Page last updated: 2024-12-07

isoteolin

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

Description

isoteolin: mixture of isomers isoboldine (RN 3019-51-0) & bracteoline (RN 25651-04-1) [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID133323
CHEMBL ID462880
CHEBI ID5986
SCHEMBL ID12140647
MeSH IDM0129202

Synonyms (44)

Synonym
NCGC00017381-01
tnp00331 ,
3019-51-0
d-isoboldine
isoboldine
nsc-113983
(+)-isoboldine
C09541
(s)-isoboldine
2,10-dimethoxy-6aalpha-aporphine-1,9-diol
NCGC00142559-01
isoteolin
95508-61-5
chebi:5986 ,
CHEMBL462880
n-methyllaurelliptine
NCGC00017381-02
ST057702 ,
4h-dibenzo(de,g)quinolinediol, 5,6,6a,7-tetrahydro-2,9(or 2,10)-dimethoxy-6-methyl-, (s)-
isoteoline
izoteolin
ai3-27548
(s)-(+)-isoboldine
m002e511aj ,
unii-m002e511aj
6aalpha-aporphine-1,9-diol, 2,10-dimethoxy-
nsc 113983
4h-dibenzo(de,g)quinoline-1,9-diol, 5,6,6a,7-tetrahydro-2,10-dimethoxy-6-methyl-, (s)-
4h-dibenzo(de,g)quinoline-1,9-diol, 5,6,6a,7-tetrahydro-2,10-dimethoxy-6-methyl-, (6as)-
6a.alpha.-aporphine-1,9-diol, 2,10-dimethoxy-
isoboldine , (+)-
SCHEMBL12140647
AKOS024282718
2,10-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinoline-1,9-diol #
LINHZVMHXABQLB-ZDUSSCGKSA-N
4h-dibenzo[de,g]quinoline-1,9-diol, 5,6,6a,7-tetrahydro-2,10-dimethoxy-6-methyl-, (s)-
(6as)-2,10-dimethoxy-6-methyl-5,6,6a,7-tetrahydro-4h-dibenzo[de,g]quinoline-1,9-diol
Q15426252
nsc785158
nsc-785158
CS-0203854
isoboldine, (+)-
DTXSID301045612
HY-N9794

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" To better understand its pharmacological activities, we need to determine its pharmacokinetic and metabolic profiles."( Pharmacokinetics and metabolism study of isoboldine, a major bioactive component from Radix Linderae in male rats by UPLC-MS/MS.
Cai, HZ; Chen, JZ; Chou, GX; Gao, Y; Jia, L; Li, Y; Shao, JW; Wu, YB; Zeng, RJ, 2015
)
0.42
" This newly developed method was successfully applied to a pharmacokinetic study after oral and intravenous dosing in rats."( Pharmacokinetics and metabolism study of isoboldine, a major bioactive component from Radix Linderae in male rats by UPLC-MS/MS.
Cai, HZ; Chen, JZ; Chou, GX; Gao, Y; Jia, L; Li, Y; Shao, JW; Wu, YB; Zeng, RJ, 2015
)
0.42
" These results have paved the way for further clarifying therapeutic ingredients and provided new knowledge regarding pharmacokinetic features of this category of isoquinoline alkaloids."( Pharmacokinetics and metabolism study of isoboldine, a major bioactive component from Radix Linderae in male rats by UPLC-MS/MS.
Cai, HZ; Chen, JZ; Chou, GX; Gao, Y; Jia, L; Li, Y; Shao, JW; Wu, YB; Zeng, RJ, 2015
)
0.42

Bioavailability

ExcerptReferenceRelevance
"isoboldine has extremely low oral bioavailability due to the strong first-pass effect by the rats, and glucuronidation and sulfonation were involved in metabolic pathways of isoboldine in rats."( Pharmacokinetics and metabolism study of isoboldine, a major bioactive component from Radix Linderae in male rats by UPLC-MS/MS.
Cai, HZ; Chen, JZ; Chou, GX; Gao, Y; Jia, L; Li, Y; Shao, JW; Wu, YB; Zeng, RJ, 2015
)
0.42

Dosage Studied

ExcerptRelevanceReference
" This newly developed method was successfully applied to a pharmacokinetic study after oral and intravenous dosing in rats."( Pharmacokinetics and metabolism study of isoboldine, a major bioactive component from Radix Linderae in male rats by UPLC-MS/MS.
Cai, HZ; Chen, JZ; Chou, GX; Gao, Y; Jia, L; Li, Y; Shao, JW; Wu, YB; Zeng, RJ, 2015
)
0.42
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
aporphine alkaloidAny benzylisoquinoline alkaloid that has a structure based on 4H-dibenzo[de,g]quinoline or its 3-methyl derivative.
[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 (37)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASEHomo sapiens (human)Potency31.62280.003245.467312,589.2998AID2517
Chain A, Putative fructose-1,6-bisphosphate aldolaseGiardia intestinalisPotency3.97160.140911.194039.8107AID2451
Chain A, HADH2 proteinHomo sapiens (human)Potency31.62280.025120.237639.8107AID886; AID893
Chain B, HADH2 proteinHomo sapiens (human)Potency31.62280.025120.237639.8107AID886; AID893
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency28.18380.177814.390939.8107AID2147
Chain A, ATP-DEPENDENT DNA HELICASE Q1Homo sapiens (human)Potency25.11890.125919.1169125.8920AID2549
TDP1 proteinHomo sapiens (human)Potency31.67680.000811.382244.6684AID686978; AID686979
Microtubule-associated protein tauHomo sapiens (human)Potency19.62210.180013.557439.8107AID1460; AID1468
aldehyde dehydrogenase 1 family, member A1Homo sapiens (human)Potency31.62280.011212.4002100.0000AID1030
cytochrome P450 2D6 isoform 1Homo sapiens (human)Potency6.30960.00207.533739.8107AID891
cellular tumor antigen p53 isoform aHomo sapiens (human)Potency31.62280.316212.443531.6228AID902
cytochrome P450 2C19 precursorHomo sapiens (human)Potency12.58930.00255.840031.6228AID899
cytochrome P450 2C9 precursorHomo sapiens (human)Potency25.11890.00636.904339.8107AID883
15-hydroxyprostaglandin dehydrogenase [NAD(+)] isoform 1Homo sapiens (human)Potency35.48130.001815.663839.8107AID894
DNA polymerase kappa isoform 1Homo sapiens (human)Potency3.16230.031622.3146100.0000AID588579
cytochrome P450 3A4 isoform 1Homo sapiens (human)Potency19.95260.031610.279239.8107AID884; AID885
caspase-1 isoform alpha precursorHomo sapiens (human)Potency31.62280.000311.448431.6228AID896; AID900
Gamma-aminobutyric acid receptor subunit piRattus norvegicus (Norway rat)Potency19.95261.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-1Rattus norvegicus (Norway rat)Potency19.95261.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit deltaRattus norvegicus (Norway rat)Potency19.95261.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)Potency19.95261.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-5Rattus norvegicus (Norway rat)Potency19.95261.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-3Rattus norvegicus (Norway rat)Potency19.95261.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-1Rattus norvegicus (Norway rat)Potency19.95261.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-2Rattus norvegicus (Norway rat)Potency19.95261.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit alpha-4Rattus norvegicus (Norway rat)Potency19.95261.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit gamma-3Rattus norvegicus (Norway rat)Potency19.95261.000012.224831.6228AID885
Caspase-1Homo sapiens (human)Potency31.62281.12209.584325.1189AID996
Gamma-aminobutyric acid receptor subunit alpha-6Rattus norvegicus (Norway rat)Potency19.95261.000012.224831.6228AID885
Histamine H2 receptorCavia porcellus (domestic guinea pig)Potency25.11890.00638.235039.8107AID883
Caspase-7Homo sapiens (human)Potency31.62283.981118.585631.6228AID889
Gamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)Potency19.95261.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-3Rattus norvegicus (Norway rat)Potency19.95261.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)Potency19.95261.000012.224831.6228AID885
Inositol monophosphatase 1Rattus norvegicus (Norway rat)Potency22.87411.000010.475628.1838AID1457; AID901
GABA theta subunitRattus norvegicus (Norway rat)Potency19.95261.000012.224831.6228AID885
Gamma-aminobutyric acid receptor subunit epsilonRattus norvegicus (Norway rat)Potency19.95261.000012.224831.6228AID885
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (38)

Processvia Protein(s)Taxonomy
cellular response to organic substanceCaspase-1Homo sapiens (human)
pattern recognition receptor signaling pathwayCaspase-1Homo sapiens (human)
proteolysisCaspase-1Homo sapiens (human)
apoptotic processCaspase-1Homo sapiens (human)
signal transductionCaspase-1Homo sapiens (human)
osmosensory signaling pathwayCaspase-1Homo sapiens (human)
protein autoprocessingCaspase-1Homo sapiens (human)
positive regulation of interleukin-1 beta productionCaspase-1Homo sapiens (human)
positive regulation of interleukin-18 productionCaspase-1Homo sapiens (human)
defense response to bacteriumCaspase-1Homo sapiens (human)
regulation of apoptotic processCaspase-1Homo sapiens (human)
positive regulation of canonical NF-kappaB signal transductionCaspase-1Homo sapiens (human)
positive regulation of cysteine-type endopeptidase activity involved in apoptotic processCaspase-1Homo sapiens (human)
icosanoid biosynthetic processCaspase-1Homo sapiens (human)
regulation of inflammatory responseCaspase-1Homo sapiens (human)
positive regulation of inflammatory responseCaspase-1Homo sapiens (human)
protein maturationCaspase-1Homo sapiens (human)
defense response to virusCaspase-1Homo sapiens (human)
pyroptosisCaspase-1Homo sapiens (human)
cellular response to lipopolysaccharideCaspase-1Homo sapiens (human)
cellular response to mechanical stimulusCaspase-1Homo sapiens (human)
cellular response to type II interferonCaspase-1Homo sapiens (human)
cytokine precursor processingCaspase-1Homo sapiens (human)
signaling receptor ligand precursor processingCaspase-1Homo sapiens (human)
AIM2 inflammasome complex assemblyCaspase-1Homo sapiens (human)
positive regulation of tumor necrosis factor-mediated signaling pathwayCaspase-1Homo sapiens (human)
proteolysisCaspase-7Homo sapiens (human)
apoptotic processCaspase-7Homo sapiens (human)
heart developmentCaspase-7Homo sapiens (human)
response to UVCaspase-7Homo sapiens (human)
protein processingCaspase-7Homo sapiens (human)
protein catabolic processCaspase-7Homo sapiens (human)
defense response to bacteriumCaspase-7Homo sapiens (human)
fibroblast apoptotic processCaspase-7Homo sapiens (human)
striated muscle cell differentiationCaspase-7Homo sapiens (human)
neuron apoptotic processCaspase-7Homo sapiens (human)
protein maturationCaspase-7Homo sapiens (human)
lymphocyte apoptotic processCaspase-7Homo sapiens (human)
cellular response to lipopolysaccharideCaspase-7Homo sapiens (human)
cellular response to staurosporineCaspase-7Homo sapiens (human)
execution phase of apoptosisCaspase-7Homo sapiens (human)
positive regulation of plasma membrane repairCaspase-7Homo sapiens (human)
positive regulation of neuron apoptotic processCaspase-7Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (15)

Processvia Protein(s)Taxonomy
endopeptidase activityCaspase-1Homo sapiens (human)
cysteine-type endopeptidase activityCaspase-1Homo sapiens (human)
protein bindingCaspase-1Homo sapiens (human)
cysteine-type endopeptidase activator activity involved in apoptotic processCaspase-1Homo sapiens (human)
kinase bindingCaspase-1Homo sapiens (human)
cytokine bindingCaspase-1Homo sapiens (human)
identical protein bindingCaspase-1Homo sapiens (human)
CARD domain bindingCaspase-1Homo sapiens (human)
caspase bindingCaspase-1Homo sapiens (human)
RNA bindingCaspase-7Homo sapiens (human)
aspartic-type endopeptidase activityCaspase-7Homo sapiens (human)
cysteine-type endopeptidase activityCaspase-7Homo sapiens (human)
protein bindingCaspase-7Homo sapiens (human)
peptidase activityCaspase-7Homo sapiens (human)
cysteine-type peptidase activityCaspase-7Homo sapiens (human)
cysteine-type endopeptidase activity involved in apoptotic processCaspase-7Homo sapiens (human)
cysteine-type endopeptidase activity involved in execution phase of apoptosisCaspase-7Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (15)

Processvia Protein(s)Taxonomy
plasma membraneGamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)
cytoplasmCaspase-1Homo sapiens (human)
cytosolCaspase-1Homo sapiens (human)
nucleolusCaspase-1Homo sapiens (human)
cytoplasmCaspase-1Homo sapiens (human)
cytosolCaspase-1Homo sapiens (human)
microtubuleCaspase-1Homo sapiens (human)
plasma membraneCaspase-1Homo sapiens (human)
canonical inflammasome complexCaspase-1Homo sapiens (human)
NLRP1 inflammasome complexCaspase-1Homo sapiens (human)
NLRP3 inflammasome complexCaspase-1Homo sapiens (human)
AIM2 inflammasome complexCaspase-1Homo sapiens (human)
protein-containing complexCaspase-1Homo sapiens (human)
IPAF inflammasome complexCaspase-1Homo sapiens (human)
protease inhibitor complexCaspase-1Homo sapiens (human)
extracellular spaceCaspase-7Homo sapiens (human)
nucleusCaspase-7Homo sapiens (human)
cytoplasmCaspase-7Homo sapiens (human)
cytosolCaspase-7Homo sapiens (human)
nucleusCaspase-7Homo sapiens (human)
nucleoplasmCaspase-7Homo sapiens (human)
cytosolCaspase-7Homo sapiens (human)
plasma membraneGamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (9)

Assay IDTitleYearJournalArticle
AID284363Inhibition of LPS-induced BALB/c mouse B cell proliferation2007Bioorganic & medicinal chemistry, Jan-15, Volume: 15, Issue:2
Discovery and synthesis of new immunosuppressive alkaloids from the stem of Fissistigma oldhamii (Hemsl.) Merr.
AID284362Inhibition of ConA-induced BALB/c mouse T cell proliferation2007Bioorganic & medicinal chemistry, Jan-15, Volume: 15, Issue:2
Discovery and synthesis of new immunosuppressive alkaloids from the stem of Fissistigma oldhamii (Hemsl.) Merr.
AID284361Cytotoxicity against BALB/c mouse spleen cells2007Bioorganic & medicinal chemistry, Jan-15, Volume: 15, Issue:2
Discovery and synthesis of new immunosuppressive alkaloids from the stem of Fissistigma oldhamii (Hemsl.) Merr.
AID284365Selectivity index, ratio of CC50 for BALB/c mouse T cells to IC50 for BALB/c mouse B cells2007Bioorganic & medicinal chemistry, Jan-15, Volume: 15, Issue:2
Discovery and synthesis of new immunosuppressive alkaloids from the stem of Fissistigma oldhamii (Hemsl.) Merr.
AID1720193Antiinflammatory activity in human neutrophils assessed as inhibition of fMLF/cytochalasin B-induced superoxide anion generation at 10 uM preincubated for 5 mins followed by fMLF addition after priming with CB for 3 mins by spectrophotometric analysis rel2020Bioorganic & medicinal chemistry letters, 07-01, Volume: 30, Issue:13
Anti-inflammatory principles from Lindera aggregata.
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.
AID1720194Antiinflammatory activity in human neutrophils assessed as inhibition of fMLF/cytochalasin B-induced superoxide anion generation preincubated for 5 mins followed by fMLF addition after priming with CB for 3 mins by spectrophotometric analysis2020Bioorganic & medicinal chemistry letters, 07-01, Volume: 30, Issue:13
Anti-inflammatory principles from Lindera aggregata.
AID284364Selectivity index, ratio of CC50 for BALB/c mouse spleen cells to IC50 for BALB/c mouse T cells2007Bioorganic & medicinal chemistry, Jan-15, Volume: 15, Issue:2
Discovery and synthesis of new immunosuppressive alkaloids from the stem of Fissistigma oldhamii (Hemsl.) Merr.
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (19)

TimeframeStudies, This Drug (%)All Drugs %
pre-19905 (26.32)18.7374
1990's7 (36.84)18.2507
2000's5 (26.32)29.6817
2010's1 (5.26)24.3611
2020's1 (5.26)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other20 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]