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Countercurrent Chromatography (CCC/CPC) as Versatile Separation ‘Tool-Box’ in the Field of Natural Product Recovery

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Natural Products Chemistry".

Deadline for manuscript submissions: 31 December 2024 | Viewed by 8291

Special Issue Editors

Dr. Gerold Jerz

E-Mail Website
Guest Editor
Institute of Food Chemistry, Technische Universität Braunschweig, Schleinitzstrasse 20, 38106 Braunschweig, Germany
Interests: off-line/ on-line hyphenation of countercurrent (CCC) and Centrifugal Partition Chromatography (CPC) to structure elucidation method; two-dimensional metabolite analysis; food and medicinal plant analysis; structural elucidation of betacyanin pigments and saponins; evaluation of biological activities; natural products from agricultural residues
Special Issues, Collections and Topics in MDPI journals
Prof. Dr. João Henrique G. Lago

E-Mail Website
Guest Editor
Center of Natural Sciences and Humanities, Federal University of ABC, 09210-580 Santo André, Brazil
Interests: structural elucidation of natural products using NMR and MS; separations of natural products using differents strategies such as CC, MPLC, HPLC, etc.; strucutre/activity studies using natural products as models; evaluation of biological activities
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Since Dr. Yoichiro Ito (NIH, Bethesda, USA) introduced “the coil planet centrifuge” in 1966 (published in Nature), countercurrent chromatography and its related techniques have started to work at higher efficiencies using stronger and faster changing gravitation force fields. This technology was originally designed for the separation of human blood cells but then evolved rapidly to become a powerful fractionation tool in the field of recovery of bioactive natural products. The use of immiscible solvent mixtures that have been specifically designed for separation problems is one of the unique features of this methodology, whereby mobile and stationary chromatographic phases are in the liquid state.

Looking back at a development period spanning more than fifty years, many innovative CCC/CPC approaches have evolved, including powerful system designs For natural product chemists, there is the potential for the direct implementation of structural elucidation technology and of off- or on-line biological evaluation in bio-assay-guided fractionation protocols.  

Therefore, this Special Issue will cover “Countercurrent chromatography (CCC/CPC) as versatile ‘tool-box’ in the field of natural product recovery” and will collect original research/ review articles dealing with innovative developments in this field.

Topics of interest include but are not limited to the following:

  • CCC and CPC in natural product recovery (all biological sources);
  • Recovery protocols and strategies for high value natural products;
  • Bio-assay-guided isolation procedures;
  • Off-line or on-line hyphenation to mass spectrometry (MS) and nuclear magnetic resonance (NMR);
  • Two-dimensional CCC or CPC (heart-cutting), or CCC/CPC x GC x LC-MS;
  • Polarity-modifying additives for solvent systems;
  • Chiral additives for enantiomer/ epimer separations;
  • Use of natural deep eutectic solvent systems (NADES);
  • Software based prediction of natural product separations;
  • Aqueous-two-phase-systems (ATPS);
  • Ion exchange and ion-pair chromatography (IP);
  • Green solvent systems for CCC/CPC;
  • New CCC/CPC column and centrifuge designs for improved natural product recovery.

Something that is highly relevant is the combination of CCC/CPC with bio-assay-guided fractionation methods for the search of lead structures in the field of natural products from all kinds of resources, as nature is still the “Fountain for the Drugs of the Future”.

Overall, the present Special Issue aims to cover novel research directions in the field of natural product recovery using CCC and CPC technologies.

Dr. Gerold Jerz
Prof. Dr. João Henrique G. Lago
Guest Editors

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • CCC and CPC in natural product recovery (all biological sources)
  • recovery protocols and strategies for high value natural products
  • bio-assay-guided isolation procedures
  • off-line or on-line hyphenation to mass spectrometry (MS) and nuclear magnetic resonance (NMR)
  • two-dimensional CCC or CPC (heart-cutting), or CCC/CPC x GC x LC-MS
  • polarity-modifying additives
  • chiral additives for enantiomer/ epimer separations
  • use of natural deep eutectic solvent systems (NADES)
  • software based prediction of natural product separations
  • aqueous-two-phase-systems (ATPS)
  • ion exchange and ion-pair chromatography (IP)
  • green solvent systems for CCC/CPC
  • new CCC/CPC column and centrifuge designs for improved natural product recovery

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Published Papers (4 papers)

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Research

14 pages, 1649 KiB  
Article
Preparative Fractionation of Brazilian Red Propolis Extract Using Step-Gradient Counter-Current Chromatography
by Begoña Gimenez-Cassina Lopez, Maria Cristina Marcucci, Silvana Aparecida Rocco, Maurício Luís Sforça, Marcos Nogueira Eberlin, Peter Hewitson, Svetlana Ignatova and Alexandra Christine Helena Frankland Sawaya
Molecules 2024, 29(12), 2757; https://doi.org/10.3390/molecules29122757 - 9 Jun 2024
Cited by 2 | Viewed by 1304
Abstract
Propolis is a resinous bee product with a very complex composition, which is dependent upon the plant sources that bees visit. Due to the promising antimicrobial activities of red Brazilian propolis, it is paramount to identify the compounds responsible for it, which, in [...] Read more.
Propolis is a resinous bee product with a very complex composition, which is dependent upon the plant sources that bees visit. Due to the promising antimicrobial activities of red Brazilian propolis, it is paramount to identify the compounds responsible for it, which, in most of the cases, are not commercially available. The aim of this study was to develop a quick and clean preparative-scale methodology for preparing fractions of red propolis directly from a complex crude ethanol extract by combining the extractive capacity of counter-current chromatography (CCC) with preparative HPLC. The CCC method development included step gradient elution for the removal of waxes (which can bind to and block HPLC columns), sample injection in a single solvent to improve stationary phase stability, and a change in the mobile phase flow pattern, resulting in the loading of 2.5 g of the Brazilian red propolis crude extract on a 912.5 mL Midi CCC column. Three compounds were subsequently isolated from the concentrated fractions by preparative HPLC and identified by NMR and high-resolution MS: red pigment, retusapurpurin A; the isoflavan 3(R)-7-O-methylvestitol; and the prenylated benzophenone isomers xanthochymol/isoxanthochymol. These compounds are markers of red propolis that contribute to its therapeutic properties, and the amount isolated allows for further biological activities testing and for their use as chromatographic standards. Full article
(This article belongs to the Special Issue Countercurrent Chromatography (CCC/CPC) as Versatile Separation ‘Tool-Box’ in the Field of Natural Product Recovery)
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15 pages, 1937 KiB  
Article
Rapid Chemical Profiling of Filipendula ulmaria Using CPC Fractionation, 2-D Mapping of 13C NMR Data, and High-Resolution LC–MS
by Steve Thomas Pannakal, Joan Eilstein, Jane Hubert, Alexis Kotland, Arpita Prasad, Amelie Gueguiniat-Prevot, Franck Juchaux, Floriane Beaumard, Ganapaty Seru, Sherluck John and Dhimoy Roy
Molecules 2023, 28(17), 6349; https://doi.org/10.3390/molecules28176349 - 30 Aug 2023
Cited by 2 | Viewed by 1758
Abstract
Filipendula ulmaria, commonly known as meadowsweet, is a wild herbaceous flowering plant that is widely distributed in Europe. A range of salicylic acid derivatives and flavonol glycosides have been previously associated with the antirheumatic and diuretic properties of F. ulmaria. In [...] Read more.
Filipendula ulmaria, commonly known as meadowsweet, is a wild herbaceous flowering plant that is widely distributed in Europe. A range of salicylic acid derivatives and flavonol glycosides have been previously associated with the antirheumatic and diuretic properties of F. ulmaria. In the present work, a hydroalcoholic extract from F. ulmaria aerial parts was extensively profiled using an efficient NMR-based dereplication strategy. The approach involves the fractionation of the crude extract by centrifugal partition chromatography (CPC), 13C NMR analysis of the fractions, 2D-cluster mapping of the entire NMR dataset, and, finally, structure elucidation using a natural metabolite database, validated by 2D NMR data interpretation and liquid chromatography coupled with mass spectrometry. The chemodiversity of the aerial parts was extensive, with 28 compounds unambiguously identified, spanning various biosynthetic classes. The F. ulmaria extract and CPC fractions were screened for their potential to enhance skin epidermal barrier function and skin renewal properties using in vitro assays performed on Normal Human Epidermal Keratinocytes. Fractions containing quercetin, kaempferol glycosides, ursolic acid, pomolic acid, naringenin, β-sitosterol, and Tellimagrandins I and II were found to upregulate genes related to skin barrier function, epidermal renewal, and stress responses. This research is significant as it could provide a natural solution for improving hydration and skin renewal properties. Full article
(This article belongs to the Special Issue Countercurrent Chromatography (CCC/CPC) as Versatile Separation ‘Tool-Box’ in the Field of Natural Product Recovery)
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18 pages, 3956 KiB  
Article
Profiling and Isolation of Ten Rare Branched-Chain Alkylresorcinols in Quinoa
by Tim Hammerschick and Walter Vetter
Molecules 2023, 28(13), 5220; https://doi.org/10.3390/molecules28135220 - 5 Jul 2023
Cited by 1 | Viewed by 1229
Abstract
Alkylresorcinols (∑ARs) are bioactive lipid compounds predominantly found in cereals. These amphiphilic compounds exist in a high structural diversity and can be divided into two main groups, i.e., 5-alkylresorcinols (ARs) and 2-methyl-5-alkylresorcinols (mARs). The pseudocereal quinoa has a very unique AR profile, consisting [...] Read more.
Alkylresorcinols (∑ARs) are bioactive lipid compounds predominantly found in cereals. These amphiphilic compounds exist in a high structural diversity and can be divided into two main groups, i.e., 5-alkylresorcinols (ARs) and 2-methyl-5-alkylresorcinols (mARs). The pseudocereal quinoa has a very unique AR profile, consisting not only of straight-chain alkyl chains but also iso- and anteiso-branched isomers. Here, we describe a method for the isolation of such methyl-branched ARs and mARs from quinoa. The enrichment of the ∑AR fraction from the lipid extracts by centrifugal partition chromatography (CPC) was followed by ∑AR profiling using countercurrent chromatography (CCC) and GC/MS analysis of CCC fractions. A total of 112 ∑ARs could be detected, 63 of which had not been previously described in quinoa. Due to this high number of ∑ARs, the direct isolation of individual ARs was not possible using conventional CCC. Instead, the more powerful heart-cut mode was applied to enrich the target compounds. A final purification step—the separation of CCC-co-eluting mARs from ARs —was performed via silver ion chromatography. Altogether, ten rare branched-chain ∑ARs (five iso-branched mARs and five anteiso-branched ARs, including mAR19:0-i and AR20:0-a) were isolated with purities up to 98% in the double-digit mg range. Full article
(This article belongs to the Special Issue Countercurrent Chromatography (CCC/CPC) as Versatile Separation ‘Tool-Box’ in the Field of Natural Product Recovery)
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17 pages, 2006 KiB  
Article
A Comparison between High-Performance Countercurrent Chromatography and Fast-Centrifugal Partition Chromatography for a One-Step Isolation of Flavonoids from Peanut Hulls Supported by a Conductor like Screening Model for Real Solvents
by Mats Kiene, Svenja Blum, Gerold Jerz and Peter Winterhalter
Molecules 2023, 28(13), 5111; https://doi.org/10.3390/molecules28135111 - 29 Jun 2023
Cited by 5 | Viewed by 3028
Abstract
Peanut hulls (Arachis hypogaea, Leguminosae), which are a side stream of global peanut processing, are rich in bioactive flavonoids such as luteolin, eriodictyol, and 5,7-dihydroxychromone. This study aimed to isolate these flavonoid derivatives by liquid-liquid chromatography with as few steps [...] Read more.
Peanut hulls (Arachis hypogaea, Leguminosae), which are a side stream of global peanut processing, are rich in bioactive flavonoids such as luteolin, eriodictyol, and 5,7-dihydroxychromone. This study aimed to isolate these flavonoid derivatives by liquid-liquid chromatography with as few steps as possible. To this end, luteolin, eriodictyol and 5,7-dihydroxychromone were isolated from peanut hulls using two different techniques, high-performance countercurrent chromatography (HPCCC) and fast-centrifugal partition chromatography (FCPC). The suitability of the biphasic solvent system composed of n-hexane/ethyl acetate/methanol/water (1.0/1.0/1.0/1.5; v/v/v/v) was determined by the Conductor like Screening Model for Real Solvents (COSMO-RS), which allowed the partition ratio KD-values of the three main flavonoids to be calculated. After a one-step HPCCC separation of ~1000 mg of an ethanolic peanut hull extract, 15 mg of luteolin and 8 mg of eriodictyol were isolated with purities over 96%. Furthermore, 3 mg of 5,7-dihydroxychromone could be isolated after purification by semi-preparative reversed-phase liquid chromatography (semi-prep. HPLC) in purity of over 99%. The compounds were identified by electrospray ionization mass spectrometry (ESI-MS) and nuclear magnetic resonance spectroscopy (NMR). Full article
(This article belongs to the Special Issue Countercurrent Chromatography (CCC/CPC) as Versatile Separation ‘Tool-Box’ in the Field of Natural Product Recovery)
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