This article is about an alkaloid chemical. For the connective-tissue fiber, see
reticular fiber .
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 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
Properties C 19 H 23 N O 4 Molar mass −1 Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Reticuline is atetrahydroisoquinoline alkaloid . It is also classified as abenzylisoquinoline alkaloid .[ 1]
Reticuline is found inopium and a variety of plants includingLindera aggregata [ 2] Annona squamosa [ 3] Ocotea fasciculata Ocotea duckei ).[ 4]
Physiological effects [ edit ] In rodents reticuline possesses potentcentral nervous system depressing effects.[ 4] morphine and many other alkaloids. It is also toxic to dopaminergic neurons causing a form ofatypical parkinsonism known as Guadeloupean Parkinsonism.[ 5]
3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase usesS -adenosyl methionineN -methyl-(S )-coclaurine to produceS -adenosylhomocysteineS )-reticuline.
Reticuline oxidase uses (S )-reticuline and O2 to produce (S )-scoulerine and H2 O2 .
Salutaridine synthase uses (R )-reticuline, NADPH, H+ , and O2 to producesalutaridine , NADP+ , and H2 O. Salutaridine can then be transformed progressively tothebaine ,oripavine , andmorphine .
1,2-dehydroreticulinium reductase (NADPH) uses (R )-reticuline and NADP+ to produce1,2-dehydroreticulinium , NADPH, and H+ .
^ Hawkins, Kristy M.; Smolke, Christina D. (2008)."Production of Benzylisoquinoline Alkaloids inSaccharomyces cerevisiae " .Nature Chemical Biology .4 (9):564– 573.doi :10.1038/nchembio.105 .PMC 2830865 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; 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 . ^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 . ^ 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 . reticuline
The dictionary definition ofreticuline at Wiktionary
