Synthesis of rebaudioside-A by enzymatic transglycosylation of stevioside present in the leaves of Stevia rebaudiana Bertoni

Food Chemistry

Volumn 200, Issue , 2016, Pages 154-158

  Adari, Bhaskar Rao ^a   Alavala, Sateesh ^a   George, Sara A ^a   Meshram, Harshadas M ^a   Tiwari, Ashok K ^a   Sarma, Akella V S ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Cellulase; Glucosyl donors; Rebaudioside A; Stevia leaves; Transglycosylation

Indexed keywords

COLUMN CHROMATOGRAPHY; GLYCOSYLATION; STARCH;

CELLULASE; GLUCOSYL DONOR; REBAUDIOSIDE-A; STEVIA LEAVES; TRANSGLYCOSYLATION;

SUGAR SUBSTITUTES;

ALPHA GLUCOSIDASE; CELLULASE; DITERPENE; GLYCOSIDE; PLANT GLYCOSIDE; REBAUDIOSIDE A; STARCH; STEVIOSIDE; UNCLASSIFIED DRUG; FOOD ADDITIVE; GLUCOSIDE; KAURANE DERIVATIVE; SWEETENING AGENT;

ARTICLE; BIOTRANSFORMATION; COLUMN CHROMATOGRAPHY; CONCENTRATION RESPONSE; DRUG ISOLATION; ENZYME GLYCOSYLATION; ENZYME INHIBITION; HYPERGLYCEMIA; IC50; MEMBRANE FILTER; PLANT LEAF; STEVIA REBAUDIANA; SWEETNESS; CHEMISTRY; STEVIA;

CELLULASE; DITERPENES, KAURANE; FOOD ADDITIVES; GLUCOSIDES; PLANT LEAVES; STEVIA; SWEETENING AGENTS;

EID: 84954357990     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2016.01.033     Document Type: Article

References (31)

1. J. Brandle Genetic control of rebaudioside A and C concentration in leaves of the sweet herb Stevia rebaudiana Canadian Journal of Plant Science 79 1999 85 91 http://pubs.aic.ca/doi/pdf/10.4141/P98-048
2. V. Chatsudthipong, and C. Muanprasat Stevioside and related compounds: Therapeutic benefits beyond sweetness Pharmacology and Therapeutics 121 2009 41 54 10.1016/j.pharmthera.2008.09.007
3. Y. Fukunaga, T. Miyata, N. Nakayasu, K. Mizutani, R. Kasai, and O. Tanaka Enzymic transglycosylation products of stevioside: Separation and sweetness evaluation Agricultural and Biological Chemistry 53 1989 1603 1607 https://www.jstage.jst.go.jp/article/bbb1961/53/6/53-6-1603/-pdf
4. H. Ishikawa, S. Kitahata, K. Ohtani, C. Ikuhara, and O. Tanaka Production of stevioside and rubusoside derivatives by transfructosylation of β-fructofuranosidase Agricultural and Biological Chemistry 54 1990 3137 3143 https://www.jstage.jst.go.jp/article/bbb1961/54/12/54-12-3137/-pdf
5. H. Ishikawa, S. Kitahata, K. Ohtani, and O. Tanaka Transfructosylation of rebaudioside A (a sweet glycoside of stevia leaves) with Microbacterium β-fructofuranosidase Chemical and Pharmaceutical Bulletin 39 1991 2043 2045 https://www.jstage.jst.go.jp/article/cpb1958/39/8/39-8-2043/-pdf
6. V. Jaitak, V.K. Kaul, Bandna, N. Kumar, B. Singh, and L.S. Savergave S. Nene Simple and efficient enzymatic transglycosylation of stevioside by β-cyclodextrin glucanotransferase from Bacillus firmus Biotechnology Letters 31 2009 1415 1420 http://link.springer.com/article/10.1007/s10529-009-0020-7
7. V. Jaitak, B.S. Badna, and V.K. Kaul An efficient microwave-assisted extraction process of stevioside and rebaudioside-A from Stevia rebaudiana (Bertoni) Phytochemical Analysis 20 2009 240 245 http://onlinelibrary.wiley.com/doi/10.1002/pca.1120/epdf
8. +-channel activity Metabolism 49 2000 208 214 http://www.ncbi.nlm.nih.gov/pubmed/10690946
9. S.W. Jung, T.K. Kim, K.W. Lee, and Y.H. Lee Catalytic properties of β-cyclodextrin glucanotransferase from alkalophilic Bacillus sp. BL-12 and intermolecular transglycosylation of stevioside Biotechnology and Bioprocess Engineering 12 2007 207 212 http://link.springer.com/article/10.1007/BF02931094
10. N. Kaneda, K. Kasa, K. Yamasaki, and O. Tanaka Chemical studies on sweet diterpene-glycosides of Stevia rebaudiana: Conversion of stevioside into rebaudioside-A Chemical and Pharmaceutical Bulletin 25 1977 2466 2472 http://doi.org/10.1248/cpb.25.2466
11. S. Kitahata, H. Ishikawa, T. Miyata, and O. Tanaka Production of rubusoside derivatives by transglycosylation of various β-galactosidases Agricultural and Biological Chemistry 53 1989 2923 2928 http://doi.org/10.1271/bbb1961.53.2923
12. V.T. Kochikyan, A.A. Markosyan, L.A. Abelyan, A.M. Balayan, and V.A. Abelyan Combined enzymatic modification of stevioside and rebaudioside A Applied Biochemistry and Microbiology 42 2006 31 37 http://link.springer.com/article/10.1134/S0003683806010030
13. R.S. Kujur, V. Singh, M. Ram, H.N. Yadava, K. Singh, S. Kumari, and B.K. Roy Antidiabetic activity and phytochemical screening of crude extract of Stevia rebaudiana in alloxan-induced diabetic rats Pharmacognosy Research 2 2010 258 263 10.4103/0974-8490.69128
14. S. Kusama, I. Kusakabe, Y. Nakamura, S. Eda, and K. Murakami Transglucosylation into stevioside by the enzyme system from Streptomyces sp Agricultural and Biological Chemistry 50 1986 2445 2451 http://doi.org/10.1271/bbb1961.50.2445
15. S. Li, W. Li, Q. Xiao, and Y. Xia Transglycosylation of stevioside to improve the edulcorant quality by lower substitution using cornstarch hydrolyzate and CGTase Food Chemistry 138 2013 2064 2069 10.1016/j.foodchem.2012.10.124
16. S.V. Lobov, R. Kasai, K. Ohtani, O. Tanaka, and K. Yamasaki Enzymic production of sweet stevioside derivatives: Transglycosylation by glucosidases Agricultural and Biological Chemistry 55 1991 2959 2965 http://doi.org/10.1271/bbb1961.55.2959
17. T. Lu, and Y. Xia Transglycosylation specificity of glycosyl donors in transglycosylation of stevioside catalyzed by cyclodextrin glucanotransferase Food Chemistry 159 2015 151 156 10.1016/j.foodchem.2014.03.017
18. B.H. Oliveira, J.F. Packer, M. Chimelli, and D.A. Jesus Enzymatic modification of stevioside by cell-free extract of Giberella fujikuroi Journal of Biotechnology 131 2007 92 97 10.1016/j.jbiotec.2007.05.035
19. I. Prakash, G.E. DuBois, J.F. Clos, K.L. Wilkens, and L.E. Fosdick Development of rebiana, a natural, non-caloric sweetener Food and Chemical Toxicology 46 2008 S75 S82 10.1016/j.fct.2008.05.004
20. M. Puri, D. Sharma, C.J. Barrow, and A.K. Tiwary Optimisation of novel method for the extraction of steviosides from Stevia rebaudiana leaves Food Chemistry 132 2012 1113 1120 10.1016/j.foodchem.2011.11.063
21. A.B. Rao, E. Prasad, G.R. Reddy, S. Sridhar, and Y.V.L. Ravikumar Simple extraction and membrane purification of process in isolation of steviosides with improved organoleptic activity Advances in Bioscience and Biotechnology 3 2012 327 335 http://file.scirp.org/Html/7-7300284-21869.htm
22. H. Shibata, S. Sonoke, H. Ochiai, H. Nishihashi, and M. Yamada Glucosylation of steviol and steviol-glucosides in extracts from Stevia rebaudiana Bertoni Plant Physiology 95 1991 152 156 http://dx.doi.org/10.1104/pp.95.1.152
23. A.N. Starratt, C.W. Kirby, R. Pocs, and J.E. Brandle Rebaudioside F, a diterpene glycoside from Stevia rebaudiana Phytochemistry 59 2002 367 370 S0031-9422(01)00416-2
24. G. Suresh, A.K. Tiwari, M.R. Krishna Murthy, D. Anand Kumar, K. Rajendra Prasad, and R. Ranga Rao K. Suresh Babu New advanced glycation end-products inhibitors from Dichrostachys cinerea Wight & Arn Journal of Natural Medicines 66 2012 213 216 http://link.springer.com/article/10.1007/s11418-011-0557-3
25. A. Tada, T. Kana, I. Kyoko, N. Sugimoto, T. Suematsu, K. Arifuku, and et al. Absolute quantitation of stevioside and rebaudioside-A in commercial standards by quantitative NMR Chemical and Pharmaceutical Bulletin 61 2013 33 38 https://www.jstage.jst.go.jp/article/cpb/61/1/61-c12-00736/-pdf
26. O. Tanaka Steviol glycosides: New natural sweeteners Trends in Analytical Chemistry 1 1982 246 248 10.1016/0165-9936(82)80079-4
27. A.K. Tiwari, S. Chintapatla, A. Zehra, K. Madhusudana, A.K. Domati, and S.B. Agawane Mitigation of starch-induced postprandial glycemic spikes in rats by antioxidants-rich extract of Cicer arietinum Linn. seeds and sprouts Journal of Pharmacy and Bioallied Sciences 5 2013 270 276 10.4103/0975-7406.120077
28. M. Upreti, G. Dubois, and I. Prakash Synthetic study on the relationship between structure and sweet taste properties of steviol glycosides Molecules 17 2012 4186 4196 10.3390/molecules1704418617, 486-4196
29. Varuzhan, H., Abelyan, V., Ghochikyan, A., Markosyan, A., Adamyan, M. O. & Abelyan, L. O. (2004). Extraction, separation and modification of sweet glycosides from the Stevia rebaudiana plant. United States Patent, Patent No US 7838044 B2.
30. Zhang, L. Y. & Li, C. K. (2013). Sweetener composition and methods of making same. United States Patent, Patent No US 20130344217 A1.
31. Y.D. Zhang, W. Li, T. Lu, and Y.M. Xia The effect of microwave irradiation on transglycosylation pathway of stevioside with starches or cyclodextrins catalyzed by a cyclodextrin glucanotransferase Journal of Molecular Catalysis B: Enzymatic 120 2015 151 157 10.1016/j.molcatb.2015.07.012