{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,4]],"date-time":"2026-06-04T10:48:49Z","timestamp":1780570129315,"version":"3.54.1"},"reference-count":15,"publisher":"Wiley","issue":"6","license":[{"start":{"date-parts":[[2014,9,3]],"date-time":"2014-09-03T00:00:00Z","timestamp":1409702400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100001691","name":"Japanese Society for the Promotion of Science","doi-asserted-by":"crossref","award":["23591659, 26461705"],"award-info":[{"award-number":["23591659, 26461705"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"crossref"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Pigment Cell Melanoma Res"],"published-print":{"date-parts":[[2014,11]]},"abstract":"<jats:title>Summary<\/jats:title><jats:p>Racemic<jats:italic><jats:styled-content style=\"fixed-case\">RS<\/jats:styled-content><\/jats:italic>\u20104\u2010(4\u2010hydroxyphenyl)\u20102\u2010butanol (rhododendrol,<jats:styled-content style=\"fixed-case\">RD<\/jats:styled-content>) was used as a topical skin\u2010whitening agent until it was recently reported to induce leukoderma. We then showed that oxidation of<jats:styled-content style=\"fixed-case\">RD<\/jats:styled-content>with mushroom tyrosinase rapidly produces<jats:styled-content style=\"fixed-case\">RD<\/jats:styled-content>\u2010quinone, which is quickly converted to<jats:styled-content style=\"fixed-case\">RD<\/jats:styled-content>\u2010cyclic quinone and<jats:styled-content style=\"fixed-case\">RD<\/jats:styled-content>\u2010hydroxy\u2010<jats:italic>p<\/jats:italic>\u2010quinone. In this study, we examined whether either or both of the enantiomers of<jats:styled-content style=\"fixed-case\">RD<\/jats:styled-content>can be oxidized by human tyrosinase. Using a chiral<jats:styled-content style=\"fixed-case\">HPLC<\/jats:styled-content>column, racemic<jats:styled-content style=\"fixed-case\">RD<\/jats:styled-content>was resolved optically to<jats:italic>R<\/jats:italic>(\u2212)\u2010<jats:styled-content style=\"fixed-case\">RD<\/jats:styled-content>and<jats:italic>S<\/jats:italic>(+)\u2010<jats:styled-content style=\"fixed-case\">RD<\/jats:styled-content>enantiomers. In the presence of a catalytic amount of<jats:sc>l<\/jats:sc>\u2010dopa, human tyrosinase, which can oxidize<jats:sc>l<\/jats:sc>\u2010tyrosine but not<jats:sc>d<\/jats:sc>\u2010tyrosine, was found to oxidize both<jats:italic>R<\/jats:italic>(\u2212)\u2010 and<jats:italic>S<\/jats:italic>(+)\u2010<jats:styled-content style=\"fixed-case\">RD<\/jats:styled-content>to give<jats:styled-content style=\"fixed-case\">RD<\/jats:styled-content>\u2010catechol and its oxidation products.<jats:italic>S<\/jats:italic>(+)\u2010<jats:styled-content style=\"fixed-case\">RD<\/jats:styled-content>was more effectively oxidized than<jats:sc>l<\/jats:sc>\u2010tyrosine, while<jats:italic>R<\/jats:italic>(\u2212)\u2010<jats:styled-content style=\"fixed-case\">RD<\/jats:styled-content>was less effective. These results support the notion that the melanocyte toxicity of<jats:styled-content style=\"fixed-case\">RD<\/jats:styled-content>depends on its tyrosinase\u2010catalyzed conversion to toxic quinones and the concomitant production of reactive oxygen species.<\/jats:p>","DOI":"10.1111\/pcmr.12300","type":"journal-article","created":{"date-parts":[[2014,7,30]],"date-time":"2014-07-30T07:53:55Z","timestamp":1406706835000},"page":"1149-1153","source":"Crossref","is-referenced-by-count":39,"title":["Human tyrosinase is able to oxidize both enantiomers of rhododendrol"],"prefix":"10.1111","volume":"27","author":[{"given":"Shosuke","family":"Ito","sequence":"first","affiliation":[{"name":"Department of Chemistry Fujita Health University School of Health Sciences Toyoake Aichi Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wolfram","family":"Gerwat","sequence":"additional","affiliation":[{"name":"Research and Development Beiersdorf AG Hamburg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ludger","family":"Kolbe","sequence":"additional","affiliation":[{"name":"Research and Development Beiersdorf AG Hamburg Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Toshiharu","family":"Yamashita","sequence":"additional","affiliation":[{"name":"Department of Dermatology Sapporo Medical University School of Medicine Sapporo Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Makoto","family":"Ojika","sequence":"additional","affiliation":[{"name":"Department of Applied Molecular Biosciences Graduate School of Bioagricultural Sciences Nagoya University Nagoya Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kazumasa","family":"Wakamatsu","sequence":"additional","affiliation":[{"name":"Department of Chemistry Fujita Health University School of Health Sciences Toyoake Aichi Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2014,9,3]]},"reference":[{"key":"e_1_2_4_2_1","doi-asserted-by":"publisher","DOI":"10.1248\/bpb.29.1970"},{"key":"e_1_2_4_3_1","doi-asserted-by":"publisher","DOI":"10.1021\/tx9902082"},{"key":"e_1_2_4_4_1","doi-asserted-by":"publisher","DOI":"10.1515\/hsz-2012-0300"},{"key":"e_1_2_4_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/0031-9422(93)85127-D"},{"key":"e_1_2_4_6_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-2006-957529"},{"key":"e_1_2_4_7_1","doi-asserted-by":"crossref","first-page":"644","DOI":"10.1016\/S0026-895X(25)13536-0","article-title":"Autoxidation versus covalent binding of quinones as the mechanism of toxicity of dopamine, 6\u2010hydroxydopamine, and related compounds toward C1300 neuroblastoma cells in vitro","volume":"14","author":"Graham D.G.","year":"1978","journal-title":"Mol. Pharmacol."},{"key":"e_1_2_4_8_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1751-1097.2007.00238.x"},{"key":"e_1_2_4_9_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bcp.2012.06.015"},{"key":"e_1_2_4_10_1","doi-asserted-by":"publisher","DOI":"10.1111\/pcmr.12275"},{"key":"e_1_2_4_11_1","doi-asserted-by":"publisher","DOI":"10.1111\/jdv.12051"},{"key":"e_1_2_4_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/tx900018q"},{"key":"e_1_2_4_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmc.2014.02.048"},{"key":"e_1_2_4_14_1","doi-asserted-by":"publisher","DOI":"10.1111\/pcmr.12269"},{"key":"e_1_2_4_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo01027a539"},{"key":"e_1_2_4_16_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1600-0749.1996.tb00095.x"}],"container-title":["Pigment Cell &amp; Melanoma Research"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1111%2Fpcmr.12300","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1111\/pcmr.12300","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,5,4]],"date-time":"2025-05-04T00:35:35Z","timestamp":1746318935000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1111\/pcmr.12300"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2014,9,3]]},"references-count":15,"journal-issue":{"issue":"6","published-print":{"date-parts":[[2014,11]]}},"alternative-id":["10.1111\/pcmr.12300"],"URL":"https:\/\/doi.org\/10.1111\/pcmr.12300","archive":["Portico"],"relation":{},"ISSN":["1755-1471","1755-148X"],"issn-type":[{"value":"1755-1471","type":"print"},{"value":"1755-148X","type":"electronic"}],"subject":[],"published":{"date-parts":[[2014,9,3]]}}}