Gypsogenin

HENRY, M., RAHIER, A., TATON, M., Effect of gypsogenin 3,0-glucuronide pretreatment of Gypsophila paniculata and Saponaria officinalis cell suspension cultures on the activities of microsomal 2,3-oxidosqualene cycloartenol and amyrin cyclases, Phytochemistry, 1992,31,3855-3859. 

Cell suspension cultures of Gypsophila paniculata and Saponaria officinalis produce very closely related triterpenoid saponins. Pretreatment of cell suspension cultures of G. paniculata with gypsogenin 3,0-glucuxonide (a triterpenoid saponin precursor in G. paniculata) followed by administration of [ C] acetate resulted in a marked reduction in incorporation of radioactivity into saponins and their precursors, but not into sterols and steryl glycosides [26]. Measurements of OSC activities revealed that there was no effect of elicitor treatment on CS levels in either species, but in G. paniculata AS levels went down while in S. officinalis they increased. This suggests that in these two species OSCs are regulating steps in the isoprenoid pathway and control the flux to sterols and triter-penes. 

Detection with AS reagent reveals one or two prominent yellow flavonoid zones at Rf 0.4-0.45 and up to five small, dark yellow-brown zones in the Rf range 0.1-0.3 due to saponin glycosides derived from niedicagenic, 16-hydroxy-medicagenic add and gypsogenin, with the main zones in and below the R, range of the reference compound aescin (T3/ R, 0.2). 

The complex mixture of bisdesmosidic triterpene saponins, derived from gypsogenin (quillaic acid), of the extracts 1-3 reveals major dark-brown bands in the R, range 0.05-0.15 four to eight minor brown or violet zones are found in the R,- range 0.2-0.75 ( A), All zones are more easily characterized by their hemolytic reactions (—>B). 

A structurally related saponin squarroside A vide supra) has been isolated from Acanthophyllum squarrosum [60]. This saponin of gypsogenin contains one more xylose linked to C-3 of the glucuronic acid. This molecule showed a concentration dependent immunomodulatory effect in the in vitro lymphocyte transformation test. 

In 1995, Liu et al. reported the isolation of three new saponins from the roots of G. oldhamiana [78], which has been used as a substitute for the well-known traditional Chinese medicinal herb Sterllaria dichotoma var. lanceo-lata in the treatment of fever, consumptive disease, and infantile malnutrition. The most polar saponin was a bisdesmoside and its structure was established as shown in Fig. (26). The other two saponins were monodesmosides derived from C-28 methyl esters of quillaic acid and gypsogenin and having identical sugar moieties at C-3. 

Acebes et al. reported the isolation of three new gypsogenin saponins from the roots of G. bermejoi, a Spanish species [82, 83] (Fig. 29). Two of them were sulfated saponins. All the three compounds possessed the same sugar chain, p-D-Glc-(l—>2)-[p-D-Glc-(l->6)]-P-D-Glc at C-28 of the aglycones. 

The roots contain 10-30 % triterpene saponins from which the glycosides gypsogenin and acanthophyllosides B, C and D were isolated (Putieva et al. 1970,1975,1979). The aboveground parts contain polysaccharides as well as many saponins (Arifkhodzhaev and Kondratenko 1983 Khodzhimatov 1989). 

Folic acid ( )onHBaa KHcnoia Gypsogenin XHncoreHHH... 

Arburinol Aescin, aescinidin etc. Gypsogenin (hi / 25) Gypsogenin lactone (hi / 85) Triterpenes from- Lycopodium Triterpene lactones... 

Segetalic acid, vaccaric acid, quillaic acid, gypsogenin, gypsogenic acid, 3,4-secogypsogenic acid... 

Gypsophilla paniculata Baby s breath Gypsogenin source Roots >10... 

As it can be clearly seen Fig. 3, the majority of saponins in the Gypsophila genus possess gypsogenin, gypsogenic acid, hederagenin, or quillaic acid as aglyconic components [23,24] (Fig. 3). 

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