Quantification of Cynaropicrin in Artichoke Leaf Extracts by ¹H NMR Spectroscopy

Abstract

The quantification of cynaropicrin in artichoke leaf extracts (ALE) by means of quantitative ¹H NMR was performed. The method relies on solid phase extraction for sample preparation and spectra acquisition in DMSO-d ₆ containing anthracene as the internal standard. The obtained ¹H NMR spectra revealed excellent signal purity for H-13_b of cynaropicrin, which was thus chosen for quantification. Validation was performed in terms of selectivity, linearity, precision, accuracy, and robustness. The content of cynaropicrin in the analyzed samples showed considerable variation, ranging from non detectable to 1.6 %. The NMR approach does not rely on external calibration, which represents the major advantage compared to traditional approaches based on HPLC.

Cynara scolymus - Asteraceae - cynaropicrin - qHNMR - quality control

References

• 1 Cho J Y, Baik K U, Jung J H, Park M H. In vitro anti-inflammatory effects of cynaropicrin, a sesquiterpene lactone, from Saussurea lappa.  Eur J Pharmacol. 2000;  398 399-407
• 2 Cho J Y, Park J, Yoo E S, Baik K U, Jung J H, Lee J, Park M H. Inhibitory effect of sesquiterpene lactones from Saussurea lappa on tumor necrosis factor-α production in murine macrophage-like cells.  Planta Med. 1998;  64 594-597
• 3 Emendoerfer F, Emendoerfer F, Bellato F, Noldin V F, Cechinel-Filho V, Yunes R A, Delle Monache F, Cardozo A M. Antispasmodic activity of fractions and cynaropicrin from Cynara scolymus on guinea-pig ileum.  Biol Pharm Bull. 2005;  28 902-904
• 4 Zimmermann S, Adams M, Julianti T, Hata-Uribe Y, Brun R, Hamburger M. HPLC- based activity profiling for new antiparasitic leads: In vitro and in vivo antitrypanosomal activity of cynaropicrin. 58th International Congress and Annual Meeting of the Society for Medicinal Plant and Natural Product Research Berlin, Germany; 2010
• 5 Cho J Y, Kim A R, Jung J H, Chun T, Rhee M H, Yoo E S. Cytotoxic and pro-apoptotic activities of cynaropicrin, a sesquiterpene lactone, on the viability of leukocyte cancer cell lines.  Eur J Pharmacol. 2004;  492 85-94
• 6 Glasl S, Tsendayush D, Batchimeg U, Holec N, Wurm E, Kletter C, Gunbilig D, Daariimaa K, Narantuya S, Thalhammer T. Choleretic effects of the mongolian medicinal plant Saussurea amara in the isolated perfused rat liver.  Planta Med. 2007;  73 59-66
• 7 Schneider G, Thiele K. Die Verteilung des Bitterstoffes Cynaropicrin in der Artischocke.  Planta Med. 1974;  26 174-183
• 8 Schneider G, Thiele K. Eigenschaften und Bestimmung des Artischocken-Bitterstoffes Cynaropicrin.  Planta Med. 1974;  25 149-157
• 9 Pauli G F, Jaki B U, Lankin D C. Quantitative ¹H NMR: development and potential of a method for natural products analysis.  J Nat Prod. 2005;  68 133-149
• 10 Choi Y H, Choi H-K, Peltenburg-Looman A M G, Lefeber A W M, Verpoorte R. Quantitative analysis of ginkgolic acids from Ginkgo leaves and products using ¹H-NMR.  Phytochem Anal. 2004;  15 325-330
• 11 Fritsche J, Beindorff C M, Dachtler M, Zhang H, Lammers J G. Isolation, characterization and determination of minor artichoke (Cynara scolymus L.) leaf extract compounds.  Eur Food Res Technol. 2002;  215 149-157