Page last updated: 2024-11-06

xanthomicrol

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

Description

Xanthomicrol is a natural product isolated from the fungus Penicillium citrinum. It exhibits a range of biological activities, including antibacterial, antifungal, and anti-inflammatory properties. Xanthomicrol is a potent inhibitor of the enzyme cyclooxygenase-2 (COX-2), which is involved in the production of prostaglandins, inflammatory mediators. This inhibitory effect makes xanthomicrol a potential therapeutic agent for inflammatory diseases. The synthesis of xanthomicrol has been achieved through various methods, including total synthesis and semi-synthesis from other natural products. Xanthomicrol is studied for its potential applications in the development of novel drugs for the treatment of bacterial infections, fungal infections, and inflammatory conditions. The unique structural features and biological activity of xanthomicrol make it an interesting target for further research and drug development.'

xanthomicrol: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

xanthomicrol : A trimethoxyflavone that is flavone substituted by methoxy groups at positions 6, 7 and 8 and hydroxy groups at positions 5 and 4'. [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 CID73207
CHEMBL ID476121
CHEBI ID35047
SCHEMBL ID6257160
MeSH IDM0434549

Synonyms (26)

Synonym
nsc79323
nsc-79323
ACON1_000922
4',5-dihydroxy-6,7,8-trimethoxyflavone
5-hydroxy-2-(4-hydroxyphenyl)-6,7,8-trimethoxy-chromen-4-one
4h-1-benzopyran-4-one, 5-hydroxy-2-(4-hydroxyphenyl)-6,7,8-trimethoxy-
xanthomicrol
16545-23-6
NCGC00169227-01
BRD-K34022850-001-01-8
5-hydroxy-2-(4-hydroxyphenyl)-6,7,8-trimethoxychromen-4-one
chebi:35047 ,
CHEMBL476121 ,
LMPK12111447
unii-3in82y8caa
5-hydroxy-2-(4-hydroxyphenyl)-6,7,8-trimethoxy-4h-1-benzopyran-4-one
3in82y8caa ,
nsc 79323
bdbm50412279
5,4'-dihydroxy-6,7,8-trimethoxyflavone
5-hydroxy-2-(4-hydroxyphenyl)-6,7,8-trimethoxy-4h-chromen-4-one
flavone, 4',5-dihydroxy-6,7,8-trimethoxy-
SCHEMBL6257160
DTXSID20167947
AKOS030525194
Q27116387

Research Excerpts

Actions

ExcerptReferenceRelevance
"Xanthomicrol was able to inhibit proliferation of a number of malignant cells."( Xanthomicrol is the main cytotoxic component of Dracocephalum kotschyii and a potential anti-cancer agent.
Ebrahimi, SA; Jahaniani, F; Mahmoudian, M; Rahbar-Roshandel, N, 2005
)
2.49

Pharmacokinetics

The plasma half-life for both agents was around 4 h, however, the volume of distribution of calycopterin appeared to be about 8 times greater than xanthomicrol.

ExcerptReferenceRelevance
"The plasma half-life for both agents was around 4 h, however, the volume of distribution of calycopterin appeared to be about 8 times greater than xanthomicrol."( Pharmacokinetics of calycopterin and xanthmicrol, two polymethoxylated hydroxyflavones with anti-angiogenic activities from Dracocephalum kotschyi Bioss.
Ebrahimi, SA; Etebari, M; Hossieni, M; Salehian, P; Zamani, SS, 2016
)
0.63
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
[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
trimethoxyflavoneA methoxyflavone that is flavone substituted by three methoxy groups.
dihydroxyflavoneAny hydroxyflavone in which two ring hydrogens are replaced by hydroxy substituents.
[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)
Aldo-keto reductase family 1 member B1Rattus norvegicus (Norway rat)IC50 (µMol)0.53700.00041.877310.0000AID342547
Peroxisome proliferator-activated receptor gammaHomo sapiens (human)IC50 (µMol)5.40000.00501.205110.0000AID1766165
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (73)

Processvia Protein(s)Taxonomy
negative regulation of gene expressionPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
positive regulation of cholesterol effluxPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
long-chain fatty acid transportPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of osteoblast differentiationPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of smooth muscle cell proliferationPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of receptor signaling pathway via STATPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
positive regulation of low-density lipoprotein receptor activityPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of signaling receptor activityPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
positive regulation of gene expressionPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of transforming growth factor beta receptor signaling pathwayPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of BMP signaling pathwayPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of MAP kinase activityPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
positive regulation of adiponectin secretionPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of miRNA transcriptionPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of cardiac muscle hypertrophy in response to stressPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of connective tissue replacement involved in inflammatory response wound healingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of transcription by RNA polymerase IIPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
placenta developmentPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
regulation of transcription by RNA polymerase IIPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
lipid metabolic processPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
activation of cysteine-type endopeptidase activity involved in apoptotic processPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
signal transductionPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
G protein-coupled receptor signaling pathwayPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
response to nutrientPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
regulation of blood pressurePeroxisome proliferator-activated receptor gammaHomo sapiens (human)
positive regulation of gene expressionPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of gene expressionPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
macrophage derived foam cell differentiationPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of macrophage derived foam cell differentiationPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of cholesterol storagePeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of lipid storagePeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of sequestering of triglyceridePeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of angiogenesisPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
monocyte differentiationPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
BMP signaling pathwayPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of transforming growth factor beta receptor signaling pathwayPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
epithelial cell differentiationPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
cellular response to insulin stimulusPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
response to lipidPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
peroxisome proliferator activated receptor signaling pathwayPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
glucose homeostasisPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
regulation of circadian rhythmPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
mRNA transcription by RNA polymerase IIPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
lipoprotein transportPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of blood vessel endothelial cell migrationPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
innate immune responsePeroxisome proliferator-activated receptor gammaHomo sapiens (human)
cell fate commitmentPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
positive regulation of fat cell differentiationPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of DNA-templated transcriptionPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
positive regulation of DNA-templated transcriptionPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
positive regulation of transcription by RNA polymerase IIPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
retinoic acid receptor signaling pathwayPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
cell maturationPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
rhythmic processPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
white fat cell differentiationPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
positive regulation of DNA-binding transcription factor activityPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
lipid homeostasisPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of type II interferon-mediated signaling pathwayPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of SMAD protein signal transductionPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
regulation of cholesterol transporter activityPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
cellular response to low-density lipoprotein particle stimulusPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
cellular response to hypoxiaPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of mitochondrial fissionPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
regulation of cellular response to insulin stimulusPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of extracellular matrix assemblyPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of miRNA transcriptionPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
positive regulation of miRNA transcriptionPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of cellular response to transforming growth factor beta stimulusPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
positive regulation of adipose tissue developmentPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of vascular associated smooth muscle cell proliferationPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
positive regulation of vascular associated smooth muscle cell apoptotic processPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of vascular endothelial cell proliferationPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
positive regulation of fatty acid metabolic processPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
fatty acid metabolic processPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
negative regulation of inflammatory responsePeroxisome proliferator-activated receptor gammaHomo sapiens (human)
cell differentiationPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
hormone-mediated signaling pathwayPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (28)

Processvia Protein(s)Taxonomy
transcription cis-regulatory region bindingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA bindingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
DNA-binding transcription factor activity, RNA polymerase II-specificPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
transcription coregulator bindingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
DNA-binding transcription activator activity, RNA polymerase II-specificPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
nucleic acid bindingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
DNA bindingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
chromatin bindingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
double-stranded DNA bindingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
DNA-binding transcription factor activityPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
nuclear receptor activityPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
prostaglandin receptor activityPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
protein bindingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
zinc ion bindingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
enzyme bindingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
peptide bindingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
identical protein bindingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
sequence-specific DNA bindingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
nuclear retinoid X receptor bindingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
arachidonic acid bindingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
DNA binding domain bindingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
LBD domain bindingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
alpha-actinin bindingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
R-SMAD bindingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
E-box bindingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
STAT family protein bindingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
DNA-binding transcription factor bindingPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
DNA-binding transcription repressor activity, RNA polymerase II-specificPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (7)

Processvia Protein(s)Taxonomy
nucleusPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
nucleusPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
nucleoplasmPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
cytosolPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
intracellular membrane-bounded organellePeroxisome proliferator-activated receptor gammaHomo sapiens (human)
RNA polymerase II transcription regulator complexPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
chromatinPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
receptor complexPeroxisome proliferator-activated receptor gammaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (16)

Assay IDTitleYearJournalArticle
AID635947Inhibition of PMA-stimulated pro MMP9 production in human SRA 01/04 cells after 24 hrs by SDS-PAGE based gelatin zymography assay2011Bioorganic & medicinal chemistry, Dec-01, Volume: 19, Issue:23
B-Ring-modified and/or 5-demethylated nobiletin congeners: inhibitory activity against pro-MMP-9 production.
AID635946Cytotoxicity against human SRA 01/04 cells at 64 uM after 24 hrs by LDH release assay2011Bioorganic & medicinal chemistry, Dec-01, Volume: 19, Issue:23
B-Ring-modified and/or 5-demethylated nobiletin congeners: inhibitory activity against pro-MMP-9 production.
AID1869580Antibacterial activity against Streptococcus mutans ATCC 25175 incubated for 48 hrs by spectrophotometric analysis
AID724431Growth inhibition of human SRA 01/04 cells at 32 uM after 4 days by Alamar blue assay2013Bioorganic & medicinal chemistry letters, Jan-01, Volume: 23, Issue:1
Polymethoxyflavones as agents that prevent formation of cataract: nobiletin congeners show potent growth inhibitory effects in human lens epithelial cells.
AID342547Inhibition of rat lens aldose reductase2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
QSAR prediction of inhibition of aldose reductase for flavonoids.
AID1869579Antibacterial activity against Staphylococcus aureus ATCC 23235 incubated for 48 hrs by spectrophotometric analysis
AID1190344Inhibition of morphine-induced analgesia in CD1 mouse model at 40 mg/kg, ip pretreated 30 mins before 5 mg/kg, sc morphine injection and measured 30 to 120 mins after morphine treatment by tail-flick assay relative to control2015Journal of natural products, Jan-23, Volume: 78, Issue:1
Methoxyflavones from Stachys glutinosa with binding affinity to opioid receptors: in silico, in vitro, and in vivo studies.
AID1190339Displacement of [3H]DPDPE from delta opioid receptor in CD1 mouse whole brain minus cerebellum membranes by liquid scintillation counting2015Journal of natural products, Jan-23, Volume: 78, Issue:1
Methoxyflavones from Stachys glutinosa with binding affinity to opioid receptors: in silico, in vitro, and in vivo studies.
AID1766165Antagonist activity at PPARgamma (unknown origin) expressed in human LNCaP cells assessed as suppression of pioglitazone-induced PPAR response element driven firefly luciferase activity measured after 24 hrs by dual luciferase reporter assay2021Bioorganic & medicinal chemistry, 09-15, Volume: 46Virtual screening and biological evaluation of PPARγ antagonists as potential anti-prostate cancer agents.
AID635943Ratio of IC50 for PMA-stimulated pro MMP9 production in human SRA 01/04 cells to IC50 for TNFalpha-stimulated pro MMP9 production in human SRA 01/04 cells2011Bioorganic & medicinal chemistry, Dec-01, Volume: 19, Issue:23
B-Ring-modified and/or 5-demethylated nobiletin congeners: inhibitory activity against pro-MMP-9 production.
AID1190343Inhibition of morphine-induced analgesia in CD1 mouse model at 80 mg/kg, ip pretreated 30 mins before 5 mg/kg, sc morphine injection and measured 30 to 120 mins after morphine treatment by tail-flick assay relative to control2015Journal of natural products, Jan-23, Volume: 78, Issue:1
Methoxyflavones from Stachys glutinosa with binding affinity to opioid receptors: in silico, in vitro, and in vivo studies.
AID1190338Displacement of [3H]DAMGO from mu opioid receptor in CD1 mouse whole brain minus cerebellum membranes by liquid scintillation counting2015Journal of natural products, Jan-23, Volume: 78, Issue:1
Methoxyflavones from Stachys glutinosa with binding affinity to opioid receptors: in silico, in vitro, and in vivo studies.
AID1190341Analgesic activity in acute pain CD1 mouse model assessed as withdrawal latency from radiant heat source at 40 to 80 mg/kg, ip by tail-flick assay2015Journal of natural products, Jan-23, Volume: 78, Issue:1
Methoxyflavones from Stachys glutinosa with binding affinity to opioid receptors: in silico, in vitro, and in vivo studies.
AID1190340Selectivity ratio of Ki for delta opioid receptor in CD1 mouse whole brain minus cerebellum membranes to Ki for mu opioid receptor in CD1 mouse whole brain minus cerebellum membranes2015Journal of natural products, Jan-23, Volume: 78, Issue:1
Methoxyflavones from Stachys glutinosa with binding affinity to opioid receptors: in silico, in vitro, and in vivo studies.
AID1869581Antibacterial activity against Treponema denticola ATCC 35405 incubated for 48 hrs by spectrophotometric analysis
AID635945Inhibition of TNFalpha-stimulated pro MMP9 production in human SRA 01/04 cells after 24 hrs by SDS-PAGE based gelatin zymography assay2011Bioorganic & medicinal chemistry, Dec-01, Volume: 19, Issue:23
B-Ring-modified and/or 5-demethylated nobiletin congeners: inhibitory activity against pro-MMP-9 production.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (21)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's4 (19.05)29.6817
2010's11 (52.38)24.3611
2020's6 (28.57)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 21.20

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 Index21.20 (24.57)
Research Supply Index3.09 (2.92)
Research Growth Index4.99 (4.65)
Search Engine Demand Index18.60 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (21.20)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (4.76%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other20 (95.24%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]