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Enzymatic synthesis and characterization of arbutin glucosides using glucansucrase from Leuconostoc mesenteroides B-1299CB

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Abstract

Two arbutin glucosides were synthesized via the acceptor reaction of a glucansucrase from Leuconostoc mesenteroides B-1299CB with arbutin and sucrose. The glucosides were purified by Bio-gel P-2 column chromatography and high-performance liquid chromatography, and the structures were elucidated as 4-hydroxyphenyl β-isomaltoside (arbutin-G1), 4-hydroxyphenyl β-isomaltotrioside (arbutin-G2), according to the results of 1H, 13C, heteronuclear single-quantum coherence, 1H-1H COSY, and heteronuclear multiple-bond correlation analyses. Arbutin glucoside (4-hydroxyphenyl β-isomaltoside) exhibited slower effects on 1,1-diphenyl-2-picrylhydrazyl radical scavenging and similar effects on tyrosinase inhibition, and increased inhibitory effect on matrix metalloproteinase-1 production induced by UVB than arbutin.

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Acknowledgment

This work was supported by 21C Frontier Microbial Genomics and the Applications Center Program, Ministry of Science and Technology (Grant MG05-0301-1-0) and partially supported by CNU Specialization Grant by Chonnam National University for students. We are also thankful to Korea Basic Science Institute Gwangju Branch for the NMR analysis.

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Authors and Affiliations

  1. School of Biological Sciences and Technology, The Research Institute for Catalysis and Institute of Bioindustrial Technology, Chonnam National University, Gwangju, 500-757, South Korea

    Young Hwan Moon, Jin Kang, Young-Min Kim, Hee-Kyung Kang & Doman Kim

  2. Jeonnam Agricultural Research & Extension Services, Jeonnam, Naju, 520-715, South Korea

    Seung Hee Nam

  3. Division of Applied Bioscience, Research Faculty of Agriculture, Hokkaido University, Sapporo, 060-8589, Japan

    Atsuo Kimura

  4. School of Dentistry, 2nd Stage of Brain Korea 21 for School of Dentistry, Chonnam National University, Gwangju, 500-757, South Korea

    Jin-Ha Lee

  5. Laboratoire de Physique Corpusculaire, Universite Blaise Pascal, Clermont-Ferrant, 63177, France

    Vincent Breton

  6. Department of Food and Nutrition, Jeonnam National University, Gwangju, 500-757, South Korea

    Woo-Jin Jun

  7. Korea Basic Science Institute Gwang-Ju Branch, Chonnam National University, Gwangju, 500-757, South Korea

    Ki-Deok Park

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  1. Young Hwan Moon
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  10. Atsuo Kimura
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Correspondence to Doman Kim.

Additional information

Young Hwan Moon and Seung Hee Nam contributed equally to this work.

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Moon, Y.H., Nam, S.H., Kang, J. et al. Enzymatic synthesis and characterization of arbutin glucosides using glucansucrase from Leuconostoc mesenteroides B-1299CB. Appl Microbiol Biotechnol 77, 559–567 (2007). https://doi.org/10.1007/s00253-007-1202-7

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  • DOI: https://doi.org/10.1007/s00253-007-1202-7

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