A fungal metabolite with diverse biological activities
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Pyrenocine A

Item No. 29622

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-methoxy-6-methyl-5-[(2E)-1-oxo-2-buten-1-yl]-2H-pyran-2-one
CAS Number
76868-97-8
Molecular Formula
C11H12O4
Formula Weight
208.2
Purity
≥70%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Dichloromethane: solubleDMSO: solubleEthanol: solubleMethanol: soluble
SMILES
O=C1OC(C)=C(C(/C=C/C)=O)C(OC)=C1
InChi Code
InChI=1S/C11H12O4/c1-4-5-8(12)11-7(2)15-10(13)6-9(11)14-3/h4-6H,1-3H3/b5-4+
InChi Key
VVYCRPVWBIEKIW-SNAWJCMRSA-N
Origin
Fungus/Penicillium sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $262

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    Product Description

    Pyrenocine A is a fungal metabolite that has been found in P. terrestris and has diverse biological activities.1 It inhibits the asexual spore germination of the plant pathogenic fungi F. oxysporum, F. solani, M. hiemalis, and R. stolonifer (EC50s = 14, 20, 20, and 25 µg/ml, respectively). Pyrenocine A is active against B. subtilis, S. aureus, and E. coli (IC50s = 30, 45, and 200 µg/ml, respectively). It inhibits onion seedling elongation (EC50 = 4 µg/ml). Pyrenocine A is also a phytotoxin that inhibits lettuce seed germination and rice seedling elongation.2,3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sparace, S.A., Reeleder, R.D., and Khanizadeh, S. Antibiotic activity of the pyrenocines. Can. J. Microbiol. 33(4), 327-330 (1987).

    2. Sato, H., Konoma, K., and Sakamura, S. Phytotoxins produced by onion pink root fungus, Pyrenochaeta terrestris. Agric. BioI. Chem. 43(11), 2409-2411 (1979).

    3. Sato, H., Konoma, K., Sakamura, S., et al. X-Ray crystal structure of pyrenocine A, a phytotoxin from Pyrenochaeta terrestris. Agric. BioI. Chem. 45(3), 795-797 (1981).