Chemistry:Reticuline
Reticuline is a tetrahydroisoquinoline alkaloid. It is also classified as a benzylisoquinoline alkaloid.[1]
Occurrence
Reticuline is found in opium and a variety of plants including Lindera aggregata,[2] Annona squamosa,[3] and Ocotea fasciculata (also known as Ocotea duckei).[4]
Physiological effects
In rodents reticuline possesses potent central nervous system depressing effects.[4] 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.[5]
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+.
References
- ↑ Hawkins, Kristy M.; Smolke, Christina D. (2008). "Production of Benzylisoquinoline Alkaloids in Saccharomyces cerevisiae". Nature Chemical Biology 4 (9): 564–573. doi:10.1038/nchembio.105. PMID 18690217.
- ↑ Han, Zheng; Zheng, Yunliang; Chen, Na; Luan, Lianjun; Zhou, Changxin; Gan, Lishe; Wu, Yongjiang (2008). "Simultaneous determination of four alkaloids in Lindera aggregata by ultra-high-pressure liquid chromatography–tandem mass spectrometry". Journal of Chromatography A 1212 (1–2): 76–81. doi:10.1016/j.chroma.2008.10.017. PMID 18951552.
- ↑ Dholvitayakhun, Achara et al. (2013). "Potential applications for Annona squamosa leaf extract in the treatment and prevention of foodborne bacterial disease". Natural Product Communications 8 (3): 385–388. doi:10.1177/1934578X1300800327. PMID 23678817.
- ↑ 4.0 4.1 de Morais, Liana Clébia Soares Lima; Barbosa-Filho, José Maria; de Almeida, Reinaldo Nóbrega (1998). "Central depressant effects of reticuline extracted from Ocotea duckei in rats and mice". Journal of Ethnopharmacology 62 (1): 57–61. doi:10.1016/S0378-8741(98)00044-0. PMID 9720612.
- ↑ Daroff, Robert B.; Jankovic, Joseph; Mazziotta, John C.; Pomeroy, Scott Loren; Bradley, W. G. (2015-10-25). Bradley's neurology in clinical practice (Seventh ed.). London: Elsevier. ISBN 9780323339162. OCLC 932031625.
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