Reticuline is a chemical compound found in a variety of plants including '' Lindera aggregata'', '' Annona squamosa'', and ''

Ocotea fasciculata ''Ocotea'' is a genus of flowering plants belonging to the family Lauraceae. Many are evergreen trees with lauroid leaves. There are over 520 species currently accepted within the genus, distributed mostly in tropical and subtropical areas of ...

'' (also known as ''Ocotea duckei''). It is based on the

benzylisoquinoline Substitution of the heterocycle isoquinoline at the C1 position by a benzyl group provides 1‑benzylisoquinoline, the most widely examined of the numerous benzylisoquinoline structural isomers. The 1-benzylisoquinoline moiety can be identified wi ...

structure. Reticuline is one of the alkaloids found in

opium Opium (or poppy tears, scientific name: ''Lachryma papaveris'') is dried latex obtained from the seed capsules of the opium poppy ''Papaver somniferum''. Approximately 12 percent of opium is made up of the analgesic alkaloid morphine, which i ...

, and experiments in rodents suggest it possesses potent central nervous system depressing effects. It is the precursor of morphine and many other alkaloids. It is also toxic to dopaminergic neurons causing a form of atypical parkinsonism known as Guadeloupean Parkinsonism.

Metabolism

3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase uses ''S''-adenosyl methionine and 3'-hydroxy-''N''-methyl-(''S'')-

coclaurine Coclaurine is a nicotinic acetylcholine receptor antagonist which has been isolated from a variety of plant sources including ''Nelumbo nucifera'', '' Sarcopetalum harveyanum'', '' Ocotea duckei'', and others. It belongs to the class of tetrahydr ...

to produce ''S''-adenosylhomocysteine and (''S'')-reticuline. Reticuline oxidase uses (''S'')-reticuline and O₂ to produce (''S'')- scoulerine and H₂O₂. Salutaridine synthase uses (''R'')-reticuline, NADPH, H⁺, and O₂ to produce salutaridine, NADP⁺, and H₂O. Salutaridine can then be transformed progressively to thebaine,

oripavine Oripavine is an opioid and the major metabolite of thebaine. It is the parent compound from which a series of semi-synthetic opioids are derived, which includes the compounds etorphine and buprenorphine. Although its analgesic potency is comp ...

, and morphine. 1,2-dehydroreticulinium reductase (NADPH) uses (''R'')-reticuline and NADP⁺ to produce 1,2-dehydroreticulinium, NADPH, and H⁺.

References

External links

{{Components of Opium Natural opium alkaloids Phenols Phenol ethers Tetrahydroisoquinolines