Natural High-Potency Sweeteners

Sweeteners and Sugar Alternatives in Food Technology

Volumn , Issue , 2012, Pages 185-212

  Lindley, Michael G ^a  

^a Lindley Consulting   (United Kingdom)

Author keywords

Brazzein; Functional and regulatory characteristics; lo han guo; Mogroside; Monatin; Natural potent sweeteners; Sensory; Steviol glycosides; Thaumatin

Indexed keywords

EID: 84887236410     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9781118373941.ch9     Document Type: Chapter

References (86)

1. D. Ming and G. Hellekant. Brazzein, a new high potency thermostable sweet protein from Pentadiplandra brazzeana B., FEBS Letters 1994, 355, 106-108.
2. H. Yamashita, S. Theerasilp and Y. Kurihara. Xth International Symposium on Olfaction and Taste, Oslo, Norway, 1989. Abstract, Purification and partial structure characterisation of a new type of sweet protein having taste modifying action, Abstract 77.
3. Z. Hu and M. He. Studies on mabinlin, a sweet protein from the seeds of Capparis masaikai, I. extraction, purification and certain characteristics. Acta Botanica Yunnanica. 1983, 5, 207-212.
4. J.A. Morris and R.H. Cagan. Purification of monellin, sweet principle in Discoreophyllum cuminsii. Biochimica Et Biophysica Acta 1972, 261, 114-122.
5. H. van der Wel, G. Larson, A. Hladik, C.M. Hladik, G. Hellekant and D. Glaser. Isolation and characterisation of pentadin, the sweet principle of Pentadiplandra brazzeana Baillon. Chemical Senses 1989, 14, 75-79.
6. W.F. Daniell. Katemfe, or the miraculous fruit of the Sudan. Pharmaceutical Journal 1855, 14, 158.
7. R. Vleggar, L.G.J. Ackerman and P.S. Steyn. Structure elucidation of monatin, a high-intensity sweetener isolated from the plant Schlerochiton ilicifolius. Journal of the Chemical Society, Perkin Transactions 1 1992, 3095-3098.
8. Y-H. Choi, R.A. Hussain, J.M. Pezzuto, A.D. Kinghorn and J.F. Morton. Abrusosides A-D, four novel sweet tasting triterpene glycosides from the leaves of Abrus precatorius. Journal of Natural Products 1989, 52, 1118-1127.
9. M. Yoshikawa, T. Morikawa, K. Nakano, Y. Pongpiriyadacha, T. Murakami and H. Matsuda. Albiziasaponins A-E, five new triterpene saponins from the stems of Albizia myriophylla. Journal of Natural Products 2002, 65, 1638-1642.
10. H. Yamada and N. Mugio. Synthetic approach to intensely sweet glycosides: baiyunoside and osladin. Studies in Plant Science 1999, 6, 360-372.
11. P.J. Hyland and J. Kosugi. Bryonoside and bryoside - new triterpene glycosides from Bryonia dioica. Phytochemistry 1982, 21, 1379-1384.
12. M. Darise, K. Mizutani, R. Kasai, O. Tanaka, S. Kitahata, S. Okada, S. Ogawa, F. Murakami and F.H. Chen. Enzymic transglucosylation of rubusoside and the structure-sweetness relationship of steviolbisglycosides. Agricultural and Biological Chemistry 1984, 48, 2483-2488.
13. R.G. Shu, L.R. Xu, L.N. Li and Z.L. Yu. Cyclocariosides II and III: two secodammarane triterpenoid saponins from Cyclocarya paliurus. Planta Medica 1995, 61, 551-553.
14. G.E. DuBois. Non-nutritive sweeteners. The search for sucrose mimics. In: H-J. Hess (ed). Annual Reports in Medicinal Chemistry, Academic Press, New York; 1982, Vol. 17, 323-332.
15. C-H. Lee. Intense sweetener from lo han kuo (Momordica grosvenorii). Experientia 1975, 31, 533-534.
16. J.R. Sun, K.C. Cheng, T.Y. Pan and X.M. Si. A new acyclic sesquiterpene oligoglycoside from pericarps of Sapindus mukurossi. Chinese Chemical Letters 2002, 13, 555-556.
17. J. Jizba, L. Dolejs, V. Herout and F. Sorm. The structure of osladin - the sweet principle of the rhizomes of Polypodium vulgare. Tetrahedron Letters 1971, 18, 1329-1332.
18. Y. Hashimoto, Y. Ohta, H. Ishizone, M. Kuriyama and M. Ogura. Periandrin, a novel sweet triterpene glycoside from Periandra dulcis. Phytochemistry 1982, 21, 2335-2337.
19. M. Katagiri, K. Ohtani, R. Kasai and O. Tanaka. Diterpenoid glycosyl esters from Phlomis younghusbandii and P. Medicinalis. Phytochemistry 1994, 35, 439-442.
20. J. Kim, J.M. Pezzuto, D.D. Soejarto, F.A. Lang and A.D. Kinghorn. Polypodoside A, an intensely sweet constituent of the rhizomes of Polyupodium glycyrrhiza. Journal of Natural Products 1988, 51, 1166-1172.
21. E.J. Kennelly, L. Cai, L. Long, L. Shannon, K. Zaw, B-N. Zhou, J.M. Pezzuto and A.D. Kinghorn. Novel highly sweet secodammarane glycosides from Pterocarya paliurus. Journal of Agricultural and Food Chemistry 1995, 43, 2602-2607.
22. J. Zhang, G-X. Chou, L-M. Liu and Z-J. Liu. Determination of rubusoside from Rubus suavissimus. Journal of Chinese Mass Spectrometry Society 2009, 30, 236-237.
23. R. Kasai, N. Kaneda, O. Tanaka, K. Yamasaki, I. Sakamoto, K. Morimoto and S. Okada. Sweet diterpene glycosides of leaves of Stevia rebaudiana - synthesis and structure sweetness relationship. Journal of The Chemical Society of Japan 1981, 726-735.
24. V.D. Huan, K. Ohtari, R. Kasai, K. Yamasaki and N.V. Tuu. Sweet pregnane glycosides from Telosma procumbens. Chemical and Pharmaceutical Bulletin 2001, 49, 453-460.
25. N.I. Baek, M.S. Chung, L. Shamon, L.B. Kardone, S. Tsauri, K. Padmawinata, J.M. Pezzuto, D.D. Soejarto and A.D. Kinghorn. Selligueain A, a novel highly sweet proanthocyanidin from the rhizomes of Selliguea feei. Journal of Natural Products 1993, 56, 1532-1538.
26. C.M. Compadre, J.M. Pezzuto, A.D. Kinghorn and S.K. Kamath. Hernandulcin: an intensely sweet compound discovered by review of ancient literature. Science 1985, 227, 417-419.
27. R.L. Nie, T. Takashi, J. Zhou and O. Tanaka. Phlorizin and trilobatin, sweet dihydrochalcone glucosides from leaves of Lithocarpus litseifolius. Agricultural and Biological Chemistry 1982, 46, 1933-1934.
28. Y. Asahina and E. Ueno. Phylodulcin, a chemical constituent of Amacha. Journal of the Pharmaceutical Society of Japan 1916, 408.
29. L. O'B. Nabors and G.E. Inglett. A review of various other alternative sweeteners. In: L.O'B. Nabors and R.C. Gelardi (eds). Alternative Sweeteners, Marcel Dekker, New York; 1986, pp. 309-323.
30. J.D. Higginbotham. Protein sweeteners. In: C.A.M. Hough, K.J. Parker, A.J. Vlitos (eds). Developments in Sweeteners 1, Applied Science, London; 1979, pp. 87-114.
31. B. Iyengar, P. Smits, F. van der Ouderaa, H. van der Wel and J. van Browersharen. Structure of the thaumatins. European Journal of Biochemistry 1979, 96, 193-204.
32. H. van der Wel, A. van der Heijden and H.G. Peer. Sweeteners. Food Reviews International, 1987, 3, 193-268.
33. J.D. Higginbotham. Talin protein (thaumatin). In: L.O'B. Nabors and R.C. Gelardi (eds). Alternative Sweeteners, Marcel Dekker, New York; 1986, pp. 103-134.
34. C.A.M. Hough and J.A. Edwardson. Antibodies to thaumatin as a model of the sweet taste receptor. Nature, 1978, 271, 381-383.
35. G.E. DuBois, D.E. Walters, S.S. Schiffman, Z.S. Warwick, B.J. Booth, S.D. Pecore, K. Gibes, B.T. Carr and L.M. Brands. Concentration-response relationships of sweeteners. In: D.E. Walters, F.T. Orthoefer and G.E. DuBois (eds). Sweeteners, Discovery, Molecular Design and Chemoreception, ACS Symposium Series 450, ACS, Washington, DC; 1991, pp. 261-276.
36. J.D. Higginbotham, M.G. Lindley and J.P. Stephens. Thaumatin. In: G. Charalambous and G.E. Inglett (eds). The Quality of Foods and Beverages, Academic Press, New York; 1981, pp. 91-113.
37. J.D. Higginbotham. Recent developments in non-nutritive sweeteners. In: T.H. Grenby, K.J. Parker and M.G. Lindley (eds.). Developments in Sweeteners II, Applied Science, London; 1983, pp. 119-155.
38. H. van derWel andW.J. Bel. Enzymatic properties of the sweet-tasting proteins thaumatin and monellin after partial reduction. European Journal of Biochemistry 1980, 104, 413-418.
39. J.D. Higginbotham, D.J. Snodin, K.K. Eaton and J.W. Daniel. Safety evaluation of thaumatin. Food and Chemical Toxicology 1983, 21, 815-823.
40. C. Green. Thaumatin: A natural flavour ingredient, In: A. Corti (ed). Low Calorie Sweeteners: Present and Future, Karger, Basel; 1991, pp. 129-132.
41. A.D. Kinghorn and D.D. Soejarto. Stevioside. In: L.O'B. Nabors and R.C. Gelardi (eds). Alternative Sweeteners, Marcel Dekker, New York; Basel, Hong Kong; 1991, pp. 157-171.
42. A.D. Kinghorn and D.D. Soejarto. Current status of stevioside as a sweetening agent for human use. In: H. Wagner, H. Hikino and N.R. Farnsworth (eds). Economic and Medicinal Plant Research, Academic Press, London; 1985, Vol. 1, pp. 1-52.
43. S-H. Kim and G.E. DuBois. Natural high potency sweeteners. In: S. Marie and J.R. Piggott (eds). Handbook of Sweeteners, Blackie, Glasgow and London; 1991, pp. 116-185.
44. G.E. DuBois, P.S. Dietrich, J.F. Lee, G.V. McGarraugh and R.A. Stephenson. Diterpenoid sweeteners, synthesis and sensory evaluation of stevioside analogues non-degradable to steviol. Journal of Medicinal Chemistry 1981, 24, 408-428.
45. R.A. Frank, S.J.S. Mize and R. Carter. An assessment of binary mixture interactions for nine sweeteners. Chemical Senses 1989, 14, 621-632.
46. A.I. Bakal and L.O'B. Nabors. Stevioside. In: L.O'B. Nabors and R.C. Gelardi (eds). Alternative Sweeteners, Marcel Dekker, New York; 1986, pp. 295-307.
47. S.S. Chang and J.M. Cook. Stability studies of stevioside and rebaudioside A in carbonated beverages. Journal of Agricultural and Food Chemistry 1983, 31, 409-412.
48. A. Roberts and A.G. Renwick. Comparative toxicokinetics and metabolism of rebaudioside A, stevioside and steviol in rats. Food and Chemical Toxicology 2008, 46(Suppl. 7), S31-S39.
49. A. Wheeler, A. Boileau, P. Winkler, J. Compton, I. Prakash, X. Jiang and D. Mandarino. Pharmacokinetics of rebaudioside A and stevioside after single oral doses in healthy men. Food and Chemical Toxicology 2008, 46(7S), S54-S60.
50. S. Marie. Sweeteners. In: J. Smith (ed). Food Additive Users Handbook, Blackie, Glasgow/AVI, New York; 1991, pp. 47-74.
51. N. Mori, M. Sakanoue, M. Takeuchi, K. Simpo and T. Tanabe. Effect of stevioside on fertility in rats. Shokuhin Eiseigaku Zasshi 1981, 22, 409-414.
52. V. Yodyingyuad and S. Bunyawong. Effect of stevioside on growth and reproduction. Human Reproduction 1991, 6, 158-165.
53. L.L. Curry and A. Roberts. Acute and subchronic toxicity of rebaudioside A. Food and Chemical Toxicology 2008, 46(Suppl. 7), S11-S20.
54. A.I. Nikiforov and A.K. Eapen. A 90-day oral (dietary) toxicity study of rebaudioside A in Sprague-Dawley rats. Internat. Journal of Toxicology 2008, 27, 65-80.
55. J.M. Pezzuto, N.P. Nanayakkara, C.M. Compadre, S.M. Swanson, A.D. Kinghorn, T.M. Guenthner, V.L. Sparnins and L.K. Lam. Characterisation of bacterial mutagenicity mediated by 13-hydroxy-entkaurenoic acid (steviol) and several structurally related derivates and evaluation of potential to induce gluthathione S-transferase in mice. Mutation Research 1986, 169, 93-103.
56. M. Suttajit, U. Vinitketkaumnuen, U. Meevate and D. Buddhasukh. Mutagenicity and human chromosomal effect of stevioside, a sweetener from Stevia rebaudiana Bertoni. Environmental Health Perspectives 1993, 101(Suppl. 3), 53-56.
57. M. Matsui, K. Matsui, T. Nohmi, H. Mizusawa and M. Ishidate. Mutagenicy of steviol: an analytical approach using the Southern blotting system. Eisei Shikenjo Hokoku 1989, 300, 83-87.
58. M. Matsui, K. Matsui,Y. Kawasaki, Y. Oda, T. Nogushi, Y. Kitagawa, M. Sawada, M.Hayashi, T. Nohmi, K. Yoshihira, M. Jr. Ishidate and T. Sofuni. Evaluation of the genotoxicity of stevioside and steviol using six in vitro and one in vivo mutagenicity assays. Mutagenesis 1996, 11, 573-579.
59. Ha-Y. Oh, E-S. Han, D-W. Choi, J-W. Kim, M-O. Eom, I-W. Kang, M-J. Kang and K-W. Ha. In vitro and in vivo evaluation of genotoxicity of stevioside and steviol natural sweetener. Yakhakhoe Chi 1999, 43, 614-622.
60. JECFA. 2006. Safety evaluation of certain food additives. Sixty-third meeting of the Joint FAO/WHO Expert Committee on Food Additives, 8-17 June, 2004. Geneva, Switzerland. World Health Organisation (WHO), International Programme on Chemical Safety (IPCS), Geneva, Switzerland, WHO Food Additives Series, No. 54.
61. A. Yamada, S. Ohgaki, T. Noda and M. Shimizu. Chronic toxicity study of dietary Stevia extracts in F344 rats. Journal of the Food Hygienic Society of Japan 1986, 27, 1-8.
62. C. Toskulkao, L. Chaturat, P. Temcharoen and T. Glinsukon. Acute toxicity of stevioside, a natural sweetener, and its metabolite, in several animal species. Drug and Chemical Toxicology 1997, 20(1-2), 31-44.
63. T. Takemoto, S. Arihara, T. Nakajima and M. Okuhira. Studies on the constituents of Fructus momordicae, III. Structure of mogrosides. Yakugaku Zasshi 1988, 103, 1155-1166.
64. G.E. Dawson. Process and composition for sweet juice from Cucurbitaceae fruit, US patent 5,411,755; 1995.
65. A.D. Kinghorn and D.D. Soejarto. Sweetening agents of plant origin. CRC Critical Reviews in Plant Sciences 1986, 4, 79-120.
66. L.O'B. Nabors and G.E. Inglett. A review of various other alternative sweeteners. In: L.O'B. Nabors and R.C. Gelardi (eds). Alternative Sweeteners, Marcel Dekker, New York; 1986, 309-323.
67. A.D. Kinghorn and D.D. Soejarto. Discovery of terpenoid and phenolic sweeteners from plants. Pure and Applied Chemistry 2002, 74, 1169-1179.
68. H. Shi. Antioxidant property of Fructus momordicae extract. Biochemistry and Molecular Biology International 1996, 40, 1111-1121.
69. T. Konoshima and M. Takasaki. Cancer-chemopreventive effects of natural sweeteners and related compounds. Pure and Applied Chemistry 2002, 74, 1309-1316.
70. A.D. Kinghorn and D.D. Soejarto. Intensely sweet compounds of natural origin. Medicinal Research Reviews 1989, 9, 91-115.
71. D. Ming and G. Hellekant. Brazzein, a new high potency thermostable sweet protein from Pentadiplandra brazzeana B. FEBS Letters 1994, 355, 106-108.
72. G. Hellekant and V. Danilova. Brazzein, a small sweet protein: discovery and physiological overview. Chemical Senses 2005, 30(Suppl 1), i88-i89.
73. H. Izawa, M. Ota, M. Kohmura and Y. Ariyoshi. Synthesis and characterization of the sweet protein brazzein. Biopolymers 1996, 39, 95-101.
74. J.F. Pfeiffer, R.B. Boulton and A.C. Noble. Modelling the sweetness response using time-intensity data. Food Quality and Preference 2000, 11, 129-138.
75. G.G. Birch. Ingredients Handbook - Sweeteners (Ingredients Handbook Series). Leatherhead Food Research Association, UK; 2000.
76. Z. Guan, G. Hellekant andW. Yan. Expression of sweet protein brazzein by Saccharomyces cerevisiae. Chemical Senses 1995, 20, 701.
77. I. Faus. Recent developments in the characterization and biotechnological production of sweet-tasting proteins. Applied Microbiology and Biotechnology 2000, 53, 145-151.
78. A. Bassoli, G. Borgonovo, G. Busnelli, G. Morini and M.G.B. Drew. Monatin and its stereoisomers: chemoenzymatic synthesis and taste properties. European Journal of Organic Chemistry 2005, 1652-1658.
79. P.J. Van Wyk and L.G. Ackerman. 3-(1-amino-1,3-dicarboxy-3-hydroxy-but-4-yl)-indole compounds. US Patent 4,975,298; 1990.
80. E. Abushanab and S. Arumugam. Synthesis of monatin - A high intensity natural sweetener. US Patent 5,994,559; 1999.
81. P.M. Hicks, S.C. McFarlan, T.W. Abraham, D.C. Cameron, J.R. Millis, J. Rosazza, L. Zhao and D.P. Weiner. Polypeptides and biosynthetic pathways for the production of monatin and its precursors. US Patent 7,572,607; 2009.
82. A.B. Khare, B.H. Hilbert, C. Solheid, S.C. McFarlan, F.A. Sanchez-Riera, K. Floy and P.M. Hicks. Methods and systems for increasing production of equilibrium reactions. US Patent 7,888,081; 2011.
83. J. Hlywka,W.A. Brathwaite, A.I. Nikiforov, M.O. Rihner and A. Eapen. A 90-day dietary toxicity study of R,R-monatin salt, a natural high potency sweetener, in rats. Poster presentation Society of Toxicology Meeting, Washington, DC, March 2011.
84. K. Mori, E. Ono and T. Takemoto. Crystal of (2R,4R)-monatin potassium salt and sweetener composition containing same. US Patent 7,553,974; 2005.
85. Y. Amino, K. Hirasawa, K. Mori and T. Takemoto. Crystals of free (2R,4R)-monatin and use thereof. US Patent 7,935,377; 2011.
86. K. Mori. Sweetener composition. US Patent 7,781,005; 2010.