| Identification | Back Directory | [Name]
cynaropicrin | [CAS]
35730-78-0 | [Synonyms]
Cynaropikrin
cynaropicrin
CYNAROPICRIN(SH)
Cynaropicrin - Cynara cardunculus (artichoke)
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
2-Propenoic acid, 2-(hydroxymethyl)-, (3aR,4S,6aR,8S,9aR,9bR)-dodecahydro-8-hydroxy-3,6,9-tris(methylene)-2-oxoazuleno[4,5-b]furan-4-yl ester
2-methylolacrylic acid [(3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-2-keto-3,6,9-trimethylene-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] ester
[(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 | [Molecular Formula]
C19H22O6 | [MDL Number]
MFCD31614147 | [MOL File]
35730-78-0.mol | [Molecular Weight]
346.37 |
| Chemical Properties | Back Directory | [Boiling point ]
566.2±50.0 °C(Predicted) | [density ]
1.28±0.1 g/cm3 (20 ºC 760 Torr) | [storage temp. ]
-20°C, protect from light | [solubility ]
DMSO:50.0(Max Conc. mg/mL);144.35(Max Conc. mM) | [form ]
Oil | [pka]
13.52±0.10(Predicted) | [color ]
Off-white to light yellow | [biological source]
plant | [Major Application]
metabolomics
vitamins, nutraceuticals, and natural products | [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]
O1[C@@H]2[C@@H]3[C@@H](C[C@@H](C3=C)O)C(=C)C[C@@H]([C@H]2C(=C)C1=O)OC(=O)C(=C)CO | [LogP]
1.340 (est) |
| Hazard Information | Back Directory | [Uses]
Cynaropicrin can inhibit lipopolysaccharide-induced TNF-α release from either murine or human macrophage cells in a dose-dependent manner with the IC50 values of 8.24 and 3.18 μM, respectively. It can also inhibit the increase of cartilage degradation factor (MMP13) and suppresses NF-κB signaling. | [Definition]
ChEBI: Cynaropicrin is a sesquiterpene lactone. | [Biological Activity]
Cynaropicrin is a potent activator of the AhR-Nrf2-Nqo1 pathwaymaking it a potential candidate for preventing UVB-induced photoaging. Additionallyit exhibits pro-apoptotic activitysuggesting its potential as an anticancer agent against certain leukocyte cancer cells such as lymphoma or leukemia. Cynaropicrin has demonstrated in vivo activity against Trypanosoma brucei and exhibits immunomodulatory effects by influencing cytokine release and nitric oxide production while also displaying immunosuppressive properties. Moreoverit has anti-inflammatory effects by inhibiting the production of inflammatory mediators and lymphocyte proliferationwhich is achieved through conjugation with sulphydryl groups of target protein(s). |
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