Reticuline

This article is about an alkaloid chemical. For the connective-tissue fiber, see reticular fiber.
Reticuline
reticuline 2D skeletal
Names
IUPAC name
3,10-Dimethoxy-8,8a-secoberbine-2,9-diol
Systematic IUPAC name
(1S)-1-[(3-Hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.006.920
KEGG
UNII
  • InChI=1S/C19H23NO4/c1-20-7-6-13-10-19(24-3)17(22)11-14(13)15(20)8-12-4-5-18(23-2)16(21)9-12/h4-5,9-11,15,21-22H,6-8H2,1-3H3/t15-/m0/s1 ☒N
    Key: BHLYRWXGMIUIHG-HNNXBMFYSA-N ☒N
  • InChI=1/C19H23NO4/c1-20-7-6-13-10-19(24-3)17(22)11-14(13)15(20)8-12-4-5-18(23-2)16(21)9-12/h4-5,9-11,15,21-22H,6-8H2,1-3H3/t15-/m0/s1
    Key: BHLYRWXGMIUIHG-HNNXBMFYBI
  • CN1CCC2=CC(=C(C=C2[C@@H]1CC3=CC(=C(C=C3)OC)O)O)OC
Properties
C19H23NO4
Molar mass 329.396 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Reticuline is a tetrahydroisoquinoline alkaloid. It is also classified as a benzylisoquinoline alkaloid.[1]

Occurrence

Riticuline 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

  1. ^ 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. PMC 2830865. PMID 18690217.
  2. ^ 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.
  3. ^ 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. doi:10.1177/1934578X1300800327. PMID 23678817.
  4. ^ 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.
  5. ^ 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.

The dictionary definition of reticuline at Wiktionary

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