Tyrosinase inhibitory activity of three new glycosides from Breynia fruticosa |
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| Institution: | 1. International Institute for Translational Chinese Medicine, Guangzhou University of Chinese Medicine, Guangzhou 510006, PR China;2. The Affiliated Zhongshan Municipal TCM Hospital, Guangzhou University of Chinese Medicine, Zhongshan 528401, PR China;1. College of Pharmacy, Jiangxi University of Traditional Chinese Medicine, Nanchang 330004, PR China;2. State Key Laboratory of Innovative Drug and Efficient Energy-Saving Pharmaceutical Equipment, Jiangxi University of Traditional Chinese Medicine, Nanchang 330006, PR China;1. National and Local Union Engineering Research Center of Veterinary Herbal Medicine Resources and Initiative, Hunan Agricultural University, Changsha, 410128, China;2. School of pharmacy, Hunan University of Chinese Medicine, Changsha 410208, China;3. Pharmaceutical Analytical & Solid-State Chemistry Research Center, Shanghai Institute of Materia Medica, Chinese Academy of Science, Shanghai 201203, China;1. Key Laboratory of Tropical Medicinal Plant Chemistry of Ministry of Education, Hainan Normal University, Haikou 571158, PR China;2. Guangxi Key Laboratory of Traditional Chinese Medicine Quality Standards, Guangxi Institute of Traditional Medical and Pharmaceutical Sciences, Nanning 530022, PR China;3. College of Pharmacy, Fujian University of Traditional Chinese Medicine, Fuzhou 350122, PR China;1. School of Pharmacy, China Medical University, Taichung 404, Taiwan;2. Chinese Medicine Research and Development Center, China Medical University Hospital, Taichung 404, Taiwan;3. Department of Medical Laboratory Science and Biotechnology, China Medical University, Taichung 404, Taiwan;4. Graduate Institute of Natural Products, Chang Gung University, Taoyuan 333, Taiwan;5. Department of Chemistry, National Cheng Kung University, Tainan 701, Taiwan;1. School of Pharmacy, Anhui University of Chinese Medicine, Anhui Key Laboratory of Modern Chinese Materia Medica, Hefei 230012, China;2. Synergetic Innovation Center of Anhui Authentic Chinese Medicine Quality Improvement, Hefei 230012, China;3. Guangdong Provincial Key Laboratory of Applied Botany, South China Botanical Garden, Chinese Academy of Sciences, Guangzhou 510650, China;4. The First Affiliated Hospital, Anhui University of Chinese Medicine, Hefei 230038, China |
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| Abstract: | Two new flavanone glycoside derivatives and one new sulfur-containing spiroacetal glycoside, (2R, 3R)-3-acetyl-7-methoxy-(−)-epicatechin 5-O-(6-isobutanoyl)-β-d-glucopyranoside (1), (2R, 3R)-3-acetyl-7-methoxy-(−)-epicatechin 5-O-6-(2-methylbutanoyl)]-β-d-glucopyranoside (2) and 4-(carboxymethyl)thio]-5′-hydroxy-phyllaemblic acid O-β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranoside ester (3), along with twelve known flavonoids and one known sulfur-containing spiroacetal glycoside, were isolated from Breynia fruticosa. Their structures were elucidated by the use of extensive spectroscopic methods (UV, IR, HR-ESI-MS, 1D and 2D NMR, and CD). The in vitro inhibition of tyrosinase activity by all of these compounds was also evaluated, and we concluded that the flavanol-containing 5-O- and 7-O-sugar moieties possessed more potent effects than the other compounds examined herein. |
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| Keywords: | Euphorbiaceae Flavonone Sulfur-containing spiroacetal glycoside Tyrosinase inhibition |
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