Synthesis of quercetin glycosides and their melanogenesis stimulatory activity in B16 melanoma cells |
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| Affiliation: | 1. The United Graduate School of Agricultural Science, Gifu University, 1-1 Yanagido, 501-1193 Gifu, Japan;2. Department of Chemistry, Faculty of Mathematics and Natural Sciences, Biopharmaca Research Center, Bogor Agricultural University, Jl. Taman Kencana No. 3, Kampus IPB Taman Kencana, Bogor 16151, Indonesia;1. Key Laboratory of Chemical Biology of Natural Products (Ministry of Education), Institute of Biochemical and Biotechnological Drug, School of Pharmaceutical Sciences, Shandong University, Jinan 250012, China;2. The State Key Laboratory of Microbial Technology, Shandong University, Jinan, 250100, China;3. National Glycoengineering Research Center, Shandong University, Jinan 250012, China;1. Laboratório de Bioconversão, Faculdade de Farmácia, Universidade Federal de Goiás, Postal Box 131, Setor Universitário, CEP: 74.605-220, Brazil;2. Laboratório de Farmacologia Cardiovascular, Faculdade de Farmácia, Universidade Federal de Goiás, Postal Box 131, Setor Universitário, CEP: 74.605-220, Brazil;3. Laboratório de Ressonância Magnética Nuclear, Instituto de Química, Universidade Federal de Goiás, Campus Samambaia, CEP: 74.001-970, Goiânia, GO, Brazil;1. College of Pharmacy and Graduate School of Pharmaceutical Sciences, Ewha Womans University, Seoul 03760, South Korea;2. Natural Products Research Unit, Department of Chemistry, Chulalongkorn University, Bangkok 10330, Thailand;1. National and Local Collaborative Engineering Center of Chinese Medicinal Resources Industrialization and Formulae Innovative Medicine, Nanjing University of Chinese Medicine, Nanjing, Jiangsu 210023, China;2. Department of Organic Chemistry, China Pharmaceutical University, Nanjing, Jiangsu 211198, China;3. Department of Pharmacology, Emory University School of Medicine, Atlanta, GA 30322, United States;1. Shandong Analysis and Test Center, Qilu University of Technology (Shandong Academy of Sciences), Jinan, 250014, PR China;2. Reyoung Pharmaceutical Co., Ltd, No. 44 Cultural West Road, Jinan, 250012, PR China;3. College of Chinese Mareria Medica, Beijing University of Chinese Medicine, Beijing, 100102, PR China |
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| Abstract: | 4′-O-β-d-Glucopyranosyl-quercetin-3-O-β-d-glucopyranosyl-(1→4)-β-d-glucopyra-noside (3) was isolated from Helminthostachys zeylanica root extract as a melanogenesis acceleration compound and was synthesized using rutin as the starting material. Related compounds were also synthesized to understand the structure–activity relationships in melanin biosynthesis.Melanogenesis activities of the glycosides were determined by measuring intracellular melanin content in B16 melanoma cells. Among the synthesized quercetin glycosides, quercetin-3-O-β-d-glucopyranoside (1), quercetin-3-O-β-d-glucopyranosyl-(1→4)-β-d-glucopyranoside (2), and 3 showed more potent intracellular melanogenesis acceleration activities than theophyline used as positive control in a dose-dependent manner with no cytotoxic effect. |
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| Keywords: | Quercetin glycoside B16 melanoma cells Tyrosinase TRP-1 |
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