title: Inhibition of tyrosinase activity and melanin production by the chalcone derivative 1-(2-cyclohexylmethoxy-6-hydroxy-phenyl)-3-(4-hydroxymethyl-phenyl)-propenone.
abstract: Abnormal accumulation of melanin pigments in the skin can be lead to hyperpigmentation disorders and melanoma. Melanin biosynthesis is ultimately regulated by the rate-limiting enzyme tyrosinase. In the present study, we synthesized chalcone derivatives and identified 1-(2-cyclohexylmethoxy-6-hydroxy-phenyl)-3-(4-hydroxymethyl-phenyl)-propenone (chalcone-21) as an anti-melanogenic substance in B16F10 melanoma cells. Chalcone-21 strongly inhibited cellular melanin production and tyrosinase activity in B16F10 melanoma cells stimulated with α-melanocyte stimulating hormone (α-MSH) or protoporphyrin IX. In addition, the compound suppressed not only the expression of tyrosinase, tyrosinase-related protein-1 (TRP-1), TRP-2, and microphthalmia-associated transcription factor (MITF), but also the transcriptional activity of tyrosinase and MITF. Our results demonstrated chalcone-21 to be an effective depigmenting agent.
authors.affiliation: Department of Pharmacology, Seoul National University College of Medicine, Seoul, 03080, Republic of Korea; CYTUS H&B Co., Ltd, Cheongju, 28160, Republic of Korea.
authors.forename: Byung-Hak
authors.initials: BH
authors.lastname: Kim
authors.affiliation: Department of Chemical & Biological Engineering, Hanbat National University, Daejeon, 34158, Republic of Korea.
authors.forename: Kyoung Chan
authors.initials: KC
authors.lastname: Park
authors.affiliation: Department of Chemical & Biological Engineering, Hanbat National University, Daejeon, 34158, Republic of Korea.
authors.forename: Jeong Ho
authors.initials: JH
authors.lastname: Park
authors.affiliation: CYTUS H&B Co., Ltd, Cheongju, 28160, Republic of Korea.
authors.forename: Chung Gi
authors.initials: CG
authors.lastname: Lee
authors.affiliation: Department of Pharmacology, Seoul National University College of Medicine, Seoul, 03080, Republic of Korea; Ischemic/Hypoxic Disease Institute, Seoul National University College of Medicine, Seoul, 03080, Republic of Korea; Neuro-Immune Information Storage Network Research Center, Seoul National University College of Medicine, Seoul, 03080, Republic of Korea. Electronic address: sangkyu@snu.ac.kr.
authors.forename: Sang-Kyu
authors.initials: SK
authors.lastname: Ye
authors.affiliation: Industry-Academic Cooperation Foundation, Hanbat National University, Daejeon, 34158, Republic of Korea. Electronic address: jypark@hanbat.ac.kr.
authors.forename: Jung Youl
authors.initials: JY
authors.lastname: Park
mesh_terms: D000818:Animals; D045744:Cell Line, Tumor; D047188:Chalcones / Q000138:chemical synthesis / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D015536:Down-Regulation / Q000187:drug effects / Q000502:physiology; D004789:Enzyme Activation / Q000187:drug effects; D004791:Enzyme Inhibitors / Q000494:pharmacology; D008543:Melanins / Q000096:biosynthesis*; D008545:Melanoma / Q000378:metabolism*; D051379:Mice; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors* / Q000378:metabolism*; D010858:Pigmentation / Q000187:drug effects*
chemical_list: D047188:Chalcones; D004791:Enzyme Inhibitors; D008543:Melanins; D014442:Monophenol Monooxygenase
keywords: 1-(2-Cyclohexylmethoxy-6-hydroxy-phenyl)-3-(4-hydroxymethyl-phenyl)-propenone (chalcone-21); Hyperpigmentation disorder; Melanin; Melanogenesis; Tyrosinase