Diterpene glycoside

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). 

HASHIMOTO K, KAWAGISHI H, NAKAYAMA T, SHIMIZU M (1997) Effect of capsianoside, a diterpene glycoside, on tight-junctional permeability. Biochim Biophys Acta. 1323 281-90. 

Kiem PV, Cai XF, Minh CV, Lee JJ, Kim YH. Kaurane-type diterpene glycoside from the stem bark of Acanthopanax trifoliatus. Planta Med 2004 70 282-284. 

A recent example demonstrates that corals rely on induced biosynthesis of terpenes as a dynamic defense strategy as well. The induction of terpenoid secondary metabolites was observed in the sea whip Pseudopterogorgia elisabethae [162]. Levels of pseudopterosins 89-92, a group of diterpene glycosides with anti-inflammatory and analgesic properties (Scheme 23) [163-165], are increased in response predation by the mollusk Cyphoma gibbosum. First bioassays indicate that these natural products are involved in the chemical defense. 

Ditellurides, 24 422 Diterpene glycosides, 24 239 Diterpenoid acids, 24 552 Diterpenoids, 24 550-555 labdane family of, 24 573 Di -ferf-alkyl peroxides, 23 439-441 as free-radical initiators, 14 288... 

The pseudopterosins and seco-pseudopterosin isolated from Bahamian specimens of Pseudopterogorgia elisabethae display strong anti-inflammatory and analgesic activity. These diterpene glycosides had potencies superior to those of... 

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...

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 ... 

Removing the eluting solvent from the two diterpene glycosides. 

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. 

Maier, H. G. and H. Wewetzer. Determination of diterpene glycosides in coffee. Z Lebensm-Unters Forsch... 

Shvets, S. A., P. K. Kintya, O. N. Gutsu, and V. 1. Grishkovets. Steroid glycosides of the seeds of Nicotiana tabacum. 11. The structures of nicotianosides C and E. Chem Nat Comp 1995 31(3) 332-335. Shinozaki, Y., T. Tobita, M. Mizutani, and T. Matsuzaki. Isolation and identification of two new diterpene glycosides from Nicotiana tabacum. Biosci Biotech Biochem 1996 60(5) 903-905. 

Lycium chinense Miller Di Gu Pi (Matrimony vine) (root bark) Cinnamic acid, betaine, peptides, acyclic diterpene glycosides, polysaccharide, kukoamines.33 Lower blood sugar and blood pressure, antipyretic, stimulate uterine contraction, antibacterial. 

Acyclic diterpene glycosides Acyl flavonol di-gycoside Adenine... 

Pseudopterosins are a series of tricyclic diterpene glycosides from the... 

The dried leaves of S. rebaudiana have been used in Paraguay for many years to sweeten bitter drinks. From 3 to 8% of the dned leaves is stevioside, which is a diterpene glycoside as shown by the formula below. 

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... 

The natural product eleutherobin (1) was isolated in 1994 by Fenical et al. from a marine soft coral from an Eleutherobia species and its structure was elucidated shortly afterwards (Figure 1) [1]. Eleutherobin is a diterpene glycoside that possesses remarkable cytotoxicity against a wide variety of cancer cells, which is likely to be based on binding to tubulin and stabilization of microtubules [2, 3]. Mitosis is interrupted and the cell division cycle is terminated. The mechanism of action of eleutherobin is comparable to that of highly potent cytostatic agents such as paclitaxel (Taxol), nonataxel, epothilones, and discodermolide. 

Munesada, K., Siddiqui, H. L., and Suga, T., 1992. Biologically active labdane-type diterpene glycosides from the root-stalks of Gleichenia japonica. Phytochemistry 31, 1533-1536... 

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... 

The diterpene glycoside eleutherobin 41373 374 was isolated from the soft coral Eleutherobia sp. collected from Bennett s shoal in Western Australia. Eleutherobin, along with the erythrolides A and B, has also been found in the... 

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