Recent advances on applications and biotechnological production of d-psicose

Abstract

d-Psicose is a hexoketose monosaccharide sweetener, which is a C-3 epimer of d-fructose and is rarely found in nature. It has 70 % relative sweetness but 0.3 % energy of sucrose, and is suggested as an ideal sucrose substitute for food products. It shows important physiological functions, such as blood glucose suppressive effect, reactive oxygen species scavenging activity, and neuroprotective effect. It also improves the gelling behavior and produces good flavor during food process. This article presents a review of recent studies on the properties, physiological functions, and food application of d-psicose. In addition, the biochemical properties of d-tagatose 3-epimerase family enzymes and the d-psicose-producing enzyme are compared, and the biotechnological production of d-psicose from d-fructose is reviewed.

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References

  1. Binkley WW (1963) The fate of cane juice simple sugars during molasses formation IV. Probable conversion of d-fructose to d-psicose. Int Sugar J 65:105–106

    CAS  Google Scholar 

  2. Choi JG, Ju YH, Yeom SJ, Oh DK (2011) Improvement in the thermostability of d-psicose 3-epimerase from Agrobacterium tumefaciens by random and site-directed mutagenesis. Appl Envrion Microbiol 77:7316–7320

    Article  CAS  Google Scholar 

  3. Cree GM, Perlin AS (1968) O-Isopropylidene derivatives of d- allulose (d-psicose) and d-erythro-hexopyranose-2, 3-diulose. Can J Biochem 46:765–770

    Article  CAS  Google Scholar 

  4. FDA (2011) GRAS Notice Inventory, GRN No. 400. http://www.accessdata.fda.gov/scripts/fcn/gras_notices/GRN000400.pdf. Accessed Aug 2011

  5. Fukada K, Ishii T, Tanaka K, Yamaji M, Yamaoka Y, Kobashi K, Izumori K (2010) Crystal structure, solubility, and mutarotation of the rare monosaccharide d-psicose. Bull Chem Soc Jpn 83:1193–1197

    Article  CAS  Google Scholar 

  6. Granstrom TB, Izumori K, Leisola M (2007) A rare sugar xylitol. Part II: biotechnological production and future applications of xylitol. Appl Microbiol Biotechnol 74:273–276

    Article  Google Scholar 

  7. Gullapalli P, Yoshihara A, Morimoto K, Rao D, Akimitsu K, Jenkinson SF, Fleet GWJ, Izumori K (2010) Conversion of l-rhamnose into ten of the sixteen 1-and 6-deoxyketohexoses in water with three reagents: d-tagatose-3-epimerase equilibrates C3 epimers of deoxyketoses. Tetrahedron Lett 51:895–898

    Article  CAS  Google Scholar 

  8. Hayashi N, Iida T, Yamada T, Okuma K, Takehara I, Yamamoto T, Yamada K, Tokuda M (2010) Study on the postprandial blood glucose suppression effect of d-psicose in borderline diabetes and the safety of long-term ingestion by normal human subjects. Biosci Biotechnol Biochem 74:510–519

    Article  CAS  Google Scholar 

  9. Hossain MA, Kitagaki S, Nakano D, Nishiyama A, Funamoto Y, Matsunaga T, Tsukamoto I, Yamaguchi F, Kamitori K, Dong Y, Hirata Y, Murao K, Toyoda Y, Tokuda M (2011) Rare sugar d-psicose improves insulin sensitivity and glucose tolerance in type 2 diabetes Otsuka Long-Evans Tokushima Fatty (OLETF) rats. Biochem Biophys Res Commun 405:7–12

    Article  CAS  Google Scholar 

  10. Hough L, Stacey BE (1966) Variation in the allitol content of Itea plants during photosynthesis. Phytochemistry 5:171–175

    Article  CAS  Google Scholar 

  11. Hu C, Li L, Zheng Y, Rui L (2011) Perspectives of biotechnological production of l-ribose and its purification. Appl Microbiol Biotechnol 92:449–455

    Article  CAS  Google Scholar 

  12. Iida T, Kishimoto Y, Yoshikawa Y, Hayashi N, Okuma K, Tohi M, Yagi K, Matsuo T, Izumori K (2008) Acute d-psicose administration decreases the glycemic responses to an oral maltodextrin tolerance test in normal adults. J Nutr Sci Vitaminol (Tokyo) 54:511–514

    Article  CAS  Google Scholar 

  13. Iida T, Hayashi N, Yamada T, Yoshikawa Y, Miyazato S, Kishimoto Y, Okuma K, Tokuda M, Izumori K (2010) Failure of d-psicose absorbed in the small intestine to metabolized into energy and its low large intestinal fermentability in humans. Metab Clin Exp 59:206–214

    Article  CAS  Google Scholar 

  14. Itoh H, Izumori K (1996) Enzymatic production of l-tagatose and l-fructose from l-sorbose and l-psicose, respectively. J Ferment Bioeng 81:351–353

    Article  CAS  Google Scholar 

  15. Itoh H, Okaya H, Khan AR, Tajima S, Hayakawa S, Izumori K (1994) Purification and characterization of d-tagatose 3-epimerase from Pseudomonas sp. ST-24. Biosci Biotechnol Biochem 58:2168–2171

    Article  CAS  Google Scholar 

  16. Itoh H, Sato T, Izumori K (1995a) Preparation of d-psicose from d-fructose by immobilized d-tagatose 3-epimerase. J Ferment Bioeng 80:101–103

    Article  CAS  Google Scholar 

  17. Itoh H, Sato T, Takeuchi T, Than AR, Izumori K (1995b) Preparation of d-sorbose from d-tagatose by immobilized d-tagatose 3-epimerase. J Ferment Bioeng 79:184–185

    Article  CAS  Google Scholar 

  18. Izumori K, Khan AR, Okaya H, Tsumura T (1993) A new enzyme, d-ketohexose 3-ppimerase, from Pseudomonas sp. ST-24. Biosci Biotechnol Biochem 57:1037–1039

    Article  CAS  Google Scholar 

  19. Kim HJ, Hyun EK, Kim YS, Lee YJ, Oh DK (2006a) Characterization of an Agrobacterium tumefaciens d-psicose 3-epimerase that converts d-fructose to d-psicose. Appl Environ Microbiol 72:981–985

    Article  CAS  Google Scholar 

  20. Kim K, Kim HJ, Oh DK, Cha SS, Rhee S (2006b) Crystal structure of d-psicose 3-epimerase from Agrobacterium tumefaciens and its complex with true substrate d-fructose: a pivotal role of metal in catalysis, an active site for the non-phosphorylated substrate, and its conformational changes. J Mol Biol 361:920–931

    Article  CAS  Google Scholar 

  21. Kim K, Kim HJ, Oh DK, Cheong JJ, Rhee S (2006c) Expression, purification, and crystallization of d-psicose 3-epimerase from Agrobacterium tumefaciens. J Microbiol Biotechnol 16:647–650

    Google Scholar 

  22. Kim NH, Kim HJ, Kang DI, Jeong KW, Lee JK, Kim Y, Oh DK (2008) Conversion shift of d-fructose to d-psicose for enzyme-catalyzed epimerization by addition of borate. Appl Environ Microbiol 74:3008–3013

    Article  CAS  Google Scholar 

  23. Kim HJ, Lim BC, Yeom SJ, Kim YS, Kim D, Oh DK (2010a) Roles of Ile66 and Ala107 of d-psicose 3-epimerase from Agrobacterium tumefaciens in binding O6 of its substrate, d-fructose. Biotechnol Lett 32:113–118

    Article  CAS  Google Scholar 

  24. Kim HJ, Yeom SJ, Kim Y, Rhee S, Kim D, Oh DK (2010b) Mutational analysis of the active site residues of a d-psicose 3-epimerase from Agrobacterium tumefaciens. Biotechnol Lett 32:261–268

    Article  CAS  Google Scholar 

  25. Lim YR, Oh DK (2011) Microbial metabolism and biotechnological production of d-allose. Appl Microbiol Biotechnol 91:229–235

    Article  CAS  Google Scholar 

  26. Lim BC, Kim HJ, Oh DK (2007) High production of d-tagatose by the addition of boric acid. Biotechnol Prog 23:824–828

    CAS  Google Scholar 

  27. Lim BC, Kim HJ, Oh DK (2009) A stable immobilized d-psicose 3-epimerase for the production of d-psicose in the presence of borate. Process Biochem 44:822–828

    Article  CAS  Google Scholar 

  28. Matsuo T (2006) Inhibitory effect of d-psicose on glycemic responses after oral carbohydrate tolerance test in rats. J Jpn Soc Nutr Food Sci 59:119–121

    Article  CAS  Google Scholar 

  29. Matsuo T, Izumori K (2009) d-psicose inhibits intestinal alpha-glucosidase and suppresses the glycemic response after ingestion of carbohydrates in rats. J Clin Biochem Nutr 45:202–206

    Article  CAS  Google Scholar 

  30. Matsuo T, Baba Y, Hashiguchi M, Takeshita K, Izumori K, Suzuki H (2001) Less body fat accumulation with d-psicose diet versus d-fructose diet. J Clin Biochem Nutr 30:55–65

    Article  CAS  Google Scholar 

  31. Matsuo T, Suzuki H, Hashiguchi M, Izumori K (2002a) d-Psicose is a rare sugar that provides no energy to growing rats. J Nutr Sci Vitaminol 48:77–80

    Article  CAS  Google Scholar 

  32. Matsuo T, Tanaka T, Hashiguchi M, Izumori K, Suzuki H (2002b) Effects of oral acute administration and subchronic feeding of several levels of d-psicose in rats. J Nutr Sci Vitaminol 48:512–516

    Article  CAS  Google Scholar 

  33. Matsuo T, Tanaka T, Hashiguchi M, Izumori K, Suzuki H (2003) Metabolic effects of d-psicose in rats: studies on faecal and urinary excretion and caecal fermentation. Asia Pac J Clin Nutr 12:225–231

    CAS  Google Scholar 

  34. Miller BS, Swain T (1969) Chromatographic analyses of the free amino acids, organic acids and sugars in wheat plant extracts. J Sci Food Agric 11:344–348

    Article  Google Scholar 

  35. Mu W, Chu F, Xing Q, Yu S, Zhou L, Jiang B (2011) Cloning, expression, and characterization of a d-psicose 3-epimerase from Clostridium cellulolyticum H10. J Agric Food Chem 59:7785–7792

    Article  CAS  Google Scholar 

  36. Murao K, Yu X, Cao WM, Imachi H, Chen K, Muraoka T, Kitanaka N, Li J, Ahmed RAM, Matsumoto K, Nishiuchi T, Tokuda M, Ishida T (2007) d-Psicose inhibits the expression of MCP-1 induced by high-glucose stimulation in HUVECs. Life Sci 81:592–599

    Article  CAS  Google Scholar 

  37. Murata A, Sekiya K, Watanabe Y, Yamaguchi F, Hatano N, Izumori K, Tokuda M (2003) A novel inhibitory effect of d-allose on production of reactive oxygen species from neutrophils. J Biosci Bioeng 96:89–91

    CAS  Google Scholar 

  38. Oh DK (2007) Tagatose: properties, applications, and biotechnological processes. Appl Microbiol Biotechnol 76:1–8

    Article  CAS  Google Scholar 

  39. Oshima H, Kimura I, Izumori K (2006) Psicose contents in various food products and its origin. Food Sci Technol Res 12:137–143

    Article  CAS  Google Scholar 

  40. Rao D, Best D, Yoshihara A, Gullapalli P, Morimoto K, Wormald MR, Wilson FX, Izumori K, Fleet GWJ (2009) A concise approach to the synthesis of all twelve 5-deoxyhexoses: d-tagatose 3-epimerase—a reagent that is both specific and general. Tetrahedron Lett 50:3559–3563

    Article  CAS  Google Scholar 

  41. Sun Y, Hayakawa IK (2004) Modification of ovalbumin with a rare ketohexose through the Maillard reaction: effect on protein structure and gel properties. J Agric Food Chem 52:1293–1299

    Article  CAS  Google Scholar 

  42. Sun Y, Hayakawa S, Izumori K (2004) Antioxidative activity and gelling rheological properties of dried egg white glycated with a rare keto-hexose through the Maillard reaction. J Food Sci 69:C427–C434

    Article  CAS  Google Scholar 

  43. Sun Y, Hayakawa S, Ogawa M, Izumori K (2005) Evaluation of the site specific protein glycation and antioxidant capacity of rare sugar-protein/peptide conjugates. J Agric Food Chem 53:10205–10212

    Article  CAS  Google Scholar 

  44. Sun Y, Hayakawa S, Jiang H, Ogawa M, Izumori K (2006) Rheological characteristics of heat-induced custard pudding gels with high antioxidative activity. Biosci Biotechnol Biochem 70:2859–2867

    Article  CAS  Google Scholar 

  45. Sun Y, Hayakawa S, Ogawa M, Izumori K (2007) Antioxidant properties of custard pudding dessert containing rare hexose, d-psicose. Food Control 18:220–227

    Article  CAS  Google Scholar 

  46. Sun Y, Hayakawa S, Ogawa M, Fukada K, Izumori K (2008) Influence of a rare sugar, d-psicose, on the physicochemical and functional properties of an aerated food system containing egg albumen. J Agric Food Chem 56:4789–4796

    Article  CAS  Google Scholar 

  47. Suna S, Yamagushi F, Kimura S, Tokuda M, Jitsunari F (2007) Preventive effect of d-psicose, one of rare ketohexoses, on di-(2-ethylhexyl) phthalate (DEHP)-induced testicular injury in rat. Tox Lett 173:107–117

    Article  CAS  Google Scholar 

  48. Takata M, Yamaguchi F, Nakanose K, Watanabe Y, Hatano N, Tsukamoto I, Nagata M, Izumori K, Tokuda M (2005) Neuroprotective effect of d-psicose on 6-hydroxydopamine-induced apoptosis in rat pheochromocytoma (PC12) cells. J Biosci Bioeng 100:511–516

    Article  CAS  Google Scholar 

  49. Takeshita K, Suga A, Takada G, Izumori K (2000) Mass production of D-psicose from D-fructose by a continuous bioreactor system using immobilized D-tagatose 3-epimerase. J Biosci Bioeng 90:453–455

    Google Scholar 

  50. Whistler RL, Singh PP, Lake WC (1974) d-Psicose metabolism in the rat. Carbohydr Res 34:200–202

    Article  CAS  Google Scholar 

  51. Yagi K, Matsuo T (2009) The study on long-term toxicity of d-psicose in rats. J Clin Biochem Nutr 45:271–277

    Article  Google Scholar 

  52. Yoshida H, Yamada M, Nishitani T, Takada G, Izumori K, Kamitori S (2007a) Crystal structures of d-tagatose 3-epimerase from Pseudomonas cichorii and its complexes with d-tagatose and d-fructose. J Mol Biol 374:443–453

    Article  CAS  Google Scholar 

  53. Yoshida H, Yamada M, Nishitani T, Takada G, Izumori K, Kamitori S (2007b) Purification, crystallization and preliminary X-ray diffraction studies of d-tagatose 3-epimerase from Pseudomonas cichorii. Acta Crystallogr Sect F Struct Biol Cryst Commun 63:123–125

    Article  Google Scholar 

  54. Zhang L, Mu W, Jiang B, Zhang T (2009) Characterization of d-tagatose-3-epimerase from Rhodobacter sphaeroides that converts d-fructose into d-psicose. Biotechnol Lett 31:857–862

    Article  CAS  Google Scholar 

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Acknowledgments

This work was supported by the Natural Science Foundation of China Project (nos. 31171705 and 20906040), the 863 Project (no. 2011AA100904), the 973 Project (no. 2012CB720802), the Support Project of Jiangsu Province (nos. BE2011622, BE2011766, BE2010678, and BE2010626), and the Innovative Research Team of Jiangnan University Project (no. 2008CXTD01).

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Correspondence to Wanmeng Mu.

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Mu, W., Zhang, W., Feng, Y. et al. Recent advances on applications and biotechnological production of d-psicose. Appl Microbiol Biotechnol 94, 1461–1467 (2012). https://doi.org/10.1007/s00253-012-4093-1

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Keywords

  • d-Psicose
  • d-Tagatose 3-epimerase family enzyme
  • Property
  • Physiological function
  • Biotechnological production