WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H584346
CAS#: 35730-78-0
Description: Cynaropicrin is the first plant natural product with in vivo activity against Trypanosoma brucei.
Hodoodo Cat#: H584346
Name: Cynaropicrin
CAS#: 35730-78-0
Chemical Formula: C19H22O6
Exact Mass: 346.14
Molecular Weight: 346.379
Elemental Analysis: C, 65.88; H, 6.40; O, 27.71
Synonym: Cynaropicrin
IUPAC/Chemical Name: 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
InChi Key: KHSCYOFDKADJDJ-NQLMQOPMSA-N
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
SMILES Code: C=C(CO)C(O[C@H]([C@](C1=C)([H])[C@]([C@@]2([H])C([C@@H](O)C[C@@]32[H])=C)([H])OC1=O)CC3=C)=O
Appearance: Solid powder
Purity: >95% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
More Info:
| Biological target: | Cynaropicrin can inhibit tumor necrosis factor (TNF-α) release with IC50s of 8.24 and 3.18 μM for murine and human macrophage cells, respectively. |
| In vitro activity: | Treatment of human melanoma cells A375 with cynaropicrin resulted in inhibition of cell proliferation and induction of caspase-3-dependent apoptosis. Reference: Phytother Res. 2021 Mar;35(3):1432-1442. https://pubmed.ncbi.nlm.nih.gov/33058354/ |
| In vivo activity: | Cynaropicrin treatment improved the survival rate of the rats with AKI. Cynaropicrin inhibits renal tissue damage and increase survival rate in AKI rat model. Reference: Dokl Biochem Biophys. 2021 Mar;497(1):151-157. https://pubmed.ncbi.nlm.nih.gov/33895932/ |
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 50.0 | 144.35 |
The following data is based on the product molecular weight 346.38 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
| Formulation protocol: | 1. De Cicco P, Busà R, Ercolano G, Formisano C, Allegra M, Taglialatela-Scafati O, Ianaro A. Inhibitory effects of cynaropicrin on human melanoma progression by targeting MAPK, NF-κB, and Nrf-2 signaling pathways in vitro. Phytother Res. 2021 Mar;35(3):1432-1442. doi: 10.1002/ptr.6906. Epub 2020 Oct 15. PMID: 33058354. 2. Liu T, Zhang J, Han X, Xu J, Wu Y, Fang J. Promotion of HeLa cells apoptosis by cynaropicrin involving inhibition of thioredoxin reductase and induction of oxidative stress. Free Radic Biol Med. 2019 May 1;135:216-226. doi: 10.1016/j.freeradbiomed.2019.03.014. Epub 2019 Mar 14. PMID: 30880248. 3. Cai D, Duan H, Fu Y, Cheng Z. Renal Tissue Damage Induced by Acute Kidney Injury in Sepsis Rat Model Is Inhibited by Cynaropicrin via IL-1β and TNF-α Down-Regulation. Dokl Biochem Biophys. 2021 Mar;497(1):151-157. doi: 10.1134/S1607672921020022. Epub 2021 Apr 24. PMID: 33895932. 4. Zheng D, Zhu Y, Shen Y, Xiao S, Yang L, Xiang Y, Dai X, Hu W, Zhou B, Liu Z, Zhao H, Zhao C, Huang X, Wang L. Cynaropicrin Shows Antitumor Progression Potential in Colorectal Cancer Through Mediation of the LIFR/STATs Axis. Front Cell Dev Biol. 2021 Jan 11;8:605184. doi: 10.3389/fcell.2020.605184. PMID: 33505963; PMCID: PMC7829511. |
| In vitro protocol: | 1. De Cicco P, Busà R, Ercolano G, Formisano C, Allegra M, Taglialatela-Scafati O, Ianaro A. Inhibitory effects of cynaropicrin on human melanoma progression by targeting MAPK, NF-κB, and Nrf-2 signaling pathways in vitro. Phytother Res. 2021 Mar;35(3):1432-1442. doi: 10.1002/ptr.6906. Epub 2020 Oct 15. PMID: 33058354. 2. Liu T, Zhang J, Han X, Xu J, Wu Y, Fang J. Promotion of HeLa cells apoptosis by cynaropicrin involving inhibition of thioredoxin reductase and induction of oxidative stress. Free Radic Biol Med. 2019 May 1;135:216-226. doi: 10.1016/j.freeradbiomed.2019.03.014. Epub 2019 Mar 14. PMID: 30880248. |
| In vivo protocol: | 1. Cai D, Duan H, Fu Y, Cheng Z. Renal Tissue Damage Induced by Acute Kidney Injury in Sepsis Rat Model Is Inhibited by Cynaropicrin via IL-1β and TNF-α Down-Regulation. Dokl Biochem Biophys. 2021 Mar;497(1):151-157. doi: 10.1134/S1607672921020022. Epub 2021 Apr 24. PMID: 33895932. 2. Zheng D, Zhu Y, Shen Y, Xiao S, Yang L, Xiang Y, Dai X, Hu W, Zhou B, Liu Z, Zhao H, Zhao C, Huang X, Wang L. Cynaropicrin Shows Antitumor Progression Potential in Colorectal Cancer Through Mediation of the LIFR/STATs Axis. Front Cell Dev Biol. 2021 Jan 11;8:605184. doi: 10.3389/fcell.2020.605184. PMID: 33505963; PMCID: PMC7829511. |
1: Zimmermann S, Kaiser M, Brun R, Hamburger M, Adams M. Cynaropicrin: the first plant natural product with in vivo activity against Trypanosoma brucei. Planta Med. 2012 Apr;78(6):553-6. doi: 10.1055/s-0031-1298241. Epub 2012 Feb 13. PubMed PMID: 22331812.
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: Sato T, Hara S, Sato M, Ogawa K, Adams M, Usuki T. Synthesis of cynaropicrin-d(4). Bioorg Med Chem Lett. 2015 Dec 1;25(23):5504-7. doi: 10.1016/j.bmcl.2015.10.065. Epub 2015 Oct 23. PubMed PMID: 26520660.
4: Emendörfer F, Emendörfer F, Bellato F, Noldin VF, Cechinel-Filho V, Yunes RA, Delle Monache F, Cardozo AM. Antispasmodic activity of fractions and cynaropicrin from Cynara scolymus on guinea-pig ileum. Biol Pharm Bull. 2005 May;28(5):902-4. PubMed PMID: 15863902.
5: Yamada K, Ishii Y, Takeda T, Kuroki H, Mitoma C, Uchi H, Furue M, Yamada H. [Effect of Cynaropicrin on 2,3,4,7,8-Pentachlorodibenzofuran-induced Wasting Syndrome and Oxidative Stress]. Fukuoka Igaku Zasshi. 2015 May;106(5):169-75. Japanese. PubMed PMID: 26226680.
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7: Elsebai MF, Koutsoudakis G, Saludes V, Pérez-Vilaró G, Turpeinen A, Mattila S, Pirttilä AM, Fontaine-Vive F, Mehiri M, Meyerhans A, Diez J. Pan-genotypic Hepatitis C Virus Inhibition by Natural Products Derived from the Wild Egyptian Artichoke. J Virol. 2015 Dec 9;90(4):1918-30. doi: 10.1128/JVI.02030-15. PubMed PMID: 26656684; PubMed Central PMCID: PMC4734011.
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9: 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.
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11: 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.
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13: Cheng CH, Costall B, Hamburger M, Hostettmann K, Naylor RJ, Wang Y, Jenner P. Toxic effects of solstitialin A 13-acetate and cynaropicrin from Centaurea solstitialis L. (Asteraceae) in cell cultures of foetal rat brain. Neuropharmacology. 1992 Mar;31(3):271-7. PubMed PMID: 1630595.
14: Mokoka TA, Xolani PK, Zimmermann S, Hata Y, Adams M, Kaiser M, Moodley N, Maharaj V, Koorbanally NA, Hamburger M, Brun R, Fouche G. Antiprotozoal screening of 60 South African plants, and the identification of the antitrypanosomal germacranolides schkuhrin I and II. Planta Med. 2013 Sep;79(14):1380-4. doi: 10.1055/s-0033-1350691. Epub 2013 Aug 8. PubMed PMID: 23929246.
15: Takei K, Hashimoto-Hachiya A, Takahara M, Tsuji G, Nakahara T, Furue M. Cynaropicrin attenuates UVB-induced oxidative stress via the AhR-Nrf2-Nqo1 pathway. Toxicol Lett. 2015 Apr 16;234(2):74-80. doi: 10.1016/j.toxlet.2015.02.007. Epub 2015 Feb 11. PubMed PMID: 25680693.
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18: Sovová H, Opletal L, Sajfrtová M, Bártlová M. Supercritical fluid extraction of cynaropicrin and 20-hydroxyecdysone from Leuzea carthamoides DC. J Sep Sci. 2008 May;31(8):1387-92. doi: 10.1002/jssc.200700496. PubMed PMID: 18383243.
19: Zimmermann S, Fouché G, De Mieri M, Yoshimoto Y, Usuki T, Nthambeleni R, Parkinson CJ, van der Westhuyzen C, Kaiser M, Hamburger M, Adams M. Structure-activity relationship study of sesquiterpene lactones and their semi-synthetic amino derivatives as potential antitrypanosomal products. Molecules. 2014 Mar 21;19(3):3523-38. doi: 10.3390/molecules19033523. PubMed PMID: 24662071.
20: Bachelier A, Mayer R, Klein CD. Sesquiterpene lactones are potent and irreversible inhibitors of the antibacterial target enzyme MurA. Bioorg Med Chem Lett. 2006 Nov 1;16(21):5605-9. Epub 2006 Aug 30. PubMed PMID: 16945528.
