Reticuline Explained

Reticuline is a chemical compound found in a variety of plants including Lindera aggregata,^[1] Annona squamosa,^[2] and Ocotea fasciculata (also known as Ocotea duckei).^[3]

Reticuline is one of the alkaloids found in opium, and experiments in rodents suggest it possesses potent central nervous system depressing effects.^[3] 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.^[4]

Metabolism

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

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

Notes and References

1. 10.1016/j.chroma.2008.10.017 . Simultaneous determination of four alkaloids in Lindera aggregata by ultra-high-pressure liquid chromatography–tandem mass spectrometry . 2008 . Han . Zheng . Zheng . Yunliang . Chen . Na . Luan . Lianjun . Zhou . Changxin . Gan . Lishe . Wu . Yongjiang . Journal of Chromatography A . 1212 . 76–81 . 18951552 . 1–2.
2. Dholvitayakhun, Achara . Trachoo, Nathanon . Sakee, Uthai . Potential applications for Annona squamosa leaf extract in the treatment and prevention of foodborne bacterial disease . Natural Product Communications . 2013 . 8 . 3 . 385–388 . 23678817 . etal. 10.1177/1934578X1300800327 . free .
3. 10.1016/S0378-8741(98)00044-0 . Central depressant effects of reticuline extracted from Ocotea duckei in rats and mice . 1998 . de Morais . Liana Clébia Soares Lima . Barbosa-Filho . José Maria . de Almeida . Reinaldo Nóbrega . Journal of Ethnopharmacology . 62 . 57–61 . 9720612 . 1.
4. Book: Bradley's neurology in clinical practice. Daroff, Robert B.,, Jankovic, Joseph,, Mazziotta, John C.,, Pomeroy, Scott Loren,, Bradley, W. G. (Walter George). 9780323339162. Seventh. London. 932031625. 2015-10-25.