Page last updated: 2024-11-12

2,4,3',5'-tetrahydroxystilbene

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

Description

oleocanthal: newly pressed extra-virgin olive oil contains oleocanthal, acting as a natural anti-inflammatory compound that has a potency and profile strikingly similar to that of ibuprofen; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

oleocanthal : A carboxylic ester that is the 2-(p-hydroxyphenyl)ethyl ester of (3S)-4-formyl-3-(2-oxoethyl)hex-4-enoic acid. Oleocanthal is found in olive oil but it is not clear whether the natural product is a mixture of E/Z isomers or a single isomer as the two isomers readily interconvert in solution; most pharmacological studies will have been performed using a mixture. [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 CID11652416
CHEMBL ID2172394
CHEBI ID85673
SCHEMBL ID137158
MeSH IDM0396164

Synonyms (32)

Synonym
2-(4-hydroxyphenyl)ethyl (e,3s)-4-formyl-3-(2-oxoethyl)hex-4-enoate
CHEMBL2172394
nsc752227
nsc-752227
(-)-oleocanthal
bdbm50431471
289030-99-5
deacetoxy-oleuropein aglycone
oleocanthal
gtpl6308
oleocanthal [inci]
oleocanthal [mi]
oleocanthal, (-)-
1246025-97-7
SCHEMBL137158
ac7qo6038o ,
deacetoxy ligstroside aglycon
4-hexenoic acid, 4-formyl-3-(2-oxoethyl)-, 2-(4-hydroxyphenyl)ethyl ester, (3s,4e)-
(3s,4e)-4-formyl-3-(2-oxoethyl)-4-hexenoic acid 2-(4-hydroxyphenyl)ethyl ester
unii-ac7qo6038o
2-(4-hydroxyphenyl)ethyl (3s,4e)-4-formyl-3-(2-oxoethyl)hex-4-enoate
(-)-deacetoxy ligstroside aglycone
(-)-deacetoxy ligstroside aglycon
CHEBI:85673
deacetoxy ligstroside aglycone
2-(4-hydroxyphenyl)ethyl (3s)-4-formyl-3-(2-oxoethyl)hex-4-enoate
DTXSID40183104
AKOS030530189
Q402613
XO162076
oxyresveratrol (cis-)
(s,e)-4-hydroxyphenethyl4-formyl-3-(2-oxoethyl)hex-4-enoate

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" However, the ability of oleocanthal to alter the toxic effect of Aβ on brain parenchymal cells is unknown."( Oleocanthal ameliorates amyloid-β oligomers' toxicity on astrocytes and neuronal cells: In vitro studies.
Al Rihani, SB; Batarseh, YS; El Sayed, KA; Kaddoumi, A; Mohamed, LA; Mousa, YM; Siddique, AB, 2017
)
0.46

Bioavailability

ExcerptReferenceRelevance
" In addition the concentration, metabolism and bioavailability of specific phenolic compounds will be discussed."( The Health Benefiting Mechanisms of Virgin Olive Oil Phenolic Compounds.
Cicerale, S; Parkinson, L, 2016
)
0.43
" Being of relevance to the clinical effects of EVOO intake, the bioavailability and biotransformation of EVOO polyphenols are addressed."( Natural Molecules for Healthy Lifestyles: Oleocanthal from Extra Virgin Olive Oil.
Francisco, V; Gómez, R; González-Gay, MA; Gualillo, O; Lago, F; Lahera, V; Mobasheri, A; Pino, J; Ruiz-Fernández, C; Scotece, M; Skaltsounis, L, 2019
)
0.51
" Data on OLC and OLE bioavailability are scarce, as most research on EVOO polyphenols has concentrated on hydroxytyrosol, tyrosol, and oleuropein."( Health-promoting properties of oleocanthal and oleacein: Two secoiridoids from extra-virgin olive oil.
Escribano-Ferrer, E; Lamuela-Raventós, RM; López-Yerena, A; Lozano-Castellón, J; Rinaldi de Alvarenga, JF; Romero Del Castillo-Alba, J; Vallverdú-Queralt, A, 2020
)
0.56
" Also discussed are OLC bioavailability and its concentration in olive oil."( Anticancer molecular mechanisms of oleocanthal.
El Haouari, M; Quintero, JE; Rosado, JA, 2020
)
0.56
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Hepatocyte growth factor receptorHomo sapiens (human)IC50 (µMol)5.15000.00040.372210.0000AID1710748; AID740157
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (27)

Processvia Protein(s)Taxonomy
endothelial cell morphogenesisHepatocyte growth factor receptorHomo sapiens (human)
signal transductionHepatocyte growth factor receptorHomo sapiens (human)
cell surface receptor signaling pathwayHepatocyte growth factor receptorHomo sapiens (human)
negative regulation of autophagyHepatocyte growth factor receptorHomo sapiens (human)
positive regulation of microtubule polymerizationHepatocyte growth factor receptorHomo sapiens (human)
negative regulation of Rho protein signal transductionHepatocyte growth factor receptorHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIHepatocyte growth factor receptorHomo sapiens (human)
hepatocyte growth factor receptor signaling pathwayHepatocyte growth factor receptorHomo sapiens (human)
branching morphogenesis of an epithelial tubeHepatocyte growth factor receptorHomo sapiens (human)
positive chemotaxisHepatocyte growth factor receptorHomo sapiens (human)
negative regulation of stress fiber assemblyHepatocyte growth factor receptorHomo sapiens (human)
excitatory postsynaptic potentialHepatocyte growth factor receptorHomo sapiens (human)
establishment of skin barrierHepatocyte growth factor receptorHomo sapiens (human)
negative regulation of thrombin-activated receptor signaling pathwayHepatocyte growth factor receptorHomo sapiens (human)
semaphorin-plexin signaling pathwayHepatocyte growth factor receptorHomo sapiens (human)
negative regulation of hydrogen peroxide-mediated programmed cell deathHepatocyte growth factor receptorHomo sapiens (human)
negative regulation of guanyl-nucleotide exchange factor activityHepatocyte growth factor receptorHomo sapiens (human)
positive regulation of endothelial cell chemotaxisHepatocyte growth factor receptorHomo sapiens (human)
liver developmentHepatocyte growth factor receptorHomo sapiens (human)
cell surface receptor protein tyrosine kinase signaling pathwayHepatocyte growth factor receptorHomo sapiens (human)
phagocytosisHepatocyte growth factor receptorHomo sapiens (human)
multicellular organism developmentHepatocyte growth factor receptorHomo sapiens (human)
neuron differentiationHepatocyte growth factor receptorHomo sapiens (human)
positive regulation of kinase activityHepatocyte growth factor receptorHomo sapiens (human)
cell migrationHepatocyte growth factor receptorHomo sapiens (human)
pancreas developmentHepatocyte growth factor receptorHomo sapiens (human)
nervous system developmentHepatocyte growth factor receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
protein tyrosine kinase activityHepatocyte growth factor receptorHomo sapiens (human)
protein bindingHepatocyte growth factor receptorHomo sapiens (human)
ATP bindingHepatocyte growth factor receptorHomo sapiens (human)
semaphorin receptor activityHepatocyte growth factor receptorHomo sapiens (human)
protein phosphatase bindingHepatocyte growth factor receptorHomo sapiens (human)
identical protein bindingHepatocyte growth factor receptorHomo sapiens (human)
molecular function activator activityHepatocyte growth factor receptorHomo sapiens (human)
hepatocyte growth factor receptor activityHepatocyte growth factor receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (7)

Processvia Protein(s)Taxonomy
extracellular regionHepatocyte growth factor receptorHomo sapiens (human)
plasma membraneHepatocyte growth factor receptorHomo sapiens (human)
basal plasma membraneHepatocyte growth factor receptorHomo sapiens (human)
cell surfaceHepatocyte growth factor receptorHomo sapiens (human)
membraneHepatocyte growth factor receptorHomo sapiens (human)
postsynapseHepatocyte growth factor receptorHomo sapiens (human)
basal plasma membraneHepatocyte growth factor receptorHomo sapiens (human)
plasma membraneHepatocyte growth factor receptorHomo sapiens (human)
receptor complexHepatocyte growth factor receptorHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (19)

Assay IDTitleYearJournalArticle
AID740163Antiinvasive activity against human MDA-MB-231 cells at 10 to 20 uM after 24 hrs by Cultrex BME assay2013Bioorganic & medicinal chemistry, Apr-01, Volume: 21, Issue:7
Olive secoiridoids and semisynthetic bioisostere analogues for the control of metastatic breast cancer.
AID703469Binding affinity to human recombinant Tau 2N4R expressed in Escherichia coli assessed as change in protein conformation at 10 mM measured for 60 mins by H/D exchange mass spectrometric analysis2012Journal of natural products, Sep-28, Volume: 75, Issue:9
Modulation of tau protein fibrillization by oleocanthal.
AID1710745Inhibition of recombinant human His-tagged c-MET expressed in baculovirus expression system assessed as reduction in c-MET phosphorylation at 5 uM using Tyr6 as substrate incubated for 1 hr by Z'-lyte assay relative to control2016Bioorganic & medicinal chemistry, Jan-15, Volume: 24, Issue:2
The indole alkaloid meleagrin, from the olive tree endophytic fungus Penicillium chrysogenum, as a novel lead for the control of c-Met-dependent breast cancer proliferation, migration and invasion.
AID740159Cytotoxicity against human MCF10A cells at IC50 in wound healing assay after 24 hrs by MTT assay2013Bioorganic & medicinal chemistry, Apr-01, Volume: 21, Issue:7
Olive secoiridoids and semisynthetic bioisostere analogues for the control of metastatic breast cancer.
AID1073064Inhibition of human recombinant 5-lipoxygenase expressed in Escherichia coli Bl21 (DE3) using arachidonic acid as substrate preincubated at 10 uM for 10 mins before substrate addition measured after 10 mins by HPLC analysis2014Journal of natural products, Mar-28, Volume: 77, Issue:3
One-step semisynthesis of oleacein and the determination as a 5-lipoxygenase inhibitor.
AID740165Antimigratory activity against human MDA-MB-231 cells at 10 uM after 24 hrs by wound healing assay2013Bioorganic & medicinal chemistry, Apr-01, Volume: 21, Issue:7
Olive secoiridoids and semisynthetic bioisostere analogues for the control of metastatic breast cancer.
AID740168Antimigratory activity against human MDA-MB-231 cells after 24 hrs by wound healing assay2013Bioorganic & medicinal chemistry, Apr-01, Volume: 21, Issue:7
Olive secoiridoids and semisynthetic bioisostere analogues for the control of metastatic breast cancer.
AID740152Competitive inhibition of c-MET phosphorylation (unknown origin) after 60 mins by Omnia kinase assay2013Bioorganic & medicinal chemistry, Apr-01, Volume: 21, Issue:7
Olive secoiridoids and semisynthetic bioisostere analogues for the control of metastatic breast cancer.
AID1710746Inhibition of recombinant human His-tagged c-MET expressed in baculovirus expression system assessed as reduction in c-MET phosphorylation at 10 uM using Tyr6 as substrate incubated for 1 hr by Z'-lyte assay relative to control2016Bioorganic & medicinal chemistry, Jan-15, Volume: 24, Issue:2
The indole alkaloid meleagrin, from the olive tree endophytic fungus Penicillium chrysogenum, as a novel lead for the control of c-Met-dependent breast cancer proliferation, migration and invasion.
AID740157Inhibition of c-MET phosphorylation (unknown origin) after 1 hr by Z'-LYTE kinase assay2013Bioorganic & medicinal chemistry, Apr-01, Volume: 21, Issue:7
Olive secoiridoids and semisynthetic bioisostere analogues for the control of metastatic breast cancer.
AID703471Inhibition of arachidonic acid-induced human recombinant Tau 2N4R fibrillation expressed in Escherichia coli assessed as alpha helix formation at 125 uM preincubated for 1 hr prior to arachidonic acid challenge measured 28 hrs post arachidonic challenge b2012Journal of natural products, Sep-28, Volume: 75, Issue:9
Modulation of tau protein fibrillization by oleocanthal.
AID1710748Inhibition of recombinant human His-tagged c-MET expressed in baculovirus expression system assessed as reduction in c-MET phosphorylation using Tyr6 as substrate incubated for 1 hr by Z'-lyte assay2016Bioorganic & medicinal chemistry, Jan-15, Volume: 24, Issue:2
The indole alkaloid meleagrin, from the olive tree endophytic fungus Penicillium chrysogenum, as a novel lead for the control of c-Met-dependent breast cancer proliferation, migration and invasion.
AID703470Inhibition of arachidonic acid-induced human recombinant Tau 2N4R fibrillation expressed in Escherichia coli preincubated for 1 hr prior to arachidonic acid challenge measured 6 hrs post arachidonic challenge by Thioflavin-S fluorescence assay2012Journal of natural products, Sep-28, Volume: 75, Issue:9
Modulation of tau protein fibrillization by oleocanthal.
AID703468Binding affinity to human recombinant Tau 2N4R expressed in Escherichia coli at 0.1 to 2.5 uM by SPR analysis2012Journal of natural products, Sep-28, Volume: 75, Issue:9
Modulation of tau protein fibrillization by oleocanthal.
AID740160Cytotoxicity against human MDA-MB-231 cells after 24 hrs by MTT assay2013Bioorganic & medicinal chemistry, Apr-01, Volume: 21, Issue:7
Olive secoiridoids and semisynthetic bioisostere analogues for the control of metastatic breast cancer.
AID740156Inhibition of c-MET phosphorylation (unknown origin) at 10 uM after 1 hr by Z'-LYTE kinase assay2013Bioorganic & medicinal chemistry, Apr-01, Volume: 21, Issue:7
Olive secoiridoids and semisynthetic bioisostere analogues for the control of metastatic breast cancer.
AID703472Inhibition of human recombinant Tau 2N4R fibrillation expressed in Escherichia coli assessed as alpha helix formation at 125 uM after 1 hr by CD spectroscopic analysis2012Journal of natural products, Sep-28, Volume: 75, Issue:9
Modulation of tau protein fibrillization by oleocanthal.
AID740158Cytotoxicity against human MCF10A cells at IC50 in MDA-MB-231 MTT assay after 24 hrs by MTT assay2013Bioorganic & medicinal chemistry, Apr-01, Volume: 21, Issue:7
Olive secoiridoids and semisynthetic bioisostere analogues for the control of metastatic breast cancer.
AID1346556Human TRPA1 (Transient Receptor Potential channels)2011The Journal of neuroscience : the official journal of the Society for Neuroscience, Jan-19, Volume: 31, Issue:3
Unusual pungency from extra-virgin olive oil is attributable to restricted spatial expression of the receptor of oleocanthal.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (113)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's10 (8.85)29.6817
2010's65 (57.52)24.3611
2020's38 (33.63)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.72

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

MetricThis Compound (vs All)
Research Demand Index10.72 (24.57)
Research Supply Index4.75 (2.92)
Research Growth Index5.47 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.72)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (1.77%)5.53%
Reviews14 (12.39%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other97 (85.84%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]