Reticuline: Difference between revisions

{{This|an alkaloid chemical|the connective-tissue fiber|reticular fiber}}

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 398757401

| Name = Reticuline

| ImageFile = [[File:Reticuline.png|frameless|reticuline 2D skeletal]]

| ImageFile2 = [[File:Reticuline 3D.png|frameless|reticuline 3D BS]]

| IUPACName = 3,10-Dimethoxy-8,8a-secoberbine-2,9-diol

| SystematicName = (1''S'')-1-[(3-Hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol

| OtherNames =

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 485-19-8

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = X35Z551WT4

| SMILES = CN1CCC2=CC(=C(C=C2[C@@H]1CC3=CC(=C(C=C3)OC)O)O)OC

| PubChem = 439653

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 388724

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C02105

| 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

| InChIKey = BHLYRWXGMIUIHG-HNNXBMFYBI

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = BHLYRWXGMIUIHG-HNNXBMFYSA-N

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 401501

|Section2={{Chembox Properties

| C=19 | H=23 | N=1 | O=4

'''Reticuline''' is a [[chemical compound]] found in a variety of plants including ''[[Lindera aggregata]]'',<ref>{{cite journal |doi=10.1016/j.chroma.2008.10.017 |title=Simultaneous determination of four alkaloids in Lindera aggregata by ultra-high-pressure liquid chromatography–tandem mass spectrometry |year=2008 |last1=Han |first1=Zheng |last2=Zheng |first2=Yunliang |last3=Chen |first3=Na |last4=Luan |first4=Lianjun |last5=Zhou |first5=Changxin |last6=Gan |first6=Lishe |last7=Wu |first7=Yongjiang |journal=Journal of Chromatography A |volume=1212 |pages=76–81 |pmid=18951552 |issue=1–2}}</ref> ''[[Annona squamosa]]'',<ref name="pmid23678817">{{cite journal|author1=Dholvitayakhun, Achara |author2=Trachoo, Nathanon |author3=Sakee, Uthai | title=Potential applications for Annona squamosa leaf extract in the treatment and prevention of foodborne bacterial disease | journal=Natural Product Communications | year= 2013 | volume= 8 | issue= 3 | pages= 385–388 | pmid=23678817 |display-authors=etal|doi=10.1177/1934578X1300800327 | doi-access=free }}</ref> and ''[[Ocotea#Selected species|Ocotea fasciculata]]'' (also known as ''Ocotea duckei'').<ref name=Morais>{{cite journal |doi=10.1016/S0378-8741(98)00044-0 |title=Central depressant effects of reticuline extracted from Ocotea duckei in rats and mice |year=1998 |last1=de Morais |first1=Liana Clébia Soares Lima |last2=Barbosa-Filho |first2=José Maria |last3=de Almeida |first3=Reinaldo Nóbrega |journal=Journal of Ethnopharmacology |volume=62 |pages=57–61 |pmid=9720612 |issue=1}}</ref> It is based on the [[benzylisoquinoline]] structure.

Reticuline is one of the [[alkaloid]]s found in [[opium]], and experiments in rodents suggest it possesses potent [[central nervous system]] [[depressant|depressing]] effects.<ref name=Morais/> It is the precursor of [[morphine]] and many other alkaloids. It is also toxic to dopaminergic neurons causing a form of [[Parkinson plus syndrome|atypical parkinsonism]] known as Guadeloupean Parkinsonism.<ref>{{Cite book|title=Bradley's neurology in clinical practice|others=Daroff, Robert B.,, Jankovic, Joseph,, Mazziotta, John C.,, Pomeroy, Scott Loren,, Bradley, W. G. (Walter George)|isbn=9780323339162|edition=Seventh|location=London|oclc=932031625|date = 2015-10-25}}</ref>

== Metabolism ==

[[3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase]] uses [[S-Adenosyl methionine|''S''-adenosyl methionine]] and 3'-hydroxy-''N''-methyl-(''S'')-[[coclaurine]] to produce [[S-Adenosyl-L-homocysteine|''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 ==

==External links==

{{Wiktionary inline|reticuline}}