Gram-Scale Purification of Two Sesquiterpene Lactones from Chartolepsis Intermedia Boiss.

Abstract

International audienceTwo sesquiterpene lactones, grosheimin and cynaropicrin, present in the aerial part of the Chartolepis intermedia Boiss. plant can be obtained from the ethyl acetate solid extract of the dried plant. A large-scale purification processing 16 kg of dry plant is presented. The first liquid-liquid extraction step of the 16 kg produced 550 g of dry extract that were divided in two equal portions. A classical low-pressure chromatography method can produce from 275 g of dry extract 13.8 g of grosheimin and 52.3 g of cynaropicrin 95 % pure lactones in 110 h using large amounts of organic solvents and 8 kg of silica gel. Another purification method employing countercurrent chromatography, with a modern hydrostatic column, and reversed phase preparative liquid chromatography were used with the second 275 g dry extract portion. It could produce 17.9 g of 99.4 % pure grosheimin and 68 g of 98.7 % pure cynaropicrin lactones in 95 h, with better yields and minimized losses in chromatographic columns, and using smaller solvent volumes than the classical method. The two purification processes are fully described and compared

The natural sesquiterpene lactones arglabin, grosheimin, agracin, parthenolide, and estafiatin inhibit T cell receptor (TCR) activation

“…The sesquiterpene lactones (achillin, arglabin, argolide, argracin, 3β-hydroxyarhalin, artesin, artemisinin, estafiatin, grosheimin, grossmisin, leucomisine, parthenolide, and taurin) were isolated as previously described from different plants of the Asteraceae family, as shown in Table I (Adekenov, 2013; Adekenov et al, 2016; Adekenov et al, 1984; Adekenov, 2017; Adekenova et al, 2016; Akyev et al, 1972; Arystan et al, 2009; Rey et al, 1992). The purity of each compound was determined to be > 98% by normalization of the peak areas detected on an automated high-performance liquid chromatography (HPLC) system (Hewlett–Packard Agilent 1100) with a Zorbax SB-C 18 column (4.6 × 150 mm) eluted with acetonitrile/water (50%/50%, v/v) or methanol/water (50%/50%, v/v) at a flow rate of 0.5 mL/min at 25 °C.…”

“…Filat. (Adekenov, 2013; Akyev et al, 1972); estafiatin ( 8 ) was isolated from Achillea nobilis L. (Adekenov et al, 1984); grosheimin ( 9 ) was isolated from Chartolepsis intermedia Boiss (Adekenova et al, 2016); leucomisine ( 11 ) was isolated from Artemisia leucodes Schrenk (Arystan et al, 2009); and parthenolide ( 12 ) was isolated from Tanacetum scopulorum (Krasch.) Tzvel (Adekenov, 2013).…”

Cynaropicrin: A Comprehensive Research Review and Therapeutic Potential As an Anti-Hepatitis C Virus Agent

“…Cynaropicrin contributes to approximately 80% of the characteristic bitter taste of artichoke, which is associated with the activation of bitter sensory receptors (Cravotto et al, 2005; Eljounaidi et al, 2015). Cynaropicrin can be isolated in gram-scale by employing countercurrent chromatography (Adekenova et al, 2015). 1 H NMR spectroscopy and titration of the lactone ring with sodium hydroxide were used for the quantitative determination of cynaropicrin (Schneider and Thiele, 1974a,b; Pieri and Stuppner, 2011).…”

Inhibition of T Cell Receptor Activation by Semi-Synthetic Sesquiterpene Lactone Derivatives and Molecular Modeling of Their Interaction with Glutathione and Tyrosine Kinase ZAP-70

“…Nova [23], 3β-hydroxyarhalin was isolated from Artemisia halophila Krasch. [24], and grosheimin was isolated from Chartolepis intermedia Boiss [25]. Dihydroargolide (ketopelenolide B) was isolated from Artemisia glabella Kar.…”

“…Arglabin, argolide, 3β-hydroxyarhalin, dihydroargolide, and grosheimin were isolated from different plants of the Asteraceae family, as previously described [23,24,25,26,55]. The purity of each compound was determined to be >98% by a normalization of the peak areas detected on an automated high-performance liquid chromatography (HPLC) system (Hewlett–Packard Agilent 1100, Santa Clara, CA, USA) with a Zorbax SB-C 18 column (4.6 × 150 mm), eluted with acetonitrile/water (50%/50%, v / v ) or methanol/water (50%/50%, v / v ) at a flow rate of 0.5 mL/min at 25 °C.…”