Digitonin is a steroidal

saponin Saponins (Latin "sapon", soap + "-in", one of), also selectively referred to as triterpene glycosides, are bitter-tasting usually toxic plant-derived organic chemicals that have a foamy quality when agitated in water. They are widely distributed ...

(saraponin) obtained from the foxglove plant ''

Digitalis purpurea ''Digitalis purpurea'', the foxglove or common foxglove, is a poisonous species of flowering plant in the plantain family Plantaginaceae, native to and widespread throughout most of temperate Europe. It has also naturalised in parts of North Ame ...

''. Its

aglycone An aglycone (aglycon or genin) is the compound remaining after the glycosyl group on a glycoside is replaced by a hydrogen atom. For example, the aglycone of a cardiac glycoside would be a steroid molecule. Detection A way to identify aglycone ...

is digitogenin, a spirostan steroid. It has been investigated as a detergent, as it effectively water-solubilizes

lipid Lipids are a broad group of naturally-occurring molecules which includes fats, waxes, sterols, fat-soluble vitamins (such as vitamins A, D, E and K), monoglycerides, diglycerides, phospholipids, and others. The functions of lipids include ...

s. As such, it has several potential

membrane A membrane is a selective barrier; it allows some things to pass through but stops others. Such things may be molecules, ions, or other small particles. Membranes can be generally classified into synthetic membranes and biological membranes. B ...

-related applications in

biochemistry Biochemistry or biological chemistry is the study of chemical processes within and relating to living organisms. A sub-discipline of both chemistry and biology, biochemistry may be divided into three fields: structural biology, enzymology and ...

, including solubilizing

membrane protein Membrane proteins are common proteins that are part of, or interact with, biological membranes. Membrane proteins fall into several broad categories depending on their location. Integral membrane proteins are a permanent part of a cell membrane ...

s, precipitating

cholesterol Cholesterol is any of a class of certain organic molecules called lipids. It is a sterol (or modified steroid), a type of lipid. Cholesterol is biosynthesized by all animal cells and is an essential structural component of animal cell mem ...

, and permeabilizing cell membranes. Digitonin is sometimes confused with the

cardiac The heart is a muscular organ in most animals. This organ pumps blood through the blood vessels of the circulatory system. The pumped blood carries oxygen and nutrients to the body, while carrying metabolic waste such as carbon dioxide to t ...

drugs

digoxin Digoxin (better known as Digitalis), sold under the brand name Lanoxin among others, is a medication used to treat various heart conditions. Most frequently it is used for atrial fibrillation, atrial flutter, and heart failure. Digoxin is on ...

and

digitoxin Digitoxin is a cardiac glycoside used for the treatment of heart failure and certain kinds of heart arrhythmia. It is a phytosteroid and is similar in structure and effects to digoxin, though the effects are longer-lasting. Unlike digoxin, which ...

; all three can be extracted from the same source.

Chemical properties

Critical micelle concentration In colloidal and surface chemistry, the critical micelle concentration (CMC) is defined as the concentration of surfactants above which micelles form and all additional surfactants added to the system will form micelles. The CMC is an important ch ...

= < 0.5 mM * Average micellar weight = 70000 *

Aggregation number An aggregation number is a description of the number of molecules present in a micelle once the critical micelle concentration (CMC) has been reached. In more detail, it has been defined as the average number of surfactant monomers in a spherical mi ...

= 60

References

{{Glycosides Spiro compounds Steroidal glycosides Saponins