Compounds > barbigerone
Page last updated: 2024-12-08

barbigerone

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

Description

barbigerone: an antioxidant; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID156793
CHEMBL ID3311038
SCHEMBL ID5094581
MeSH IDM0539739

Synonyms (18)

Synonym
4h,8h-benzo(1,2-b:3,4-b')dipyran-4-one, 8,8-dimethyl-3-(2,4,5-trimethoxyphenyl)-
barbigerone
LMPK12050076
8,8-dimethyl-3-(2,4,5-trimethoxyphenyl)pyrano[2,3-f]chromen-4-one
9be3f2b4gd ,
75425-27-3
unii-9be3f2b4gd
SCHEMBL5094581
CHEMBL3311038 ,
DTXSID30226352
bdbm50505210
ncgc00386021-01!8,8-dimethyl-3-(2,4,5-trimethoxyphenyl)pyrano[2,3-f]chromen-4-one
Q4859690
j6l ,
ionchocarpusone
4h,8h-benzo[1,2-b:3,4-b']dipyran-4-one, 8,8-dimethyl-3-(2,4,5-trimethoxyphenyl)-
8,8-dimethyl-3-(2,4,5-trimethoxyphenyl)-4h,8h-benzo(1,2-b:3,4-b')dipyran-4-one
AKOS040745595

Research Excerpts

Overview

Barbigerone is a naturally occurring isoflavone with antioxidant activity. It is mainly found in the genus Milletti, such as the edible leguminous plant Millettia ferruginea.

ExcerptReferenceRelevance
"Barbigerone is an isoflavone mainly found in the genus Milletti, such as the edible leguminous plant Millettia ferruginea, with anticancer activity. "( Crystal structure of tubulin-barbigerone complex enables rational design of potent anticancer agents with isoflavone skeleton.
Chen, L; Li, Y; Liu, Y; Pei, H; Wen, Y; Yan, W; Yang, J, 2023)		2.64
"Barbigerone is a naturally occurring isoflavone with antioxidant activity. "( Barbigerone, a natural isoflavone, induces apoptosis in murine lung-cancer cells via the mitochondrial apoptotic pathway.
Cao, ZX; Chen, LJ; Jiang, PD; Li, ZG; Mao, YQ; Peng, A; Wei, YQ; Wu, X; Ye, HY; Zhao, X; Zhao, YL; Zheng, YZ, 2009)		3.24

Actions

ExcerptReferenceRelevance
"Both barbigerone and 0412 inhibit cancer cell proliferation, tubulin polymerization, migration of HeLa cells and capillary-like tube formation of HUVECs, induce G2/M phase cell cycle arrest and apoptosis, and exhibit anticancer activity in an H460 xenograft model."( Crystal structure of tubulin-barbigerone complex enables rational design of potent anticancer agents with isoflavone skeleton.
Chen, L; Li, Y; Liu, Y; Pei, H; Wen, Y; Yan, W; Yang, J, 2023)		1.66
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
CholinesteraseHomo sapiens (human)IC50 (µMol)21.77000.00001.559910.0000AID1524946
AcetylcholinesteraseHomo sapiens (human)IC50 (µMol)121.60000.00000.933210.0000AID1524945
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (25)

Processvia Protein(s)Taxonomy
xenobiotic metabolic processCholinesteraseHomo sapiens (human)
learningCholinesteraseHomo sapiens (human)
negative regulation of cell population proliferationCholinesteraseHomo sapiens (human)
neuroblast differentiationCholinesteraseHomo sapiens (human)
peptide hormone processingCholinesteraseHomo sapiens (human)
response to alkaloidCholinesteraseHomo sapiens (human)
cocaine metabolic processCholinesteraseHomo sapiens (human)
negative regulation of synaptic transmissionCholinesteraseHomo sapiens (human)
response to glucocorticoidCholinesteraseHomo sapiens (human)
response to folic acidCholinesteraseHomo sapiens (human)
choline metabolic processCholinesteraseHomo sapiens (human)
acetylcholine catabolic processCholinesteraseHomo sapiens (human)
acetylcholine catabolic process in synaptic cleftAcetylcholinesteraseHomo sapiens (human)
regulation of receptor recyclingAcetylcholinesteraseHomo sapiens (human)
osteoblast developmentAcetylcholinesteraseHomo sapiens (human)
acetylcholine catabolic processAcetylcholinesteraseHomo sapiens (human)
cell adhesionAcetylcholinesteraseHomo sapiens (human)
nervous system developmentAcetylcholinesteraseHomo sapiens (human)
synapse assemblyAcetylcholinesteraseHomo sapiens (human)
receptor internalizationAcetylcholinesteraseHomo sapiens (human)
negative regulation of synaptic transmission, cholinergicAcetylcholinesteraseHomo sapiens (human)
amyloid precursor protein metabolic processAcetylcholinesteraseHomo sapiens (human)
positive regulation of protein secretionAcetylcholinesteraseHomo sapiens (human)
retina development in camera-type eyeAcetylcholinesteraseHomo sapiens (human)
acetylcholine receptor signaling pathwayAcetylcholinesteraseHomo sapiens (human)
positive regulation of cold-induced thermogenesisAcetylcholinesteraseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (15)

Processvia Protein(s)Taxonomy
amyloid-beta bindingCholinesteraseHomo sapiens (human)
catalytic activityCholinesteraseHomo sapiens (human)
acetylcholinesterase activityCholinesteraseHomo sapiens (human)
cholinesterase activityCholinesteraseHomo sapiens (human)
protein bindingCholinesteraseHomo sapiens (human)
hydrolase activity, acting on ester bondsCholinesteraseHomo sapiens (human)
enzyme bindingCholinesteraseHomo sapiens (human)
choline bindingCholinesteraseHomo sapiens (human)
identical protein bindingCholinesteraseHomo sapiens (human)
amyloid-beta bindingAcetylcholinesteraseHomo sapiens (human)
acetylcholinesterase activityAcetylcholinesteraseHomo sapiens (human)
cholinesterase activityAcetylcholinesteraseHomo sapiens (human)
protein bindingAcetylcholinesteraseHomo sapiens (human)
collagen bindingAcetylcholinesteraseHomo sapiens (human)
hydrolase activityAcetylcholinesteraseHomo sapiens (human)
serine hydrolase activityAcetylcholinesteraseHomo sapiens (human)
acetylcholine bindingAcetylcholinesteraseHomo sapiens (human)
protein homodimerization activityAcetylcholinesteraseHomo sapiens (human)
laminin bindingAcetylcholinesteraseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (16)

Processvia Protein(s)Taxonomy
extracellular regionCholinesteraseHomo sapiens (human)
nuclear envelope lumenCholinesteraseHomo sapiens (human)
endoplasmic reticulum lumenCholinesteraseHomo sapiens (human)
blood microparticleCholinesteraseHomo sapiens (human)
plasma membraneCholinesteraseHomo sapiens (human)
extracellular spaceCholinesteraseHomo sapiens (human)
extracellular regionAcetylcholinesteraseHomo sapiens (human)
basement membraneAcetylcholinesteraseHomo sapiens (human)
extracellular spaceAcetylcholinesteraseHomo sapiens (human)
nucleusAcetylcholinesteraseHomo sapiens (human)
Golgi apparatusAcetylcholinesteraseHomo sapiens (human)
plasma membraneAcetylcholinesteraseHomo sapiens (human)
cell surfaceAcetylcholinesteraseHomo sapiens (human)
membraneAcetylcholinesteraseHomo sapiens (human)
neuromuscular junctionAcetylcholinesteraseHomo sapiens (human)
synaptic cleftAcetylcholinesteraseHomo sapiens (human)
synapseAcetylcholinesteraseHomo sapiens (human)
perinuclear region of cytoplasmAcetylcholinesteraseHomo sapiens (human)
side of membraneAcetylcholinesteraseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (19)

Assay IDTitleYearJournalArticle
AID1524947Selectivity index, ratio of IC50 for inhibition of AChE (unknown origin) to IC50 for inhibition of BChE (unknown origin)2019Bioorganic & medicinal chemistry letters, 05-15, Volume: 29, Issue:10
Bioactivity-guided identification of flavonoids with cholinesterase and β-amyloid peptide aggregation inhibitory effects from the seeds of Millettia pachycarpa.
AID1178590Antimigratory activity in HUVEC assessed as migration into wound area at 1 uM after 24 hrs relative to vehicle treated control2014Bioorganic & medicinal chemistry letters, Jul-15, Volume: 24, Issue:14
Synthesis, structure-activity relationships and biological evaluation of barbigerone analogues as anti-proliferative and anti-angiogenesis agents.
AID1524946Inhibition of BChE (unknown origin) using butyrylthiocholine iodide as substrate by spectrophotometry based Ellman's method2019Bioorganic & medicinal chemistry letters, 05-15, Volume: 29, Issue:10
Bioactivity-guided identification of flavonoids with cholinesterase and β-amyloid peptide aggregation inhibitory effects from the seeds of Millettia pachycarpa.
AID1524944Inhibition of BChE (unknown origin) at 20 ug/mL using butyrylthiocholine iodide as substrate by spectrophotometry based Ellman's method2019Bioorganic & medicinal chemistry letters, 05-15, Volume: 29, Issue:10
Bioactivity-guided identification of flavonoids with cholinesterase and β-amyloid peptide aggregation inhibitory effects from the seeds of Millettia pachycarpa.
AID1524943Inhibition of AChE (unknown origin) at 20 ug/mL using acetylthiocholine iodide as substrate by spectrophotometry based Ellman's method2019Bioorganic & medicinal chemistry letters, 05-15, Volume: 29, Issue:10
Bioactivity-guided identification of flavonoids with cholinesterase and β-amyloid peptide aggregation inhibitory effects from the seeds of Millettia pachycarpa.
AID1524945Inhibition of AChE (unknown origin) using acetylthiocholine iodide as substrate by spectrophotometry based Ellman's method2019Bioorganic & medicinal chemistry letters, 05-15, Volume: 29, Issue:10
Bioactivity-guided identification of flavonoids with cholinesterase and β-amyloid peptide aggregation inhibitory effects from the seeds of Millettia pachycarpa.
AID1178592Antiangiogenic activity against HUVEC assessed as inhibition of capillary-like tube formation at 5 uM after 8 hrs by Matrigel assay relative to control2014Bioorganic & medicinal chemistry letters, Jul-15, Volume: 24, Issue:14
Synthesis, structure-activity relationships and biological evaluation of barbigerone analogues as anti-proliferative and anti-angiogenesis agents.
AID1178589Antimigratory activity in HUVEC assessed as migration into wound area at 0.5 uM after 24 hrs relative to vehicle treated control2014Bioorganic & medicinal chemistry letters, Jul-15, Volume: 24, Issue:14
Synthesis, structure-activity relationships and biological evaluation of barbigerone analogues as anti-proliferative and anti-angiogenesis agents.
AID1178585Antiproliferative activity against mouse B16 cells after 24 hrs by MTT assay2014Bioorganic & medicinal chemistry letters, Jul-15, Volume: 24, Issue:14
Synthesis, structure-activity relationships and biological evaluation of barbigerone analogues as anti-proliferative and anti-angiogenesis agents.
AID1178591Antiangiogenic activity against HUVEC assessed as inhibition of capillary-like tube formation at 1 uM after 8 hrs by Matrigel assay relative to control2014Bioorganic & medicinal chemistry letters, Jul-15, Volume: 24, Issue:14
Synthesis, structure-activity relationships and biological evaluation of barbigerone analogues as anti-proliferative and anti-angiogenesis agents.
AID1524955Inhibition of amyloid beta (1 to 42) (unknown origin) self-aggregation at 80 uM incubated for 48 hrs by thioflavin-T fluorescence method2019Bioorganic & medicinal chemistry letters, 05-15, Volume: 29, Issue:10
Bioactivity-guided identification of flavonoids with cholinesterase and β-amyloid peptide aggregation inhibitory effects from the seeds of Millettia pachycarpa.
AID1178587Antiproliferative activity against HUVEC after 24 hrs by MTT assay2014Bioorganic & medicinal chemistry letters, Jul-15, Volume: 24, Issue:14
Synthesis, structure-activity relationships and biological evaluation of barbigerone analogues as anti-proliferative and anti-angiogenesis agents.
AID1524953Inhibition of amyloid beta (1 to 42) (unknown origin) self-aggregation at 20 uM incubated for 48 hrs by thioflavin-T fluorescence method2019Bioorganic & medicinal chemistry letters, 05-15, Volume: 29, Issue:10
Bioactivity-guided identification of flavonoids with cholinesterase and β-amyloid peptide aggregation inhibitory effects from the seeds of Millettia pachycarpa.
AID1178588Antiangiogenic activity in Flk-1-GFP transgenic zebrafish embryo after 24 hrs2014Bioorganic & medicinal chemistry letters, Jul-15, Volume: 24, Issue:14
Synthesis, structure-activity relationships and biological evaluation of barbigerone analogues as anti-proliferative and anti-angiogenesis agents.
AID1178584Antiproliferative activity against human U251 cells after 24 hrs by MTT assay2014Bioorganic & medicinal chemistry letters, Jul-15, Volume: 24, Issue:14
Synthesis, structure-activity relationships and biological evaluation of barbigerone analogues as anti-proliferative and anti-angiogenesis agents.
AID1178582Antiproliferative activity against human HepG2 cells after 24 hrs by MTT assay2014Bioorganic & medicinal chemistry letters, Jul-15, Volume: 24, Issue:14
Synthesis, structure-activity relationships and biological evaluation of barbigerone analogues as anti-proliferative and anti-angiogenesis agents.
AID1524954Inhibition of amyloid beta (1 to 42) (unknown origin) self-aggregation at 40 uM incubated for 48 hrs by thioflavin-T fluorescence method2019Bioorganic & medicinal chemistry letters, 05-15, Volume: 29, Issue:10
Bioactivity-guided identification of flavonoids with cholinesterase and β-amyloid peptide aggregation inhibitory effects from the seeds of Millettia pachycarpa.
AID1178586Antiproliferative activity against human HCT116 cells after 24 hrs by MTT assay2014Bioorganic & medicinal chemistry letters, Jul-15, Volume: 24, Issue:14
Synthesis, structure-activity relationships and biological evaluation of barbigerone analogues as anti-proliferative and anti-angiogenesis agents.
AID1178583Antiproliferative activity against human A375 cells after 24 hrs by MTT assay2014Bioorganic & medicinal chemistry letters, Jul-15, Volume: 24, Issue:14
Synthesis, structure-activity relationships and biological evaluation of barbigerone analogues as anti-proliferative and anti-angiogenesis agents.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (10)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (10.00)29.6817
2010's8 (80.00)24.3611
2020's1 (10.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 17.81

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 Index17.81 (24.57)
Research Supply Index2.40 (2.92)
Research Growth Index5.03 (4.65)
Search Engine Demand Index10.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (17.81)

All Compounds (24.57)

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%
Other10 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
galantamine
Galantamine: A benzazepine derived from norbelladine. It is found in GALANTHUS and other AMARYLLIDACEAE. It is a cholinesterase inhibitor that has been used to reverse the muscular effects of GALLAMINE TRIETHIODIDE and TUBOCURARINE and has been studied as a treatment for ALZHEIMER DISEASE and other central nervous system disorders.. galanthamine : A benzazepine alkaloid isolated from certain species of daffodils.		2.2110benzazepine alkaloid fundamental parent;
benzazepine alkaloid;
organic heterotetracyclic compound;
tertiary amino compound		antidote to curare poisoning;
cholinergic drug;
EC 3.1.1.7 (acetylcholinesterase) inhibitor;
EC 3.1.1.8 (cholinesterase) inhibitor;
plant metabolite
rotenolone
rotenolone: decomposition product of rotenone; RN given refers to (2 alpha,6a beta,12a beta)-isomer		2.2110organic molecular entitymetabolite
deguelin
deguelin: a natural product from Mundulea sericea; RN refers to (7aS-cis)-isomer; structure given in first source. deguelin : A rotenone that is 13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chromen-7(7aH)-one substituted by methoxy groups at positions 9 and 10, and by two methyl groups at position 3 (the 7aS,13aS-stereoisomer). It exists in abundant quantities in the bark, roots, and leaves of the Leguminosae family of plants and reported to exert anti-tumour effects in various cancers.		2.2110aromatic ether;
diether;
organic heteropentacyclic compound;
rotenones		angiogenesis inhibitor;
anti-inflammatory agent;
antineoplastic agent;
antiviral agent;
apoptosis inducer;
EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor;
mitochondrial NADH:ubiquinone reductase inhibitor;
plant metabolite
tephrosin
tephrosin: RN given for (7aR-cis)-isomer; has insecticidal activity; structure in first source. tephrosin : A member of the class of rotenones that is 13,13a-dihydro-3H-chromeno[3,4-b]pyrano[2,3-h]chromen-7(7aH)-one substituted with geminal methyl groups at position 3, hydroxy group at position 7a and methoxy groups at positions 9 and 10 (the 7aR,13aR stereoisomer). It is isolated from the leaves and twigs of Antheroporum pierrei and exhibits antineoplastic and pesticidal activities.		2.2110aromatic ether;
cyclic ketone;
organic heteropentacyclic compound;
rotenones		antineoplastic agent;
metabolite;
pesticide
betadex
beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.		2.110cyclodextrin
curcumin
Curcumin: A yellow-orange dye obtained from tumeric, the powdered root of CURCUMA longa. It is used in the preparation of curcuma paper and the detection of boron. Curcumin appears to possess a spectrum of pharmacological properties, due primarily to its inhibitory effects on metabolic enzymes.. curcumin : A beta-diketone that is methane in which two of the hydrogens are substituted by feruloyl groups. A natural dyestuff found in the root of Curcuma longa.		2.2110aromatic ether;
beta-diketone;
diarylheptanoid;
enone;
polyphenol		anti-inflammatory agent;
antifungal agent;
antineoplastic agent;
biological pigment;
contraceptive drug;
dye;
EC 1.1.1.205 (IMP dehydrogenase) inhibitor;
EC 1.1.1.21 (aldehyde reductase) inhibitor;
EC 1.1.1.25 (shikimate dehydrogenase) inhibitor;
EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor;
EC 1.8.1.9 (thioredoxin reductase) inhibitor;
EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor;
EC 3.5.1.98 (histone deacetylase) inhibitor;
flavouring agent;
food colouring;
geroprotector;
hepatoprotective agent;
immunomodulator;
iron chelator;
ligand;
lipoxygenase inhibitor;
metabolite;
neuroprotective agent;
nutraceutical;
radical scavenger
4-hydroxylonchocarpin
4-hydroxylonchocarpin: structure in first source		2.2110
4-Methoxylonchocarpin
[no description available]		2.2110chalcones
cytochrome c-t
Cytochromes c: Cytochromes of the c type that are found in eukaryotic MITOCHONDRIA. They serve as redox intermediates that accept electrons from MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX III and transfer them to MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX IV.		2.0510
ConditionIndicatedRelationship StrengthStudiesTrials
Breast Cancer
[description not available]		02.1710
Breast Neoplasms
Tumors or cancer of the human BREAST.		02.1710
Cancer of Lung
[description not available]		02.7630
B16 Melanoma
[description not available]		02.110
Angiogenesis, Pathologic
[description not available]		02.4920
Lung Neoplasms
Tumors or cancer of the LUNG.		02.7630
Adjuvant Arthritis
[description not available]		02.110
Carcinoma, Non-Small Cell Lung
[description not available]		02.0710
Carcinoma, Non-Small-Cell Lung
A heterogeneous aggregate of at least three distinct histological types of lung cancer, including SQUAMOUS CELL CARCINOMA; ADENOCARCINOMA; and LARGE CELL CARCINOMA. They are dealt with collectively because of their shared treatment strategy.		02.0710