Prevention of degradation of the natural high potency sweetener (2R,4R)-monatin in mock beverage solutions

Food Chemistry

Volumn 173, Issue , 2015, Pages 645-651

  Storkey, Corin ^a,b   Pattison, David I ^a,b   Koehler, Jamie A ^c   Gaspard, Dan S ^c   Evans, Jeff C ^c   Hagestuen, Erik D ^c   Davies, Michael J ^a,b  

^a HEART RESEARCH INSTITUTE   (Australia)

^b University of Sydney   (Australia)

^c CARGILL INC   (United States)

Author keywords

Keywords Monatin Tryptophan Photo oxidation Sweetener Metal ions Radicals Singlet oxygen

Indexed keywords

ADDITIVES; AMINO ACIDS; BEVERAGES; CHELATION; LIGHT ABSORPTION; METAL IONS; POLYCYCLIC AROMATIC HYDROCARBONS; POLYETHYLENE TEREPHTHALATES;

ABSORBANCES; CHELATING RESIN; DESFERRIOXAMINE; HIGH-POTENCY SWEETENERS; LIGHT FILTERING; METAL ION REMOVAL; NATURALLY OCCURRING; PROTECTIVE EFFECTS;

METALS;

CHELATING AGENT; DEFEROXAMINE; EDETIC ACID; INDOLE; LACTAM; LACTONE; METAL ION; MONATIN; RESIN; SWEETENING AGENT; TANNIN; UNCLASSIFIED DRUG; 4-HYDROXY-4-(INDOL-3-YLMETHYL)GLUTAMIC ACID; ANTIOXIDANT; GLUTAMIC ACID; INDOLE DERIVATIVE;

ANTIOXIDANT ACTIVITY; ARTICLE; BEVERAGE; CATALYST; CHELATION; DEGRADATION; LIGHT ABSORPTION; PHOTOOXIDATION; SWEETNESS; ULTRA PERFORMANCE LIQUID CHROMATOGRAPHY; ANALOGS AND DERIVATIVES; ANALYSIS; CHEMISTRY; LIGHT;

ANTIOXIDANTS; BEVERAGES; CHELATING AGENTS; EDETIC ACID; GLUTAMIC ACID; INDOLES; LIGHT; SWEETENING AGENTS;

EID: 84911449947     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2014.10.054     Document Type: Article

References (23)

1. Abraham, T. W., Cameron, D. C., Goulson, M. J., Hicks, P. M., Lindley, M. G., McFarlan, S. C., Millis, J. R., Rosazza, J., Zhao, L., & Weiner, D. P. (2005). Beverage compositions comprising monatin and methods of making same. US Patent US/2005/0106305.
2. R.G. Andrade Jr., J.S. Ginani, G.K. Lopes, F. Dutra, A. Alonso, and M. Hermes-Lima Tannic acid inhibits in vitro iron-dependent free radical formation Biochimie 88 2006 1287 1296
3. J. Bao, Y. Cai, M. Sun, G. Wang, and H. Corke Anthocyanins, flavonols, and free radical scavenging activity of Chinese bayberry (Myrica rubra) extracts and their color properties and stability Journal of Agricultural and Food Chemistry 53 2005 2327 2332
4. A. Bassoli, G. Borgonovo, and G. Morini Lost and found in sweeteners: forgotten molecules and unsolved problems in the chemistry of sweet compounds Flavour and Fragrance Journal 26 2011 269 273
5. Buddoo, S., Rousseau, A. L., & Gordon, G. E. R. (2009). Production of monatin enantiomers. World Intellectual Property Organization, World Patent: WO/2009/044245.
6. G.E. DuBois, and I. Prakash Non-caloric sweeteners, sweetness modulators, and sweetener enhancers Annual Reviews of Food Science and Technology 3 2012 353 380
7. V.B. Duffy, and G. Anderson Position of the American Dietetic Association: use of nutritive and nonnutritive sweeteners Journal of the American Dietetic Association 98 1998 580 587
8. Evans, J. C., & Goulson, M. J. (2010). Shelf stable monatin sweetened beverage. World Intellectual Property Organization, World Patent: WO/2010/138513.
9. Evans, J. C., & Goulson, M. J. (2012). Shelf stable monatin sweetened beverage. European Patent Office, Patent: EP2434910.
10. V. Fogliano, V. Verde, G. Randazzo, and A. Ritieni Method for measuring antioxidant activity and its application to monitoring the antioxidant capacity of wines Journal of Agricultural and Food Chemistry 47 1999 1035 1040
11. J.C. Fry, N. Yurttas, K.L. Biermann, M.G. Lindley, and M.J. Goulson The sweetness concentration-response of R, R-monatin, a naturally occurring high-potency sweetener Journal of Food Science 77 2012 S362 364
12. M. Gracanin, C.L. Hawkins, D.I. Pattison, and M.J. Davies Singlet oxygen-mediated amino acid and protein oxidation: formation of tryptophan peroxides and decomposition products Free Radical Biology and Medicine 47 2009 92 102
13. A. Hopia, and M. Heinonen Antioxidant activity of flavonol aglycones and their glycosides in methyl linoleate Journal of the American Oil Chemists Society 76 1999 139 144
14. S. Khokhar, and R.K. Owusu Apenten Iron binding characteristics of phenolic compounds: some tentative structure-activity relations Food Chemistry 81 2003 133 140
15. G.K.B. Lopes, H.M. Schulman, and M. Hermes-Lima Polyphenol tannic acid inhibits hydroxyl radical formation from Fenton reaction by complexing ferrous ions Biochimica Et Biophysica Acta-General Subjects 1472 1999 142 152
16. Prakash, I., Upreti, M., DuBois, G. E., King, G. A., Klucik, J., & San Miguel, R. (2008). Sweetness enhancers, sweetness enhanced sweetener compositions, methods for their formulation, and uses. World Intellectual Property Organization, World Patent: WO/2008/147727.
17. R. Pulido, L. Bravo, and F. Saura-Calixto Antioxidant activity of dietary polyphenols as determined by a modified ferric reducing/antioxidant power assay Journal of Agricultural and Food Chemistry 48 2000 3396 3402
18. G.E. Ronsein, M.C. de Oliveira, M.H. de Medeiros, and P. Di Mascio Characterization of O(2) ((1)delta(g))-derived oxidation products of tryptophan: a combination of tandem mass spectrometry analyses and isotopic labeling studies Journal of the American Society of Mass Spectrometrists 20 2009 188 197
19. G.E. Ronsein, M.C. de Oliveira, M.H. de Medeiros, and P. Di Mascio Mechanism of dioxindolylalanine formation by singlet molecular oxygen-mediated oxidation of tryptophan residues Photochemical and Photobiological Sciences 10 2011 1727 1730
20. G.E. Ronsein, M.C. Oliveira, S. Miyamoto, M.H. Medeiros, and P. Di Mascio Tryptophan oxidation by singlet molecular oxygen [O2(1Delta(g))]: mechanistic studies using 18O-labeled hydroperoxides, mass spectrometry, and light emission measurements Chemical Research in Toxicology 21 2008 1271 1283
21. Roy, G. M. (2010). Beverage composition and method of reducing degradation of monatin. World Intellectual Property Organization, World Patent: WO/2010/036576.
22. C. Storkey, D.I. Pattison, D.S. Gaspard, E.D. Hagestuen, and M.J. Davies Mechanisms of degradation of the natural high-potency sweetener (2R,4R)-monatin in mock beverage solutions Journal of Agricultural and Food Chemistry 62 2014 3476 3487
23. M. Upreti, K.V. Somayajula, D.J. Milanowski, P. Kowalenko, U. Mocek, and R. San Miguel Photostability study of natural high-potency sweetener Monatin in a model beverage system and characterization of the degradation products Food Chemistry 131 2012 413 421