title: Free-Radical-Scavenging, Antityrosinase, and Cellular Melanogenesis Inhibitory Activities of Synthetic Isoflavones.
abstract: In this study, we examined the potential of synthetic isoflavones for application in cosmeceuticals. Twenty-five isoflavones were synthesized and their capacities of free-radical-scavenging and mushroom tyrosinase inhibition, as well as their impact on cell viability of B16F10 murine melanoma cells and HaCaT human keratinocytes were evaluated. Isoflavones that showed significant mushroom tyrosinase inhibitory activities were further studied on reduction of cellular melanin formation and antityrosinase activities in B16F10 melanocytes in vitro. Among the isoflavones tested, 6-hydroxydaidzein (2) was the strongest scavenger of both ABTS(.+) and DPPH(.) radicals with SC50 values of 11.3 ± 0.3 and 9.4 ± 0.1 μM, respectively. Texasin (20) exhibited the most potent inhibition of mushroom tyrosinase (IC50 14.9 ± 4.5 μM), whereas retusin (17) showed the most efficient inhibition both of cellular melanin formation and antityrosinase activity in B16F10 melanocytes, respectively. In summary, both retusin (17) and texasin (20) exhibited potent free-radical-scavenging capacities as well as efficient inhibition of cellular melanogenesis, suggesting that they are valuable hit compounds with potential for advanced cosmeceutical development.
authors.affiliation: Department of Pharmacy, Tajen University, No. 20 Wei-Xin Rd., Yanpu, Pingtung 907, Taiwan, ROC, (phone: +886-8-7624002 ext. 2727; fax: +886-8-7625308). tzminglu@gmail.com, cmlu@tajen.edu.tw.
authors.forename: Tzy-Ming
authors.initials: TM
authors.lastname: Lu
authors.affiliation: Department of Fragrance and Cosmetic Science, Kaohsiung Medical University, Kaohsiung 807, Taiwan, ROC.
authors.forename: Horng-Huey
authors.initials: HH
authors.lastname: Ko
authors.affiliation: Department of Agricultural Chemistry, National Taiwan University, Taipei 106, Taiwan, ROC.
authors.forename: Lean-Teik
authors.initials: LT
authors.lastname: Ng
authors.affiliation: Department of Pharmacy, Fooyin University Hospital, Pingtung 917, Taiwan, ROC.
authors.forename: Yen-Pin
authors.initials: YP
authors.lastname: Hsieh
mesh_terms: D000363:Agaricales / Q000201:enzymology; D000818:Animals; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D016166:Free Radical Scavengers / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D006801:Humans; D007529:Isoflavones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D015603:Keratinocytes / Q000187:drug effects; D008543:Melanins / Q000037:antagonists & inhibitors* / Q000096:biosynthesis; D051379:Mice; D015394:Molecular Structure; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors* / Q000378:metabolism; D013329:Structure-Activity Relationship
chemical_list: D004791:Enzyme Inhibitors; D016166:Free Radical Scavengers; D007529:Isoflavones; D008543:Melanins; D014442:Monophenol Monooxygenase
keywords: Cosmeceuticals; Free radicals; Isoflavones; Melanins; Tyrosinase