pigment Cell & Melanoma Research
#698
of 1,272 outputs
Outputs of similar age
#123,018
of 242,870 outputs
Outputs of similar age from Pigment Cell & Melanoma Research
#11
of 28 outputs
Altmetric has tracked 25,554,853 research outputs across all sources so far. This one is in the 40th percentile – i.e., 40% of other outputs scored the same or lower than it.
So far Altmetric has tracked 1,272 research outputs from this source. They typically receive a little more attention than average, with a mean Attention Score of 5.8. This one is in the 44th percentile – i.e., 44% of its peers scored the same or lower than it.
Older research outputs will score higher simply because they've had more time to accumulate mentions. To account for age we can compare this Altmetric Attention Score to the 242,870 tracked outputs that were published within six weeks on either side of this one in any source. This one is in the 49th percentile – i.e., 49% of its contemporaries scored the same or lower than it.
We're also able to compare this research output to 28 others from the same source and published within six weeks on either side of this one. This one has gotten more attention than average, scoring higher than 64% of its contemporaries.