A sesquiterpene lactone
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Cynaropicrin

Item No. 25099

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-(hydroxymethyl)-2-propenoic acid, (3aR,4S,6aR,8S,9aR,9bR)-dodecahydro-8-hydroxy-3,6,9-tris(methylene)-2-oxoazuleno[4,5-b]furan-4-yl ester
CAS Number
35730-78-0
Molecular Formula
C19H22O6
Formula Weight
346.4
Purity
≥98%
Formulation (Request formulation change)
A 1 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: miscibleDMSO: miscibleEthanol: miscibleEthanol:PBS(pH 7.2) (1:1): 0.5 mg/ml
SMILES
C=C([C@@H](O)C1)[C@@]2([H])[C@]1([H])C(C[C@H](OC(C(CO)=C)=O)[C@](C3=C)([H])[C@]2([H])OC3=O)=C
InChi Code
InChI=1S/C19H22O6/c1-8-5-14(24-18(22)9(2)7-20)16-11(4)19(23)25-17(16)15-10(3)13(21)6-12(8)15/h12-17,20-21H,1-7H2/t12-,13-,14-,15-,16+,17+/m0/s1
InChi Key
KHSCYOFDKADJDJ-NQLMQOPMSA-N
Origin
Plant/Cynara scolymus leaf
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    Cynaropicrin is a sesquiterpene lactone originally isolated from artichoke (C. scolymus) that has diverse biological activities.1,2,3,4,5 It inhibits the growth of SKOV3, LOX-IMVI, A549, MCF-7, HCT15, and PC-3 cancer cells (IC50s = 1.1-8.7 μg/ml).1 Cynaropicrin inhibits hepatitis C virus (HCV) replication in Huh7.5 cells with EC50 values ranging from 0.4 to 1.4 μM for genotypes 1a, 1b, 2b, 3a, 4a, 5a, 6a, and 7a.2 It inhibits release of TNF-α and nitric oxide (NO) from LPS-stimulated RAW264.7 cells (IC50s = 8.24 and 1.1 μM, respectively) as well as LPS-induced lymphocyte proliferation (IC50 = 0.9 μM).3 Cynaropicrin inhibits the growth of T. cruzi bloodstream trypomastigotes isolated from infected mice (EC50 = 1 μg/ml).4 It also exhibits antifeedant activity against S. granarius beetles, T. confusum larvae, and T. granarium larvae.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Elsebai, M.F., Mocan, A., and Atanasov, A.G. Cynaropicrin: A comprehensive research review and therapeutic potential as an anti-hepatitis C virus agent. Front. Pharmacol. 7:472, (2016).

    2. Elsebai, M.F., Koutsoudakis, G., Saludes, V., et al. Pan-genotypic hepatitis C virus inhibition by natural products derived from the wild egyptian artichoke. J. Virol. 90(4), 1918-1930 (2015).

    3. Cho, J.Y., Baik, K.U., Jung, J.H., et al. In vitro anti-inflammatory effects of cynaropicrin, a sesquiterpene lactone, from Saussurea lappa. Eur. J. Pharmacol. 398(3), 399-407 (2000).

    4. da Silva, C.F., Batista Dda, G., De Araújo, J.S., et al. Activities of psilostachyin A and cynaropicrin against Trypanosoma cruzi in vitro and in vivo. Antimicrob. Agents Chemother. 57(11), 5307-5314 (2013).

    5. Cis, J., Nowark, G., and Kisiel, W. Antifeedant properties and chemotaxonomic implications of sesquiterpene lactones and syringin from Rhaponticum pulchrum. Biochem. System. Ecol. 34(12), 862-867 (2006).