Glycosides diterpene, stevia

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 ... 

Kohda H, Kasai R, Yamasaki K, Murakami K, Tanaka O, New Sweet diterpene glycosides from stevia rebaudiana, Phytochemistry 15 981—983, 1976. 

Dobberstein RH, Ahmed MS, Extraction, separation and recovery of diterpene glycosides from Stevia rebauAiana plants. US Patent No. 4,361,697, 1982. 

Kohda, H., R. Kasai, K. Yamasaki, K. Murakami, and O. Tanaka New sweet diterpene glycosides from Stevia rebaudiana, Phytochem. 15, 981 (1976). 

Kohda, H., O. Tanaka, and K. Nishi Diterpene—glycosides of Stevia paniculata Lag. Structures of aglycones. Chem. Pharm. Bull. 24, 1040 (1976). 

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). 

Ent-kaurene Diterpene Glycosides from the Leaves of Stevia rebaudiana... 

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. 

Table 1. Diterpene Glycosides Isolated from Stevia Leaves...

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... 

Several cwt-kaurenoid diterpene glycosides with steviol as a common aglycon have been isolated from Stevia rebaudiana, which is native to subtropical and tropical South America and Central America.23-27 Among the... 

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.

Stevioside is a diterpene glycoside occurring in Stevia rebaudiana Bertoni leaves. It is a high intensity sweetener that is about 300 times... 

Stevioside or stevia [XI] is the name given to a group of sweet diterpene glycosides extracted from the leaves of Stevia Rebaudiana plant (native of South America). Steviosides show good stability in the solid form. They are also quite stable in acidic condition beverages at 22°C. Steviosides are approved for food use in several South American and Asian countries, but lack approval in Europe and North America. 

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 phenolic constituents, including galloylglucoses and ac l-glucoses, in rhubarb (Rhei Rhizoma) have been determined by reversed-phase h-p-Lc.," and the stevia food sweeteners, diterpene oligosaccharide glycoside/glycosyl esters such as stevioside, by h.pJ.c. on a primary amine bonded silica column. ... 

Figure 21. Structures of cwMabdane and c /-kauranoid diterpenes isolated from Stevia (Eupatorieae) e -labdanes and kaurene mono- and di-glycosides (Scheme A) C-13-kaurene-glycosides (Scheme B).

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). 

Yamasaki, K., H. Kohda, T. Kobayashi, N. Kaneda, R. Kasai, O. Tanaka, and K. Nishi Application of 13C nuclear magnetic resonance spectroscopy to chemistry of glycosides structures of paniculosides-I, -II, -III, -IV, and -V, diterpene glucosides of Stevia paniculata Lag. Chem. Pharm. Bull. 25, 2895 (1977). 

---