A fungal metabolite with diverse biological activities
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Fuscin

Item No. 27485

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9,10-dihydro-5-hydroxy-4,8,8-trimethyl-2H,4H-benzo[1,2-b:4,3-c']dipyran-2,6(8H)-dione
CAS Number
83-85-2
Molecular Formula
C15H16O5
Formula Weight
276.3
Purity
≥95%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMSO: Soluble
SMILES
O=C1OC(C)C(C2=C1)=C(O)C(C3=C2CCC(C)(C)O3)=O
InChi Code
InChI=1S/C15H16O5/c1-7-11-9(6-10(16)19-7)8-4-5-15(2,3)20-14(8)13(18)12(11)17/h6-7,17H,4-5H2,1-3H3
InChi Key
OSJKAGRXDVEZQO-UHFFFAOYSA-N
Origin
Fungi
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $182

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    5 mg

    $820

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    10 mg

    $1,089

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    Cayman Chemical
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    Product Description

    Fuscin is a quinonoid fungal metabolite originally isolated from O. fuscum that has diverse biological activities.1,2,3 It inhibits binding of the ADP/ATP translocase inhibitor atractyloside (Item No. 44522) to rat liver mitochondria in an ADP-dependent manner when used at a concentration of 50 μM in a radioligand binding assay.1 Fuscin (20 μM) reduces the glutathione content of rat liver mitochondria to 28% of controls and inhibits NADH oxidation in sonicated pigeon heart mitochondria preparations in a concentration-dependent manner.2 It competes with macrophage inflammatory protein 1α (MIP-1α) for binding to CCR5 chemokine receptors in vitro with an IC50 value of 21 μM.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Vignais, P.V., and Vignais, P.M. Effect of SH reagents on atractyloside binding to mitochondria and ADP translocation. Potentiation by ADP and its prevention by uncoupler FCCP. FEBS Lett. 26(1), 27-31 (1972).

    2. Vignais, P.M., and Vignais, P.V. Fuscin, an inhibitor of mitochondrial SH-dependent transport-linked functions. Biochim. Biophys. Acta 325(3), 357-374 (1973).

    3. Yoganathan, K., Rossant, C., Ng, S., et al. 10-Methoxydihydrofuscin, fuscinarin, and fuscin, novel antagonists of the human CCR5 receptor from Oidiodendron griseum. J. Nat. Prod. 66(8), 1116-1117 (2003).