title: Effects of resveratrol, oxyresveratrol, and their acetylated derivatives on cellular melanogenesis.
abstract: Resveratrol and oxyresveratrol are naturally occurring phenolic compounds with various bioactivities, but their uses in cosmetics have been partly limited by their chemical instabilities. This study was performed to examine the anti-melanogenic effects of the acetylated derivatives from resveratrol and oxyresveratrol. Resveratrol and oxyresveratrol were chemically modified to triacetyl resveratrol and tetraacetyl oxyresveratrol, respectively. The acetylated compounds were less susceptible than the parent compounds to oxidative discoloration. The acetylated compounds inhibited the activities of tyrosinases less than parent compounds in vitro, but they were as effective at cellular melanogenesis inhibition, indicating bioconversion to parent compounds inside cells. Supporting this notion, the parent compounds were regenerated when the acetylated compounds were digested with cell lysates. Although resveratrol and triacetyl resveratrol inhibited tyrosinase activity less effectively than oxyresveratrol and tetraacetyl oxyresveratrol in vitro, they inhibited cellular melanogenesis more effectively. This discrepancy was explained by strong inhibition of tyrosinase expression by resveratrol and triacetyl resveratrol. Experiments using a reconstituted skin model indicated that resveratrol derivatives can affect melanin synthesis and cell viability to different extents. Collectively, this study suggests that acetylated derivatives of resveratrol have great potential as anti-melanogenic agents for cosmetic use in terms of efficacy, safety, and stability.
authors.affiliation: Department of Molecular Medicine and Cell and Matrix Research Institute, BK21 plus program, Kyungpook National University School of Medicine, 101 Dongin-dong 2-ga, Jung-gu, Daegu, 700-422, Republic of Korea.
authors.forename: Jiaa
authors.initials: J
authors.lastname: Park
authors.forename: Joon Heum
authors.initials: JH
authors.lastname: Park
authors.forename: Hwa-Jin
authors.initials: HJ
authors.lastname: Suh
authors.forename: In Chul
authors.initials: IC
authors.lastname: Lee
authors.forename: Jaesook
authors.initials: J
authors.lastname: Koh
authors.forename: Yong Chool
authors.initials: YC
authors.lastname: Boo
mesh_terms: D000107:Acetylation; D000818:Animals; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D057809:HEK293 Cells; D006801:Humans; D017495:Hyperpigmentation / Q000188:drug therapy*; D008543:Melanins / Q000096:biosynthesis*; D008546:Melanoma, Experimental; D051379:Mice; D008954:Models, Biological; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors / Q000096:biosynthesis; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology*; D000077185:Resveratrol; D012879:Skin Physiological Phenomena / Q000187:drug effects; D012880:Skin Pigmentation / Q000187:drug effects*; D013267:Stilbenes / Q000737:chemistry / Q000494:pharmacology*; D014466:Ultraviolet Rays / Q000009:adverse effects
chemical_list: D008543:Melanins; D010936:Plant Extracts; D013267:Stilbenes; C034912:puag-haad; D014442:Monophenol Monooxygenase; D000077185:Resveratrol