Page last updated: 2024-11-06

medicagenic acid

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Description

Medicagenic acid is a naturally occurring triterpenoid saponin found in plants of the genus *Medicago*, such as alfalfa (*Medicago sativa*). It has been shown to possess various biological activities, including anti-inflammatory, anti-cancer, and immunomodulatory effects. Research suggests that medicagenic acid might act as a selective inhibitor of NF-κB, a key transcription factor involved in inflammation. This inhibition contributes to its anti-inflammatory properties. The compound's potential anti-cancer effects are linked to its ability to induce apoptosis in cancer cells. Medicagenic acid is also investigated for its immunomodulatory potential, as it can influence the activity of immune cells like macrophages and lymphocytes. The structural complexity and diverse biological activities of medicagenic acid make it a promising candidate for further investigation as a potential therapeutic agent in various diseases.'

medicagenic acid: aglycone constituent of lucerne saponins, upon which their fungastatic & hemolytic activity depends [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID65048
CHEMBL ID520726
CHEBI ID167977
SCHEMBL ID1050033
MeSH IDM0047910

Synonyms (32)

Synonym
NCI60_003635
(2s,3r,4s,4ar,6ar,6bs,8as,12as,14ar,14br)-2,3-dihydroxy-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4,8a-dicarboxylic acid
olean-12-ene-23,28-dioic acid, 2,3-dihydroxy-, (2.beta.,3.beta.,4.alpha.)-
medicagenic acid
NSC382024 ,
nsc-382024
olean-12-ene-23, 2,3-dihydroxy-, (2.beta.,3.beta.4.alpha.)-
599-07-5
nsc 382024
ccris 6615
2-beta,3-beta-dihydroxyolean-12-ene-23,28-dioic acid
CHEBI:167977
CHEMBL520726 ,
S3305
7x05537i17 ,
unii-7x05537i17
SCHEMBL1050033
(4s)-2beta,3beta-dihydroxyolean-12-ene-23,28-dioic acid
LMPR0106150034
castanogenin
medicagenicacid
AC-34519
medicagensaure
medicogenic acid
CS-0022742
HY-N2472
AKOS032946034
mfcd02752364
Q27268960
MS-29340
bdbm50531256
DTXSID301032043
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
triterpenoidAny terpenoid derived from a triterpene. The term includes compounds in which the C30 skeleton of the parent triterpene has been rearranged or modified by the removal of one or more skeletal atoms (generally methyl groups).
[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)
Polyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)IC50 (µMol)30.40000.00011.68479.3200AID1617774
Prostaglandin G/H synthase 2Homo sapiens (human)IC50 (µMol)40.00000.00010.995010.0000AID1617780
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (88)

Processvia Protein(s)Taxonomy
negative regulation of endothelial cell proliferationPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
leukocyte chemotaxis involved in inflammatory responsePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
leukocyte migration involved in inflammatory responsePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
leukotriene production involved in inflammatory responsePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
leukotriene metabolic processPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
humoral immune responsePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
negative regulation of angiogenesisPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
leukotriene biosynthetic processPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
lipoxygenase pathwayPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
positive regulation of bone mineralizationPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
dendritic cell migrationPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
glucose homeostasisPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
long-chain fatty acid biosynthetic processPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
regulation of fat cell differentiationPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
regulation of inflammatory responsePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
negative regulation of inflammatory responsePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
regulation of insulin secretionPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
negative regulation of vascular wound healingPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
negative regulation of wound healingPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
regulation of inflammatory response to woundingPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
regulation of cytokine production involved in inflammatory responsePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
regulation of cellular response to oxidative stressPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
leukotriene A4 biosynthetic processPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
regulation of reactive oxygen species biosynthetic processPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
negative regulation of response to endoplasmic reticulum stressPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
negative regulation of sprouting angiogenesisPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
positive regulation of leukocyte adhesion to arterial endothelial cellPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
lipoxin biosynthetic processPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
arachidonic acid metabolic processPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
lipid oxidationPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
prostaglandin biosynthetic processProstaglandin G/H synthase 2Homo sapiens (human)
angiogenesisProstaglandin G/H synthase 2Homo sapiens (human)
response to oxidative stressProstaglandin G/H synthase 2Homo sapiens (human)
embryo implantationProstaglandin G/H synthase 2Homo sapiens (human)
learningProstaglandin G/H synthase 2Homo sapiens (human)
memoryProstaglandin G/H synthase 2Homo sapiens (human)
regulation of blood pressureProstaglandin G/H synthase 2Homo sapiens (human)
negative regulation of cell population proliferationProstaglandin G/H synthase 2Homo sapiens (human)
response to xenobiotic stimulusProstaglandin G/H synthase 2Homo sapiens (human)
response to nematodeProstaglandin G/H synthase 2Homo sapiens (human)
response to fructoseProstaglandin G/H synthase 2Homo sapiens (human)
response to manganese ionProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of vascular endothelial growth factor productionProstaglandin G/H synthase 2Homo sapiens (human)
cyclooxygenase pathwayProstaglandin G/H synthase 2Homo sapiens (human)
bone mineralizationProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of prostaglandin biosynthetic processProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of fever generationProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of synaptic plasticityProstaglandin G/H synthase 2Homo sapiens (human)
negative regulation of synaptic transmission, dopaminergicProstaglandin G/H synthase 2Homo sapiens (human)
prostaglandin secretionProstaglandin G/H synthase 2Homo sapiens (human)
response to estradiolProstaglandin G/H synthase 2Homo sapiens (human)
response to lipopolysaccharideProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of peptidyl-serine phosphorylationProstaglandin G/H synthase 2Homo sapiens (human)
response to vitamin DProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to heatProstaglandin G/H synthase 2Homo sapiens (human)
response to tumor necrosis factorProstaglandin G/H synthase 2Homo sapiens (human)
maintenance of blood-brain barrierProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of protein import into nucleusProstaglandin G/H synthase 2Homo sapiens (human)
hair cycleProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of apoptotic processProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of nitric oxide biosynthetic processProstaglandin G/H synthase 2Homo sapiens (human)
negative regulation of cell cycleProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of vasoconstrictionProstaglandin G/H synthase 2Homo sapiens (human)
negative regulation of smooth muscle contractionProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of smooth muscle contractionProstaglandin G/H synthase 2Homo sapiens (human)
decidualizationProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of smooth muscle cell proliferationProstaglandin G/H synthase 2Homo sapiens (human)
regulation of inflammatory responseProstaglandin G/H synthase 2Homo sapiens (human)
brown fat cell differentiationProstaglandin G/H synthase 2Homo sapiens (human)
response to glucocorticoidProstaglandin G/H synthase 2Homo sapiens (human)
negative regulation of calcium ion transportProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of synaptic transmission, glutamatergicProstaglandin G/H synthase 2Homo sapiens (human)
response to fatty acidProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to mechanical stimulusProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to lead ionProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to ATPProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to hypoxiaProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to non-ionic osmotic stressProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to fluid shear stressProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of transforming growth factor beta productionProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of cell migration involved in sprouting angiogenesisProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of fibroblast growth factor productionProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of brown fat cell differentiationProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of platelet-derived growth factor productionProstaglandin G/H synthase 2Homo sapiens (human)
cellular oxidant detoxificationProstaglandin G/H synthase 2Homo sapiens (human)
regulation of neuroinflammatory responseProstaglandin G/H synthase 2Homo sapiens (human)
negative regulation of intrinsic apoptotic signaling pathway in response to osmotic stressProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to homocysteineProstaglandin G/H synthase 2Homo sapiens (human)
response to angiotensinProstaglandin G/H synthase 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (13)

Processvia Protein(s)Taxonomy
arachidonate 5-lipoxygenase activityPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
arachidonate 12(S)-lipoxygenase activityPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
iron ion bindingPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
protein bindingPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
hydrolase activityPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
arachidonate 8(S)-lipoxygenase activityPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
peroxidase activityProstaglandin G/H synthase 2Homo sapiens (human)
prostaglandin-endoperoxide synthase activityProstaglandin G/H synthase 2Homo sapiens (human)
protein bindingProstaglandin G/H synthase 2Homo sapiens (human)
enzyme bindingProstaglandin G/H synthase 2Homo sapiens (human)
heme bindingProstaglandin G/H synthase 2Homo sapiens (human)
protein homodimerization activityProstaglandin G/H synthase 2Homo sapiens (human)
metal ion bindingProstaglandin G/H synthase 2Homo sapiens (human)
oxidoreductase activity, acting on single donors with incorporation of molecular oxygen, incorporation of two atoms of oxygenProstaglandin G/H synthase 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (20)

Processvia Protein(s)Taxonomy
extracellular regionPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
extracellular spacePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
nuclear envelopePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
nuclear envelope lumenPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
nucleoplasmPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
cytosolPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
nuclear matrixPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
nuclear membranePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
secretory granule lumenPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
perinuclear region of cytoplasmPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
ficolin-1-rich granule lumenPolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
nuclear envelopePolyunsaturated fatty acid 5-lipoxygenaseHomo sapiens (human)
nuclear inner membraneProstaglandin G/H synthase 2Homo sapiens (human)
nuclear outer membraneProstaglandin G/H synthase 2Homo sapiens (human)
cytoplasmProstaglandin G/H synthase 2Homo sapiens (human)
endoplasmic reticulumProstaglandin G/H synthase 2Homo sapiens (human)
endoplasmic reticulum lumenProstaglandin G/H synthase 2Homo sapiens (human)
endoplasmic reticulum membraneProstaglandin G/H synthase 2Homo sapiens (human)
caveolaProstaglandin G/H synthase 2Homo sapiens (human)
neuron projectionProstaglandin G/H synthase 2Homo sapiens (human)
protein-containing complexProstaglandin G/H synthase 2Homo sapiens (human)
neuron projectionProstaglandin G/H synthase 2Homo sapiens (human)
cytoplasmProstaglandin G/H synthase 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (12)

Assay IDTitleYearJournalArticle
AID1617781Inhibition of human recombinant COX2 expressed in baculovirus infected sf21 cells assessed as residual activity at 42 uM using arachidonic acid as substrate preincubated for 10 mins followed by substrate addition measured after 45 mins by LC-MS analysis r2019Journal of natural products, 12-27, Volume: 82, Issue:12
Structure-Activity Relationships of Pentacyclic Triterpenoids as Inhibitors of Cyclooxygenase and Lipoxygenase Enzymes.
AID1617780Inhibition of human recombinant COX2 expressed in baculovirus infected sf21 cells assessed as decrease in PGE2 formation using arachidonic acid as substrate preincubated for 10 mins followed by substrate addition measured after 45 mins by LC-MS analysis2019Journal of natural products, 12-27, Volume: 82, Issue:12
Structure-Activity Relationships of Pentacyclic Triterpenoids as Inhibitors of Cyclooxygenase and Lipoxygenase Enzymes.
AID1617779Inhibition of ovine recombinant COX1 assessed as residual activity at 42 uM using arachidonic acid as substrate preincubated for 10 mins followed by substrate addition measured after 45 mins by LC-MS analysis2019Journal of natural products, 12-27, Volume: 82, Issue:12
Structure-Activity Relationships of Pentacyclic Triterpenoids as Inhibitors of Cyclooxygenase and Lipoxygenase Enzymes.
AID365156Binding affinity to photoactivated rhodopsin in bovine retinal rod outer-segment membranes assessed as induction of extra receptor MII state stabilization at 250 uM by UV/visible difference spectroscopy2008Journal of medicinal chemistry, Sep-11, Volume: 51, Issue:17
Modulating G-protein coupled receptor/G-protein signal transduction by small molecules suggested by virtual screening.
AID1617778Inhibition of ovine recombinant COX1 assessed as decrease in formation of PGE2 using arachidonic acid as substrate preincubated for 10 mins followed by substrate addition measured after 45 mins by LC-MS analysis2019Journal of natural products, 12-27, Volume: 82, Issue:12
Structure-Activity Relationships of Pentacyclic Triterpenoids as Inhibitors of Cyclooxygenase and Lipoxygenase Enzymes.
AID1617777Inhibition of human recombinant N-terminal His-tagged 15-LOX2 expressed in Escherichia coli assessed as residual activity at 42 uM using arachidonic acid as substrate preincubated for 5 mins followed by substrate addition measured after 20 mins in dark by2019Journal of natural products, 12-27, Volume: 82, Issue:12
Structure-Activity Relationships of Pentacyclic Triterpenoids as Inhibitors of Cyclooxygenase and Lipoxygenase Enzymes.
AID1651392Neuroprotective activity against H2O2-induced cell death in human SH-SY5Y cells assessed as cell viability at 50 uM preincubated for 1 hr followed by H2O2 addition and measured after 4 hrs by CCK8 assay (Rvb = 61.14 +/- 1.05%)2020Bioorganic & medicinal chemistry letters, 02-15, Volume: 30, Issue:4
Isolation of triterpenoid saponins from Medicago sativa L. with neuroprotective activities.
AID1617776Inhibition of human recombinant N-terminal His-tagged 15-LOX2 expressed in Escherichia coli using arachidonic acid as substrate preincubated for 5 mins followed by substrate addition measured after 20 mins in dark by ferric ion oxidation-xylenol orange as2019Journal of natural products, 12-27, Volume: 82, Issue:12
Structure-Activity Relationships of Pentacyclic Triterpenoids as Inhibitors of Cyclooxygenase and Lipoxygenase Enzymes.
AID1651393Neuroprotective activity against H2O2-induced cell death in human SH-SY5Y cells assessed as cell viability at 100 uM preincubated for 1 hr followed by H2O2 addition and measured after 4 hrs by CCK8 assay (Rvb = 61.14 +/- 1.05%)2020Bioorganic & medicinal chemistry letters, 02-15, Volume: 30, Issue:4
Isolation of triterpenoid saponins from Medicago sativa L. with neuroprotective activities.
AID1617775Inhibition of human recombinant 5-LOX expressed in insect cells assessed residual activity using arachidonic acid at 42 uM as substrate preincubated for 5 mins followed by substrate addition measured after 20 mins in dark by ferric ion oxidation-xylenol o2019Journal of natural products, 12-27, Volume: 82, Issue:12
Structure-Activity Relationships of Pentacyclic Triterpenoids as Inhibitors of Cyclooxygenase and Lipoxygenase Enzymes.
AID1617774Inhibition of human recombinant 5-LOX expressed in insect cells assessed as decrease in production of 5-HPETE and 5-HETE using arachidonic acid as substrate preincubated for 5 mins followed by substrate addition measured after 20 mins in dark by ferric io2019Journal of natural products, 12-27, Volume: 82, Issue:12
Structure-Activity Relationships of Pentacyclic Triterpenoids as Inhibitors of Cyclooxygenase and Lipoxygenase Enzymes.
AID1651391Neuroprotective activity against H2O2-induced cell death in human SH-SY5Y cells assessed as cell viability at 25 uM preincubated for 1 hr followed by H2O2 addition and measured after 4 hrs by CCK8 assay (Rvb = 61.14 +/- 1.05%)2020Bioorganic & medicinal chemistry letters, 02-15, Volume: 30, Issue:4
Isolation of triterpenoid saponins from Medicago sativa L. with neuroprotective activities.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (23)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (13.04)18.7374
1990's6 (26.09)18.2507
2000's3 (13.04)29.6817
2010's8 (34.78)24.3611
2020's3 (13.04)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 23.51

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 Index23.51 (24.57)
Research Supply Index3.18 (2.92)
Research Growth Index5.05 (4.65)
Search Engine Demand Index23.28 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (23.51)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (8.70%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other21 (91.30%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]