A homoisoflavonoid with diverse biological activities
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Sappanone A

Item No. 23205

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-[(3,4-dihydroxyphenyl)methylene]-2,3-dihydro-7-hydroxy-4H-1-benzopyran-4-one
CAS Number
102067-84-5
Molecular Formula
C16H12O5
Formula Weight
284.3
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 15 mg/mlEthanol: 5 mg/mlPBS (pH 7.2): 0.25 mg/ml
λmax
271, 374 nm
SMILES
OC1=CC=C(C(/C(CO2)=C/C3=CC=C(O)C(O)=C3)=O)C2=C1
InChi Code
InChI=1S/C16H12O5/c17-11-2-3-12-15(7-11)21-8-10(16(12)20)5-9-1-4-13(18)14(19)6-9/h1-7,17-19H,8H2/b10-5+
InChi Key
KVYZXXBTJHJISR-BJMVGYQFSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

    $36

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    10 mg

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    Product Description

    Sappanone A is a homoisoflavonoid with diverse biological activities that has been isolated from the aerial parts of C. pulcherrima, the heartwood of C. sappan, and the stems of H. campechianum.1,2,3,4,5 In vitro, sappanone A inhibits 76.2, 59.2, 37.4, and 35.4% of FGFR1, KDR, c-Met, and c-Kit kinase activity, respectively, when used at a concentration of 10 μM.1 It also inhibits influenza viral neuraminidase (NA) with IC50 values of 0.7, 1.1, and 1 μM for H1N1, H3N2, and H9N2 influenza viral NAs, respectively.2 Sappanone A has antibacterial activity against Gram-positive B. subtilis, B. sphaericus, and S. aureus as well as Gram-negative K. aerogenes and C. violaceum.3 It also inhibits the growth of A. niger and C. albicans fungi. Sapannone A inhibits LPS-induced inflammatory responses in vitro and in vivo, reducing nitric oxide (NO), interleukin-6 (IL-6), and prostaglandin E2 (PGE2; Item No. 14010) production in RAW264.7 cells as well as LPS-induced mortality in mice.4 It also attenuates airway inflammation and mucus hypersecretion via activation of the Nrf2 signaling pathway in a mouse model of ovalbumin-induced asthma.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lin, L.-G., Xie, H., Li, H.-L., et al. Naturally occurring homoisoflavonoids function as potent protein tyrosine kinase inhibitors by c-Src-based high-throughput screening. J. Med. Chem. 51(15), 4419-4429 (2008).

    2. Jeong, H.J., Kim, Y.M., Kim, J.H., et al. Homoisoflavonoids from Caesalpinia sappan displaying viral neuraminidases inhibition. Biol. Pharm. Bull. 35(5), 786-790 (2012).

    3. Das, B.C., Thirupathi, P., Ravikanth, B., et al. Isolation, synthesis, and bioactivity of homoisoflavonoids from Caesalpinia pulcherrima. Chem. Pharm. Bull. (Tokyo) 57(10), 1139-1141 (2009).

    4. Lee, S., Choi, S.-Y., Choo, Y.-Y., et al. Sappanone A exhibits anti-inflammatory effects via modulation of Nrf2 and NF-κB. Int. Immunopharmacol. 28(1), 328-336 (2015).

    5. Liu, X., Yu, D., and Wang, T. Sappanone A attenuates allergic airway inflammation in ovalbumin-induced asthma. Int. Arch. Allergy. Immunol. 170(3), 180-186 (2016).