Page last updated: 2024-11-12

monascin

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

Description

monascin: a pigment isolated from Monascus pilosus fermented rice; has antineoplastic activity; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

monascin : An organic heterotricyclic compound that is 3a,4,8,9a-tetrahydro-2H-furo[3,2-g][2]benzopyran-2,9(3H)-dione that is substituted at positions 3, 6, and 9a by hexanoyl, (1E)-prop-1-en-1-yl and methyl groups, respectively (the 3S,3aR,9aR diastereoisomer). One of the azaphilonoid pigments in extracts of Monascus pilosus-fermented rice (red-mould rice), it is a potent inhibitor of carcinogenesis measured against chemical- or UV-initiated, phorbol-promoted mouse skin tumours. [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 CID12118082
CHEMBL ID1215463
CHEBI ID82621
SCHEMBL ID13100009
MeSH IDM0507570

Synonyms (23)

Synonym
monascoflavin
monascin
CHEMBL1215463
chebi:82621 ,
w74d2m37fx ,
ccris 9138
21516-68-7
unii-w74d2m37fx
(3s,3ar,9ar)-3-hexanoyl-9a-methyl-6-[(1e)-prop-1-en-1-yl]-3a,4,8,9a-tetrahydro-2h-furo[3,2-g][2]benzopyran-2,9(3h)-dione
SCHEMBL13100009
(3s,3ar,9ar)-3a,4,8,9a-tetrahydro-9a-methyl-3-(1-oxohexyl)-6-(1e)-1-propen-1-yl-2h-furo(3,2-g)(2)benzopyran-2,9(3h)-dione
2h-furo(3,2-g)(2)benzopyran-2,9(3h)-dione, 3a,4,8,9a-tetrahydro-9a-methyl-3-(1-oxohexyl)-6-(1e)-1-propen-1-yl-, (3s,3ar,9ar)-
monascoflavine
monascin [mi]
monascin, >=97.0% (hplc)
AKOS037515362
Q27156138
(3s,3ar,9ar)-3-hexanoyl-9a-methyl-6-((e)-prop-1-en-1-yl)-3a,4,8,9a-tetrahydro-2h-furo[3,2-g]isochromene-2,9(3h)-dione
HY-N6641
CS-0062869
(3s,3ar,9ar)-3-hexanoyl-9a-methyl-6-[(e)-prop-1-enyl]-3,3a,4,8-tetrahydrofuro[3,2-g]isochromene-2,9-dione
DTXSID50944127
XM161521

Research Excerpts

Overview

Monascin is an azaphilonoid pigment extracted from Monascus-fermented rice with a potential anti-inflammatory effect reported in various preclinical studies. Monascin acts as a novel natural Nrf2 activator with PPARγ-agonist activity.

ExcerptReferenceRelevance
"Monascin (MS) is a yellow lipid-soluble azaphilonoid pigment identified from Monascus-fermented products with promising biological activities. "( Molecular insight on the binding of monascin to bovine serum albumin (BSA) and its effect on antioxidant characteristics of monascin.
Bao, Y; Chen, M; Guo, Q; Li, Z; Liu, H; Peng, X; Wang, C; Wang, X; Wu, S; Zhang, C, 2020
)
2.28
"Monascin is an azaphilonoid pigment extracted from Monascus-fermented rice with a potential anti-inflammatory effect reported in various preclinical studies."( Monascin inhibits IL-1β induced catabolism in mouse chondrocytes and ameliorates murine osteoarthritis.
Chen, T; Li, X; Tang, Q; Tian, N; Wang, H; Wang, J; Wang, X; Wu, D; Wu, Y; Xu, H; Zhan, Y; Zhang, X; Zheng, F; Zheng, G; Zhou, Y, 2018
)
2.64
"Monascin (MS) is a yellow compound isolated from Monascus-fermented products that has pancreatic protective, anti-inflammatory, anti-oxidative, and hypolipidemic activity. "( Monascin improves diabetes and dyslipidemia by regulating PPARγ and inhibiting lipogenesis in fructose-rich diet-induced C57BL/6 mice.
Chang, YY; Hsu, WH; Hsu, YW; Huang, T; Lee, BH; Pan, TM, 2013
)
3.28
"Monascin acts as a novel natural Nrf2 activator with PPARγ-agonist activity were confirmed by Nrf2 and PPARγ reporter assays in Hep G2 cells."( A novel natural Nrf2 activator with PPARγ-agonist (monascin) attenuates the toxicity of methylglyoxal and hyperglycemia.
Chang, YY; Hsu, WH; Hsu, YW; Lee, BH; Pan, TM, 2013
)
1.36
"Monascin (MS) is a novel compound proposed for antioxidative stress applications and is derived from an edible fungus secondary metabolite."( Monascin from Monascus-Fermented Products Reduces Oxidative Stress and Amyloid-β Toxicity via DAF-16/FOXO in Caenorhabditis elegans.
Liao, VH; Pan, TM; Shi, YC, 2016
)
2.6
"Monascin is a major yellow compound from red mold dioscorea. "( Monascin from red mold dioscorea as a novel antidiabetic and antioxidative stress agent in rats and Caenorhabditis elegans.
Liao, VH; Pan, TM; Shi, YC, 2012
)
3.26

Effects

ExcerptReferenceRelevance
"Monascin has been shown to prevent or ameliorate several conditions, including hypercholesterolemia, hyperlipidemia, diabetes, and obesity."( A novel PPARgamma agonist monascin's potential application in diabetes prevention.
Hsu, WH; Pan, TM, 2014
)
1.42

Treatment

ExcerptReferenceRelevance
"Monascin-treated rats showed higher serum insulin level, lower reactive oxygen species production, and higher activities of glutathione peroxidase, superoxide dismutase, and catalase in the pancreas compared to diabetic control rats."( Monascin from red mold dioscorea as a novel antidiabetic and antioxidative stress agent in rats and Caenorhabditis elegans.
Liao, VH; Pan, TM; Shi, YC, 2012
)
2.54

Toxicity

ExcerptReferenceRelevance
" Monacolin K also serves as a well-known hypolipidemic medication, but its side effect myopathy is a concern."( Monascin and ankaflavin have more anti-atherosclerosis effect and less side effect involving increasing creatinine phosphokinase activity than monacolin K under the same dosages.
Hsu, YW; Hung, YP; Lee, CL; Pan, TM, 2013
)
1.83

Dosage Studied

The high dosage of monascin significantly improved neurological deficits, reduced the volume of hematoma in 1-7days after ICH, decreased BBB permeability and edema formation.

ExcerptRelevanceReference
"The high dosage of monascin significantly improved neurological deficits, reduced the volume of hematoma in 1-7days after ICH, decreased BBB permeability and edema formation in 1-3days following ICH."( The effect of monascin on hematoma clearance and edema after intracerebral hemorrhage in rats.
Dong, L; Duan, S; Li, T; Sun, XG; Wang, G; Wang, J; Xu, Y; Yi, J, 2017
)
1.14
"Our study demonstrated that the high dosage of monascin played a neuroprotective role in ICH through reducing BBB permeability, edema and hematoma volume."( The effect of monascin on hematoma clearance and edema after intracerebral hemorrhage in rats.
Dong, L; Duan, S; Li, T; Sun, XG; Wang, G; Wang, J; Xu, Y; Yi, J, 2017
)
1.07
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (4)

RoleDescription
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
PPARgamma agonistA PPAR modulator which activates the peroxisome proliferator-activated receptor-gamma.
antilipemic drugA substance used to treat hyperlipidemia (an excess of lipids in the blood).
fungal metaboliteAny eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
[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 (4)

ClassDescription
organic heterotricyclic compoundAn organic tricyclic compound in which at least one of the rings of the tricyclic skeleton contains one or more heteroatoms.
gamma-lactoneA lactone having a five-membered lactone ring.
alpha,beta-unsaturated ketoneA ketone of general formula R(1)R(2)C=CR(3)-C(=O)R(4) (R(4) =/= H) or R(1)C#C-C(=O)R(2) (R(2) =/= H) in which the ketonic C=O function is conjugated to an unsaturated C-C bond at the alpha,beta position.
polyketideNatural and synthetic compounds containing alternating carbonyl and methylene groups ('beta-polyketones'), biogenetically derived from repeated condensation of acetyl coenzyme A (via malonyl coenzyme A), and usually the compounds derived from them by further condensations, etc. Considered by many to be synonymous with the less frequently used terms acetogenins and ketides.
[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]

Bioassays (6)

Assay IDTitleYearJournalArticle
AID499309Antiproliferative activity against human JR8 cells after 72 hrs2010Bioorganic & medicinal chemistry, Aug-15, Volume: 18, Issue:16
Natural and semisynthetic azaphilones as a new scaffold for Hsp90 inhibitors.
AID499308Antiproliferative activity against human A431 cells after 72 hrs2010Bioorganic & medicinal chemistry, Aug-15, Volume: 18, Issue:16
Natural and semisynthetic azaphilones as a new scaffold for Hsp90 inhibitors.
AID499312Binding affinity to HSP90 after 4 hrs by fluorescence polarization assay2010Bioorganic & medicinal chemistry, Aug-15, Volume: 18, Issue:16
Natural and semisynthetic azaphilones as a new scaffold for Hsp90 inhibitors.
AID499311Inhibition of yeast full-length recombinant HSP90 ATPase activity expressed in Escherichia coli strain BL21(DE3) assessed as inorganic phosphate release after 3 hrs2010Bioorganic & medicinal chemistry, Aug-15, Volume: 18, Issue:16
Natural and semisynthetic azaphilones as a new scaffold for Hsp90 inhibitors.
AID499307Antiproliferative activity against human NCI-H460 cells after 72 hrs2010Bioorganic & medicinal chemistry, Aug-15, Volume: 18, Issue:16
Natural and semisynthetic azaphilones as a new scaffold for Hsp90 inhibitors.
AID499310Antiproliferative activity against human IGROV1 cells after 72 hrs2010Bioorganic & medicinal chemistry, Aug-15, Volume: 18, Issue:16
Natural and semisynthetic azaphilones as a new scaffold for Hsp90 inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (47)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (2.13)29.6817
2010's38 (80.85)24.3611
2020's8 (17.02)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 24.43

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 Index24.43 (24.57)
Research Supply Index3.89 (2.92)
Research Growth Index5.49 (4.65)
Search Engine Demand Index43.31 (26.88)
Search Engine Supply Index3.90 (0.95)

This Compound (24.43)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (6.25%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other45 (93.75%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]