An azaphilonoid pigment with diverse biological activities
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Monascin

Item No. 39510

Technical Information
Formal Name
(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
CAS Number
21516-68-7
Molecular Formula
C21H26O5
Formula Weight
Purity
≥95%
Formulation
A solid
Acetonitrile: SolubleChloroform: Soluble
SMILES
C[C@]12[C@@](CC3=C(COC(/C=C/C)=C3)C2=O)([H])[C@H](C(O1)=O)C(CCCCC)=O
InChi Code
InChI=1S/C21H26O5/c1-4-6-7-9-17(22)18-16-11-13-10-14(8-5-2)25-12-15(13)19(23)21(16,3)26-20(18)24/h5,8,10,16,18H,4,6-7,9,11-12H2,1-3H3/b8-5+/t16-,18+,21-/m1/s1
InChi Key
XXKNHBAFFJINCK-RVEJDSBJSA-N
Origin
Fungus/Monascus sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    Monascin is an azaphilonoid pigment that has been found in the fungus Monascus and has diverse biological activities.1,2,3 It induces peroxisome proliferator-activated receptor α (PPARα) activity in a coactivator assay (IC50 = 2,038 nM) and inhibits oleic acid-induced fatty acid uptake, lipogenesis, and fatty acid oxidation in FL83B mouse hepatocytes.1 In vivo, monascin reduces hepatic IL-6, TNF-α, and TGF-β levels, plasma levels of total cholesterol, triglycerides, free fatty acids, and alanine transaminase (ALT), and hepatic macrovesicular steatosis in a mouse model of high-fat diet-induced non-alcoholic steatohepatitis (NASH). Monascin reduces the number of papillomas per mouse and the number of mice with papillomas in a mouse model of two-stage carcinogenesis induced by phorbol 12-myristate 13-acetate (TPA; Item No. 10008014) and UVB or peroxynitrite when administered in the drinking water at a concentration of 0.0025%.2 It also reduces serum insulin, triglyceride, total cholesterol, and HDL concentrations in a rat model of diabetes induced by streptozotocin (STZ; Item No. 13104).3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hsu, W.-H., Chen, T.-H., Lee, B.-H., et alMonascin and ankaflavin act as natural AMPK activators with PPARα agonist activity to down-regulate nonalcoholic steatohepatitis in high-fat diet-fed C57BL/6 mice. Food Chem. Toxicol. 64, 94-103 (2014).

    2. Akihisa, T., Tokuda, H., Ukiya, M., et alAnti-tumor-initiating effects of monascin, an azaphilonoid pigment from the extract of Monascus pilosus fermented rice (red-mold rice). Chem. Biodivers. 2(10), 1305-1309 (2005).

    3. Shi, Y.-C., Liao, V.H.-C., and Pan, T.-M. Monascin from red mold dioscorea as a novel antidiabetic and antioxidative stress agent in rats and Caenorhabditis elegans. Free Radic. Biol. Med. 52(1), 109-117 (2012).