Reticuline

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Reticuline
Reticuline.png
Identifiers
CAS number 485-19-8 YesY
PubChem 439653
ChemSpider 388724 N
ChEMBL CHEMBL401501 N
Jmol-3D images Image 1
Properties
Molecular formula C19H23NO4
Molar mass 329.39 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

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]

Metabolism[edit]

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.

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

References[edit]

  1. ^ 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. 
  2. ^ Dholvitayakhun, Achara; Trachoo, Nathanon; Sakee, Uthai 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. PMID 23678817. 
  3. ^ a b 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.