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
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
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
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
FDA (2011) GRAS Notice Inventory, GRN No. 400. http://www.accessdata.fda.gov/scripts/fcn/gras_notices/GRN000400.pdf. Accessed Aug 2011
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
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
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
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
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
Hough L, Stacey BE (1966) Variation in the allitol content of Itea plants during photosynthesis. Phytochemistry 5:171–175
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
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
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
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
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
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
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
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
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
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
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
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
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
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
Lim YR, Oh DK (2011) Microbial metabolism and biotechnological production of d-allose. Appl Microbiol Biotechnol 91:229–235
Lim BC, Kim HJ, Oh DK (2007) High production of d-tagatose by the addition of boric acid. Biotechnol Prog 23:824–828
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
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
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
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
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
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
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
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
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
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
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
Oh DK (2007) Tagatose: properties, applications, and biotechnological processes. Appl Microbiol Biotechnol 76:1–8
Oshima H, Kimura I, Izumori K (2006) Psicose contents in various food products and its origin. Food Sci Technol Res 12:137–143
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
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
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
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
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
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
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
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
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
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
Whistler RL, Singh PP, Lake WC (1974) d-Psicose metabolism in the rat. Carbohydr Res 34:200–202
Yagi K, Matsuo T (2009) The study on long-term toxicity of d-psicose in rats. J Clin Biochem Nutr 45:271–277
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
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
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
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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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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DOI: https://doi.org/10.1007/s00253-012-4093-1