Page last updated: 2024-11-13

epi-maslinic acid

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

Description

epi-maslinic acid : A pentacyclic triterpenoid that is 3alpha-hydroxy epimer of maslinic acid. Isolated from Prunella vulgaris and Isodon japonicus, it exhibits anti-inflammatory activity. [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
PrunellagenusA plant genus of the family LAMIACEAE. Members contain TRITERPENES. Heal all is another common name.[MeSH]LamiaceaeThe mint plant family. They are characteristically aromatic, and many of them are cultivated for their oils. Most have square stems, opposite leaves, and two-lipped, open-mouthed, tubular corollas (united petals), with five-lobed, bell-like calyxes (united sepals).[MeSH]
IsodongenusA plant genus of the family LAMIACEAE used in TRADITIONAL CHINESE MEDICINE.[MeSH]LamiaceaeThe mint plant family. They are characteristically aromatic, and many of them are cultivated for their oils. Most have square stems, opposite leaves, and two-lipped, open-mouthed, tubular corollas (united petals), with five-lobed, bell-like calyxes (united sepals).[MeSH]
Prunella vulgarisspecies[no description available]LamiaceaeThe mint plant family. They are characteristically aromatic, and many of them are cultivated for their oils. Most have square stems, opposite leaves, and two-lipped, open-mouthed, tubular corollas (united petals), with five-lobed, bell-like calyxes (united sepals).[MeSH]
Isodon japonicusspecies[no description available]LamiaceaeThe mint plant family. They are characteristically aromatic, and many of them are cultivated for their oils. Most have square stems, opposite leaves, and two-lipped, open-mouthed, tubular corollas (united petals), with five-lobed, bell-like calyxes (united sepals).[MeSH]

Cross-References

ID SourceID
PubMed CID25564831
CHEMBL ID383749
CHEBI ID66683
SCHEMBL ID5797455

Synonyms (19)

Synonym
2,3-dihydroxy-12-oleanen-28-oic acid
CHEMBL383749 ,
chebi:66683 ,
3-epimaslinic acid
3-epi-maslinic acid
3-epi-masilinic acid
bdbm50175873
(2alpha,3alpha)-2,3-dihydroxyolean-12-en-28-oic acid
epi-maslinic acid
LMPR0106150030
SCHEMBL5797455
Q27135304
FS-9686
DTXSID201315975
HY-N1827
CS-0017681
PD181373
(4as,6ar,6as,6br,8ar,10s,11r,12ar,14bs)-10,11-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
AKOS040760980
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
anti-inflammatory agentAny compound that has anti-inflammatory effects.
[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 (2)

ClassDescription
dihydroxy monocarboxylic acidAny hydroxy monocarboxylic acid carrying at least two hydroxy groups.
pentacyclic triterpenoid
[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 (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Glycogen phosphorylase, muscle formOryctolagus cuniculus (rabbit)IC50 (µMol)144.18130.01405.93249.0000AID404873; AID603224
Tyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)IC50 (µMol)14.33000.00053.49849.7600AID437763
Tyrosyl-DNA phosphodiesterase 1Homo sapiens (human)IC50 (µMol)100.00000.01203.32138.4300AID1662670
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (30)

Processvia Protein(s)Taxonomy
positive regulation of JUN kinase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein dephosphorylationTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
insulin receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of signal transductionTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of signal transductionTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
actin cytoskeleton organizationTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of endocytosisTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of vascular endothelial growth factor receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
endoplasmic reticulum unfolded protein responseTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of intracellular protein transportTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cellular response to unfolded proteinTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
peptidyl-tyrosine dephosphorylationTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
platelet-derived growth factor receptor-beta signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
IRE1-mediated unfolded protein responseTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
insulin receptor recyclingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of MAP kinase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of insulin receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of type I interferon-mediated signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
growth hormone receptor signaling pathway via JAK-STATTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
positive regulation of protein tyrosine kinase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of ERK1 and ERK2 cascadeTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of hepatocyte growth factor receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of endoplasmic reticulum stress-induced intrinsic apoptotic signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
positive regulation of IRE1-mediated unfolded protein responseTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of PERK-mediated unfolded protein responseTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
peptidyl-tyrosine dephosphorylation involved in inactivation of protein kinase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
positive regulation of receptor catabolic processTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
single strand break repairTyrosyl-DNA phosphodiesterase 1Homo sapiens (human)
DNA repairTyrosyl-DNA phosphodiesterase 1Homo sapiens (human)
double-strand break repairTyrosyl-DNA phosphodiesterase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (16)

Processvia Protein(s)Taxonomy
RNA bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein tyrosine phosphatase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
insulin receptor bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
zinc ion bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
enzyme bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein kinase bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
receptor tyrosine kinase bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cadherin bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
ephrin receptor bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein phosphatase 2A bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
non-membrane spanning protein tyrosine phosphatase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
double-stranded DNA bindingTyrosyl-DNA phosphodiesterase 1Homo sapiens (human)
single-stranded DNA bindingTyrosyl-DNA phosphodiesterase 1Homo sapiens (human)
exonuclease activityTyrosyl-DNA phosphodiesterase 1Homo sapiens (human)
protein bindingTyrosyl-DNA phosphodiesterase 1Homo sapiens (human)
3'-tyrosyl-DNA phosphodiesterase activityTyrosyl-DNA phosphodiesterase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (14)

Processvia Protein(s)Taxonomy
plasma membraneTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cytoplasmTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
mitochondrial matrixTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
early endosomeTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
endoplasmic reticulumTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cytosolTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
mitochondrial cristaTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
endosome lumenTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
sorting endosomeTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cytoplasmic side of endoplasmic reticulum membraneTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein-containing complexTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
endoplasmic reticulumTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cytoplasmTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
early endosomeTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
nucleoplasmTyrosyl-DNA phosphodiesterase 1Homo sapiens (human)
cytoplasmTyrosyl-DNA phosphodiesterase 1Homo sapiens (human)
plasma membraneTyrosyl-DNA phosphodiesterase 1Homo sapiens (human)
intracellular membrane-bounded organelleTyrosyl-DNA phosphodiesterase 1Homo sapiens (human)
nucleusTyrosyl-DNA phosphodiesterase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (23)

Assay IDTitleYearJournalArticle
AID1246452Antiinflammatory activity in IRC mouse assessed as inhibition of TPA-induced IL-23 mRNA expression in epidermis at 2 umol administered topically 30 mins prior to TPA challenge for twice weekly over 2 weeks measured 6 hrs post last TPA challenge by qRT-PCR2015Bioorganic & medicinal chemistry letters, Oct-01, Volume: 25, Issue:19
Synthesis of oxygenated oleanolic and ursolic acid derivatives with anti-inflammatory properties.
AID1165539Anti-inflammatory activity in mouse RAW264.7 cells assessed as inhibition of lipopolysaccharide-induced nitric oxide production incubated for 24 hrs by Griess reagent based assay2014Journal of natural products, Oct-24, Volume: 77, Issue:10
Anti-inflammatory ursane- and oleanane-type triterpenoids from Vitex negundo var. cannabifolia.
AID603224Inhibition of rabbit muscle glycogen phosphorylase A assessed as release of phosphate from glucose-1-phosphate after 25 mins by microplate reader based method2011European journal of medicinal chemistry, Jun, Volume: 46, Issue:6
Identification of pentacyclic triterpenes derivatives as potent inhibitors against glycogen phosphorylase based on 3D-QSAR studies.
AID437763Inhibition of GST-tagged human PTP 1B2009Bioorganic & medicinal chemistry letters, Dec-01, Volume: 19, Issue:23
Synthesis and biological evaluation of heterocyclic ring-substituted maslinic acid derivatives as novel inhibitors of protein tyrosine phosphatase 1B.
AID464581Cytotoxicity against human SK-MEL-2 cells by SRB assay2010Bioorganic & medicinal chemistry letters, Mar-15, Volume: 20, Issue:6
Bioactivity-guided isolation of cytotoxic triterpenoids from the trunk of Berberis koreana.
AID1662676Inhibition of TDP1 (unknown origin) expressed in Escherichia coli BL21 (DE3) at 100 uM using 5'-FAM-AGGATCTAAAAGACTT-BHQ-3' as substrate preincubated for 30 mins followed by substrate addition by fluorescence assay relative to control2020Bioorganic & medicinal chemistry, 06-01, Volume: 28, Issue:11
Secondary metabolites from Isodon ternifolius (D. Don) Kudo and their anticancer activity as DNA topoisomerase IB and Tyrosyl-DNA phosphodiesterase 1 inhibitors.
AID1165541Cytotoxicity against mouse RAW264.7 cells assessed as cell viability at 40 uM by MTT assay2014Journal of natural products, Oct-24, Volume: 77, Issue:10
Anti-inflammatory ursane- and oleanane-type triterpenoids from Vitex negundo var. cannabifolia.
AID1246451Antiinflammatory activity in IRC mouse assessed as inhibition of TPA-induced IL-6 mRNA expression in epidermis at 2 umol administered topically 30 mins prior to TPA challenge for twice weekly over 2 weeks measured 6 hrs post last TPA challenge by qRT-PCR 2015Bioorganic & medicinal chemistry letters, Oct-01, Volume: 25, Issue:19
Synthesis of oxygenated oleanolic and ursolic acid derivatives with anti-inflammatory properties.
AID1662673Cytotoxicity against human HCT116 cells assessed as growth inhibition after 72 hrs by MTT assay2020Bioorganic & medicinal chemistry, 06-01, Volume: 28, Issue:11
Secondary metabolites from Isodon ternifolius (D. Don) Kudo and their anticancer activity as DNA topoisomerase IB and Tyrosyl-DNA phosphodiesterase 1 inhibitors.
AID1662669Inhibition of calf thymus Top1 assessed as reduction in supercoiled pBR322 DNA relaxation at 100 uM measured after 30 mins by agarose gel electrophoresis relative to camptothecin2020Bioorganic & medicinal chemistry, 06-01, Volume: 28, Issue:11
Secondary metabolites from Isodon ternifolius (D. Don) Kudo and their anticancer activity as DNA topoisomerase IB and Tyrosyl-DNA phosphodiesterase 1 inhibitors.
AID404873Inhibition of rabbit muscle glycogen phosphorylase A assessed as phosphate release from glucose-1-phosphate2008Journal of medicinal chemistry, Jun-26, Volume: 51, Issue:12
Naturally occurring pentacyclic triterpenes as inhibitors of glycogen phosphorylase: synthesis, structure-activity relationships, and X-ray crystallographic studies.
AID437762Inhibition of GST-tagged human TCPTP2009Bioorganic & medicinal chemistry letters, Dec-01, Volume: 19, Issue:23
Synthesis and biological evaluation of heterocyclic ring-substituted maslinic acid derivatives as novel inhibitors of protein tyrosine phosphatase 1B.
AID1364712Anti-inflammatory in mouse BV2 cells assessed as inhibition of LPS-induced nitric oxide production pre-incubated before LPS challenge for 24 hrs by Griess reagent based assay2017Journal of natural products, 04-28, Volume: 80, Issue:4
Bioactive Triterpenoids from the Twigs of Chaenomeles sinensis.
AID1364713Cytotoxicity in mouse BV2 cells assessed as cell viability at 20 uM incubated for 24 hrs by MTT assay relative to untreated control2017Journal of natural products, 04-28, Volume: 80, Issue:4
Bioactive Triterpenoids from the Twigs of Chaenomeles sinensis.
AID464580Cytotoxicity against human SKOV3 cells by SRB assay2010Bioorganic & medicinal chemistry letters, Mar-15, Volume: 20, Issue:6
Bioactivity-guided isolation of cytotoxic triterpenoids from the trunk of Berberis koreana.
AID1662672Cytotoxicity against human A549 cells assessed as growth inhibition after 72 hrs by MTT assay2020Bioorganic & medicinal chemistry, 06-01, Volume: 28, Issue:11
Secondary metabolites from Isodon ternifolius (D. Don) Kudo and their anticancer activity as DNA topoisomerase IB and Tyrosyl-DNA phosphodiesterase 1 inhibitors.
AID464582Cytotoxicity against human HCT15 cells by SRB assay2010Bioorganic & medicinal chemistry letters, Mar-15, Volume: 20, Issue:6
Bioactivity-guided isolation of cytotoxic triterpenoids from the trunk of Berberis koreana.
AID1246449Antiinflammatory activity in IRC mouse assessed as inhibition of TPA-induced IL-1alpha mRNA expression in epidermis at 2 umol administered topically 30 mins prior to TPA challenge for twice weekly over 2 weeks measured 6 hrs post last TPA challenge by qRT2015Bioorganic & medicinal chemistry letters, Oct-01, Volume: 25, Issue:19
Synthesis of oxygenated oleanolic and ursolic acid derivatives with anti-inflammatory properties.
AID464579Cytotoxicity against human A549 cells by SRB assay2010Bioorganic & medicinal chemistry letters, Mar-15, Volume: 20, Issue:6
Bioactivity-guided isolation of cytotoxic triterpenoids from the trunk of Berberis koreana.
AID1662670Inhibition of TDP1 (unknown origin) expressed in Escherichia coli BL21 (DE3) using 5'-FAM-AGGATCTAAAAGACTT-BHQ-3' as substrate preincubated for 30 mins followed by substrate addition by fluorescence assay2020Bioorganic & medicinal chemistry, 06-01, Volume: 28, Issue:11
Secondary metabolites from Isodon ternifolius (D. Don) Kudo and their anticancer activity as DNA topoisomerase IB and Tyrosyl-DNA phosphodiesterase 1 inhibitors.
AID1246450Antiinflammatory activity in IRC mouse assessed as inhibition of TPA-induced IL-1beta mRNA expression in epidermis at 2 umol administered topically 30 mins prior to TPA challenge for twice weekly over 2 weeks measured 6 hrs post last TPA challenge by qRT-2015Bioorganic & medicinal chemistry letters, Oct-01, Volume: 25, Issue:19
Synthesis of oxygenated oleanolic and ursolic acid derivatives with anti-inflammatory properties.
AID1662671Cytotoxicity against human MCF7 cells assessed as reduction in cell viability after 72 hrs by MTT assay2020Bioorganic & medicinal chemistry, 06-01, Volume: 28, Issue:11
Secondary metabolites from Isodon ternifolius (D. Don) Kudo and their anticancer activity as DNA topoisomerase IB and Tyrosyl-DNA phosphodiesterase 1 inhibitors.
AID260787Inhibitory activity against rabbit muscle GPa2006Bioorganic & medicinal chemistry letters, Feb, Volume: 16, Issue:3
Pentacyclic triterpenes. Part 2: Synthesis and biological evaluation of maslinic acid derivatives as glycogen phosphorylase inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's3 (33.33)29.6817
2010's5 (55.56)24.3611
2020's1 (11.11)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.27

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 Index12.27 (24.57)
Research Supply Index2.30 (2.92)
Research Growth Index4.57 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.27)

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%
Other9 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]