Bufanolide
Encyclopedia
Bufadienolide is a type of 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...

. Its derivatives are collectively known as bufadienolides, including many in the form of bufadienolide glycosides (bufadienolides that contain structural groups derived from sugars). These are a type of cardiac glycoside
Cardiac glycoside
Cardiac glycosides are drugs used in the treatment of congestive heart failure and cardiac arrhythmia. These glycosides are found as secondary metabolites in several plants, but also in some animals, such as the milkweed butterflies. -Function:...

, the other being the cardenolide
Cardenolide
Cardenolide is a type of steroid. Many plants contain derivatives, collectively known as cardenolides, including many in the form of cardenolide glycosides...

 gylcosides. Both bufadienolides and their glycosides are toxic; specifically, they are heart-arresting
Cardiac arrest
Cardiac arrest, is the cessation of normal circulation of the blood due to failure of the heart to contract effectively...

.

Etymology

The term derives from the toad genus Bufo
Bufo
Bufo is a large genus of about 150 species of true toads in the amphibian family Bufonidae. Bufo is a Latin word for toad.- Description :...

that contains bufadienolide glycosides, the suffix -adien- that refers to the two double bonds in the lactone ring, and the ending -olide that denotes the lactone
Lactone
In chemistry, a lactone is a cyclic ester which can be seen as the condensation product of an alcohol group -OH and a carboxylic acid group -COOH in the same molecule...

 structure. Consequently, related structures with only one double bond are called bufenolides, and the saturated
Saturation (chemistry)
In chemistry, saturation has six different meanings, all based on reaching a maximum capacity...

 equivalent is bufanolide.

Classification

According to MeSH
Medical Subject Headings
Medical Subject Headings is a comprehensive controlled vocabulary for the purpose of indexing journal articles and books in the life sciences; it can also serve as a thesaurus that facilitates searching...

, bufadienolides and bufanolides are classified as follows:
  • Polycyclic compound
    Polycyclic compound
    In organic chemistry, a polycyclic compound is a cyclic compound with more than one hydrocarbon loop or ring structures . In general, the term includes all polycyclic aromatic compounds, including the polycyclic aromatic hydrocarbons, the heterocyclic aromatic compounds containing sulfur,...

    s
  • 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...

    s
  • Cardanolide
    Cardanolide
    Cardanolide is a steroid with a molecular weight of 344.531....

    s
  • Cardenolide
    Cardenolide
    Cardenolide is a type of steroid. Many plants contain derivatives, collectively known as cardenolides, including many in the form of cardenolide glycosides...

    s
  • Cardiac glycoside
    Cardiac glycoside
    Cardiac glycosides are drugs used in the treatment of congestive heart failure and cardiac arrhythmia. These glycosides are found as secondary metabolites in several plants, but also in some animals, such as the milkweed butterflies. -Function:...

    s
  • Bufanolides
  • Bufenolides
  • Bufadienolides
  • Proscillaridin
    Proscillaridin
    Proscillaridin is a bufanolide glycoside that can be obtained from plants of the genus Scilla....

  • Daigremontianin
    Daigremontianin
    Daigremontianin is a bufadienolide. Bufadienolides are steroids and cardiac glycoside aglycones that are similar to cardenolides, differing only in the structure of the C-17 substituent on the D ring. This chemical has been found to be toxic in experiments on mice...

  • Cardenolides


Note that cardenolides have been classified under cardanolides as well as cardiac glycosides in this classification.
The source of this article is wikipedia, the free encyclopedia.  The text of this article is licensed under the GFDL.
 
x
OK