Digitonin

From Wikipedia, the free encyclopedia

This is an old revision of this page, as edited by PlethoraChutney (talk | contribs) at 21:12, 8 January 2016 ("It's" to "Its"). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Digitonin
Names
Other names
digitin
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.031.129 Edit this at Wikidata
EC Number
  • 234-255-6
KEGG
  • 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
  • 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
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]
-40 ° (Wavlen: 589.3 nm; Temp: 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).
☒N verify (what is checkY☒N ?)


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. ^ a b 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.
  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.
Retrieved from "https://en.wikipedia.org/w/index.php?title=Digitonin&oldid=698885767"