An inhibitor of mitochondrial complex II
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Harzianopyridone

Item No. 19620

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-hydroxy-5,6-dimethoxy-3-[(2S,4E)-2-methyl-1-oxo-4-hexen-1-yl]-2(1H)-pyridinone
CAS Number
137813-88-8
Synonyms
  • (-)-Harzianopyridone
Molecular Formula
C14H19NO5
Formula Weight
281.3
Purity
≥95%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Methanol: Soluble
SMILES
O=C1NC(OC)=C(OC)C(O)=C1C([C@@H](C)C/C=C/C)=O
InChi Code
InChI=1S/C14H19NO5/c1-5-6-7-8(2)10(16)9-11(17)12(19-3)14(20-4)15-13(9)18/h5-6,8H,7H2,1-4H3,(H2,15,17,18)/b6-5+/t8-/m0/s1
InChi Key
FPYAYFJAGDIMEX-GJIOHYHPSA-N
Origin
Fungus/Trichoderma harzianum sp. FKI-1509
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    250 µg

    $69

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    1 mg

    $238

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    Product Description

    Harzianopyridone is an atpenin-like inhibitor of mammalian and nematode mitochondrial complex II (succinate:ubiquinone oxidoreductase; SQR) with IC50 values of 0.017, 0.2, and 2 μM for bovine, rat, and nematode complex II, respectively.1 It also inhibits nematode quinol-fumarate reductase (QFR; IC50 = 0.36 μM). Harzianopyridone is selective for complex II over complexes I and III in rats and cattle and complex I in nematodes (IC50s >100 μM). It has antibacterial and antifungal activity (EC50s = 35.9, 42.2, 60.4, and 50.2 μg/ml against R. solani, S. rolfsii, M. phaseolina, and F. oxysporum, respectively).2,3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Miyadera, H., Shiomi, K., Ui, H., et al. Atpenins, potent and specific inhibitors of mitochondrial complex II (succinate-ubiquinone oxidoreductase). Proc. Natl. Acad. Sci. USA 100(2), 473-477 (2003).

    2. Cutler, H.G., and Jacyno, J.M. Biological activity of (−)-harzianopyridone isolated from Trichoderma harzianum. Agric. Biol. Chem. 55(10), 2629-2631 (1991).

    3. Ahluwalia, V., Kumar, J., Rana, V.S., et al. Comparative evaluation of two Trichoderma harzianum strains for major secondary metabolite production and antifungal activity. Nat. Prod. Res. 29(10), 914-920 (2015).