A microbial metabolite with diverse biological activities
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Ankaflavin

Item No. 39546

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3S,3aR,9aR)-3a,4,8,9a-tetrahydro-(1-oxooctyl)-6-(1E)-1-propen-1-yl-2H-furo[3,2-g][2]benzopyran-2,9(3H)-dione
CAS Number
50980-32-0
Molecular Formula
C23H30O5
Formula Weight
386.5
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Methanol: Soluble
SMILES
C[C@]12[C@@](CC3=C(COC(/C=C/C)=C3)C2=O)([H])[C@H](C(O1)=O)C(CCCCCCC)=O
InChi Code
InChI=1S/C23H30O5/c1-4-6-7-8-9-11-19(24)20-18-13-15-12-16(10-5-2)27-14-17(15)21(25)23(18,3)28-22(20)26/h5,10,12,18,20H,4,6-9,11,13-14H2,1-3H3/b10-5+/t18-,20+,23-/m1/s1
InChi Key
AQTJNEHGKRUSLT-ODTNPMSZSA-N
Origin
Fungus/Monascus sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    OBESITY RESEARCH SOLUTIONS
    Product Description

    Ankaflavin is a microbial metabolite that has been found in M. ruber and has diverse biological activities.1,2,3 It induces cytotoxicity in HepG2 hepatic carcinoma and A549 lung cancer cells (IC50 = ~15 µg/ml for both).1 Ankaflavin (15 µg/ml) induces cell cycle arrest at the G0 phase in HepG2 cells. It reduces nitric oxide (NO) production in LPS-stimulated RAW 264.7 macrophages when used at concentrations of 5, 10, and 15 µg/ml.2 Ankaflavin (10 µM) increases lipolysis in 3T3-L1 adipocytes matured by isobutylmethylxanthine (IBMX; Item No. 13347), dexamethasone (Item No. 11015), and insulin.3 In vivo, ankaflavin (5 mg/kg per day) reduces blood glucose and serum insulin levels in mice fed a high-fat diet.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Su, N.-W., Lin, Y.-L., Lee, M.-H., et al. Ankaflavin from Monascus-fermented red rice exhibits selective cytotoxic effect and induces cell death on Hep G2 cells. J. Agric. Food Chem. 53(6), 1949-1954 (2005).

    2. Hsu, L.-C., Hsu, Y.-W., Liang, Y.-H., et al. Anti-tumor and anti-inflammatory properties of ankaflavin and monaphilone A from Monascus purpureus NTU 568. J. Agric. Food Chem. 59(4), 1124-1130 (2011).

    3. Hsu, W.-H., Liao, T.-H., Lee, B.-H., et al. Ankaflavin regulates adipocyte function and attenuates hyperglycemia caused by high-fat diet via PPAR-γ activation. J. Funct. Foods 5(1), (2012).