Synthesis and characterization of ampelopsin glucosides using dextransucrase from Leuconostoc mesenteroides B-1299CB4: Glucosylation enhancing physicochemical properties |
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| Affiliation: | 1. Department of Biotechnology and Bioengineering and Research Institute for Catalysis, Chonnam National University, Gwang-Ju 500-757, Republic of Korea;2. Samyang Group Food R&D Center, Samyang Genex Corporation, Daejeon 305-717, Republic of Korea;3. Eco-Friendly Biomaterial Research Center, Korea Research Institute of Bioscience and Biotechnology (KRIBB), Jeongeup 580-185, Republic of Korea;4. Skin Research Institute, AmorePacific R&D Center, 314-1, Gyeonggido 449-729, Republic of Korea;5. Department of Food Science and Technology and Functional Food Research Center, Chonnam National University, Gwangju 500-757, Republic of Korea;6. Department of Microbiology, College of Natural Sciences, Pusan National University, Busan 609-735, Republic of Korea;7. Audubon Sugar Institute, LSU AgCenter, Saint Gabriel, LA 70803, USA;8. Jeonnam Agricultural Research & Extension Services, Jeonnam 520-715, Republic of Korea;9. State Key Laboratory of Food Science and Technology, Jiangnan University, Jiangsu 214122, China;10. Research Faculty of Agriculture, Hokkaido University, Sapporo 060-8589, Japan;1. Eco-Friendly Bio-material Research Center, Korea Research Institute of Bioscience and Biotechnology, Jeongeup 580-185, Korea;2. Institute of Health Science, Department of Biomedical Sciences, College of Health Sciences, Korea University, Seoul 136-703, South Korea;3. The Institute of Food Research and Industrialization, Institute of Green Bio Science & Technology and Department of Agricultural Biotechnology, Seoul National University, Pyeongchang-gun, Gangwon-do 232-916, Korea;4. Department of Food Science & Technology and Functional Food Research Center, Chonnam National University, Gwangju 500-757, Korea;1. Department of Chemical Biology, Helmholtz Centre for Infection Research, Braunschweig, Germany;2. Department of Molecular Structural Biology, Helmholtz Centre for Infection Research, Braunschweig, Germany;3. Laboratorio de Microbiología Molecular y Biotecnología Ambiental, Departamento de Química & Centro de Biotecnología Daniel Alkalay Lowitt & Center of Nanotechnology and Systems Biology, Universidad Técnica Federico Santa María, Valparaíso, Chile;4. Laboratorio de Investigación Científica Emory Black, Escuela de Medicina, Facultad de Ciencias Médicas, Universidad de Santiago de Chile, Casilla 442, Correo 2 Santiago, Chile |
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| Abstract: | Novel ampelopsin glucosides (AMPLS-Gs) were enzymatically synthesized and purified using a Sephadex LH-20 column. Each structure of the purified AMPLS-Gs was determined by nuclear magnetic resonance, and the ionic product of AMPLS-G1 was observed at m/z 505 (C21H22O13·Na)+ using matrix-assisted laser desorption ionization time-of-flight mass spectrometry. AMPLS-G1 was identified as ampelopsin-4′-O-α-d-glucopyranoside. The optimum condition for AMPLS-G1, determined using response surface methodology, was 70 mM ampelopsin, 150 mM sucrose, and 1 U/mL dextransucrase, which resulted in an AMPLS-G1 yield of 34 g/L. The purified AMPLS-G1 displayed 89-fold increased water solubility and 14.5-fold browning resistance compared to those of AMPLS and competitive inhibition against tyrosinase with a Ki value of 40.16 μM. This value was smaller than that of AMPLS (Ki = 62.56 μM) and much smaller than that of β-arbutin (Ki = 514.84 μM), a commercial active ingredient of whitening cosmetics. These results indicate the potential of AMPLS and AMPLS-G1 as superior ingredients for functional cosmetics. |
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