Coclaurine
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| Preferred IUPAC name
(1S)-1-[(4-Hydroxyphenyl)methyl]-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol | |
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| Properties | |
| C17H19NO3 | |
| Molar mass | 285.343 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Coclaurine is a nicotinic acetylcholine receptor antagonist[1] which has been isolated from a variety of plant sources including Nelumbo nucifera, Sarcopetalum harveyanum,[2] Ocotea duckei,[3] and others. It belongs to the class of tetrahydroisoquinoline alkaloids. Dimerization of coclaurine leads to the biscoclaurine alkaloids such as cepharanthine.
Biosynthesis
-norcoclaurine_synthesis.svg)
(S)-coclaurine is produced from (S)-norcoclaurine as part of the general alkaloid biosynthesis pathway to isoquinolines. The precursor is a tetrahydroisoquinoline, arising from the condensation of two tyrosine derivatives, dopamine and 4-hydroxyphenylacetaldehyde.[4]
In this methylation reaction, the enzyme (RS)-norcoclaurine 6-O-methyltransferase uses the cofactor, S-adenosyl methionine (SAM) which transfers a methyl group, giving S-adenosyl-L-homocysteine (SAH) as a by-product.[4]
-higenamine.svg)
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:[5]
-N-methylcoclaurine.svg)
Subsequent reactions lead to (S)-reticuline, from which many other alkaloids are derived.[4]
Coclaurine can also be incorporated into dimeric alkaloids via an oxidation reaction. The enzyme 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.[4][6]
-N-methylcoclaurine.svg)
References
- ^ Cock, Ian Edwin; Cheesman, Matthew J. (May 2016). "Oceania: Antidepressant Medicinal Plants" (PDF). ResearchGate. p. 503.
- ^ Sowemimo BO, Beal JL, Doskotch RW, Svoboda GH (1972). "The isolation of stepharine and coclaurine from Sarcopetalum harveyanum". Lloydia. 35 (1): 90–91. PMID 5037484.
- ^ 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. doi:10.1016/s0305-1978(02)00024-8.
- ^ a b c d 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. PMID 39360417.
- ^ Loeffler S, Deus-Neumann B, Zenk MH (1995). "S-Adenosyl-L-methionine: (S)-coclaurine-N-methyltransferase from Tinospora cordifolia". Phytochemistry. 38 (6): 1387–1395. Bibcode:1995PChem..38.1387L. doi:10.1016/0031-9422(94)00813-9.
- ^ Rogosnitzky M, Danks R (2011). "Therapeutic potential of the biscoclaurine alkaloid, cepharanthine, for a range of clinical conditions" (PDF). Pharmacological Reports. 63 (2): 337–47. doi:10.1016/S1734-1140(11)70500-X. PMID 21602589.