Recent advances in d-allulose: Physiological functionalities, applications, and biological production

Trends in Food Science and Technology

Volumn 54, Issue , 2016, Pages 127-137

  Zhang, Wenli ^a   Yu, Shuhuai ^a   Zhang, Tao ^a   Jiang, Bo ^a   Mu, Wanmeng ^a  

^a JIANGNAN UNIVERSITY   (China)

Author keywords

Biochemical properties; Biological production; D allulose; Ketose 3 epimerase; Physiological functions; Structural analysis

Indexed keywords

ENZYME ACTIVITY; FRUCTOSE; PHYSIOLOGY; STRUCTURAL ANALYSIS; SUGAR (SUCROSE);

BIOCHEMICAL PROPERTIES; BIOLOGICAL PRODUCTION; CATALYTIC MECHANISMS; KETOSE 3-EPIMERASE; MOLECULAR MODIFICATION; PHYSIOLOGICAL FUNCTIONS; SITE DIRECTED MUTAGENESIS; SUSTAINED ATTENTION;

BIOLOGY;

EID: 84974667022     PISSN: 09242244     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tifs.2016.06.004     Document Type: Review

References (95)

1. Ayers B.J., Hollinshead J., Saville A.W., Nakagawa S., Adachi I., Kato A., et al. Iteamine, the first alkaloid isolated from Itea virginica L. inflorescence. Phytochemistry 2014, 100:126-131.
2. Bilik V., Tihlarik K. Reaction of saccharides catalyzed by molybdate ions. IX. Epimerization of ketohexoses. Chemical Papers 1973, 28:106-109.
3. Binkley W.W., Wolfrom M.L. Composition of cane juice and cane final molasses. Advances in Carbohydrate Chemistry 1952, 8:291-314.
4. Bosshart A., Hee C.S., Bechtold M., Schirmer T., Panke S. Directed divergent evolution of a thermostable D-tagatose epimerase towards improved activity for two hexose substrates. Chembiochem 2015, 16:592-601.
5. Chan H.C., Zhu Y., Hu Y., Ko T.P., Huang C.H., Ren F., et al. Crystal structures of D-psicose 3-epimerase from Clostridium cellulolyticum H10 and its complex with ketohexose sugars. Protein & Cell 2012, 3:123-131.
6. Choi J.G., Ju Y.H., Yeom S.J., Oh D.K. Improvement in the thermostability of D-Psicose 3-epimerase from Agrobacterium tumefaciens by random and site-directed mutagenesis. Applied and Environmental Microbiology 2011, 77:7316-7320.
7. Chung Y.M., Lee J.H., Kim D.Y., Hwang S.H., Hong Y.H., Kim S.B., et al. Dietary D-psicose reduced visceral fat mass in high-fat diet-induced obese rats. Journal of Food Science 2012, 77:H53-H58.
8. Chung M.Y., Oh D.K., Lee K.W. Hypoglycemic health benefits of D-psicose. Journal of Agricultural and Food Chemistry 2012, 60:863-869.
9. Cree G., Perlin A. O-isopropylidene derivatives of D-allulose (D-psicose) and D-erythro-hexopyranos-2, 3-diulose. Canadian Journal of Biochemistry 1968, 46:765-770.
10. Doner L.W. Isomerization of D-fructose by base: Liquid-chromatographic evaluation and the isolation of D-psicose. Carbohydrate Research 1979, 70:209-216.
11. Eble T., Hoeksema H., Boyack G., Savage G. Psicofuranine. I. Discovery, isolation, and properties. Antibiotics & Chemotherapy 1959, 9:419-420.
12. Feng Z., Mu W., Jiang B. Characterization of ribose-5-phosphate isomerase converting D-psicose to D-allose from Thermotoga lettingae TMO. Biotechnology Letters 2013, 35:719-724.
13. Fukada K., Ishii T., Tanaka K., Yamaji M., Yamaoka Y., Kobashi K., et al. Crystal structure, solubility, and mutarotation of the rare monosaccharide D-Psicose. Bulletin of the Chemical Society of Japan 2010, 83:1193-1197.
14. Granstrom T.B., Takata G., Tokuda M., Izumori K. Izumoring: A novel and complete strategy for bioproduction of rare sugars. Journal of Bioscience and Bioengineering 2004, 97:89-94.
15. Han W., Zhu Y., Men Y., Yang J., Liu C., Sun Y. Production of allitol from D-psicose by a novel isolated strain of Klebsiella oxytoca G4A4. Journal of Basic Microbiology 2014, 54:1073-1079.
16. Harada M., Kondo E., Hayashi H., Suezawa C., Suguri S., Arai M. D-Allose and D-psicose reinforce the action of metronidazole on trichomonad. Parasitology Research 2012, 110:1565-1567.
17. Hayashi N., Iida T., Yamada T., Okuma K., Takehara I., Yamamoto T., et al. 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. Bioscience Biotechnology and Biochemistry 2010, 74:510-519.
18. Hishiike T., Ogawa M., Hayakawa S., Nakajima D., O'Charoen S., Ooshima H., et al. Transepithelial transports of rare sugar D-Psicose in human intestine. Journal of Agricultural and Food Chemistry 2013, 61:7381-7386.
19. Hossain M.A., Kitagaki S., Nakano D., Nishiyama A., Funamoto Y., Matsunaga T., et al. Rare sugar D-psicose improves insulin sensitivity and glucose tolerance in type 2 diabetes Otsuka Long-Evans Tokushima Fatty (OLETF) rats. Biochemical and Biophysical Research Communications 2011, 405:7-12.
20. Hossain A., Yamaguchi F., Hirose K., Matsunaga T., Sui L., Hirata Y., et al. Rare sugar D-psicose prevents progression and development of diabetes in T2DM model Otsuka Long-Evans Tokushima Fatty rats. Drug Design Development and Therapy 2015, 9:525-535.
21. Hossain A., Yamaguchi F., Matsunaga T., Hirata Y., Kamitori K., Dong Y.Y., et al. Rare sugar D-psicose protects pancreas beta-islets and thus improves insulin resistance in OLETF rats. Biochemical and Biophysical Research Communications 2012, 425:717-723.
22. Hossain A., Yamaguchi F., Matsuo T., Tsukamoto I., Toyoda Y., Ogawa M., et al. Rare sugar D-allulose: Potential role and therapeutic monitoring in maintaining obesity and type 2 diabetes mellitus. Pharmacology & Therapeutics 2015, 155:49-59.
23. Iida T., Hayashi N., Yamada T., Yoshikawa Y., Miyazato S., Kishimoto Y., et al. Failure of D-psicose absorbed in the small intestine to metabolize into energy and its low large intestinal fermentability in humans. Metabolism-Clinical and Experimental 2010, 59:206-214.
24. Iida T., Kishimoto Y., Yoshukawa Y., Hayashi N., Okuma K., Tohi M., et al. Acute D-psicose administration decreases the glycemic responses to an oral maltodextrin tolerance test in normal adults. Journal of Nutritional Science and Vitaminology 2008, 54:511-514.
25. Iida T., Yamada T., Hayashi N., Okuma K., Izumori K., Ishii R., et al. Reduction of abdominal fat accumulation in rats by 8-week ingestion of a newly developed sweetener made from high fructose corn syrup. Food Chemistry 2013, 138:781-785.
26. Itoh H., Okaya H., Khan A.R., Tajima S., Hayakawa S., Izumori K. Purification and characterization of D-tagatose 3-epimerase from Pseudomonas sp, St-24. Bioscience Biotechnology and Biochemistry 1994, 58:2168-2171.
27. Itoh H., Sato T., Izumori K. Preparation of D-psicose from D-fructose by immobilized D-tagatose 3-epimerase. Journal of Fermentation and Bioengineering 1995, 80:101-103.
28. Izumori K. Bioproduction strategies for rare hexose sugars. Naturwissenschaften 2002, 89:120-124.
29. Izumori K. Izumoring: A strategy for bioproduction of all hexoses. Journal of Biotechnology 2006, 124:717-722.
30. Izumori K., Khan A.R., Okaya H., Tsumura T. A new enzyme, D-ketohexose 3-epimerase, from Pseudomonas sp. ST-24. Bioscience, Biotechnology, and Biochemistry 1993, 57:1037-1039.
31. Jia M., Mu W., Chu F., Zhang X., Jiang B., Zhou L., et al. A D-psicose 3-epimerase with neutral pH optimum from Clostridium bolteae for D-psicose production: Cloning, expression, purification, and characterization. Applied Microbiology and Biotechnology 2014, 98:717-725.
32. Kawakami K., Hasegawa Y., Deguchi K., Ohki S., Shimizu T., Yoshihashi Y., et al. Competition of thermodynamic and dynamic factors during formation of multicomponent particles via spray drying. Journal of Pharmaceutical Sciences 2013, 102:518-529.
33. Kawakami K., Hasegawa Y., Zhang S.L., Yoshihashi Y., Yonemochi E., Terada K. Low-density microparticles with petaloid surface structure for pulmonary drug delivery. Journal of Pharmaceutical Sciences 2014, 103:1309-1313.
34. Kim H.J., Hyun E.K., Kim Y.S., Lee Y.J., Oh D.K. Characterization of an Agrobacterium tumefaciens D-psicose 3-epimerase that converts D-fructose to D-psicose. Applied and Environmental Microbiology 2006, 72:981-985.
35. Kim N.H., Kim H.J., Kang D.I., Jeong K.W., Lee J.K., Kim Y., et al. Conversion shift of D-fructose to D-psicose for enzyme-catalyzed epimerization by addition of borate. Applied and Environmental Microbiology 2008, 74:3008-3013.
36. Kim K., Kim H.J., Oh D.K., Cha S.S., Rhee S. 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. Journal of Molecular Biology 2006, 361:920-931.
37. Kim H.J., Lim B.C., Yeom S.J., Kim Y.S., Kim D., Oh D.K. Roles of Ile66 and Ala107 of D-psicose 3-epimerase from Agrobacterium tumefaciens in binding O6 of its substrate, D-fructose. Biotechnology Letters 2010, 32:113-118.
38. Kim H.J., Yeom S.J., Kim K., Rhee S., Kim D., Oh D.K. Mutational analysis of the active site residues of a D-psicose 3-epimerase from Agrobacterium tumefaciens. Biotechnology Letters 2010, 32:261-268.
39. Lee D.W., Choe E.A., Kim S.B., Eom S.H., Hong Y.H., Lee S.J., et al. Distinct metal dependence for catalytic and structural functions in the L-arabinose isomerases from the mesophilic Bacillus halodurans and the thermophilic Geobacillus stearothermophilus. Archives of Biochemistry and Biophysics 2005, 434:333-343.
40. Li Z., Li Y., Duan S.L., Liu J., Yuan P., Nakanishi H., et al. Bioconversion of D-glucose to D-psicose with immobilized D-xylose isomerase and D-psicose 3-epimerase on Saccharomyces cerevisiae spores. Journal of Industrial Microbiology & Biotechnology 2015, 42:1117-1128.
41. Lim B.C., Kim H.J., Oh D.K. A stable immobilized D-psicose 3-epimerase for the production of D-psicose in the presence of borate. Process Biochemistry 2009, 44:822-828.
42. Li X., Zhu Y., Zeng Y., Zhang T., Sun Y. Overexpression of D-psicose 3-epimerase from Clostridium cellulolyticum H10 in Bacillus subtilis and its prospect for D-psicose production. Advance Journal of Food Science & Technology 2013, 5:264-269.
43. Long N.V.D., Le T.H., Kim J.L., Lee J.W., Koo Y.M. Separation of D-psicose and D-fructose using simulated moving bed chromatography. Journal of Separation Science 2009, 32:1987-1995.
44. Luger A., Steinhart H. Carbohydrates in steam treated coffee. Seizième Colloque Scientifique International sur le Café 1995.
45. Matsuo T., Baba Y., Hashiguchi M., Takeshita K., Izumori K., Suzuki H. Dietary D-psicose, a C-3 epimer of D-fructose, suppresses the activity of hepatic lipogenic enzymes in rats. Asia Pacific Journal of Clinical Nutrition 2001, 10:233-237.
46. Matsuo T., Izumori K. D-Psicose inhibits intestinal alpha-glucosidase and suppresses the glycemic response after ingestion of carbohydrates in rats. Journal of Clinical Biochemistry and Nutrition 2009, 45:202-206.
47. Matsuo T., Shirai Y., Izumori K. Effects of dietary D-psicose on diurnal variation in plasma glucose and insulin concentrations of rats. FASEB Journal 2006, 20. A594-A594.
48. Matsuo T., Tanaka T., Hashiguchi M., Izumori K., Suzuki H. Metabolic effects of D-psicose in rats: Studies on faecal and urinary excretion and caecal fermentation. Asia Pacific Journal of Clinical Nutrition 2003, 12:225-231.
49. McDonald E.J. A new synthesis of D-psicose (D-ribo-hexulose). Carbohydrate Research 1967, 5:106-108.
50. Menavuvu B.T., Poonperm W., Takeda K., Morimoto K., Granstrom T.B., Takada G., et al. Novel substrate specificity of D-arabinose isomerase from Klebsiella pneumoniae and its application to production of D-altrose from D-psicose. Journal of Bioscience and Bioengineering 2006, 102:436-441.
51. Men Y., Zhu Y., Zeng Y., Izumori K., Sun Y., Ma Y. Co-expression of D-glucose isomerase and D-psicose 3-epimerase: Development of an efficient one-step production of D-psicose. Enzyme and Microbial Technology 2014, 64-65:1-5.
52. Miller B.S., Swain T. Chromatographic analyses of the free amino-acids, organic acids and sugars in wheat plant extracts. Journal of the Science of Food and Agriculture 1960, 11:344-348.
53. Moller D., Berger J. Role of PPARs in the regulation of obesity-related insulin sensitivity and inflammation. International Journal of Obesity 2003, 27:S17-S21.
54. Mozhaev V.V. Mechanism-based strategies for protein thermostabilization. Trends in biotechnology 1993, 11:88-95.
55. Mu W., Chu F., Xing Q.C., Yu S., Zhou L., Jiang B. Cloning, expression, and characterization of a D-psicose 3-epimerase from Clostridium cellulolyticum H10. Journal of Agricultural and Food Chemistry 2011, 59:7785-7792.
56. Murao K., Yu X., Cao W.M., Imachi H., Chen K., Muraoka T., et al. D-Psicose inhibits the expression of MCP-1 induced by high-glucose stimulation in HUVECs. Life Sciences 2007, 81:592-599.
57. Mu W., Yu L., Zhang W., Zhang T., Jiang B. Isomerases for biotransformation of D-hexoses. Applied Microbiology and Biotechnology 2015, 99:6571-6584.
58. Mu W., Zhang W., Fang D., Zhou L., Jiang B., Zhang T. Characterization of a D-psicose-producing enzyme, D-psicose 3-epimerase, from Clostridium sp. Biotechnology Letters 2013, 35:1481-1486.
59. Mu W., Zhang W., Feng Y., Jiang B., Zhou L. Recent advances on applications and biotechnological production of D-psicose. Applied Microbiology and Biotechnology 2012, 94:1461-1467.
60. Nagata Y., Kanasaki A., Tamaru S., Tanaka K. D-Psicose, an epimer of D-fructose, favorably alters lipid metabolism in sprague-dawley rats. Journal of Agricultural and Food Chemistry 2015, 63:3168-3176.
61. O'Charoen S., Hayakawa S., Ogawa M. Food properties of egg white protein modified by rare ketohexoses through Maillard reaction. International Journal of Food Science and Technology 2015, 50:194-202.
62. Ochiai M., Nakanishi Y., Yamada T., Iida T., Matsuo T. Inhibition by dietary D-psicose of body fat accumulation in adult rats fed a high-sucrose diet. Bioscience Biotechnology and Biochemistry 2013, 77:1123-1126.
63. Ochiai M., Onishi K., Yamada T., Iida T., Matsuo T. D-Psicose increases energy expenditure and decreases body fat accumulation in rats fed a high-sucrose diet. International Journal of Food Sciences and Nutrition 2014, 65:245-250.
64. Oshima H., Kimura I., Izumori K. Psicose contents in various food products and its origin. Food Science and Technology Research 2006, 12:137-143.
65. Oshima H., Kimura I., Kitakubo Y., Hayakawa S., Izumori K. Factors affecting psicose formation in food products during cooking. Food Science and Technology Research 2014, 20:423-430.
66. Sakuraba H., Yoneda K., Satomura T., Kawakami R., Ohshima T. Structure of a D-tagatose 3-epimerase-related protein from the hyperthermophilic bacterium Thermotoga maritima. Acta Crystallographica Section F-Structural Biology and Crystallization Communications 2009, 65:199-203.
67. Sasahara H., Mine M., Izumori K. Production of D-talitol from D-psicose by Candida famata R28. Journal of Fermentation and Bioengineering 1998, 85:84-88.
68. Sato M., Kurose H., Yamasaki T., Izumori K. Potential anthelmintic: D-psicose inhibits motility, growth and reproductive maturity of L1 larvae of Caenorhabditis elegans. Journal of Natural Medicines 2008, 62:244-246.
69. Soengas R., Izumori K., Simone M.I., Watkin D.J., Skytte U.P., Soetaert W., et al. Kiliani reactions on ketoses: Branched carbohydrate building blocks from D-tagatose and D-psicose. Tetrahedron Letters 2005, 46:5755-5759.
70. Suna S., Yamaguchi F., Kimura S., Tokuda M., Jitsunari F. Preventive effect of D-psicose, one of rare ketohexoses, on di-(2-ethylhexyl) phthalate (DEHP)-induced testicular injury in rat. Toxicology Letters 2007, 173:107-117.
71. Sun Y., Hayakawa S., Ogawa M., Fukada K., Izumori K. Influence of a rare sugar, D-psicose, on the physicochemical and functional properties of an aerated food system containing egg albumen. Journal of Agricultural and Food Chemistry 2008, 56:4789-4796.
72. Takata M.K., Yamaguchi F., Nakanose Y., Watanabe Y., Hatano N., Tsukamoto I., et al. Neuroprotective effect of D-psicose on 6-hydroxydopamine-induced apoptosis in rat pheochromocytoma (PC12) cells. Journal of Bioscience and Bioengineering 2005, 100:511-516.
73. Takei S., Hanabata M. Eco-friendly, water-repellent, light-transparent film derived from psicose using nanoimprint lithography. Materials Letters 2015, 143:197-200.
74. Takeshita K., Suga A., Takada G., Izumori K. Mass production of D-psicose from D-fructose by a continuous bioreactor system using immobilized D-tagatose 3-epimerase. Journal of Bioscience and Bioengineering 2000, 90:453-455.
75. Thacker J., Toyoda Y. Lung and heart-lung transplantation at University of Pittsburgh: 1982-2009. Clinical Transplants 2008, 179-195.
76. Toyoda Y., Mori S., Umemura N., Nimura Y., Inoue H., Hata T. Suppression of blood glucose levels by D-psicose in glucose tolerance test in diabetic rats. Japanese Pharmacology & Therapeutics 2010, 38:261-269.
77. Tseng C.W., Liao C.Y., Sun Y., Peng C.C., Tzen J.T.C., Guo R.T., et al. Immobilization of Clostridium cellulolyticum D-psicose 3-epimerase on artificial oil bodies. Journal of Agricultural and Food Chemistry 2014, 62:6771-6776.
78. Tsukamoto K., Hossain A., Yamaguchi F., Hirata Y., Dong Y., Kamitori K., et al. Intestinal absorption, organ distribution, and urinary excretion of the rare sugar D-psicose. Drug Design Development and Therapy 2014, 8:1955-1964.
79. Uechi K., Sakuraba H., Yoshihara A., Morimoto K., Takata G. Structural insight into L-ribulose 3-epimerase from Mesorhizobium loti. Acta Crystallographica Section D-Biological Crystallography 2013, 69:2330-2339.
80. Uechi K., Takata G., Fukai Y., Yoshihara A., Morimoto K. Gene cloning and characterization of L-ribulose 3-epimerase from Mesorhizobium loti and its application to rare sugar production. Bioscience Biotechnology and Biochemistry 2013, 77:511-515.
81. Uechi K., Takata G., Yoneda K., Ohshima T., Sakuraba H. Structure of D-tagatose 3-epimerase-like protein from Methanocaldococcus jannaschii. Acta Crystallographica Section F-Structural Biology Communications 2014, 70:890-895.
82. Xu Z., Li S., Feng X., Liang J., Xu H. L-Arabinose isomerase and its use for biotechnological production of rare sugars. Applied Microbiology and Biotechnology 2014, 98:8869-8878.
83. Yagi K., Matsuo T. The study on long-term toxicity of D-psicose in rats. Journal of Clinical Biochemistry and Nutrition 2009, 45:271-277.
84. Yang J., Zhu Y., Li J., Men Y., Sun Y., Ma Y. Biosynthesis of rare ketoses through constructing a recombination pathway in an engineered Corynebacterium glutamicum. Biotechnology and Bioengineering 2015, 112:168-180.
85. Yeom S.J., Seo E.S., Kim Y.S., Oh D.K. Increased D-allose production by the R132E mutant of ribose-5-phosphate isomerase from Clostridium thermocellum. Applied Microbiology and Biotechnology 2011, 89:1859-1866.
86. Yoshida H., Yamada M., Nishitani T., Takada G., Izumori K., Karnitori S. Crystal structures of D-tagatose 3-epimerase from Pseudomonas cichorii and its complexes with D-tagatose and D-fructose. Journal of Molecular Biology 2007, 374:443-453.
87. Yoshihara K., Shinohara Y., Hirotsu T., Izumori K. Chitosan productivity enhancement in Rhizopus oryzae YPF-61A by D-psicose. Journal of Bioscience and Bioengineering 2003, 95:293-297.
88. Yoshihara K., Shinohara Y., Hirotsu T., Izumori K. Bioconversion of D-psicose to D-tagatose and D-talitol by Mucoraceae fungi. Journal of Bioscience and Bioengineering 2006, 101:219-222.
89. Zeng Y., Zhang H., Guan Y., Zhang L., Sun Y. Comparative study on the effects of D-psicose and D-fructose in the Maillard reaction with beta-lactoglobulin. Food Science and Biotechnology 2013, 22:341-346.
90. Zhang W., Fang D., Xing Q., Zhou L., Jiang B., Mu W. Characterization of a novel metal-dependent D-psicose 3-epimerase from Clostridium scindens 35704. Plos One 2013, 8.
91. Zhang W., Fang D., Zhang T., Zhou L., Jiang B., Mu W. Characterization of a metal-dependent D-psicose 3-epimerase from a novel strain, Desmospora sp. 8437. Journal of Agricultural and Food Chemistry 2013, 61:11468-11476.
92. Zhang W., Li H., Zhang T., Jiang B., Zhou L., Mu W. Characterization of a D-psicose 3-epimerase from Dorea sp CAG317 with an acidic pH optimum and a high specific activity. Journal of Molecular Catalysis B-Enzymatic 2015, 120:68-74.
93. Zhang L., Mu W., Jiang B., Zhang T. Characterization of D-tagatose-3-epimerase from Rhodobacter sphaeroides that converts D-fructose into D-psicose. Biotechnology Letters 2009, 31:857-862.
94. Zhang W., Zhang T., Jiang B., Mu W. Biochemical characterization of a D-psicose 3-epimerase from Treponema primitia ZAS-1 and its application on enzymatic production of D-psicose. Journal of the Science of Food and Agriculture 2016, 96:49-56.
95. Zhu Y., Men Y., Bai W., Li X., Zhang L., Sun Y., et al. Overexpression of D-psicose 3-epimerase from Ruminococcus sp. in Escherichia coli and its potential application in D-psicose production. Biotechnology Letters 2012, 34:1901-1906.