Digitonin

Digitonin

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Digitonin is a glycoside
Glycoside
In chemistry, a glycoside is a molecule in which a sugar is bound to a non-carbohydrate moiety, usually a small organic molecule. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. These can be activated by enzyme...

 obtained from Digitalis purpurea
Digitalis purpurea
Digitalis purpurea , is a flowering plant in the family Plantaginaceae , native to most of Europe.-Description:...

; the aglycone
Aglycone
An aglycone is the non-sugar compound remaining after replacement of the glycosyl group from a glycoside by a hydrogen atom. The spelling aglycon is sometimes encountered .Classes of phytochemicals found in the aglycone and glycosides forms :...

 is digitogenin, a spirostan steroid
Steroid
A steroid is a type of organic compound that contains a characteristic arrangement of four cycloalkane rings that are joined to each other. Examples of steroids include the dietary fat cholesterol, the sex hormones estradiol and testosterone, and the anti-inflammatory drug dexamethasone.The core...

. Used as a detergent, it effectively water-solubilizes lipid
Lipid
Lipids constitute a broad group of naturally occurring molecules that include fats, waxes, sterols, fat-soluble vitamins , monoglycerides, diglycerides, triglycerides, phospholipids, and others...

s. As such, it has several membrane
Biological membrane
A biological membrane or biomembrane is an enclosing or separatingmembrane that acts as a selective barrier, within or around a cell. It consists of a lipid bilayer with embedded proteins that may constitute close to 50% of membrane content...

-related applications in biochemistry
Biochemistry
Biochemistry, sometimes called biological chemistry, is the study of chemical processes in living organisms, including, but not limited to, living matter. Biochemistry governs all living organisms and living processes...

, including solubilizing membrane protein
Membrane protein
A membrane protein is a protein molecule that is attached to, or associated with the membrane of a cell or an organelle. More than half of all proteins interact with membranes.-Function:...

s, precipitating cholesterol
Cholesterol
Cholesterol is a complex isoprenoid. Specifically, it is a waxy steroid of fat that is produced in the liver or intestines. It is used to produce hormones and cell membranes and is transported in the blood plasma of all mammals. It is an essential structural component of mammalian cell membranes...

, and permeabilizing cell membranes.

Digitonin is sometimes confused with the cardiac drug digoxin
Digoxin
Digoxin INN , also known as digitalis, is a purified cardiac glycoside and extracted from the foxglove plant, Digitalis lanata. Its corresponding aglycone is digoxigenin, and its acetyl derivative is acetyldigoxin...

 (sometimes also called digitalis or digitoxin), but has no heart-related effects.

Physical, chemical and biological properties


Critical micelle concentration
Critical micelle concentration
In colloidal and surface chemistry, the critical micelle concentration is defined as the concentration of surfactants above which micelles form and almost all additional surfactants added to the system go to micelles....

= < 0.5 mM

Average micellar weight = 70000

Appearance = White to off-white powder

Boiling Point/Melting Point = 230 °C to 240 °C

Aggregation number = 60

Rat-LD50 = 4 mg/kg body weight (IVN), 51 mg/kg body weight (ORAL)