Cordycepin, or 3'-deoxyadenosine, is a

derivative In mathematics, the derivative of a function of a real variable measures the sensitivity to change of the function value (output value) with respect to a change in its argument (input value). Derivatives are a fundamental tool of calculus. ...

of the

nucleoside Nucleosides are glycosylamines that can be thought of as nucleotides without a phosphate group. A nucleoside consists simply of a nucleobase (also termed a nitrogenous base) and a five-carbon sugar ( ribose or 2'-deoxyribose) whereas a nucleoti ...

adenosine Adenosine (symbol A) is an organic compound that occurs widely in nature in the form of diverse derivatives. The molecule consists of an adenine attached to a ribose via a β-N9-glycosidic bond. Adenosine is one of the four nucleoside buildin ...

, differing from the latter by the replacement of the

hydroxy group In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydrox ...

in the 3' position with a hydrogen. It was initially extracted from the

fungus A fungus (plural, : fungi or funguses) is any member of the group of Eukaryote, eukaryotic organisms that includes microorganisms such as yeasts and Mold (fungus), molds, as well as the more familiar mushrooms. These organisms are classified ...

Cordyceps militaris ''Cordyceps militaris'' is a species of fungus in the family Cordycipitaceae, and the type species of the genus '' Cordyceps''. It was originally described by Carl Linnaeus in 1753 as ''Clavaria militaris''. Description Macroscopic characteris ...

'', but can now be produced synthetically. It is also found in other ''

Cordyceps ''Cordyceps'' is a genus of ascomycete fungi (sac fungi) that includes about 600 species. Most ''Cordyceps'' species are endoparasitoids, parasitic mainly on insects and other arthropods (they are thus entomopathogenic fungi); a few are parasit ...

'' species as well as ''

Ophiocordyceps sinensis ''Ophiocordyceps sinensis'' (formerly known as ''Cordyceps sinensis''), known colloquially as caterpillar fungus, is an entomopathogenic fungus (a fungus that grows on insects) in the family Ophiocordycipitaceae. It is mainly found in the me ...

''. Because cordycepin is similar to

, some

enzyme Enzymes () are proteins that act as biological catalysts by accelerating chemical reactions. The molecules upon which enzymes may act are called substrate (chemistry), substrates, and the enzyme converts the substrates into different molecule ...

s cannot discriminate between the two. It can therefore participate in certain biochemical reactions (for example, 3-dA can trigger the premature termination of mRNA synthesis). By acting as an adenosine analog, cordycepin was found to be the most potent molecular circadian clock resetter out of several screened compounds. Cordycepin has displayed cytotoxicity against some

leukemic Leukemia ( also spelled leukaemia and pronounced ) is a group of blood cancers that usually begin in the bone marrow and result in high numbers of abnormal blood cells. These blood cells are not fully developed and are called ''blasts'' or '' ...

cell lines ''in vitro''. Cordycepin has been found to produce rapid, robust

imipramine Imipramine, sold under the brand name Tofranil, among others, is a tricyclic antidepressant (TCA) mainly used in the treatment of depression. It is also effective in treating anxiety and panic disorder. The drug is also used to treat bedwetting. ...

-like

antidepressant Antidepressants are a class of medication used to treat major depressive disorder, anxiety disorders, chronic pain conditions, and to help manage addictions. Common side-effects of antidepressants include dry mouth, weight gain, dizziness ...

effects in

animal models of depression Animal models of depression are research tools used to investigate depression and action of antidepressants as a simulation to investigate the symptomatology and pathophysiology of depressive illness or used to screen novel antidepressants. In ...

, and these effects, similarly to those of imipramine, are dependent on enhancement of

AMPA receptor The α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor (also known as AMPA receptor, AMPAR, or quisqualate receptor) is an ionotropic transmembrane receptor for glutamate (iGluR) that mediates fast synaptic transmission in the ce ...

signaling.

References

{{Reflist, 2 Alkaloids Alkaloids found in fungi Antidepressants Nucleosides

See also

References