Page last updated: 2024-12-08

reticuline

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

reticuline: opium alkaloid; dopamine receptor blocker; RN given refers to (S)-isomer; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

(S)-reticuline : The (S)-enantiomer of reticuline. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID439653
CHEMBL ID235212
CHEBI ID16718
SCHEMBL ID147597
MeSH IDM0044318

Synonyms (40)

Synonym
reticline
(1s)-1-(3-hydroxy-4-methoxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol
CHEBI:16718 ,
(s)-(+)-reticuline
l-(+)-reticuline
d-reticuline
brn 4299976
einecs 207-611-3
7-isoquinolinol, 1,2,3,4-tetrahydro-1-((3-hydroxy-4-methoxyphenyl)methyl)-6-methoxy-2-methyl-,(s)-
s-(+)-reticuline
(s)-1,2,3,4-tetrahydro-1-((3-hydroxy-4-methoxyphenyl)methyl)-6-methoxy-2-methylisoquinolin-7-ol
reticuline
REN ,
(s)-reticuline
485-19-8
(+)-reticuline
C02105
S-RETICULINE ,
CHEMBL235212
5-21-06-00046 (beilstein handbook reference)
x35z551wt4 ,
unii-x35z551wt4
7-isoquinolinol, 1,2,3,4-tetrahydro-1 ((3-hydroxy-4-methoxyphenyl)methyl)-6-methoxy-2-methyl-, (s)-
7-isoquinolinol, 1,2,3,4-tetrahydro-1-((3-hydroxy-4-methoxyphenyl)methyl)-6-methoxy-2-methyl-, (1s)-
reticuline, s-(+)-
reticuline [mi]
reticuline, (+)-
SCHEMBL147597
(s)-1,2,3,4-tetrahydro-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methylisoquinolin-7-ol
AC-35156
(1s)-1-[(3-hydroxy-4-methoxyphenyl)methyl]-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol
bdbm50187681
AKOS032948461
Q6122828
HY-N1356
F14598
CS-0016764
MS-24943
A871916
DTXSID001317199

Research Excerpts

Overview

Reticuline is a key compound in the biosynthetic pathway for isoquinoline alkaloids in plants. These include morphine, codeine and berberine.

ExcerptReferenceRelevance
"(S)-Reticuline is an important precursor for BIAs biosynthesis."( Development of an artificial biosynthetic pathway for biosynthesis of (S)-reticuline based on HpaBC in engineered Escherichia coli.
Guo, D; Kong, S; Li, X; Pan, H; Sun, Y, 2021
)
1.33
"With reticuline, there is a 3 minute delay, which is followed by an extended release period."( Reticuline exposure to invertebrate ganglia increases endogenous morphine levels.
Mantione, KJ; Stefano, GB; Zhu, W, 2004
)
2.22
"Reticuline is a key compound in the biosynthetic pathway for isoquinoline alkaloids in plants, which include morphine, codeine and berberine. "( Knockdown of berberine bridge enzyme by RNAi accumulates (S)-reticuline and activates a silent pathway in cultured California poppy cells.
Fujii, N; Inui, T; Iwasa, K; Morishige, T; Sato, F, 2007
)
2.02
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
EC 2.1.1.116 [3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase] inhibitorAn EC 2.1.1.* (methyltransferases) inhibitor that interferes with the action of 3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase (EC 2.1.1.116).
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
reticuline
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
AcetylcholinesteraseElectrophorus electricus (electric eel)IC50 (µMol)301.01000.00000.94539.9400AID1312273
CholinesteraseEquus caballus (horse)IC50 (µMol)65.04000.00002.22149.4000AID1312274
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (27)

Assay IDTitleYearJournalArticle
AID301054Selectivity index, ratio of CC50 for human Hep G2.2.15 cells to IC50 for HBV e antigen secretion in HBV transfected Hep G2.2.15 cells2007Bioorganic & medicinal chemistry letters, Oct-01, Volume: 17, Issue:19
Two new alkaloids and active anti-hepatitis B virus constituents from Hypserpa nitida.
AID354885Inhibition of arachidonic acid-induced platelet aggregation in rabbit platelet-rich plasma at 100 ug/ml by turbidimetric method1996Journal of natural products, May, Volume: 59, Issue:5
Antiplatelet of vasorelaxing actions of some benzylisoquinoline and phenanthrene alkaloids.
AID1170646Antitubercular activity against Mycobacterium tuberculosis H37Rv by MABA assay2014Journal of natural products, Dec-26, Volume: 77, Issue:12
Tetrahydroxanthene-1,3(2H)-dione derivatives from Uvaria valderramensis.
AID1312272Inhibition of equine serum BChE at 100 ug/ml preincubated for 15 mins followed by addition of S-butyrylthiocholine chloride as substrate measured after 30 mins by Ellman's microplate assay2016Bioorganic & medicinal chemistry, 09-15, Volume: 24, Issue:18
Cholinesterase inhibitory activity of isoquinoline alkaloids from three Cryptocarya species (Lauraceae).
AID301052Antiviral activity against HBV transfected Hep G2.2.15 cells assessed as inhibition of e antigen HBsAg secretion2007Bioorganic & medicinal chemistry letters, Oct-01, Volume: 17, Issue:19
Two new alkaloids and active anti-hepatitis B virus constituents from Hypserpa nitida.
AID354898Vasorelaxant activity against norepinephrine-induced phasic contraction in Wistar rat thoracic aorta at 100 ug/ml1996Journal of natural products, May, Volume: 59, Issue:5
Antiplatelet of vasorelaxing actions of some benzylisoquinoline and phenanthrene alkaloids.
AID354891Inhibition of platelet-activity factor-induced platelet aggregation in rabbit platelet-rich plasma at 100 ug/ml by turbidimetric method1996Journal of natural products, May, Volume: 59, Issue:5
Antiplatelet of vasorelaxing actions of some benzylisoquinoline and phenanthrene alkaloids.
AID1312275Selectivity ratio, ratio of IC50 for equine serum BChE to electric eel AChE2016Bioorganic & medicinal chemistry, 09-15, Volume: 24, Issue:18
Cholinesterase inhibitory activity of isoquinoline alkaloids from three Cryptocarya species (Lauraceae).
AID301053Selectivity index, ratio of CC50 for human Hep G2.2.15 cells to IC50 for surface antigen HBsAg secretion in HBV transfected Hep G2.2.15 cells2007Bioorganic & medicinal chemistry letters, Oct-01, Volume: 17, Issue:19
Two new alkaloids and active anti-hepatitis B virus constituents from Hypserpa nitida.
AID354688Antimalarial activity against chloroquine-resistant Plasmodium falciparum W2 as [3H]hypoxanthine uptake1996Journal of natural products, Jun, Volume: 59, Issue:6
Costaricine, a new antiplasmodial bisbenzylisoquinoline alkaloid from Nectandra salicifolia trunk bark.
AID1312276Selectivity ratio, ratio of IC50 for electric eel AChE to equine serum BChE2016Bioorganic & medicinal chemistry, 09-15, Volume: 24, Issue:18
Cholinesterase inhibitory activity of isoquinoline alkaloids from three Cryptocarya species (Lauraceae).
AID301050Cytotoxicity against human Hep G2.2.15 cells2007Bioorganic & medicinal chemistry letters, Oct-01, Volume: 17, Issue:19
Two new alkaloids and active anti-hepatitis B virus constituents from Hypserpa nitida.
AID354902Vasorelaxant activity against norepinephrine-induced tonic contraction in Wistar rat thoracic aorta at 100 ug/ml1996Journal of natural products, May, Volume: 59, Issue:5
Antiplatelet of vasorelaxing actions of some benzylisoquinoline and phenanthrene alkaloids.
AID493705Cytotoxicity against human A549 cells by SRB assay2010Bioorganic & medicinal chemistry letters, Aug-01, Volume: 20, Issue:15
Benzylisoquinoline alkaloids from the tubers of Corydalis ternata and their cytotoxicity.
AID493708Cytotoxicity against human HCT15 cells by SRB assay2010Bioorganic & medicinal chemistry letters, Aug-01, Volume: 20, Issue:15
Benzylisoquinoline alkaloids from the tubers of Corydalis ternata and their cytotoxicity.
AID1312271Inhibition of electric eel AChE at 100 ug/ml preincubated for 15 mins followed by addition of acetylthiocholine iodide as substrate measured after 30 mins by Ellman's microplate assay2016Bioorganic & medicinal chemistry, 09-15, Volume: 24, Issue:18
Cholinesterase inhibitory activity of isoquinoline alkaloids from three Cryptocarya species (Lauraceae).
AID335151Antimalarial activity after 24 hrs against chloroquine-sensitive Plasmodium falciparum D6 infected type A+ human erythrocytes by [3H]hypoxanthine uptake1993Journal of natural products, Sep, Volume: 56, Issue:9
Cytotoxic and antimalarial alkaloids from the tubers of Stephania pierrei.
AID1312273Inhibition of electric eel AChE preincubated for 15 mins followed by addition of acetylthiocholine iodide as substrate measured after 30 mins by Ellman's microplate assay2016Bioorganic & medicinal chemistry, 09-15, Volume: 24, Issue:18
Cholinesterase inhibitory activity of isoquinoline alkaloids from three Cryptocarya species (Lauraceae).
AID1312274Inhibition of equine serum BChE preincubated for 15 mins followed by addition of S-butyrylthiocholine chloride as substrate measured after 30 mins by Ellman's microplate assay2016Bioorganic & medicinal chemistry, 09-15, Volume: 24, Issue:18
Cholinesterase inhibitory activity of isoquinoline alkaloids from three Cryptocarya species (Lauraceae).
AID493706Cytotoxicity against human SKOV3 cells by SRB assay2010Bioorganic & medicinal chemistry letters, Aug-01, Volume: 20, Issue:15
Benzylisoquinoline alkaloids from the tubers of Corydalis ternata and their cytotoxicity.
AID301051Antiviral activity against HBV transfected Hep G2.2.15 cells assessed as inhibition of surface antigen HBsAg secretion2007Bioorganic & medicinal chemistry letters, Oct-01, Volume: 17, Issue:19
Two new alkaloids and active anti-hepatitis B virus constituents from Hypserpa nitida.
AID354882Inhibition of adenosine diphosphate-induced platelet aggregation in rabbit platelet-rich plasma at 100 ug/ml by turbidimetric method1996Journal of natural products, May, Volume: 59, Issue:5
Antiplatelet of vasorelaxing actions of some benzylisoquinoline and phenanthrene alkaloids.
AID335152Antimalarial activity after 24 hrs against chloroquine-resistant Plasmodium falciparum W2 infected type A+ human erythrocytes by [3H]hypoxanthine uptake1993Journal of natural products, Sep, Volume: 56, Issue:9
Cytotoxic and antimalarial alkaloids from the tubers of Stephania pierrei.
AID354894Vasorelaxant activity against high potassium-induced contraction in Wistar rat thoracic aorta at 100 ug/ml1996Journal of natural products, May, Volume: 59, Issue:5
Antiplatelet of vasorelaxing actions of some benzylisoquinoline and phenanthrene alkaloids.
AID354687Antimalarial activity against chloroquine-sensitive Plasmodium falciparum D6 as [3H]hypoxanthine uptake1996Journal of natural products, Jun, Volume: 59, Issue:6
Costaricine, a new antiplasmodial bisbenzylisoquinoline alkaloid from Nectandra salicifolia trunk bark.
AID354888Inhibition of collagen-induced platelet aggregation in rabbit platelet-rich plasma at 100 ug/ml by turbidimetric method1996Journal of natural products, May, Volume: 59, Issue:5
Antiplatelet of vasorelaxing actions of some benzylisoquinoline and phenanthrene alkaloids.
AID493707Cytotoxicity against human SK-MEL-2 cells by SRB assay2010Bioorganic & medicinal chemistry letters, Aug-01, Volume: 20, Issue:15
Benzylisoquinoline alkaloids from the tubers of Corydalis ternata and their cytotoxicity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (70)

TimeframeStudies, This Drug (%)All Drugs %
pre-19906 (8.57)18.7374
1990's8 (11.43)18.2507
2000's24 (34.29)29.6817
2010's28 (40.00)24.3611
2020's4 (5.71)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 40.89

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index40.89 (24.57)
Research Supply Index4.29 (2.92)
Research Growth Index4.91 (4.65)
Search Engine Demand Index57.35 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (40.89)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (2.78%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other70 (97.22%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]