CCC Publications

Recent CCC-related Publications from the
Pauli & Friesen Laboratory

Classic Paper: G.U.E.S.S. in CCC

  • Ramos R, Wan B, Inui T, Franzblau S, Pauli GF, Jaki B
    Airborne Anti-TB activity of Eucalyptus citriodora Hook. Essential Oil
    Journal of Natural Products 77: in press (2014)
  • Liu Y, Chen SN, McAlpine JB, Klein LL, Friesen JB, Lankin DC,
    Pauli G
    Quantification of a Botanical Negative Marker without an Identical
    Standard: Ginkgotoxin in Ginkgo biloba
    Journal of Natural Products 77: in press (2014)
  • Simmler C, Jones T, Anderson J, Nikolic D, van Breemen R, Soejarto D, Chen SN, Pauli GF
    Species-specific Standardization of Licorice by Metabolomic Profiling of Flavanones and Chalcones
    Phytochemical Analysis 26: in press (2014)
  • Qiu F, Friesen JB, McAlpine JB, Pauli GF
    Design of Countercurrent Separation of Ginkgo biloba Terpene Lactones by Nuclear Magnetic Resonance
    Journal of Chromatography A 1242: 26-34 (2012)
  • McAlpine JB, Friesen JB, Pauli GF [Book Chapter]
    Separation of Natural Products by Countercurrent Chromatography
    In: Natural Products Isolation
    Springer, New York/Vienna (2012)

    Editor: S. Sarker
  • Friesen JB, Pauli GF
    Binary concepts and standardization in counter-current separation technology.
    Journal of Chromatography A 1116: 4237-44
  • Gödecke T, Chen SN, Lankin D, Nikolic D, van Breemen R, Pauli GF
    Phytochemistry of Cimicifugic Acids and Associated Bases in Cimicifuga racemosa Root Extracts
    Phytochemical Analysis 20: 120-131 (2009)
  • Friesen JB, Pauli GF
    GUESSmix-guided optimization of elution–extrusion counter-current separations.
    Journal of Chromatography A 1216: 4225-4231
  • Pauli GF, Pro S, Friesen B [REVIEW with 240 citations]
    Countercurrent Separation of Natural Products
    Journal of Natural Products 71: 1489-1508 (2008)
    An assessment of the technology and method development in countercurrent chromatography (CCC) and centrifugal partition chromatography (CPC), collectively referred to as countercurrent separation (CS), is provided. More than six decades of CS theory and applications are critically reviewed and developed into a practical guide to CS for natural products research. The necessary theoretical foundation is given for better use of CS in the separation of biological molecules of any size, small to large, and from any matrix, simple to complex. The three operational fundamentals of CSinstrumentation, biphasic solvent systems, and theoryare covered in a prismatic fashion. The goal of this review is to provide the necessary background and references for an up-to-date perspective of CS and to point out its potential for the natural products scientist for applications in natural products chemistry, metabolome, and proteome research involving organisms from terrestrial and marine sources.
  • Schinkovitz A, Pro S, Main M, Chen SN, Jaki BU, Lankin DC, Pauli GF
    The Dynamic Nature of the Ligustilide Complex
    Journal of Natural Products 71: 1606-1611 (2008)
  • Friesen B & Pauli GF
    Performance Characteristics of Countercurrent Separation in Natural Product Analysis
    Journal of Agricultural & Food Chemistry 56: 19-28 (2008)
  • Friesen JB & Pauli GF
    Reciprocal Symmetry Plots as a Representation of Countercurrent Chromatograms.
    Analytical Chemistry 79: 2320-2324 (2007)
    Traditionally, chromatograms in countercurrent chromatography (CCC) have been plotted with retention volume or time on the x-axis. However, the distribution constant (K) is a more appropriate, reproducible value for the x-axis, because it is a physicochemical property of a particular analyte in a particular solvent system. Therefore, K is independent of both the total column volume and the stationary-phase volume ratio (SF) of the column. Going one step beyond simple K plots, the reciprocal symmetry (ReS) plot, with K and 1/K positioned on either side of a line of symmetry on the x-axis, represents all K values, zero to infinity. Based on experimental evidence, using a mixture of CCC reference standards, the ReS plot demonstrates both the invertible and “symmetric” nature of CCC, a consequence of the exchange of the mobile and stationary phases by reversing the direction of the flow and the symmetry of the liquid−liquid partitioning process between two immiscible phases, respectively. Moreover, the interval of optimal resolution can be centered on the ReS plot to focus on K values of interest, establishing the reciprocal shifted symmetry (ReSS) plots in CCC. Improved representation of peak shape across the whole CCC polarity range is an added advantage of ReSS plots over both K and classical retention volume plots.
  • Berthod A, Friesen JB, Inui T, Pauli, GF
    Elution-Extrusion Countercurrent Chromatography: Theory and Concepts in Metabolic Analysis.
    Analytical Chemistry 79: 3371-3382 (2007)
    Featured article in May 2007, “Research Profile: Revisiting liquid stationary phases"
    Elution−extrusion countercurrent chromatography (EECCC) takes full advantage of the liquid nature of the stationary phase in CCC by combining regular chromatographic elution with stationary-phase extrusion. EECCC is shown to be a three-stage process consisting of classical elution (I), sweeping elution (II), and extrusion (III). After only two column volumes of solvent, it rapidly yields a high-resolution chromatogram that covers an extended polarity range of solutes. As hydrophilicity/lipophilicity balance is a crucial discriminatory property of analytes in highly complex mixtures such as metabolomic samples, the precise determination of CCC distribution constants (KD) is vital to the analysis of metabolomes and other complex biological matrixes. This work builds the EECCC concept by performing a full theoretical treatment and providing equations for retention volumes, peak widths, resolution factors, and distribution constants. Experimental validation utilizes natural products standards that resemble the zero to infinity range of the polarity continuum. EECCC extends the “sweet spot” of high resolution in CCC and provides access to the otherwise practically unapproachable high-KD portion of the high-resolution chromatograms in CCC. Its improved capabilities of KD targeting make EECCC a promising tool for the specific analysis of “small” molecules in complex samples such as in metabolomic fingerprinting and footprinting.
  • Friesen JB, Pauli GF
    Rational Development of Solvent System Families in Counter-current Chromatography.
    Journal of Chromatography A 1151: 51-59
  • Inui T, Wang Y, Smith D, Franzblau S, Pauli GF
    Counter-Current Chromatography-Based Analysis of Synergy in an Anti-tuberculosis Ethnobotanical.
    Journal of Chromatography A 1151: 211-215 (2007)
  • Case R, Wang Y, Franzblau SG, Matainaho L, Piskaut P, Soejarto D, Pauli GF
    Advanced Applications of CCC in the isolation of anti-TB constituents from
    Dracaena angustifolia.
    Journal of Chromatography A 1151: 169-174 (2007)
  • Berthod A, Conway W, Ito Y, Pauli GF, Sutherland I
    CCC 2006 - The Fourth International Conference on Countercurrent Chromatography
    in Bethesda (MD): Natural Products and Scale-up Applications
    Journal of Chromatography A 1151: 1-5 (2007)
    G.U.E.S.S. to make Generally Useful Estimations of Solvent Systems in CCC.
    Journal of Liquid Chromatography & Relat. Technologies 28: 2777-2806 (2005)
  • Pauli GF, Case R, Inui T, Wang Y, Cho S, Fischer N, Franzblau S. 2005.
    New perspectives on natural products in TB drug research
    Life Sciences 78: 485-494 (2005)
  • Conway W, Chadwick L, Fong HHS, Farnsworth N, Pauli GF
    Extra-Column dead volume in countercurrent chromatography
    Journal of Liquid Chromatography and Related Technologies 28: 1799-1818 (2005)
  • Chadwick L, Fong HHS, Farnsworth NR, Pauli GF
    CCC sample cutting for isolation of prenylated phenolics from hopsJournal of Liquid Chromatography and Related Technologies 28: 1959-1969 (2005)
  • Inui T, Case R, Chou E, Soejarto D, Fong HHS, Franzblau S, Smith D, Pauli GF. 2005.
    Anti-TB ethnobotanicals and plants from Alaska and Asia - The potential of CCC
    Journal of Liquid Chromatography and Related Technologies 28: 2017-2028 (2005)


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