A fungal macrolactone
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Curvularin

Item No. 21758

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(4S)-4,5,6,7,8,9-hexahydro-11,13-dihydroxy-4-methyl-2H-3-benzoxacyclododecin-2,10(1H)-dione
CAS Number
10140-70-2
Synonyms
  • (−)-Curvularin
  • (S)-Curvularin
  • NSC 166071
Molecular Formula
C16H20O5
Formula Weight
292.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2)(1:9): 0.1 mg/mlEthanol: 10 mg/ml
λmax
222, 272, 303 nm
SMILES
O=C(CCCCC[C@H](C)O1)C(C(O)=CC(O)=C2)=C2CC1=O
InChi Code
InChI=1S/C16H20O5/c1-10-5-3-2-4-6-13(18)16-11(8-15(20)21-10)7-12(17)9-14(16)19/h7,9-10,17,19H,2-6,8H2,1H3/t10-/m0/s1
InChi Key
VDUIGYAPSXCJFC-JTQLQIEISA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $81

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    5 mg

    $297

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    Product Description

    Curvularin is a natural fungal macrolactone that has cytotoxic activity against select cancer cell lines.1,2 It inhibits cytokine-induced expression of induced nitric oxide synthase (iNOS; IC50 = 9.5 µM) in vitro and reduces proinflammatory gene expression in a mouse model of rheumatoid arthritis.3,4 Curvularin also blocks TGF-β signaling in HepG2 and MDA-MB-231 cells.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kumar, C.G., Mongolla, P., Sujitha, P., et al. Metabolite profiling and biological activities of bioactive compounds produced by Chrysosporium lobatum strain BK-3 isolated from Kaziranga National Park, Assam, India. Springerplus 2(1), 122 (2013).

    2. Zhan, J., Wijeratne, E.M., Seliga, C.J., et al. A new anthraquinone and cytotoxic curvularins of a Penicillium sp. from the rhizosphere of Fallugia paradoxa of the Sonoran desert. J. Antibiot. (Tokyo) 57(5), 341-344 (2004).

    3. Yao, Y., Hausding, M., Erkel, G., et al. Sporogen, S14-95, and S-curvularin, three inhibitors of human inducible nitric-oxide synthase expression isolated from fungi. Mol. Pharmacol. 63(2), 383-391 (2003).

    4. Schmidt, N., Art, J., Forsch, I., et al. The anti-inflammatory fungal compound (S)-curvularin reduces proinflammatory gene expression in an in vivo model of rheumatoid arthritis. J. Pharm. Exp. Ther. 343(1), 106-114 (2012).

    5. Rudolph, K., Serwe, A., and Erkel, G. Inhibition of TGF-β signaling by the fungal lactones (S)-curvularin, dehydrocurvularin, oxacyclododecindione and galiellalactone. Cytokine 61(1), 285-296 (2013).