Page last updated: 2024-11-13

kurarinol

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

Description

kurarinol: from Sophora flavescens; has inhibitory effect on tyrosinase and melanin synthesis; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

kurarinol : A trihydroxyflavanone that is (2S)-flavanone substituted by hydroxy groups at positions 7, 2' and 4' , a methoxy group at position 5 and a (2S)-5-hydroxy-5-methyl-2-(prop-1-en-2-yl)hexyl group at position 8 respectively. [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]

FloraRankFlora DefinitionFamilyFamily Definition
SophoragenusA plant genus of the family FABACEAE.[MeSH]FabaceaeThe large family of plants characterized by pods. Some are edible and some cause LATHYRISM or FAVISM and other forms of poisoning. Other species yield useful materials like gums from ACACIA and various LECTINS like PHYTOHEMAGGLUTININS from PHASEOLUS. Many of them harbor NITROGEN FIXATION bacteria on their roots. Many but not all species of beans belong to this family.[MeSH]

Cross-References

ID SourceID
PubMed CID44563198
CHEMBL ID455667
CHEBI ID81093
MeSH IDM0518054

Synonyms (16)

Synonym
kurarinol
C17444
CHEMBL455667
chebi:81093 ,
bdbm50366788
855746-98-4
(2s)-2-(2,4-dihydroxyphenyl)-7-hydroxy-8-[(2r)-5-hydroxy-5-methyl-2-(prop-1-en-2-yl)hexyl]-5-methoxy-2,3-dihydro-4h-1-benzopyran-4-one
Q27155049
(s)-2-(2,4-dihydroxyphenyl)-7-hydroxy-8-((r)-5-hydroxy-5-methyl-2-(prop-1-en-2-yl)hexyl)-5-methoxychroman-4-one
GLXC-18739
(2s)-2-(2,4-dihydroxyphenyl)-7-hydroxy-8-[(2r)-5-hydroxy-5-methyl-2-prop-1-en-2-ylhexyl]-5-methoxy-2,3-dihydrochromen-4-one
HY-122933
DTXSID401318587
CS-0090489
AKOS040760508
FS-7789

Research Excerpts

Overview

Kurarinol is a flavonoid isolated from roots of the medical plant Sophora flavescens.

ExcerptReferenceRelevance
"Kurarinol is a flavonoid isolated from roots of the medical plant Sophora flavescens. "( Kurarinol induces hepatocellular carcinoma cell apoptosis through suppressing cellular signal transducer and activator of transcription 3 signaling.
Hong, Z; Mei, Z; Shu, G; Xu, C; Yang, J; Yang, X; Zhao, W, 2014
)
3.29

Actions

ExcerptReferenceRelevance
"Kurarinol can increase level of HBV specific CTL by down-regulating peripheral blood HBV specific CTL surface PD-1 expression of CHB patients, which may be one of the possible mechanisms that kurarinol can remove or inhibit HBV of CHB patients."( [Effect of kurarinol on peripheral blood CTL surface PD-1 expression of patients with chronic hepatitis B].
Chen, HK; Gu, XB; Hua, Z; Jiang, YM; Lu, ZH; Pei, H; Wu, HY; Xu, YQ; Yang, XJ; Zang, B; Zhu, YF, 2012
)
2.21

Compound-Compound Interactions

Kurarinol combined with Diammonium Glycyrrhizinate can further increase HBV specific CTL, CD4+ and Th1 level of CHB patients.

ExcerptReferenceRelevance
"To explore effects of kurarinol combined with Diammonium Glycyrrhizinate on specific cellular immunity of patients with chronic hepatitis B (CHB)."( [Study on effects of kurarinol combined with glycyrrhizic acid on cellular immunity of patients with chronic hepatitis B].
Chen, HK; Gu, XB; Hua, Z; Jiang, XH; Jiang, YM; Lu, ZH; Pei, H; Wu, HY; Yang, XJ; Zhang, B; Zhou, YL; Zhu, YF, 2012
)
1.01
"Sixty-three CHB patients were randomly divided into two groups, 32 cases in group of kurarinol combined with Diammonium Glycyrrhizinate group (combined therapy group) were treated with 600 mg kurarinol glucose injection intravenously, once a day for one month, then 200 mg kurarinol capsule was used orally, three times a day for two months."( [Study on effects of kurarinol combined with glycyrrhizic acid on cellular immunity of patients with chronic hepatitis B].
Chen, HK; Gu, XB; Hua, Z; Jiang, XH; Jiang, YM; Lu, ZH; Pei, H; Wu, HY; Yang, XJ; Zhang, B; Zhou, YL; Zhu, YF, 2012
)
0.92
"Kurarinol combined with Diammonium Glycyrrhizinate can further increase HBV specific CTL, CD4+ and Th1 level of CHB patients."( [Study on effects of kurarinol combined with glycyrrhizic acid on cellular immunity of patients with chronic hepatitis B].
Chen, HK; Gu, XB; Hua, Z; Jiang, XH; Jiang, YM; Lu, ZH; Pei, H; Wu, HY; Yang, XJ; Zhang, B; Zhou, YL; Zhu, YF, 2012
)
2.14

Dosage Studied

ExcerptRelevanceReference
" 38 cases in control group, only Silybin Meglumine Tablets was used, method and dosage were the same as treatment group."( [Influence of Kurarinol on specific and non-specific cell immunity in patients with chronic hepatitis B].
Ding, H; Gu, XB; Wang, D; Wu, HY; Xu, YQ; Yang, XJ; Zhang, B; Zhu, YF, 2009
)
0.71
" 150 mg Diammonium Glycyrrhizinate for Injection was added to 250 ml 10% glucose injection for intravenous drip, once a day for one month, then 150 mg Diammonium Glycyrrhizinate capsule was used orally, three times a day for two months; 31 case in kurarinol group (single drug group) only used kurarinol, methods and dosage were the same as those of treatment group."( [Study on effects of kurarinol combined with glycyrrhizic acid on cellular immunity of patients with chronic hepatitis B].
Chen, HK; Gu, XB; Hua, Z; Jiang, XH; Jiang, YM; Lu, ZH; Pei, H; Wu, HY; Yang, XJ; Zhang, B; Zhou, YL; Zhu, YF, 2012
)
0.88
" 35 cases in control group, only silibin meglumine tablet was used, method and dosage were the same as those of treatment group."( [Effect of kurarinol on peripheral blood CTL surface PD-1 expression of patients with chronic hepatitis B].
Chen, HK; Gu, XB; Hua, Z; Jiang, YM; Lu, ZH; Pei, H; Wu, HY; Xu, YQ; Yang, XJ; Zang, B; Zhu, YF, 2012
)
0.77
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (3)

RoleDescription
anti-inflammatory agentAny compound that has anti-inflammatory effects.
antioxidantA substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
[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 (3)

ClassDescription
trihydroxyflavanoneA hydroxyflavanone carrying three hydroxy substituents.
monomethoxyflavanoneAny methoxyflavanone that is flavanone substituted by a methoxy group.
4'-hydroxyflavanonesAny hydroxyflavanone having a hydroxy substituent located at position 4'.
[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 (6)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
cGMP-specific 3',5'-cyclic phosphodiesteraseRattus norvegicus (Norway rat)IC50 (µMol)6.10000.00031.35116.1000AID158109
cAMP-specific 3',5'-cyclic phosphodiesterase 4D Rattus norvegicus (Norway rat)IC50 (µMol)6.59000.00032.723210.0000AID160105
cAMP-specific 3',5'-cyclic phosphodiesterase 4CRattus norvegicus (Norway rat)IC50 (µMol)6.59000.00032.723210.0000AID160105
cAMP-specific 3',5'-cyclic phosphodiesterase 4BRattus norvegicus (Norway rat)IC50 (µMol)6.59000.00032.663810.0000AID160105
cAMP-specific 3',5'-cyclic phosphodiesterase 4ARattus norvegicus (Norway rat)IC50 (µMol)6.59000.00032.723210.0000AID160105
Beta-secretase 1Homo sapiens (human)IC50 (µMol)39.20000.00061.619410.0000AID344054
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (16)

Processvia Protein(s)Taxonomy
proteolysisBeta-secretase 1Homo sapiens (human)
membrane protein ectodomain proteolysisBeta-secretase 1Homo sapiens (human)
response to lead ionBeta-secretase 1Homo sapiens (human)
protein processingBeta-secretase 1Homo sapiens (human)
amyloid-beta formationBeta-secretase 1Homo sapiens (human)
amyloid precursor protein catabolic processBeta-secretase 1Homo sapiens (human)
positive regulation of neuron apoptotic processBeta-secretase 1Homo sapiens (human)
amyloid-beta metabolic processBeta-secretase 1Homo sapiens (human)
detection of mechanical stimulus involved in sensory perception of painBeta-secretase 1Homo sapiens (human)
prepulse inhibitionBeta-secretase 1Homo sapiens (human)
cellular response to copper ionBeta-secretase 1Homo sapiens (human)
cellular response to manganese ionBeta-secretase 1Homo sapiens (human)
presynaptic modulation of chemical synaptic transmissionBeta-secretase 1Homo sapiens (human)
signaling receptor ligand precursor processingBeta-secretase 1Homo sapiens (human)
cellular response to amyloid-betaBeta-secretase 1Homo sapiens (human)
amyloid fibril formationBeta-secretase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
amyloid-beta bindingBeta-secretase 1Homo sapiens (human)
endopeptidase activityBeta-secretase 1Homo sapiens (human)
aspartic-type endopeptidase activityBeta-secretase 1Homo sapiens (human)
protein bindingBeta-secretase 1Homo sapiens (human)
peptidase activityBeta-secretase 1Homo sapiens (human)
beta-aspartyl-peptidase activityBeta-secretase 1Homo sapiens (human)
enzyme bindingBeta-secretase 1Homo sapiens (human)
protein serine/threonine kinase bindingBeta-secretase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (20)

Processvia Protein(s)Taxonomy
lysosomeBeta-secretase 1Homo sapiens (human)
endosomeBeta-secretase 1Homo sapiens (human)
early endosomeBeta-secretase 1Homo sapiens (human)
late endosomeBeta-secretase 1Homo sapiens (human)
multivesicular bodyBeta-secretase 1Homo sapiens (human)
endoplasmic reticulum lumenBeta-secretase 1Homo sapiens (human)
Golgi apparatusBeta-secretase 1Homo sapiens (human)
trans-Golgi networkBeta-secretase 1Homo sapiens (human)
plasma membraneBeta-secretase 1Homo sapiens (human)
synaptic vesicleBeta-secretase 1Homo sapiens (human)
cell surfaceBeta-secretase 1Homo sapiens (human)
endosome membraneBeta-secretase 1Homo sapiens (human)
membraneBeta-secretase 1Homo sapiens (human)
axonBeta-secretase 1Homo sapiens (human)
dendriteBeta-secretase 1Homo sapiens (human)
neuronal cell bodyBeta-secretase 1Homo sapiens (human)
membrane raftBeta-secretase 1Homo sapiens (human)
recycling endosomeBeta-secretase 1Homo sapiens (human)
Golgi-associated vesicle lumenBeta-secretase 1Homo sapiens (human)
hippocampal mossy fiber to CA3 synapseBeta-secretase 1Homo sapiens (human)
endosomeBeta-secretase 1Homo sapiens (human)
plasma membraneBeta-secretase 1Homo sapiens (human)
trans-Golgi networkBeta-secretase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (11)

Assay IDTitleYearJournalArticle
AID344054Inhibition of human BACE12008Bioorganic & medicinal chemistry, Jul-15, Volume: 16, Issue:14
BACE1 inhibitory effects of lavandulyl flavanones from Sophora flavescens.
AID159374Relative inhibition of Phosphodiesterase 3 and Phosphodiesterase 52002Bioorganic & medicinal chemistry letters, Sep-02, Volume: 12, Issue:17
A prenylated flavonol, sophoflavescenol: a potent and selective inhibitor of cGMP phosphodiesterase 5.
AID410032Inhibition of Clostridium perfringens neuraminidase by Lineweaver-Burke plot2008Bioorganic & medicinal chemistry letters, Dec-01, Volume: 18, Issue:23
Pterocarpans and flavanones from Sophora flavescens displaying potent neuraminidase inhibition.
AID159373Inhibition of Phosphodiesterase 3 from rat diaphragm2002Bioorganic & medicinal chemistry letters, Sep-02, Volume: 12, Issue:17
A prenylated flavonol, sophoflavescenol: a potent and selective inhibitor of cGMP phosphodiesterase 5.
AID403550Antiviral activity against HSV2 in african green monkey Vero cells assessed as virus-induced cytopathic effect after 3 days by MTT assay1998Journal of natural products, Dec, Volume: 61, Issue:12
A new prenylated flavonol from the roots of Sophora flavescens.
AID160105Inhibition of Phosphodiesterase 4 from rat liver2002Bioorganic & medicinal chemistry letters, Sep-02, Volume: 12, Issue:17
A prenylated flavonol, sophoflavescenol: a potent and selective inhibitor of cGMP phosphodiesterase 5.
AID160123Relative inhibition of Phosphodiesterase 4 and Phosphodiesterase 52002Bioorganic & medicinal chemistry letters, Sep-02, Volume: 12, Issue:17
A prenylated flavonol, sophoflavescenol: a potent and selective inhibitor of cGMP phosphodiesterase 5.
AID403549Antiviral activity against HSV1 in african green monkey Vero cells assessed as virus-induced cytopathic effect after 3 days by MTT assay1998Journal of natural products, Dec, Volume: 61, Issue:12
A new prenylated flavonol from the roots of Sophora flavescens.
AID1260925Inhibition of Staphylococcus aureus SrtA2015Journal of medicinal chemistry, Dec-10, Volume: 58, Issue:23
Sortase A Inhibitors: Recent Advances and Future Perspectives.
AID410031Inhibition of Clostridium perfringens neuraminidase2008Bioorganic & medicinal chemistry letters, Dec-01, Volume: 18, Issue:23
Pterocarpans and flavanones from Sophora flavescens displaying potent neuraminidase inhibition.
AID158109Inhibition of Phosphodiesterase 5 from rat diaphragm2002Bioorganic & medicinal chemistry letters, Sep-02, Volume: 12, Issue:17
A prenylated flavonol, sophoflavescenol: a potent and selective inhibitor of cGMP phosphodiesterase 5.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (13)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (7.69)18.2507
2000's6 (46.15)29.6817
2010's6 (46.15)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 17.47

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index17.47 (24.57)
Research Supply Index2.83 (2.92)
Research Growth Index5.12 (4.65)
Search Engine Demand Index10.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (17.47)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials3 (23.08%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other10 (76.92%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]