Coclaurine: Difference between revisions

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'''Coclaurine''' is a [[benzylisoquinoline alkaloid]] found in various plants, including members of the [[Papaveraceae]] and [[Menispermaceae]] families. It is a precursor in the biosynthesis of many other plant alkaloids.
{{DISPLAYTITLE:Coclaurine}}


==Chemistry==
== Coclaurine ==
[[File:Coclaurine.svg|thumb|right|Chemical structure of Coclaurine]]
Coclaurine is a [[benzylisoquinoline alkaloid]] that is found in various plant species, particularly within the [[Lauraceae]] family. It is a secondary metabolite that plays a role in the plant's defense mechanisms against herbivores and pathogens.


Coclaurine is a [[dimer]] of two [[dopamine]] molecules, and is the first committed step in the biosynthesis of benzylisoquinoline alkaloids. The formation of coclaurine from dopamine is catalyzed by the enzyme [[N-methyltransferase]].
== Chemical Structure ==
Coclaurine is characterized by its [[isoquinoline]] backbone, which is a common feature among alkaloids in this class. The structure includes a benzyl group attached to the nitrogen atom of the isoquinoline ring, which is a defining feature of benzylisoquinoline alkaloids.


==Biosynthesis==
== Biosynthesis ==
The biosynthesis of coclaurine involves the condensation of two [[tyrosine]]-derived molecules, leading to the formation of the basic benzylisoquinoline structure. This process is catalyzed by the enzyme [[norcoclaurine synthase]], which facilitates the Pictet-Spengler reaction, a key step in the formation of the isoquinoline ring.


The biosynthesis of coclaurine begins with the decarboxylation of [[L-tyrosine]] to tyramine by the enzyme [[tyrosine decarboxylase]]. Tyramine is then converted to dopamine by the enzyme [[tyramine hydroxylase]]. Dopamine is then methylated by the enzyme [[N-methyltransferase]] to form N-methyl dopamine. Two molecules of N-methyl dopamine are then coupled by the enzyme [[dopamine N-methyltransferase]] to form coclaurine.
== Biological Activity ==
Coclaurine exhibits various biological activities, including [[antimicrobial]], [[antioxidant]], and [[anti-inflammatory]] effects. These properties make it a compound of interest in the development of new pharmaceuticals and therapeutic agents.


==Pharmacology==
== Occurrence ==
Coclaurine is found in several plant species, including those in the [[Magnolia]] and [[Cinnamomum]] genera. These plants have been traditionally used in herbal medicine, and the presence of coclaurine contributes to their medicinal properties.


Coclaurine has been found to have [[antioxidant]] properties, and has been studied for its potential use in the treatment of [[neurodegenerative diseases]]. It has also been found to have [[anti-inflammatory]] properties, and has been studied for its potential use in the treatment of [[inflammatory diseases]].
== Related Compounds ==
Coclaurine is structurally related to other benzylisoquinoline alkaloids such as [[norcoclaurine]], [[reticuline]], and [[morphine]]. These compounds share a common biosynthetic pathway and have diverse pharmacological activities.


==See also==
== Related Pages ==
 
* [[Benzylisoquinoline alkaloid]]
* [[Benzylisoquinoline]]
* [[Isoquinoline]]
* [[Alkaloid]]
* [[Lauraceae]]
* [[Dopamine]]
* [[Norcoclaurine synthase]]
* [[N-methyltransferase]]
 
==References==
 
{{reflist}}


[[Category:Alkaloids]]
[[Category:Alkaloids]]
[[Category:Benzylisoquinolines]]
[[Category:Isoquinoline alkaloids]]
[[Category:Pharmacology]]
[[Category:Phytochemicals]]
{{Pharma-stub}}
{{Chem-stub}}

Latest revision as of 03:41, 13 February 2025


Coclaurine[edit]

Chemical structure of Coclaurine

Coclaurine is a benzylisoquinoline alkaloid that is found in various plant species, particularly within the Lauraceae family. It is a secondary metabolite that plays a role in the plant's defense mechanisms against herbivores and pathogens.

Chemical Structure[edit]

Coclaurine is characterized by its isoquinoline backbone, which is a common feature among alkaloids in this class. The structure includes a benzyl group attached to the nitrogen atom of the isoquinoline ring, which is a defining feature of benzylisoquinoline alkaloids.

Biosynthesis[edit]

The biosynthesis of coclaurine involves the condensation of two tyrosine-derived molecules, leading to the formation of the basic benzylisoquinoline structure. This process is catalyzed by the enzyme norcoclaurine synthase, which facilitates the Pictet-Spengler reaction, a key step in the formation of the isoquinoline ring.

Biological Activity[edit]

Coclaurine exhibits various biological activities, including antimicrobial, antioxidant, and anti-inflammatory effects. These properties make it a compound of interest in the development of new pharmaceuticals and therapeutic agents.

Occurrence[edit]

Coclaurine is found in several plant species, including those in the Magnolia and Cinnamomum genera. These plants have been traditionally used in herbal medicine, and the presence of coclaurine contributes to their medicinal properties.

Related Compounds[edit]

Coclaurine is structurally related to other benzylisoquinoline alkaloids such as norcoclaurine, reticuline, and morphine. These compounds share a common biosynthetic pathway and have diverse pharmacological activities.

Related Pages[edit]