# Coclaurine

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**Coclaurine** is a [nicotinic acetylcholine receptor](/source/Nicotinic_acetylcholine_receptor) [antagonist](/source/Receptor_antagonist)[1] which has been isolated from a variety of plant sources including *[Nelumbo nucifera](/source/Nelumbo_nucifera)*, *[Sarcopetalum harveyanum](/source/Sarcopetalum_harveyanum)*,[2] *[Ocotea duckei](/source/Ocotea_duckei)*,[3] and others. It belongs to the class of [tetrahydroisoquinoline](/source/Tetrahydroisoquinoline) [alkaloids](/source/Alkaloid). [Dimerization](/source/Dimer_(chemistry)) of coclaurine leads to the biscoclaurine alkaloids such as [cepharanthine](/source/Cepharanthine).

## Biosynthesis

(*S*)-coclaurine is produced from (*S*)-norcoclaurine as part of the general [alkaloid biosynthesis](/source/Alkaloid_biosynthesis) pathway to [isoquinolines](/source/Isoquinolines). The precursor is a [tetrahydroisoquinoline](/source/Tetrahydroisoquinoline), arising from the [condensation](/source/Condensation_reaction) of two [tyrosine](/source/Tyrosine) derivatives, [dopamine](/source/Dopamine) and [4-hydroxyphenylacetaldehyde](/source/4-hydroxyphenylacetaldehyde).[4]

In this [methylation](/source/Methylation) reaction, the enzyme [(RS)-norcoclaurine 6-O-methyltransferase](/source/(RS)-norcoclaurine_6-O-methyltransferase) uses the [cofactor](/source/Cofactor_(biochemistry)), [S-adenosyl methionine](/source/S-adenosyl_methionine) (SAM) which transfers a [methyl group](/source/Methyl_group), giving [S-adenosyl-L-homocysteine](/source/S-adenosyl-L-homocysteine) (SAH) as a by-product.[4]

## Metabolism

The next stage of the biosynthesis of alkaloids derived from (*S*)-coclaurine involves a second methylation reaction to give (S)-N-methylcoclaurine, which is formed by the action of the enzyme [(S)-coclaurine-N-methyltransferase](/source/(S)-coclaurine-N-methyltransferase):[5]

Subsequent reactions lead to [(*S*)-reticuline](/source/Reticuline), from which many other alkaloids are derived.[4]

Coclaurine can also be incorporated into [dimeric](/source/Dimer_(chemistry)) alkaloids via an [oxidation reaction](/source/Redox). The enzyme [berbamunine synthase](/source/Berbamunine_synthase) combines coclaurine and a related N-methyl compound, (*R*)-N-methylcoclaurine, to give 2'-norberbamunine. Further elaboration leads to examples such as [cepharanthine](/source/Cepharanthine).[4][6]

## References

1. Cock, Ian Edwin & Cheesman, Matthew J. (May 2016). ["Oceania: Antidepressant Medicinal Plants"](https://www.researchgate.net/profile/Matthew_Cheesman4/publication/303689274_Oceania_Antidepressant_Medicinal_Plants/links/5aa85083a6fdcc1b59c63bda/Oceania-Antidepressant-Medicinal-Plants.pdf). *ResearchGate*. p. 503.

1. Sowemimo BO, Beal JL, Doskotch RW, Svoboda GH (1972). "The isolation of stepharine and coclaurine from Sarcopetalum harveyanum". *[Lloydia](/source/Lloydia)*. **35** (1): 90–91. [PMID 5037484](https://pubmed.ncbi.nlm.nih.gov/5037484)

1. I.G da Silva; J.M Barbosa-Filho; M.S da Silva; C.D.G de Lacerda; E.V.L da-Cunha (2002). "Coclaurine from Ocotea duckei". *Biochemical Systematics and Ecology*. **30** (9): 881–883. [Bibcode:2002BioSE..30..881D](https://ui.adsabs.harvard.edu/abs/2002BioSE..30..881D). [doi:10.1016/s0305-1978(02)00024-8](https://doi.org/10.1016/s0305-1978(02)00024-8)

1. Tian, Ya; Kong, Lingzhe; Li, Qi; Wang, Yifan; Wang, Yongmiao; An, Zhoujie; Ma, Yuwei; Tian, Lixia; Duan, Baozhong; Sun, Wei; Gao, Ranran; Chen, Shilin; Xu, Zhichao (2024). "Structural diversity, evolutionary origin, and metabolic engineering of plant specialized benzylisoquinoline alkaloids". *Natural Product Reports*. **41** (11): 1787–1810. [doi:10.1039/d4np00029c](https://doi.org/10.1039/d4np00029c). [PMID 39360417](https://pubmed.ncbi.nlm.nih.gov/39360417)

1. Loeffler S, Deus-Neumann B, Zenk MH (1995). "S-Adenosyl-L-methionine: (S)-coclaurine-N-methyltransferase from Tinospora cordifolia". *[Phytochemistry](/source/Phytochemistry_(journal))*. **38** (6): 1387–1395. [Bibcode:1995PChem..38.1387L](https://ui.adsabs.harvard.edu/abs/1995PChem..38.1387L). [doi:10.1016/0031-9422(94)00813-9](https://doi.org/10.1016/0031-9422(94)00813-9)

1. Rogosnitzky M, Danks R (2011). ["Therapeutic potential of the biscoclaurine alkaloid, cepharanthine, for a range of clinical conditions"](http://www.if-pan.krakow.pl/pjp/pdf/2011/2_337.pdf). *Pharmacological Reports*. **63** (2): 337–47. [doi:10.1016/S1734-1140(11)70500-X](https://doi.org/10.1016/S1734-1140(11)70500-X). [PMID 21602589](https://pubmed.ncbi.nlm.nih.gov/21602589)

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Adapted from the Wikipedia article [Coclaurine](https://en.wikipedia.org/wiki/Coclaurine) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Coclaurine?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.