A natural COX and glucose-6-phosphatase inhibitor
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Thielavin A

Item No. 21767

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
4-[(2,4-dihydroxy-3,6-dimethylbenzoyl)oxy]-2-hydroxy-3,5,6-trimethyl-benzoic acid, 4-carboxy-3-hydroxy-2,5,6-trimethylphenyl ester
CAS Number
71950-66-8
Molecular Formula
C29H30O10
Formula Weight
538.5
Purity
≥95%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
DMF: SolubleDMSO: SolubleEthanol: Soluble
SMILES
CC1=C(O)C=C(C)C(C(OC2=C(C)C(C)=C(C(OC3=C(C)C(C)=C(C(O)=O)C(O)=C3C)=O)C(O)=C2C)=O)=C1O
InChi Code
InChI=1S/C29H30O10/c1-10-9-18(30)15(6)22(31)19(10)28(36)38-26-14(5)12(3)21(24(33)17(26)8)29(37)39-25-13(4)11(2)20(27(34)35)23(32)16(25)7/h9,30-33H,1-8H3,(H,34,35)
InChi Key
MGGMNKJGDSNTKZ-UHFFFAOYSA-N
Origin
Fungus/Unidentified sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $314

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    2.5 mg

    $1,490

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    Product Description

    Thielavin A is a fungal metabolite originally isolated from T. terricola that is related to thielavin B (Item No. 18770).1 Thielavin A inhibits COX, blocking both the conversion of arachidonic acid (Item No. 90010) to prostaglandin H2 (PGH2; Item No. 17020) and the conversion of PGH2 to PGE2 (Item No. 14010; IC50s = 10 and 40 µM, respectively).2 Thielavin A also inhibits glucose-6-phosphatase in rat liver microsomes (IC50 = 4.6 µM).3 It is a non-competitive inhibitor of α-glucosidase from S. cerevisiae (IC50 = 23.8 µM; Ki = 27.8 µM).4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kitahara, N., Haruyama, H., Hata, T., et al. The structures of thielavins A, B and C. Prostaglandin synthetase inhibitors from fungi. J. Antibiot. (Tokyo) 36(5), 599-600 (1983).

    2. Kitahara, N., Endo, A., Furuya, K., et al. Thielavin A and B, new inhibitors of prostaglandin biosynthesis produced by Thielavia terricola. J. Antibiot. (Tokyo) 34(12), 1562-1568 (1981).

    3. Sakemi, S., Hirai, H., Ichiba, T., et al. Thielavins as glucose-6-phosphatase (G6Pase) inhibitors: Producing strain, fermentation, isolation, structural elucidation and biological activities. J. Antibiot. (Tokyo) 55(11), 941-951 (2002).

    4. Take, Y., Inouye, Y., and Nakamura, S. Comparative studies of the inhibitory properties of antibiotics on human immunodeficiency virus and avian myeloblastosis virus reverse transcriptases and cellular DNA polymerases. J. Antibiot. (Tokyo) 42(1), 107-115 (1989).

    5. Rivera-Chávez, J., González-Andrade, M., González Mdel, C., et al. Thielavins A, J and K: α-Glucosidase inhibitors from MEXU 27095, an endophytic fungus from Hintonia latiflora. Phytochemistry 94, 198-205 (2013).