Digitonin

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Digitonin
Digitonin CASCC.png
Chemical structure of digitonin
Digitonin.png
Alternate depiction using sugar abbreviations (Gal = galactose, Glc = glucose, Xyl = xylose
Names
Other names
Digitin
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.031.129
EC Number
  • 234-255-6
KEGG
PubChem CID
UNII
Properties
C56H92O29
Molar mass 1229.323 g·mol−1
AppearanceWhite to off-white powder
Melting point 244.0–248.5 °C (471.2–479.3 °F; 517.1–521.6 K) [1]
-40° (589.3 nm; 20 °C) [1]
Hazards
Lethal dose or concentration (LD, LC):
23 mg/kg (rat, intravenous) [2]

4 mg/kg (mouse, intravenous) [3]

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Digitonin is a steroidal saponin (saraponin) obtained from the foxglove plant Digitalis purpurea . Its aglycone is digitogenin, a spirostan steroid. It has been investigated as a detergent, as it effectively water-solubilizes lipids. As such, it has several potential membrane-related applications in biochemistry, including solubilizing membrane proteins, precipitating cholesterol, and permeabilizing cell membranes. [4] [5]

Digitonin is sometimes confused with the cardiac drugs digoxin and digitoxin and all three can be extracted from the same source.

Chemical properties

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References

  1. 1 2 Tschesche, R.; Wulff, G. (January 1963). "Über saponine der spirostanolreihe—IX". Tetrahedron (in German). 19 (4): 621–634. doi:10.1016/S0040-4020(01)98548-5.
  2. Segal, Ruth; Milo-Goldzweig, Ilana; Kaplan, Gideon; Weisenberg, Emil (April 1977). "The protective action of glycyrrhizin against saponin toxicity". Biochemical Pharmacology. 26 (7): 643–645. doi:10.1016/0006-2952(77)90039-9.
  3. Pitha, Josef; Szente, Lajos (February 1984). "Digitonin derivatives of low toxicity: Potential solubilizers for lipophilic compounds". Journal of Pharmaceutical Sciences. 73 (2): 240–243. doi:10.1002/jps.2600730224.
  4. Geelen, Math J.H. (December 2005). "The use of digitonin-permeabilized mammalian cells for measuring enzyme activities in the course of studies on lipid metabolism". Analytical Biochemistry. 347 (1): 1–9. doi:10.1016/j.ab.2005.03.032. PMID   16291302.
  5. Fiskum, Gary (April 1985). "Intracellular levels and distribution of Ca2+ in digitonin-permeabilized cells". Cell Calcium. 6 (1–2): 25–37. doi:10.1016/0143-4160(85)90032-6.