Digitonin is a steroidal

saponin Saponins (Latin ''sapon'', 'soap' + ''-in'', 'one of') are bitter-tasting, usually toxic plant-derived secondary metabolites. They are organic chemicals that become foamy when agitated in water and have high molecular weight. They are present ...

(saraponin) obtained from the foxglove plant ''

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

''. Its

aglycone An aglycone (aglycon or genin) is the chemical 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 A steroid is an organic compoun ...

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

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

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. Bi ...

-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, a ...

, 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 the principal sterol of all higher animals, distributed in body Tissue (biology), tissues, especially the brain and spinal cord, and in Animal fat, animal fats and oils. Cholesterol is biosynthesis, biosynthesized by all anima ...

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

cardiac The heart is a muscular organ found in humans and other animals. This organ pumps blood through the blood vessels. The heart and blood vessels together make the circulatory system. The pumped blood carries oxygen and nutrients to the tissu ...

drugs

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

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, whic ...

; all three can be extracted from the same source.

Chemical properties

Critical micelle concentration In colloidal chemistry, 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 ...

= < 0.5 mM * Average micellar weight = 70000 *

Aggregation number In colloidal chemistry, 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 ...

= 60

References

{{Glycosides Spiro compounds Steroidal glycosides Saponins