Counter-Current Chromatography in Natural Products Isolation

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Topic Information

Dear Colleagues,

Counter-current chromatography (CCC) is a unique liquid–liquid partition chromatography. Without use of solids as support matrices, CCC eliminates many complications resulting from solid-supporting materials, such as irreversible absorption, constituent losses and deactivation, tailing of solute peaks and contamination. In addition, by comparison with other solid-support chromatography including silica column chromatography and reversed-phase liquid chromatography, CCC has more advantages such as a higher retention of a stationary phase, a better selection and more solvent-saving. Therefore, CCC has been widely employed for separation and preparation of natural and synthetic compounds from complex mixtures in many fields. In discussing this topic, we will focus on the separation and purification of bioactive natural products by CCC or CCC-involved separation techniques. Novel CCC instruments and separation methods developments are encouraged, and general reviews and experimental reports are welcome.

Dr. Shihua Wu
Dr. Zhi Yang
Dr. Xinyi Huang
Topic Editors

Keywords

Participating Journals

Journal Name	Impact Factor	CiteScore	Launched Year	First Decision (median)	APC
Analytica analytica	-	1.8	2020	17.9 Days	CHF 1000
Metabolites metabolites	3.5	5.7	2011	16.1 Days	CHF 2700
Molecules molecules	4.2	7.4	1996	15.1 Days	CHF 2700
Separations separations	2.5	3.0	2014	15.1 Days	CHF 2600
Toxins toxins	3.9	7.5	2009	20.3 Days	CHF 2700

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Published Papers (4 papers)

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All Analytica Metabolites Molecules Separations Toxins

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12 pages, 3852 KiB  

Open AccessArticle

Screening and Isolating Acetylcholinesterase Inhibitors from Olea europaea L. Fruit Using Ultrafiltration–Liquid Chromatography Coupled with High-Speed Counter-Current Chromatography

by Xingcui Wang, Yingshan Zhang, Jules Muhire, Duolong Di, Xinyi Huang and Dong Pei

Separations 2025, 12(4), 96; https://doi.org/10.3390/separations12040096 - 12 Apr 2025

Viewed by 171

Abstract

Alzheimer’s disease (AD) is a progressive neurodegenerative condition and one of the most prevalent types of dementia in older adults. Currently, the primary drugs used to treat AD are acetylcholinesterase (AChE) inhibitors. The development of natural substances has become a research hotspot due [...] Read more.

Alzheimer’s disease (AD) is a progressive neurodegenerative condition and one of the most prevalent types of dementia in older adults. Currently, the primary drugs used to treat AD are acetylcholinesterase (AChE) inhibitors. The development of natural substances has become a research hotspot due to the high number of adverse effects of synthetic drugs. In this study, a new assay based on ultrafiltration–liquid chromatography–high-speed counter-current chromatography (UF-HPLC-HSCCC) was developed for the rapid screening and identification of AChE inhibitors from Olea europaea L. fruit. In this research, we screened and isolated two AChE inhibitors from O. europaea fruit extracts, identified by EI-MS and NMR as secologanoside and oleuroside-11-methyl ester. These compounds were identified for the first time from O. europaea and found to possess AChE inhibitory activity using an in vitro AChE inhibition assay and molecular docking. The IC₅₀ values of the two compounds were 0.76 ± 0.04 mM and 1.08 ± 0.05 mM. The results demonstrated that secologanoside showed better AChE inhibition activity than oleuroside-11-methyl ester, suggesting that this compound is a promising AChE inhibitor. At the same time, the results showed that the combination of UF-HPLC- HSCCC provides a powerful tool for screening and isolating AChE inhibitors in complex samples. Full article

(This article belongs to the Topic Counter-Current Chromatography in Natural Products Isolation)

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13 pages, 1492 KiB  

Open AccessFeature PaperArticle

Screening of Solvent Systems for Countercurrent Chromatography Separation of Polar Constituents from Ginkgo biloba L. Seeds

by Ruxi Hu, Zhuo Liu, Yi Zhou, Peng Tian, Luqi Li, Zhi Yang and Yatuan Ma

Molecules 2025, 30(2), 409; https://doi.org/10.3390/molecules30020409 - 19 Jan 2025

Viewed by 740

Abstract

The separation of large polar constituents presents a substantial challenge in natural product research when employing column chromatography techniques, as the process is both complex and time-consuming. In this study, an acetonitrile/tetrahydrofuran/di-(2-ethylhexyl) phosphoric acid/aqueous saturated sodium chloride solvent system was developed and utilized [...] Read more.

The separation of large polar constituents presents a substantial challenge in natural product research when employing column chromatography techniques, as the process is both complex and time-consuming. In this study, an acetonitrile/tetrahydrofuran/di-(2-ethylhexyl) phosphoric acid/aqueous saturated sodium chloride solvent system was developed and utilized for the countercurrent chromatography of polar constituents from Ginkgo biloba L. seeds. Five polar constituents were effectively isolated using an acetonitrile/tetrahydrofuran/di-(2-ethylhexyl) phosphoric acid/aqueous saturated sodium chloride (2:2:0.8:3, v/v) solvent system using a two-step countercurrent chromatography method. In the initial countercurrent chromatography process, three constituents were successfully purified from the methanol extract: compound 1, compound 4, and compound 5. Compounds 2 and 3, co-eluted from the column, were further subjected to three inner-recycling chromatographic procedures. At last, five constituents were purified and identified, including 4′-O-methylpyridoxine (1); two indole alkaloid N-glucosides, ginkgoside B (2) and ginkgoside A (3); 2-(4-hydroxybenzyl) malic acid (4); and coniferyl alcohol (5). The results demonstrated that the acetonitrile/tetrahydrofuran/di-(2-ethylhexyl) phosphoric acid/aqueous saturated sodium chloride solvent system serves as a feasible system for the efficient countercurrent chromatography separation of polar components. Full article

(This article belongs to the Topic Counter-Current Chromatography in Natural Products Isolation)

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25 pages, 6169 KiB  

Open AccessArticle

Synthesis and Isolation of Phenol- and Thiol-Derived Epicatechin Adducts Prepared from Avocado Peel Procyanidins Using Centrifugal Partition Chromatography and the Evaluation of Their Antimicrobial and Antioxidant Activity

by Barbara Berrios-Henríquez, Matías Venegas-Toloza, María Reyes-Fuentes, Felipe Zúñiga-Arbalti, Luis Bustamante, Apolinaria García-Cancino, Julio Alarcón-Enos and Edgar Pastene-Navarrete

Molecules 2024, 29(12), 2872; https://doi.org/10.3390/molecules29122872 - 17 Jun 2024

Cited by 1 | Viewed by 1858

Abstract

Polyphenols from agro-food waste represent a valuable source of bioactive molecules that can be recovered to be used for their functional properties. Another option is to use them as starting material to generate molecules with new and better properties through semi-synthesis. A proanthocyanidin-rich [...] Read more.

Polyphenols from agro-food waste represent a valuable source of bioactive molecules that can be recovered to be used for their functional properties. Another option is to use them as starting material to generate molecules with new and better properties through semi-synthesis. A proanthocyanidin-rich (PACs) extract from avocado peels was used to prepare several semi-synthetic derivatives of epicatechin by acid cleavage in the presence of phenol and thiol nucleophiles. The adducts formed by this reaction were successfully purified using one-step centrifugal partition chromatography (CPC) and identified by chromatographic and spectroscopic methods. The nine derivatives showed a concentration-dependent free radical scavenging activity in the DPPH assay. All compounds were also tested against a panel of pathogenic bacterial strains formed by Listeria monocytogenes (ATCC 7644 and 19115), Staphylococcus aureus (ATCC 9144), Escherichia coli (ATCC 11775 and 25922), and Salmonella enterica (ATCC 13076). In addition, adducts were tested against two no-pathogenic strains, Limosilactobacillus fermentum UCO-979C and Lacticaseibacillus rhamnosus UCO-25A. Overall, thiol-derived adducts displayed antimicrobial properties and, in some specific cases, inhibited biofilm formation, particularly in Listeria monocytogenes (ATCC 7644). Interestingly, phenolic adducts were inactive against all the strains and could not inhibit its biofilm formation. Moreover, depending on the structure, in specific cases, biofilm formation was strongly promoted. These findings contribute to demonstrating that CPC is a powerful tool to isolate new semi-synthetic molecules using avocado peels as starting material for PACc extraction. These compounds represent new lead molecules with antioxidant and antimicrobial activity. Full article

(This article belongs to the Topic Counter-Current Chromatography in Natural Products Isolation)

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13 pages, 1715 KiB  

Open AccessArticle

Bioactivity-Guided High Performance Counter-Current Chromatography and Following Semi-Preparative Liquid Chromatography Method for Rapid Isolation of Anti-Inflammatory Lignins from Dai Medicinal Plant, Zanthoxylum acanthopodium var. timbor

by Qing-Fei Fan, Lan Zhou, Pian-Chou Gongpan, Chuan-Li Lu, Hua Chang and Xun Xiang

Molecules 2023, 28(6), 2592; https://doi.org/10.3390/molecules28062592 - 13 Mar 2023

Cited by 3 | Viewed by 2031

Abstract

The development of Dai medicine is relatively slow, and Zanthoxylum has great economic and medicinal value. It is still difficult to obtain medicinal components from the low-polarity parts of Zanthoxylum belonging to Dai medicine. In this study, we introduced one simple and quick [...] Read more.

The development of Dai medicine is relatively slow, and Zanthoxylum has great economic and medicinal value. It is still difficult to obtain medicinal components from the low-polarity parts of Zanthoxylum belonging to Dai medicine. In this study, we introduced one simple and quick strategy of separating target compounds from the barks of Z. acanthopodium var. timbor by high-performance countercurrent chromatography (HPCCC) with an off-line anti-inflammatory activity screening mode. The development of this strategy was based on the TLC-based generally useful estimation of solvent systems (GUESS) method and HPCCC in combination. This paper presented a rapid method for obtaining target anti-inflammatory compounds. Three lignins were enriched by HPCCC with an off-line inhibition mode of nitric oxide production in lipopolysaccharide-stimulated RAW264.7 macrophage cells, using petroleum ether–ethyl acetate–methanol–water (3:2:3:2) as the solvent system. The results showed that this method was simple and practical and could be applied to trace the anti-inflammatory components of the low-polarity part in Dai medicine. Full article

(This article belongs to the Topic Counter-Current Chromatography in Natural Products Isolation)

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