Reticuline

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Reticuline
(S)-reticuline.svg
(S)-reticuline
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 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
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 Yes check.svgY
    Key: BHLYRWXGMIUIHG-HNNXBMFYSA-N Yes check.svgY
  • 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).

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 . [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]

Biosynthesis

1,2-dehydroreticulinium reductase (NADPH) is an enzyme that catalyzes the chemical reaction which produces (R)-reticuline in Papaver somniferum : [6]

Reticulinylium.svg
reticulinylium cation
+ NADPH
 
 
H+
 
Reticuline
 
 
 
(R)-reticuline.svg
(R)-reticuline
+ NADP+
 

This is an irreversible step in the biosynthesis of morphinan alkaloids. [7]

(S)-reticuline is formed by the enzyme 3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase, which methylates 3'-hydroxy-N-methyl-(S)-coclaurine using S-adenosyl methionine as its cofactor. [8]

Metabolism

Reticuline oxidase uses (S)-reticuline and oxygen to produce the benzylisoquinoline scoulerine, with hydrogen peroxide as a by-product. [9]

(S)-reticuline.svg
(S)-reticuline
 
O2
2 H2O
Reticuline
 
 
 
Scoulerine-S.png
scoulerine

Salutaridine synthase uses (R)-reticuline, NADPH, and oxygen to produce salutaridine. [10]

(R)-reticuline.svg
(R)-reticuline
+ NADPH
 
 
O2
2 H2O
Reticuline
 
 
 
Salutaridine.svg
salutaridine
+ NADP+
 

Salutaridine can then be transformed progressively to thebaine, oripavine, and morphine.

References

  1. ↑ Hawkins, Kristy M.; Smolke, Christina D. (2008). "Production of Benzylisoquinoline Alkaloids in Saccharomyces cerevisiae". Nature Chemical Biology. 4 (9): 564–573. Bibcode:2008NatCB...4..564H. 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. 1 2 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. (25 October 2015). Bradley's neurology in clinical practice (Seventh ed.). London: Elsevier. ISBN   9780323339162. OCLC   932031625.
  6. ↑ De-Eknamkul W, Zenk MH (1992). "Purification and properties of 1,2-dehydroreticulinium reductase from Papaver somniferum seedlings". Phytochemistry . 31 (3): 813–821. Bibcode:1992PChem..31..813D. doi:10.1016/0031-9422(92)80020-F.
  7. ↑ Enzyme 1.5.1.27 at KEGG Pathway Database.
  8. ↑ Frenzel T, Zenk MH (1990). "S-Adenosyl-L-methionine: 3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase, a regio- and stereoselective enzyme of the (S)-reticuline pathway". Phytochemistry . 29 (11): 3505–3511. doi:10.1016/0031-9422(90)85265-H.
  9. ↑ Kutchan TM, Dittrich H (1995). "Characterization and mechanism of the berberine bridge enzyme, a covalently flavinylated oxidase of benzophenanthridine alkaloid biosynthesis in plants". J. Biol. Chem. 270 (41): 24475–81. doi: 10.1074/jbc.270.41.24475 . PMID   7592663.
  10. ↑ Gerady R, Zenk MH (1993). "Formation of salutaridine from (R)-reticuline by a membrane-bound cytochrome P-450 enzyme from Papaver somniferum". Phytochemistry . 32: 79–86. doi:10.1016/0031-9422(92)80111-Q.

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