Page last updated: 2024-09-26

cirsimarin

Description

cirsimarin: a flavone glycoside from Microtea debilis; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
Microteagenus[no description available]Microteaceae[no description available]

Cross-References

ID SourceID
PubMed CID159460
CHEMBL ID517637
CHEBI ID192417
SCHEMBL ID2016369
MeSH IDM0280270

Synonyms (25)

Synonym
4h-1-benzopyran-4-one, 2-(4-(beta-d-glucopyranosyloxy)phenyl)-5-hydroxy-6,7-dimethoxy-
cirsitakaoside
cirsimarin
2-(4-(beta-d-glucopyranosyloxy)phenyl)-5-hydroxy-6,7-dimethoxy-4h-1-benzopyran-4-one
bdbm50250467
CHEMBL517637 ,
13020-19-4
CHEBI:192417
5-hydroxy-6,7-dimethoxy-2-[4-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one
SCHEMBL2016369
DTXSID80926633
4-(5-hydroxy-6,7-dimethoxy-4-oxo-4h-1-benzopyran-2-yl)phenyl hexopyranoside
HY-N7272
CS-0111105
Q63399214
MS-28836
STARBLD0000899
E80544
AKOS040732824
5,4'-dihydroxy-6,7-dimethoxyflavone 4'-o-beta-d-glucoside
72U3YNK7DV
cirsimaretin
2-[4-(beta-d-glucopyranosyloxy)phenyl]-5-hydroxy-6,7-dimethoxy-4h-1-benzopyran-4-one
4h-1-benzopyran-4-one, 2-[4-(beta-d-glucopyranosyloxy)phenyl]-5-hydroxy-6,7-dimethoxy-
cirsimaritin 4'-glucoside

Drug Classes (2)

ClassDescription
glycosideA glycosyl compound resulting from the attachment of a glycosyl group to a non-acyl group RO-, RS-, RSe-, etc. The bond between the glycosyl group and the non-acyl group is called a glycosidic bond. By extension, the terms N-glycosides and C-glycosides are used as class names for glycosylamines and for compounds having a glycosyl group attached to a hydrocarbyl group respectively. These terms are misnomers and should not be used. The preferred terms are glycosylamines and C-glycosyl compounds, respectively.
flavonoidsAny organic molecular entity whose stucture is based on derivatives of a phenyl-substituted 1-phenylpropane possessing a C15 or C16 skeleton, or such a structure which is condensed with a C6-C3 lignan precursors. The term is a 'superclass' comprising all members of the classes of flavonoid, isoflavonoid, neoflavonoid, chalcones, dihydrochalcones, aurones, pterocarpan, coumestans, rotenoid, flavonolignan, homoflavonoid and flavonoid oligomers. Originally restricted to natural products, the term is also applied to synthetic compounds related to them.
[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 (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Xanthine dehydrogenase/oxidaseHomo sapiens (human)IC50 (µMol)100.00000.00132.81389.8200AID399340
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (27)

Processvia Protein(s)Taxonomy
allantoin metabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
negative regulation of protein phosphorylationXanthine dehydrogenase/oxidaseHomo sapiens (human)
negative regulation of endothelial cell proliferationXanthine dehydrogenase/oxidaseHomo sapiens (human)
guanine catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
inosine catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
deoxyinosine catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
adenosine catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
deoxyadenosine catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
deoxyguanosine catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
AMP catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
IMP catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
activation of cysteine-type endopeptidase activity involved in apoptotic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
lactationXanthine dehydrogenase/oxidaseHomo sapiens (human)
hypoxanthine catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
xanthine catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
negative regulation of gene expressionXanthine dehydrogenase/oxidaseHomo sapiens (human)
iron-sulfur cluster assemblyXanthine dehydrogenase/oxidaseHomo sapiens (human)
amide catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
negative regulation of endothelial cell differentiationXanthine dehydrogenase/oxidaseHomo sapiens (human)
GMP catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
dGMP catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
dAMP catabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
negative regulation of phosphatidylinositol 3-kinase/protein kinase B signal transductionXanthine dehydrogenase/oxidaseHomo sapiens (human)
positive regulation of p38MAPK cascadeXanthine dehydrogenase/oxidaseHomo sapiens (human)
negative regulation of vascular endothelial growth factor signaling pathwayXanthine dehydrogenase/oxidaseHomo sapiens (human)
positive regulation of reactive oxygen species metabolic processXanthine dehydrogenase/oxidaseHomo sapiens (human)
negative regulation of vasculogenesisXanthine dehydrogenase/oxidaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (11)

Processvia Protein(s)Taxonomy
xanthine dehydrogenase activityXanthine dehydrogenase/oxidaseHomo sapiens (human)
xanthine oxidase activityXanthine dehydrogenase/oxidaseHomo sapiens (human)
iron ion bindingXanthine dehydrogenase/oxidaseHomo sapiens (human)
protein bindingXanthine dehydrogenase/oxidaseHomo sapiens (human)
protein homodimerization activityXanthine dehydrogenase/oxidaseHomo sapiens (human)
molybdopterin cofactor bindingXanthine dehydrogenase/oxidaseHomo sapiens (human)
flavin adenine dinucleotide bindingXanthine dehydrogenase/oxidaseHomo sapiens (human)
2 iron, 2 sulfur cluster bindingXanthine dehydrogenase/oxidaseHomo sapiens (human)
hypoxanthine dehydrogenase activityXanthine dehydrogenase/oxidaseHomo sapiens (human)
hypoxanthine oxidase activityXanthine dehydrogenase/oxidaseHomo sapiens (human)
FAD bindingXanthine dehydrogenase/oxidaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
cytosolXanthine dehydrogenase/oxidaseHomo sapiens (human)
extracellular spaceXanthine dehydrogenase/oxidaseHomo sapiens (human)
peroxisomeXanthine dehydrogenase/oxidaseHomo sapiens (human)
cytosolXanthine dehydrogenase/oxidaseHomo sapiens (human)
sarcoplasmic reticulumXanthine dehydrogenase/oxidaseHomo sapiens (human)
extracellular spaceXanthine dehydrogenase/oxidaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (6)

Assay IDTitleYearJournalArticle
AID399341Antioxidant activity assessed as superoxide-scavenging activity by nitrite method1998Journal of natural products, Jan, Volume: 61, Issue:1
Structure-activity relationship and classification of flavonoids as inhibitors of xanthine oxidase and superoxide scavengers.
AID403920Displacement of [3H]DPCPX from adenosine A1 receptor in rat forebrain membrane in presence of GTP1997Journal of natural products, Jun, Volume: 60, Issue:6
Adenosine-1 active ligands: cirsimarin, a flavone glycoside from Microtea debilis.
AID403919Displacement of [3H]DPCPX from adenosine A1 receptor in rat forebrain membrane1997Journal of natural products, Jun, Volume: 60, Issue:6
Adenosine-1 active ligands: cirsimarin, a flavone glycoside from Microtea debilis.
AID338974Inhibition of cow milk xanthine oxidase at 50 ug/mL
AID403918Displacement of [3H]DPCPX from adenosine A1 receptor in rat forebrain membrane assessed as fraction of receptor bound radioligand at 100 ug/mL1997Journal of natural products, Jun, Volume: 60, Issue:6
Adenosine-1 active ligands: cirsimarin, a flavone glycoside from Microtea debilis.
AID399340Inhibition of xanthine oxidase assessed as decrease in uric acid production by spectrophotometry1998Journal of natural products, Jan, Volume: 61, Issue:1
Structure-activity relationship and classification of flavonoids as inhibitors of xanthine oxidase and superoxide scavengers.
[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's4 (40.00)18.2507
2000's1 (10.00)29.6817
2010's3 (30.00)24.3611
2020's2 (20.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

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%
Other11 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]