Page last updated: 2024-11-13

meleagrin

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Description

meleagrin: low molecular weight protein found in turkey (Meleagris gallopavo) ovomucoid preparation; amino acid sequence given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

meleagrine : An indole alkaloid with a heterotetracyclic skeleton isolated from Penicillium oxalicum. [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 CID23728435
CHEMBL ID4746496
MeSH IDM0168470

Synonyms (27)

Synonym
MEGXM0_000075
ACON1_001969
MEGXM0_000097
ACON0_001257
ACON1_001373
ACON0_001256
meleagrin
71751-77-4
unii-5780k492k3
5780k492k3 ,
1h,5h-imidazo(1',2':1,2)pyrido(2,3-b)indole-2,5(3h)-dione, 7a-(1,1-dimethyl-2-propenyl)-7a,12-dihydro-6-hydroxy-3-(1h-imidazol-4-ylmethylene)-12-methoxy-, (7ar-(3e,7ar*,12as*))-
meleagrine
meleagrin, (-)-
6-o-demethyloxaline
1h,5h-imidazo(1',2':1,2)pyrido(2,3-b)indole-2,5(3h)-dione, 7a-(1,1-dimethyl-2-propen-1-yl)-7a,12-dihydro-6-hydroxy-3-(1h-imidazol-5-ylmethylene)-12-methoxy-, (3e,7ar,12as)-
(3e,7ar,12as)-7a-(1,1-dimethyl-2-propen-1-yl)-7a,12-dihydro-6-hydroxy-3-(1h-imidazol-5-ylmethylene)-12-methoxy-1h,5h-imidazo(1',2':1,2)pyrido(2,3-b)indole-2,5(3h)-dione
AKOS027307612
DTXSID80891812
bdbm50558000
chembl4746496 ,
BCP14992
Q63409166
(7ar,12as,e)-3-((1h-imidazol-5-yl)methylene)-6-hydroxy-12-methoxy-7a-(2-methylbut-3-en-2-yl)-7a,12-dihydro-1h,5h-imidazo[1',2':1,2]pyrido[2,3-b]indole-2,5(3h)-dione
CS-0100053
HY-N6797
(1s,9r,14e)-11-hydroxy-14-(1h-imidazol-5-ylmethylidene)-2-methoxy-9-(2-methylbut-3-en-2-yl)-2,13,16-triazatetracyclo[7.7.0.01,13.03,8]hexadeca-3,5,7,10-tetraene-12,15-dione
BM162737

Research Excerpts

Overview

Meleagrin is a potential nontoxic antifoulant that is isolated from the fungus Penicillium sp.; however, its mechanistic effect mode of action on larval settlement remains unknown.

ExcerptReferenceRelevance
"Meleagrin B is a terpene-alkaloid hybrid natural product that contains both the conidiogenone and meleagrin scaffold. "( An Enzyme-Mediated Aza-Michael Addition Is Involved in the Biosynthesis of an Imidazoyl Hybrid Product of Conidiogenone B.
Chein, RJ; Chen, YJ; Hewage, RT; Huang, RJ; Lai, SJ; Li, D; Lien, YC; Lin, HC; Weng, SH; Wu, SH, 2021
)
2.06
"Meleagrin is a potential nontoxic antifoulant that is isolated from the fungus Penicillium sp.; however, its mechanistic effect mode of action on larval settlement remains unknown."( iTRAQ-based proteomic profiling of the barnacle Balanus amphitrite in response to the antifouling compound meleagrin.
Han, Z; He, F; He, LS; Matsumura, K; Qi, SH; Qian, PY; Qiu, JW; Sun, J; Xu, Y; Zhang, Y, 2013
)
1.32

Treatment

ExcerptReferenceRelevance
"Meleagrin treatment potently suppressed the invasive triple negative breast tumor cell growth in an orthotopic athymic nude mice model, promoting this unique natural product from hit to a lead rank."( 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.
Ebrahim, HY; El Sayed, KA; Elsayed, HE; Haggag, EG; Houssen, WE; Mady, MS; Mohyeldin, MM; Soliman, RF, 2016
)
1.48
[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)3.15000.00040.372210.0000AID1710748; AID1710749
[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 (29)

Assay IDTitleYearJournalArticle
AID1710732Antiproliferative activity against human BT-474 cells expressing c-MET assessed as reduction in cell viability incubated for 72 hrs by MTT 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.
AID1710749Inhibition of recombinant human His-tagged c-MET M1250T mutant 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.
AID1710752Antiinvasive activity against human MDA-MB-231 cells assessed as reduction in HGF-induced cell invasion incubated for 24 hrs by fluorescence based 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.
AID1710738Cytotoxicity against human MCF-10A cells assessed as cell viability at 10 uM incubated for 72 hrs by MTT 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.
AID1710734Antiproliferative activity against human MDA-MB-231 cells expressing c-MET assessed as reduction in cell viability incubated for 72 hrs by MTT 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.
AID1710740Cytotoxicity against human MCF-10A cells assessed as cell viability at 30 uM incubated for 72 hrs by MTT 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.
AID1710744Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell viability at 50 uM incubated for 24 hrs by LDH 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.
AID1710757Toxicity in athymic nude-Foxn1nu/Fox1+ mouse assessed as effect on body weight at 10 mg/kg, ip dosed 3 times per week for 3 weeks treatment started 14 days of post inoculation2016Bioorganic & 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.
AID1710758Antiinvasive activity against human MDA-MB-231 cells assessed as reduction in HGF-mediate cell invasion at 4 uM incubated for 24 hrs by fluorescence based 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.
AID1710736Antiproliferative activity against human T47D cells assessed as reduction in cell viability incubated for 72 hrs by MTT 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.
AID1710727Cytotoxicity against human HL-60 cells assessed as reduction in cell viability incubated for 72 hrs by MTT 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.
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.
AID1710731Antiproliferative activity against human MCF7-DOX cells expressing c-MET assessed as reduction in cell viability incubated for 72 hrs by MTT 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.
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.
AID1710751Antimigratory activity against human MDA-MB-231 cells assessed as inhibition of HGF-induced cell migration incubated for 24 hrs by Giemsa-staining based wound healing 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.
AID1710759Antiinvasive activity against human MDA-MB-231 cells assessed as reduction in HGF-mediate cell invasion at 8 uM incubated for 24 hrs by fluorescence based 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.
AID1710750Selectivity index, ratio of IC50 for recombinant human His-tagged c-MET expressed in baculovirus expression system to IC50 for recombinant human His-tagged c-MET M1250T mutant expressed in baculovirus expression system2016Bioorganic & 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.
AID1710743Cytotoxicity against human MDA-MB-231 cells assessed as reduction in cell viability at 25 uM incubated for 24 hrs by LDH 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.
AID1710755Antitumor activity against GFP-tagged human MDA-MB-231 cells xenografted in athymic nude-Foxn1nu/Fox1+ mouse assessed as the reduction in tumor volume at 10 mg/kg, ip dosed 3 times per week for 3 weeks treatment started 14 days of post inoculation2016Bioorganic & 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.
AID1710739Cytotoxicity against human MCF-10A cells assessed as cell viability at 20 uM incubated for 72 hrs by MTT 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.
AID1710726Cytotoxicity against human A549 cells assessed as reduction in cell viability incubated for 72 hrs by MTT 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.
AID1710754Inhibition of c-MET in human MDA-MB-231 cells assessed as reduction in c-MET phosphorylation level at 15 to 30 uM incubated for 48 hrs by Western blot analysis2016Bioorganic & 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.
AID1710756Antitumor activity against GFP-tagged human MDA-MB-231 cells xenografted in athymic nude-Foxn1nu/Fox1+ mouse assessed as the reduction in tumor growth at 10 mg/kg, ip dosed 3 times per week for 3 weeks treatment started 14 days of post inoculation2016Bioorganic & 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.
AID1710735Antiproliferative activity against human MDA-MB-468 cells expressing c-MET assessed as reduction in cell viability incubated for 72 hrs by MTT 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.
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.
AID1710737Cytotoxicity against human MCF-10A cells assessed as cell viability at 5 uM incubated for 72 hrs by MTT 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.
AID1710730Antiproliferative activity against human MCF7 cells expressing c-MET assessed as reduction in cell viability incubated for 72 hrs by MTT 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.
AID1710733Antiproliferative activity against human SK-BR-3 cells expressing c-MET assessed as reduction in cell viability incubated for 72 hrs by MTT 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.
AID1710753Reduction of c-MET expression level in human MDA-MB-231 cells at 15 to 30 uM incubated for 48 hrs by Western blot analysis2016Bioorganic & 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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (12)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (8.33)18.7374
1990's0 (0.00)18.2507
2000's1 (8.33)29.6817
2010's8 (66.67)24.3611
2020's2 (16.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 22.16

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 Index22.16 (24.57)
Research Supply Index2.64 (2.92)
Research Growth Index5.50 (4.65)
Search Engine Demand Index18.60 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (22.16)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (7.69%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other12 (92.31%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]