Journal of Microbiology and Biotechnology

The Korean Society for Microbiology and Biotechnology (한국미생물·생명공학회)
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Glucosyl Rubusosides by Dextransucrases Improve the Quality of Taste and Sweetness

  • Ko, Jin-A (Eco-Friendly Bio-material Research Center, Korea Research Institute of Bioscience and Biotechnology) ;
  • Ryu, Young Bae (Eco-Friendly Bio-material Research Center, Korea Research Institute of Bioscience and Biotechnology) ;
  • Park, Ji-Young (Eco-Friendly Bio-material Research Center, Korea Research Institute of Bioscience and Biotechnology) ;
  • Kim, Cha Young (Eco-Friendly Bio-material Research Center, Korea Research Institute of Bioscience and Biotechnology) ;
  • Kim, Joong Su (Eco-Friendly Bio-material Research Center, Korea Research Institute of Bioscience and Biotechnology) ;
  • Nam, Seung-Hee (Department of Food Science and Technology and BK21 Plus Program, Graduate School of Chonnam National University and Bioenergy Research Center) ;
  • Lee, Woo Song (Eco-Friendly Bio-material Research Center, Korea Research Institute of Bioscience and Biotechnology) ;
  • Kim, Young-Min (Department of Food Science and Technology and BK21 Plus Program, Graduate School of Chonnam National University and Bioenergy Research Center)
  • Received : 2016.01.04
  • Accepted : 2016.01.25
  • Published : 2016.03.28
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Abstract

Glucosyl rubusosides were synthesized by two dextransucrases. LcDexT was obtained from Leuconosotoc citreum, that LlDexT was obtained from Leuconostoc lactis. LcDexT and LlDexT regioselectively transferred a glucosyl residue to the 13-O-glucosyl moiety of rubusoside with high yield of 59-66% as analyzed by TLC and HPLC. Evaluation of the sweetness of these glucosyl rubusosides showed that their quality of taste, in particular, was superior to that of rubusoside. These results indicate that transglucosylation at the 13-O-glucosyl moiety of rubusoside by different regioselective dextransucrases can be applicable for increasing its sweetness and quality of taste.

Keywords

References

  1. Darise M, Mizutani K, Kasai R, Tanaka O, Kitahata S, Okada S, et al. 1984. Enzymic transglucosylation of rubusoside and the structure-sweetness relationship of steviol-bisglycosides. Agric. Biol. Chem. 48: 2483-2488.
  2. George Thompson AM, Lancu CV, Naguyen TT, Kim D, Choe JY. 2015. Inhibition of human GLUT1 and GLUT5 by plant carbohydrate products; insights into transport specificity. Sci. Rep. 5: 12804. https://doi.org/10.1038/srep12804
  3. Ishikawa H, Kitahata S, Ohtani K, Ikuhara C, Tanaka O. 1990. Production of stevioside and rubusoside derivatives by transfructosylation of β-fructofuranosidase. Agric. Biol. Chem. 54: 3137-3143.
  4. Kim YM, Yeon MJ, Choi NS, Chang YH, Jung MY, Song JJ, Kim JS. 2010. Purification and characterization of a novel glucansucrase from Leuconostoc lactis EG001. Microbiol. Res. 165: 384-391. https://doi.org/10.1016/j.micres.2009.08.005
  5. Kitahata S, Ishikawa H, Miyata T, Tanaka O. 1989. Production of rubusoside derivatives by transgalactosylation of various α-galactosidases. Agric. Biol. Chem. 53: 2929-2934.
  6. Ko JA, Jeong HJ, Ryu YB, Park SJ, Wee YJ, Kim D, et al. 2012. Large increase in Leuconostoc citreum KM20 dextransucrase activity achieved by changing the strain/inducer combination in an E. coli expression system. J. Microbiol. Biotechnol. 22: 510-515. https://doi.org/10.4014/jmb.1111.11032
  7. Lee HY, Jung KH. 2014. Enzymatic synthesis of 2-phenoxyethanol galactoside by whole cells of β-galactosidase-containing Escherichia coli. J. Microbiol. Biotechnol. 24: 1254-1259. https://doi.org/10.4014/jmb.1404.04004
  8. Miller GL. 1959. Use of dinitrosalicylic acid reagent for determination of reducing sugar. Anal. Chem. 31: 426-428. https://doi.org/10.1021/ac60147a030
  9. Moon YH, Kim G, Lee JH, Jin XJ, Kim DW, Kim D. 2006. Enzymatic synthesis and characterization of novel epigallocatechin gallate glucosides. J. Mol. Catal. B Enzym. 40: 1-7. https://doi.org/10.1016/j.molcatb.2006.01.030
  10. Nguyen TT, Jung SJ, Kim HK, Kim YM, Moon YH, Kim H, Kim D. 2014. Production of rubusoside from stevioside by using a thermostable lactase from Thermus thermophiles and solubility enhancement of liquiritin and teniposide. Enzyme Microb. Technol. 64-65: 38-43. https://doi.org/10.1016/j.enzmictec.2014.07.001
  11. Ohtani K, Aikawa Y, Ishikawa H, Kasai R, Kitahata S, Mizutani K, et al. 1991. Further study on the 1,4-alpha-transglucosylation of rubusoside, a sweet steviol-biglucoside from Rubus suavissimus. Agric. Biol. Chem. 55: 449-453.
  12. Seo ES, Kim D, Robyt JF, Day DF, Kim DW, Park HJ, Park HJ. 2004. Modified oligosaccharides as potential dental plaque control materials. Biotechnol. Prog. 20: 1550-1554. https://doi.org/10.1021/bp049883e
  13. Su D, Robyt JF. 1993. Control of the synthesis of dextan and acceptor-products by Leuconosotc mesenteroides B-512FM dextransucrase. Carbohydr. Res. 248: 471-476. https://doi.org/10.1016/0008-6215(93)84139-W
  14. Tanaka O. 1997. Improvement of taste of natural sweeteners. Pure Appl. Chem. 69: 675-683. https://doi.org/10.1351/pac199769040675
  15. Tanaka T, Kohda H, Tanaka O, Chen FH, Chou WH, Leu JL. 1981. Rubusoside (β-D-glucosyl ester of 13-O-β-D-glucosyl-steviol), a sweet principle of Rubus chingii Hu (Rosaceae). Agric. Biol. Chem. 45: 2165-2166.
  16. Yoon SH, Robyt JF. 2002. Synthesis of acarbose analogues by transglycosylation reactions of Leuconostoc mesenterioides B-512FMC and B-742CB dextransucrase. Carbohydr. Res. 24: 2427-2435. https://doi.org/10.1016/S0008-6215(02)00350-6
  17. Zhang F, Koh GY, Hollingsworth J, Russo PS, Stout RW, Liu Z. 2012. Reformulation of etoposide with solubility-enhancing rubusoside. Int. J. Pharm. 434: 453-459. https://doi.org/10.1016/j.ijpharm.2012.06.013

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