Flavanoids from Dalea elegans: Chemical reassignment and determination of kinetics parameters related to their anti-tyrosinase activity |
| |
| Institution: | 1. Key Laboratory of Plants Resources and Chemistry of Arid Zone, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing South Road 40-1, Urumqi 830011, Xinjiang, PR China;2. S. Yu. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashken, Uzbekistan;3. State Key Laboratory Basis of Xinjiang Indigenous Medicinal Plants Resource Utilization, Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Urumqi 830011, PR China;4. University of Chinese Academy of Sciences, Beijing 100039, PR China;1. Department of Biochemistry, Faculty of Science, Khon Kaen University, 123 Mittraphap Road, Muang District, Khon Kaen 40002, Thailand;2. Protein and Proteomics Research Center for Commercial and Industrial Purposes (ProCCI), Faculty of Science, Khon Kaen University, 123 Mittraphap Road, Muang District, Khon Kaen 40002, Thailand;3. Department of Integrated Science, Forensic Science Program, Faculty of Science, Khon Kaen University, 123 Mittraphap Road, Muang District, Khon Kaen 40002, Thailand;4. Department of Biochemistry, Faculty of Science, Kasetsart University, Ngam Wong Wan Road, Chatuchak, Bangkok 10900, Thailand;5. Department of Biotechnology, Faculty of Agricultural Technology, Kalasin University, 62/1 Kasetsomboon Road, Muang District, Kalasin 46000, Thailand;6. Department of Pharmaceutical Technology, Faculty of Pharmaceutical Sciences, Naresuan University, 99 Moo 9 Phitsanulok-Nakhonsawan Road, Tapho Sub-District, Muang District, Phitsanulok 65000, Thailand;7. Center of Excellence for Innovation in Chemistry, Naresuan University, 99 Moo 9 Phitsanulok-Nakhonsawan Road, Tapho Sub-District, Muang District, Phitsanulok 65000, Thailand;1. A.V. Nikolaev Institute of Inorganic Chemistry, The Siberian Branch of the Russian Academy of Sciences, Av. Lavrentyev 3, Novosibirsk 630090, Russia;2. National Research Tomsk Polytechnic University, Lenin Avenue 30, Tomsk 634050, Russia;3. Novosibirsk State University, Pirogova 2, Novosibirsk 630090, Russia;4. N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, The Siberian Branch of the Russian Academy of Sciences, Av. Lavrentyev 9, 630090 Novosibirsk, Russia;1. Shaanxi Collaborative Innovation Center of Chinese Medicinal Resource Industrialization, School of Pharmacy, Shaanxi College of Traditional Chinese Medicine, Xianyang 712046, China;2. Key Laboratory of Gastrointestinal Pharmacology of Chinese Materia Medica of the State Administration of Traditional Chinese Medicine, Collaborative Innovation Center for Chinese Medicine in Qinba Mountains, School of Pharmacy, The Fourth Military Medical University, Xi’an 710032, China;3. The First Hospital of Xi’an, Xi’an 710002, China |
| |
| Abstract: | In the first chemical investigation developed on the species Dalea elegans twenty years ago, the occurrence of two prenylated derivatives of pinocembrin was reported: 2′,4′-dihydroxy-5′-(1?,1?-dimethylallyl)-6-prenylpinocembrin (6PP) given as a new structure in this family of compounds, and another derivative of already known structure, 6-prenylpinocembrin (6P). In the present paper, their structures were again analyzed by using spectroscopic techniques, especially 2D NMR. Based on the evidence obtained it is proposed the reassignment of both flavanones as: 2′,4′-dihydroxy-5′-(1?,1?-dimethylallyl)-8-prenylpinocembrin (8PP) for the first and 8-prenylpinocembrin (8P) for the last. Additionally, triangularin, demethoxymatteucinol, comptonin and 7-hydroxy-5-methoxy-6,8-dimethylflavanone were isolated from aerial parts of D. elegans and informed by the first time for this species. All of these compounds were evaluated in vitro in relation to the antityrosinase effect by using a spectrophotometric method. Compound 8PP (IC50 2.32 ± 0.01 μM) exhibited the most potency and was two times more active than Kojic acid (IC50 4.93 ± 0.01 μM) used as a positive control. Triangularin also has shown an important inhibitory activity. Kinetic studies were performed for both compounds. Hence, new tyrosinase inhibitors with potential applications in pharmacy and cosmetic industry are presented. |
| |
| Keywords: | Fabaceae Prenyalted flavanones C-methyl flavonoids Chemical reassignment Antityrosinase activity |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
