Glycosides rebaudioside

Sakamoto, I., K. Yamasaki, and O. Tanaka Application of NMR spectroscopy to chemistry of plant glycosides rebaudiosides-D and -E, new sweet diterpene-glucosides of Stevia rebaudiana Bertoni. Chem. Pharm. Bull. 25, 3437 (1977). 

Stevioside and rebaudioside A are diterpene glycosides. The sweetness is tainted with a bitter and undesirable aftertaste. The time—intensity profile is characteristic of naturally occurring sweeteners slow onset but lingering. The aglycone moiety, steviol [471 -80-7] (10), which is the principal metaboHte, has been reported to be mutagenic (79). Wide use of stevia ia Japan for over 20 years did not produce any known deleterious side effects. However, because no food additive petition has been presented to the FDA, stevioside and related materials caimot be used ia the United States. An import alert against stevia was issued by the FDA ia 1991. In 1995, however, the FDA revised this import alert to allow the importation and use of stevia as a diet supplement (80), but not as a sweetener or an ingredient for foods. Several comprehensive reviews of stevia are available (81,82). 

The plant Stevia rebaudiana bertoni has been studied in depth because it was discovered that this plant is the source of six sweet-tasting diterpene glycosides. They are stevioside, rebaudiosides A, C, D, E and dulcoside A. (Table 1). These sweet diterpene glycosides, as well as a complex mixture of organic compounds of which more than a hundred compounds have been identified, are found mainly in the leaves of the plant. The leaves contain a complex mixture of labdane diterpenes, triterpenes, stigmasterol, tannins and volatile oils. There is an abundance of reviews and patents relating to these sweet diterpene glycosides. 

There are many patents and journal articles that describe processes to produce the principal sweet diterpene glycosides stevioside and in particular, rebaudioside A. Many of the reported methods of production require the use of ion exchange columns or gases and are not satisfactory if the scale-up to commercial quantities are required. Most methods for extraction and purification of the sweet diterpene glycosides from Stevia use complicated processing of the crude extracts. Generally, the recovery processes of the principal two diterpene glycosides stevioside and rebaudioside A involve ... 

The leaves of Stevia rebaudiana (Compositae) are a source of several sweet glycosides of steviol (26) (Fig. 15) [1, 61]. The major glycoside, stevioside (27), is used in oriental countries as a food sweetener and the second major glycoside named rebaudioside (28), which is sweeter and more delicious than stevioside, is utilized in beverages. 

Stevia sweeteners are extracted from the leaves of Stevia rebaudiana Bertoni (Compositae), an herb native to Paraguay but cultivated in Southeast Asia, Japan, Paraguay, Brazil, Israel, and the United States. The sweet constituents of stevia include eight diterpene glycosides stevioside, ste-violbioside, rebaudiosides A, B, C, D, E, and dulcoside A, which collectively are 100-300 times... 

Detection of stevia glycosides after separation by HPLC has been performed by high-sensitivity refractive index (106,116) and by UV at 210 nm (110,115-118). The use of UV at 210 nm allowed detection of 0.4 fig for stevioside, steviolbioside, rebaudioside B, and dulcoside A and 0.8 fig for rebaudiosides A and C-E. This sensitivity is higher than that obtained with the RI detector-2 /ig of stevioside and rebaudioside A (116). 

In Japan, the largest market for the S. rebaudiana sweeteners to date, three different forms of stevia sweetener products are commercially available, namely, stevia extract , sugar-transferred stevia extract , and rebaudioside A-enriched stevia extract . Stevia extract is a powder or granule made by several industrial steps and standardized so as to contain more than 80% of steviol glycosides, inclusive of dulcoside A (3-5%), rebaudioside A (20-25%), rebaudioside C (5-10%), and stevioside (50-55%) [31]. Sugar-transferred stevia extract is made by... 

Fig. 2A In a Steviae folium BuOll extract (.1) the. sweet-tasting diterpene glycosides are found as four grey zones in the R, range 0.1-0.3 with rebaudioside A (T2) at R, 0.2 and stevioside (Tl) at R, 0.3. The three weak grey zones in the upper R, range 0,75 up to the. solvent front are due to less polar diterpene glycosides and aglycones.

Carakostas, M.C., L.L. Curry, A.C. Boileau, and D.J. Brusick. 2008. Overview The history, technical function and safety of rebaudioside A, a naturally occurring steviol glycoside, for use in food and beverages. Food Chem. Foxicol. 46(Suppl. 7) S1-S10. 

Stevia species are members of the family of Asteraceae. Stevia rebaudiana contains steviol glycosides, such as stevioside and rebaudioside A, used as artificial sweeteners and 100-300 times sweeter than sucrose [72, 73 ]. Their clinical pharmacology and therapeutic actions have been reviewed [74, 75 ]. 

Stevioside is an ent-kaurene type diteipenoid glycoside isolated from leaves of Stevia rebaudiana Bertoni. Leaves of this plant produce zero-calorie diterpene glycosides (stevioside and rebaudioside), a nmi-nutiitive, high-potency sweetener. Stevioside content in leaves will vary in field grown plants and is also influenced by agroclimatic conditions. Stevia leaves are also in use for their medicinal benefits. In this chapter, natural distribution and cultivation of Stevia,... 

The full paper on the C n.m.r. of the glycosides derived from Stevia panF culata LAG has appeared (see Vol. 10, p. 182), and the structures of two sweet glucosides from S. rebaudiana Bertoni, rebaudioside-D and -E, have been studied by means of C n.m.r. and enzymic and chemical hydrolysis. A report of a study of C n.m.r. spectra of a wide range of pyranoside epoxides has confirmed that the presence of the epoxide ring leads to an upheld... 

Rebaudioside A, a naturally occurring glycoside about 400 times sweeter than table sugar, is obtained from the leaves of the stevia plant, a shrub native to Central and South America. 

---