title: Ov-16 [4-(3,4-dihydroxybenzoyloxymethyl)phenyl-O-β-D-glucopyranoside] inhibits melanin synthesis by regulating expressions of melanogenesis-regulated gene and protein.
abstract: Ov-16 (4-(3,4-dihydroxybenzoyloxymethyl)phenyl-O-β-D-glucopyranoside), a polyphenolic glycoside that is isolated from oregano (Origanum vulgare L.), can scavenge 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radicals. This investigation is the first to study in detail the hypopigmentary properties of Ov-16. It demonstrates that 0-1000 μg/ml Ov-16 inhibits the activity of mushroom tyrosinase (Tyr) in a concentration-dependent manner. The inhibitionary Tyr kinetics of Ov-16 towards the oxidation of L-DOPA was found to be uncompetitive. Following the treatment of human skin premalignant kerationcyte HaCaT cells, human skin fibroblast Hs68 cells and mice melanoma B16 cells with Ov-16 (0-100 μg/ml), cell viability was >98%, suggesting that Ov-16 is non-toxic. Ov-16 can reduce cellular Tyr activity, DOPA oxidase activity and melanin synthesis in B16 cells that are stimulated by the α-melanocyte-stimulating hormone (α-MSH). Moreover, Ov-16 inhibited the production of melanin in Streptomyces bikiniensis without affecting the growth of the microorganism. The treatment of B16 cells with Ov-16 considerably reduced the gene expressions of melanocortin-1 receptor (Mc1r), microphthalmia-associated transcription factor (Mitf), Tyr, tyrosinase-related proteins-2 (Trp-2) and Trp-1, as determined by RT-PCR. The expressions of Mc1r, Mift, Tyr, Trp-2 and TrpP-1 protein in Ov-16-treated B16 cells were also significantly reduced, as determined by western blotting and fluorescent staining analysis. These results suggest that Ov-16 exhibits hypopigmentary performance.
authors.affiliation: Department of Cosmetic Science, Chia Nan University of Pharmacy and Science, 60 Erh-Jen Road Sec. 1, Pao-An, Jen-Te Hsiang, Tainan, Taiwan. tinna_ling@mail.chna.edu.tw
authors.forename: Chia-Hua
authors.initials: CH
authors.lastname: Liang
mesh_terms: D000363:Agaricales / Q000201:enzymology; D000818:Animals; D000975:Antioxidants / Q000494:pharmacology; D001483:Base Sequence; D002460:Cell Line; D017931:DNA Primers / Q000235:genetics; D004365:Drugs, Chinese Herbal / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000494:pharmacology; D005786:Gene Expression Regulation / Q000187:drug effects; D006801:Humans; D019746:Intramolecular Oxidoreductases / Q000235:genetics; D008543:Melanins / Q000037:antagonists & inhibitors* / Q000096:biosynthesis*; D008546:Melanoma, Experimental / Q000188:drug therapy / Q000235:genetics / Q000378:metabolism; D008562:Membrane Glycoproteins / Q000235:genetics; D008757:Methylglucosides / Q000494:pharmacology*; D051379:Mice; D051739:Microphthalmia-Associated Transcription Factor / Q000235:genetics; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors / Q000235:genetics; D010088:Oxidoreductases / Q000235:genetics; D044102:Receptor, Melanocortin, Type 1 / Q000235:genetics; D020133:Reverse Transcriptase Polymerase Chain Reaction; D012880:Skin Pigmentation / Q000187:drug effects / Q000235:genetics / Q000502:physiology; D013302:Streptomyces / Q000187:drug effects / Q000378:metabolism
chemical_list: C529825:4-(3,4-dihydroxybenzoyloxymethyl)phenyl-O-beta-D-glucopyranoside; D000975:Antioxidants; D017931:DNA Primers; D004365:Drugs, Chinese Herbal; D004791:Enzyme Inhibitors; D008543:Melanins; D008562:Membrane Glycoproteins; D008757:Methylglucosides; D051739:Microphthalmia-Associated Transcription Factor; C497235:Mitf protein, mouse; D044102:Receptor, Melanocortin, Type 1; D010088:Oxidoreductases; C079621:Tyrp1 protein, mouse; D014442:Monophenol Monooxygenase; D019746:Intramolecular Oxidoreductases; C042501:dopachrome isomerase