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INFORMATION to Top This is a sweetener that is approximately 250 times sweeter than table sugar. It is a plant, Stevia rebaudiana that has been used historically in Paraguay as both a sweetener and herbal remedy. As noted the chemical structure is a stevioside, rebaudiosideA, and oat least six other sweet compounds that have glucoside groups attached to a three-carbon-ring central structure. Grenby (1987) indicates that this was first described in the scientific literature as Eupatorium rebaudianum by Moise Santiago Brtoni, Director of the College of Aggriculture in Asuncion in 1899. This is periodic continued interest in this plant. ALT="variation of formula"> From Phillips, K.C. 1987. Stevia: Steps in developing a new sweetener. IN Grenby, T.H. 1987. Developments in Sweeteners - 3. Elsevier Applied Science, New York. pp. 4. REFERENCES to Top Alves, L.M. and M. Ruddat. 1979. The presence of gibberellin A in Stevia rebaudiana and its significance for the biological activity of steviol. Plant and Cell Physiol. 20: 123 - 130. Avent, Anthony G.; Hanson, James R.; de Oliveira, Bras H. 1990. Hydrolysis of the diterpenoid glycoside, stevioside Phytochemistry 29(8): 2712-15 Bearder, J.R., J. MacMillan, C.M. Wells and B.O. Phinney. 1973. Metabolism of steviol and its derivatives by Gibberella fujikuroi mutant B1-41A. Journal Chem. Soc. Chem. Commun. 20: 778-779. Blumenthal,-M. 1995Fall. FDA lifts import alert on stevia. Herb can be imported only as dietary supplement; future use as a sweetener is still unclear. HerbalGram. Austin, TX : American Botanical Council and the Herb Research Foundation. (35) p. 17-18. Brandle, J. E.; Rosa, N. 1992Ocrober. Heritability for yield, leaf:stem ratio and stevioside content estimated from a landrace cultivar of Stevia rebaudiana. Canadian Journal of Plant Science 72:1263-6 Brandle, J. 1999 Genetic control of rebaudioside A and C concentration in leaves of the sweet herb, Stevia rebaudiana. Canadian journal of plant science. 79(1):85-92. Chang,-S.S.; Cook,-J.M. 1983Mar/April. Stability studies of stevioside and rebaudioside A in carbonated beverages Sweet-tasting compounds in the leaves of Stevia rebaudiana. J-Agric-Food-Chem. 31 (2) p. 409-412. Crosby, G.A. and R.E. Wingard. 1979. A survey of the less common sweeteners. IN Developments in Sweeteners. Ed. by C.A.M. Nough, K.J. Parker and A.J. Uletos. Darise, Muchsin; Mizutani, Kenji; Kasai, Ryoji 1984October. Enzymic transglucosylation of rubusoside and the structure-sweetness relationship of steviol-bisglycosides. Agricultural and Biological Chemistry 48: 2483-8. Esaki, Sachiko; Tanaka, Reiko; Kamiya, Shintaro 1984July. Synthesis and taste of certain steviol glycosides. Agricultural and Biological Chemistry 48: 1831-4 Fuh, Wea-Shang; Chikang, Been-Huang 1990October. Purification of steviosides by membrane and ion exchange processes. Journal of Food Science 55: 1454-7. Fujinuma,-K.; Saito,-K.; Nakazato,-M.; Kikuchi,-Y.; Ibe,-A.; Nichima,-T. 1986Sept/Oct. Thin layer chromatographic detection and liquid chromatographic determination of stevioside and rebaudioside A in beverages and foods following reverse phase column chromatography. Assoc-Off-Anal-Chem-J. 69 (5):799-802. Fukunaga, Yuichiro; Miyata, Takeshi; Nakayasu, Noriko 1989June. Enzymic transglucosylation products of stevioside: separation and sweetness-evaluation. Agricultural and Biological Chemistry 53: 1603-7 Grashoff, J.L. 1972. A systematic study of the North and Central American species of Stevia. University of Texas at Austin thesis. Handro,-W; Hell,-K-G; Kerbauy,-G-B 1977September. Tissue culture of Stevia rebaudiana, a sweetening plant. Plant-Med.32 (2): 115-117. Inglett,-G-E 1970June. Natural and synthetic sweeteners.[Richardella dulcifica, Stevia rebaudiana, Dioscoreophyllum cumminsii]. Hortscience 5 (3): 139-141. Inglett,-G.E. 1981March. Sweeneners--a review. Food-Technol. 35 (3):37-38,40-41. Kamiya,-S.; Konishi,-F.; Esaki,-S. 1979September. Synthesis and taste of some analogs of stevioside a sweet diterpene glycoside obtainable from Stevia rebaudiana, food additives. Agric-Biol-Chem. Tokyo 43 (9): 1863-1867. Kaneda,-N; Kasai,-R; Yamasaki,-K; Tanaka,-O. 1977. Chemical studies on sweet diterpene-glycosides of Stevia rebaudiana: conversion of stevioside into rebaudioside-A. Chem-Pharm-Bull. 25 (9): 2466-2467. Kitada,-Y.; Sasaki,-M.; Yamazoe,-Y.; Nakazawa,-H. 1989July19. Simultaneous determination of stevioside, rebaudioside A and C and dulcoside A in foods by high-performance liquid chromatography. J-Chromatogr. 474 (2): 447-451. Kobayashi,-M; Horikawa,-S; Degrandi,-I-H; Ueno,-J; Mitsuhashi,-H 1977. Dulcosides A and B, new diterpene glycosides from Stevia rebaudiana [Natural sweetening agents]. Phytochemistry 16 (9): 1405-1408. Kohda,-H; Kasai,-R; Yamasaki,-K; Murakami,-K; Tanaka,-O 1976. New sweet diterpene glucosides from Stevia rebaudiana. Phytochemistry 15 (6): 981-983. Kusakabe, Isao; Kusama, Satoru; Murakami, Kazuo 1987August. An easy method for the preparation of sophorose from stevioside. Agricultural and Biological Chemistry 51: 2255-6 Kusakabe, Isao; Watanabe, Satoru; Morita, Reiko 1992February. Formation of a transfer product from stevioside by the cultures of actinomycete. Bioscience, Biotechnology, and Biochemistry 56: 233-7 Metiyier, J. and A.M. Viana. 1979. The effect of long and short day length upon the growth of whole plants and the level of soluble proteins, sugars, and stevioside in leaves of Stevia rebaudiana.. Bert. Jour. of Exp. Botany 30: 1211-1222. Metivier,-J.; Viana,-A.M. 1979August. Determination of microgram quantities of stevioside from leaves of Stevia rebaudiana Bert. by two-dimensional thin layer chromatography. J-Exp-Bot. 30 (117):805-810. Mizukami,-H.; Shiba,-K.; Ohashi,-H. 1982. Enzymatic determination of stevioside in Stevia rebaudiana. Phytochemistry 21 (8):1927-1930. Nabeta,-K; Kasai,-T; Sugisawa,-H 1976October. Phytosterol from the callus of Stevia rebaudiana Bertoni. Agric-Biol-Chem. 40 (10): 2103-2104. Nakahara,-Y; Mori,-K; Matsui,-M 1971. Diterpenoid total synthesis. xVI. alternative synthetic routes to (+)-steviol and (+)-kaur-16-en-19-oic acid. [Stevia rebaudiana]. Agric-Biol-Chem. 35 (6): 918-928. Nakamura, S., S. Ishiguro, and M. Komuro. 1978. High-performance liquid chromatographic determination of Stevia components on a hydrophilic packed column. Journal of Chromatography 161: 403-405. Nanayakkara,-N.P.D.; Klocke,-J.A.; Compadre,-C.M.; Hussain,-R.A.; Pezzuto,-J.M.; Kinghorn,-A.D. 1987May/June. Characterization and feeding deterrent effects on the aphid, Schizaphis graminum, of some derivatives of the sweet compounds, stevioside and rebaudioside A. J-Nat-Prod. 50 (3):434-441. Sakamoto,-I; Yamasaki,-K; Tanaka,-O 1977December. Application of 13C NMR [carbon isotope, nuclear magnetic resonance] spectroscopy to chemistry of plant glycosides: rebaudiosides-D and -E, new sweet diterpene-glucosides of Stevia rebaudiana Bertoni. Chem-Pharm-Bull. 25 (12): 3437-3439. Schneider,-G; Miersch,-O; Liebisch,-H-W 1977January. Synthesis of O-beta-D-glucopyranosyl-gibberellin-O-D-glucopyranosyl esters [Stevia rebaudiana] (Synthese von O-beta-D-glucopyranosyl-gibberellin-O-beta-D-glucopyranosylestern. Tetrahedron-Lett. 5: 405-406. Shibata,-H.; Sonoke,-S.; Ochiai,-H.; Nishihashi,-H.; Yamada,-M. 1991January. Glucosylation of steviol and steviol-glucosides in extracts from Stevia rebaudiana Bertoni. Plant-Physiol. 95 (1):152-156. ABSTRACT: To evaluate and characterize stevioside biosynthetic pathway in Stevia rebaudiana Bertoni cv Houten, two enzyme fractions that catalyze glucosylation of steviol (ent-13-hydroxy kaur-16-en-19-oic acid) and steviol-glucosides (steviol-13-O-glucopyranoside, steviolbioside and stevioside), utilizing UDP-glucose as the glucose donor, were prepared from the soluble extracts of S. rebaudians leaves. Enzyme fraction I, passed through DEAE-Toyopearl equilibrated with 50 millimolar K-phosphate pH 7.5, catalyzed the glucosylation to steviol and 19-O-methylsteviol, but not to isosteviol and 13-O-methylsteviol, indicating that 13-hydroxyl group of the steviol skeleton is glucosylated first from UDP-glucose to produce steviol-13-O-glucopyranoside. Enzyme fraction II, eluted from the DEAE-Toyopearl column with 0.15 molar KCl, catalyzed the glucose transfer from UDP-glucose to steviol-13-O-glucopyranoside, steviolbioside and stevioside, but not to rubusoside (13,19-di-O-glucopyranoside) and rebaudioside A. The reaction products glucosylated from steviol-13-O-glucopyranoside, steviolbioside and stevioside were identified to be steviolbioside, stevioside and rebaudioside A, respectively. These results indicate that in the steviol-glucoside biosynthetic pathway, steviol-13-O-glucopyranoside produced from the steviol glucosylation is successively glucosylated to steviolbioside, then to stevioside producing rebaudioside A. Shibata,-H.; Sawa,-Y.; Oka,-T.; Sonoke,-S.; Kim,-K.K.; Yoshioka,-M. 1995August 20. Steviol and steviol-glycoside: glucosyltransferase activities in Stevia rebaudiana Bertoni--purification and partial characterization. Arch-biochem-biophys. 321 (2): 390-396. ABSTRACT: The leaves of Stevia rebaudiana Bertoni contain sweet compounds which are glycosides of diterpene derivative steviol (ent-13-hydroxykaur-16-en-19-oic acid). Its main constituents are stevioside (triglucosylated steviol; 13-O-beta-sophorosyl-19-O-beta-glucosyl-steviol) and rebaudioside-A (tetraglucosylated steviol; 2'-O-beta-glucosyl-13-O-beta-sophorosyl-19-O-beta-glucosyl steviol). From the extracts of S. rebaudiana Bertoni, two glucosyltransferases (GTases I and IIB) acting on steviol and steviol-glycosides were isolated, and another distinct activity (GTase IIA) acting on steviol was detected. Purified GTase I (subunit Mr 24,600) catalyzed glucose transfer from UDP-glucose to steviol and steviolmonoside (steviol-13-O-glucopyranoside), but not to other steviol-glycosides. Apparent Km values were 71.4 micromolar for steviol and 360 micromolar for UDP-glucose. GTase IIB (subunit Mr 30,700) showed a broad substrate specificity, acting on steviol, steviolmonoside, steviolbioside (13-O-beta-sophorosyl-steviol), and stevioside. Apparent Km values were 182 micromolar for steviol, 44 micromolar for steviolbioside, 95 micromolar for stevioside, and 385 micromolar for UDP-glucose. The two enzymes had a similar optimum pH at 6.5. They also acted effectively on ubiquitous flavonol aglycones, quercetin, and kaempferol and utilized kaempferol at a higher rate than steviol and steviol-glycosides. The apparent Km values of GTase I and IIB for kaempferol were 12 and 31 micromolar respectively. Shock, C.C. 1982, September-October. Rebaudi's stevia: natural noncaloric sweeteners. California Agriculture p. 4-5. Suzuki,-H; Ikeda,-T; Matsumoto,-T; Noguchi,-M 1976. Isolation and identification of rutin from cultured cells of Stevia rebaudiana Bertoni. Agric-Biol-Chem. 40 (4): 819-820. Toskulkao, Chaivat; Sutheerawattananon, Monthaporn 1994November. Effects of stevioside, a natural sweetener, on intestinal glucose absorption in hamsters. Nutrition Research14: 1711-20 Vasquez,-E.; Jakinovich,-W.-Jr. 1993Aug. Stimulation of the gerbil's gustatory receptors by some potently sweet terpenoids. J-agric-food-chem. 41 (8):1305-1310. ABSTRACT: The gerbil was investigated as a model for sweet taste among several highly sweet plant terpenoids and the sweet dihydroisocoumarin phyllodulcin. Although the gerbil's chorda tympani nerve did not respond in electrophysiological experiments to rebaudiosides B and C, steviolbioside, and phyllodulcin, concentration-response curves were obtained for the stimulatory sweeteners hernandulcin, mogroside V, periandrin III, rebaudioside A, and stevioside. These compounds were more effective stimuli in the gerbil than sucrose, in the following order of potency: rebaudioside A=stevioside=periandrin III > hernandulcin > mogroside V > sucrose. In conditioned-taste aversion studies, gerbils trained to avoid these five stimulatory compounds generalized an avoidance to sucrose but not to hydrochloric acid, and except for the perception of a concomitant salty taste, our data show that these substances taste like sucrose to gerbils, as in humans. Support is thus provided for the potential involvement of this methodology to guide the purification of natural sweeteners from plant extracts. Updated: Saturday, September 24, 2005.

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