A flavonoid with diverse biological activities
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Sakuranetin

Item No. 19761

Technical Information
Formal Name
2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4H-1-benzopyran-4-one
CAS Number
520-29-6
Molecular Formula
C16H14O5
Formula Weight
Purity
≥98%
A crystalline solid
DMF: 30 mg/mlDMF:PBS(pH 7.2)(1:1): 0.5 mg.mlDMSO: 25 mg/ml
λmax
215, 287 nm
SMILES
O=C1C2=C(O)C=C(OC)C=C2OC(C3=CC=C(O)C=C3)C1
InChi Code
InChI=1S/C16H14O5/c1-20-11-6-12(18)16-13(19)8-14(21-15(16)7-11)9-2-4-10(17)5-3-9/h2-7,14,17-18H,8H2,1H3
InChi Key
DJOJDHGQRNZXQQ-UHFFFAOYSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Sakuranetin is a flavonoid and phytoalexin that has been found in rice and has diverse biological activities.1,2,3,4 It reduces blast fungus mycelium growth in vitro and decreases the number of fungal lesions and fungal DNA in blast fungus-infected rice leaves when applied at concentrations of 0.1 and 0.2 mM.1 Sakuranetin is active against M. luteus and B. subtilis (MICs = 2 and 0.5 µg/ml, respectively).2 It is cytotoxic to KB nasopharyngal carcinoma cells (EC50 = 10 µg/ml). Sakuranetin (20 mg/kg) reduces alveolar enlargement, collagen and elastic fiber deposition, and bronchoalveolar lavage fluid (BALF) levels of TNF-α, IL-1β, and M-CSF in a mouse model of elastase-induced emphysema.3 It also reduces collagen fiber deposition and lung inflammation in a mouse model of LPS-induced acute lung injury.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Hasegawa, M., Mitsuhara, I., Seo, S., et alAnalysis on blast fungus-responsive characters of a flavonoid phytoalexin sakuranetin; accumulation in infected rice leaves, antifungal activity and detoxification by fungus. Molecules 19(8), 11404-11418 (2014).

    2. Orjala, J., Wright, A.D., Behrends, H., et alCytotoxic and antibacterial dihydrochalcones from Piper aduncum. J. Nat. Prod. 57(1), 18-26 (1994).

    3. Taguchi, L., Pinheiro, N.M., Olivo, C.R., et alA flavanone from Baccharis retusa (Asteraceae) prevents elastase-induced emphysema in mice by regulating NF-κB, oxidative stress and metalloproteinases. Respir. Res. 16(79), 1-15 (2015).

    4. Bittencourt-Mernak, M.I., Pinheiro, N.M., Santana, F.P., et alProphylactic and therapeutic treatment with the flavonone sakuranetin ameliorates LPS-induced acute lung injury. Am. J. Physiol. Lung Cell Mol. Physiol. 312(2), L217-L230 (2017).