Cynaropicrin

• CAT Number: M006402
• CAS Number: 35730-78-0
• Molecular Formula: C19H22O6
• Molecular Weight: 346.37
• Purity: ≥95%
• Synonyms: cynaropicrin;2-Hydroxymethylpropenoic acid (3aR,4S,6aβ,9aβ,9bα)-dodecahydro-8α-hydroxy-3,6,9-tris(methylene)-2-oxoazuleno[4,5-b]furan-4-yl ester;Cynaropikrin;[(3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroa
• Storage: -20°C
• IUPAC Name: [(3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] 2-(hydroxymethyl)prop-2-enoate
• InChI: 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
• InChIKey: KHSCYOFDKADJDJ-NQLMQOPMSA-N
• SMILES: C=C1C[C@@H]([C@@H]2[C@@H]([C@@H]3[C@H]1C[C@@H](C3=C)O)OC(=O)C2=C)OC(=O)C(=C)CO

Cynaropicrin（Cat No.:M006402）is a sesquiterpene lactone found in artichoke (Cynara scolymus), known for its anti-inflammatory, antioxidant, and antimicrobial properties. It exhibits potent biological activity by inhibiting the NF-κB signaling pathway, thereby reducing the production of pro-inflammatory cytokines. Cynaropicrin has also shown cytotoxic effects against cancer cells, making it a promising compound in cancer research. Additionally, it has hepatoprotective effects and is being explored for its potential benefits in liver health and gastrointestinal disorders. Its diverse therapeutic properties make it valuable for medicinal and pharmacological research.

Reference

1: da Silva CF, Batista Dda G, De Araújo JS, Batista MM, Lionel J, de Souza EM, Hammer ER, da Silva PB, De Mieri M, Adams M, Zimmermann S, Hamburger M, Brun R, Schühly W, Soeiro Mde N. Activities of psilostachyin A and cynaropicrin against Trypanosoma cruzi in vitro and in vivo. Antimicrob Agents Chemother. 2013 Nov;57(11):5307-14. doi: 10.1128/AAC.00595-13. Epub 2013 Aug 12. PubMed PMID: 23939901; PubMed Central PMCID: PMC3811247.
2: Pieri V, Stuppner H. Quantification of cynaropicrin in artichoke leaf extracts by 1H NMR spectroscopy. Planta Med. 2011 Oct;77(15):1756-8. doi: 10.1055/s-0030-1271083. Epub 2011 May 12. PubMed PMID: 21567361.
3: Zimmermann S, Oufir M, Leroux A, Krauth-Siegel RL, Becker K, Kaiser M, Brun R, Hamburger M, Adams M. Cynaropicrin targets the trypanothione redox system in Trypanosoma brucei. Bioorg Med Chem. 2013 Nov 15;21(22):7202-9. doi: 10.1016/j.bmc.2013.08.052. Epub 2013 Sep 5. PubMed PMID: 24080104.
4: Usuki T, Sato M, Hara S, Yoshimoto Y, Kondo R, Zimmermann S, Kaiser M, Brun R, Hamburger M, Adams M. Antitrypanosomal structure-activity-relationship study of synthetic cynaropicrin derivatives. Bioorg Med Chem Lett. 2014 Feb 1;24(3):794-8. doi: 10.1016/j.bmcl.2013.12.099. Epub 2014 Jan 2. PubMed PMID: 24433861.
5:Elsebai, M.F., Koutsoudakis, G., Saludes, V., et al. Pan-<wbr style=”box-sizing: border-box;” />genotypic hepatitis C virus inhibition by natural products derived from the wild egyptian artichoke. J. Virol.  90(4),1918-1930 (2015).
6: Tanaka YT, Tanaka K, Kojima H, Hamada T, Masutani T, Tsuboi M, Akao Y. Cynaropicrin from Cynara scolymus L. suppresses photoaging of skin by inhibiting the transcription activity of nuclear factor-kappa B. Bioorg Med Chem Lett. 2013 Jan 15;23(2):518-23. doi: 10.1016/j.bmcl.2012.11.034. Epub 2012 Nov 21. PubMed PMID: 23232059.
7:Elsebai, M.F., Mocan, A., and Atanasov, A.G. Cynaropicrin: A comprehensive research review and therapeutic potential as an anti-<wbr style=”box-sizing: border-box;” />hepatitis C virus agent. Front. Pharmacol. 7:472,(2016).