Digitonin

Digitonin
Names

Other names digitin
Identifiers
CAS Number	11024-24-1^Y
ChEMBL	ChEMBL404811^N
ChemSpider	23753^Y
EC Number	234-255-6
Jmol interactive 3D	Image
KEGG	C00765^N
PubChem	25444
InChI InChI=1S/C56H92O29/c1-19-7-10-56(75-17-19)20(2)31-45(85-56)37(67)32-22-6-5-21-11-26(24(61)12-55(21,4)23(22)8-9-54(31,32)3)76-50-42(72)39(69)44(30(16-60)80-50)81-53-48(47(36(66)29(15-59)79-53)83-49-40(70)33(63)25(62)18-74-49)84-52-43(73)46(35(65)28(14-58)78-52)82-51-41(71)38(68)34(64)27(13-57)77-51/h19-53,57-73H,5-18H2,1-4H3/t19-,20+,21+,22-,23+,24-,25-,26-,27-,28-,29-,30-,31+,32-,33+,34-,35+,36?,37+,38+,39-,40-,41-,42-,43-,44+,45-,46+,47+,48-,49+,50-,51+,52+,53+,54-,55+,56-/m1/s1^N Key: UVYVLBIGDKGWPX-YCCXZQINSA-N^N InChI=1/C56H92O29/c1-19-7-10-56(75-17-19)20(2)31-45(85-56)37(67)32-22-6-5-21-11-26(24(61)12-55(21,4)23(22)8-9-54(31,32)3)76-50-42(72)39(69)44(30(16-60)80-50)81-53-48(47(36(66)29(15-59)79-53)83-49-40(70)33(63)25(62)18-74-49)84-52-43(73)46(35(65)28(14-58)78-52)82-51-41(71)38(68)34(64)27(13-57)77-51/h19-53,57-73H,5-18H2,1-4H3/ t19-,20+,21+,22-,23+,24-,25-,26-,27-,28-,29-,30-,31+,32-,33+,34-,35+,36?,37+,38+,39-,40-,41-,42-,43-,44+,45-,46+,47+,48-,49+,50-,5 1+,52+,53+,54-,55+,56-/m1/s1
SMILES O[C@@H]%11[C@@H](O)[C@H](O)[C@H](O[C@H]%11O[C@@H]1[C@@H](O)[C@@H](O[C@H](CO)[C@@H]1O)O[C@@H]%10[C@@H](O[C@@H]2OC[C@@H](O)[C@H](O)[C@H]2O)C(O)[C@H](O[C@H]%10O[C@@H]3[C@H](O)[C@@H](O)[C@@H](O[C@@H]3CO)O[C@H]9[C@H](O)C[C@@]8(C)[C@@H](CC[C@@H]6[C@@H]8CC[C@@]7([C@@H]5[C@@H](O[C@@]4(OC[C@@H](CC4)C)[C@H]5C)[C@@H](O)[C@@H]67)C)C9)CO)CO
Properties
Chemical formula	C₅₆H₉₂O₂₉
Molar mass	1229.3 g/mol
Melting point	244.0–248.5 °C (471.2–479.3 °F; 517.1–521.6 K)^[1]
Chiral rotation ([α]_D)	-40 ° (Wavlen: 589.3 nm; Temp: 20 °C)^[1]
Hazards
Lethal dose or concentration (LD, LC):
LD₅₀ (Median dose)	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).
N verify (what is ^YN ?)
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 drug digoxin (sometimes also called digitalis or digitoxin) and both can be extracted from the same source.

Structure of Digitonin using sugar abbreviations (Gal = Galactose, Glc = Glucose, Xyl = Xylose)

Physical, chemical and biological properties

Critical micelle concentration = < 0.5 mM
Average micellar weight = 70000
Appearance = White to off-white powder
Boiling Point/Melting Point = 230 to 240 °C
Aggregation number = 60
Rat-LD₅₀ = 4 mg/kg body weight (IVN), 51 mg/kg body weight (ORAL)

References

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.
↑ 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.
↑ 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.
↑ 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.
↑ 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.

Glycosides

Bond	O-glycosidic bond N-glycosidic bond S-glycosidic bond C-glycosidic bond

Geometry	α-Glycoside β-Glycoside 1,4-Glycoside 1,6-Glycoside

Glycone	Fructoside Galactoside Glucoside Glucuronide Rhamnoside Riboside

Aglycone	Alcoholic glycoside Cardiac glycoside Bufadienolide Cardenolide Cyanogenic glycoside Glycosylamine Phenolic glycoside Anthraquinone glycoside Coumarin glycoside Flavonoid glycoside Saponin Steviol glycoside Thioglycoside

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