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Like chemical drugs, research and development of herbal medicine also have a need to resolve enantiomers. To help illustrating the antiviral bioactivity of Isatidis Radix, a widely used traditional Chinese medicine (TCM), supercritical fluid chromatography (SFC) was used for analytical and preparative separation of (R,S)-goitrin, which was reported...
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... The (R, S)-goitrin, the mixture of epigoitrin [(R)-goitrin] and goitrin [(S)-goitrin-] (Nie et al., 2016(Nie et al., , 2017, was one of the most characteristic sulfur-containing compounds in Isatidis Radix and was acknowledged as the quality marker of this herb (Chinese Pharmacopoeia Commission, 2020). Epigoitrin and goitrin were verified as the breakdown products of their glucosinolate prototypes, epiprogoitrin and progoitrin, which also existed in Isatidis Radix (Nie et al., 2011). ...
For a long history, herbal medicines have made significant contributions to human health all around the world. However, the exploration of an effective approach to illustrate their inner quality remains a challenge. So, it is imperative to develop new methods and technologies to characterize and identify quality markers of herbal medicines. Taking Isatidis Radix, the dried root of Isatis indigotica as an example, desorption electrospray ionization (DESI), in combination with quadrupole-time-of-flight mass spectrometry (Q-TOF/MS), was applied in this work for the first time to reveal the comprehensive spatial distribution of metabolites and, further, to illustrate quality characters of this herbal medicine. After simple pretreatment, 102 metabolites including alkaloids, sulfur-containing compounds, phenylpropanoids, nucleosides, amino acids, organic acids, flavonoids, phenols, terpenes, saccharides, peptides, and sphingolipids were characterized, some of which were successfully localized and visualized in the transverse section of the root. Based on the ion images, samples with different quality characters were distinguished unambiguously by the pattern recognition method of orthogonal partial least squares discrimination analysis (OPLS-DA). Simultaneously, 11 major influencing components exerting higher ion intensities in superior samples were identified as the potential quality markers of Isatidis Radix. Desorption electrospray ionization (DESI) mass spectrometry imaging (MSI), together with chemometric analysis could not only improve the understanding of the plant biology of herbal medicines but also be beneficial in the identification of quality markers, so as to carry out better quality control of herbal medicines.
... Shorter run time increases the sample throughput in terms of both analytical and preparative scale along with the huge range of different column solvent conditions. [86,87] Nie et al. [88] developed a supercritical fluid chromatography (SFC) method analytical and preparative for the separation of (R,S)-goitrin enantiomers which is widely used as traditional Chinese medicine (TCM). The best resolution was observed on Chiralpak IC (20 mm  250 mm, 5 mm) column, and acetonitrile was used as the organic modifier to enhance the speed with respect to the previous normal phase HPLC (NPLC) methods. ...
... This technique of SFC can be applied in chiral research of traditional Chinese medicine. [88] In the pharmaceutical industry, the separation of enantiomers is very common for both analytical and preparative scales. SFC technique is used for method development, optimization, and monitoring of compounds for rapid chiral separation. ...
The supercritical fluid chromatography technique is one of the most promising and innovative technologies used in the analysis as well as the separation of various racemates. The various enantiomers have been separated using SFC due to its several merits over conventional HPLC methods such as low cost, wide polarity compatibility, higher column efficiency, and fast analyzing capability, which are desirable features for the pharmaceutical industry. Therefore, it was considered worthwhile to review the applications of SFC in achiral and chiral separations. This review encompasses the latest literature exploration of various practical aspects of SFC for enantiomeric separation, purification, and applications to the pharmaceutical industry. A detailed discussion of SFC was made in terms of productivity, stacked injections, sample solubility, particle size, green incentive, organic solvent, recycle solvents, and economical aspects. Besides, future perspectives of SFC have also been highlighted. A comparison was also made between SFC and HPLC. SFC has been found better technique than HPLC for the chiral separations on a preparative scale. This article will be highly useful for chiral chromatography in pharmaceutical industries and research laboratories.
... In addition, ethanol used in the SFC method is the benchmark green solvent while hexane used for the HPLC method was highly toxic and hazardous. Another example of preparative chiral SFC has been introduced by Nie et al. [67] for the improvement of the chiral separation of (R, S)-goitrin (Fig. 4). SFC was adopted on a Chiralpak IC column by means of Co 2 /acetonitrile (80/20) as the eluent at 35°C/100 bar. ...
Purification of active pharmaceutical ingredients is a crucial step in pharmaceutical
manufacturing. The elimination of by-products, impurities, catalysts, coloring agents, and
residual solvents is critical for the production of high-quality pharmaceutical products.
This step is traditionally time-consuming, expensive, and consumes plentiful toxic
organic solvents. With the global concern about green chemistry and sustainability, it
becomes mandatory for the pharmaceutical industry to depend on greener purification
techniques. This chapter highlights the green chromatographic techniques for purification
of pharmaceuticals including counter-current chromatography, high-performance thin
layer chromatography, gas chromatography, and supercritical fluid chromatography. As
well, the most up-to-date applications of these green chromatographic purification
techniques are included.
... It is imperative to adopt reliable and efficient analytical platforms to fully resolve them and facilitate quality assessment of raw medicinal plants [96]. Nie et al. [97] isolated (R, S)-goitrin by SFC-DAD and screened five polysaccharide CSP columns (ADH, ASH, ODH, IA and IC columns) to evaluate their separation efficiency. The separation achieved best when the Chiralpak IC column and acetonitrile was selected. ...
Medicinal plants with complex matrices are endowed with a wide scope of biological activities. The separation, quantification, characterization and purification of bioactive components from herbal medicine extracts have always challenged analysts. Fortunately, the advancement of various emerging techniques has provided potent support for improving the method selectivity, sensitivity and run speeds in medicinal plants analyses. In recent years, the advent of new-generation supercritical fluid chromatography (SFC) instruments and a wide diversity of column chemistries, coupled with the intrinsic technical features of SFC, have made it an alternative and prominent analytical platform in the medicinal plant research area. This work aims to give a comprehensive overview of the fundamentals, technical advancement and investigating parameters of SFC in combination with three prevalent detectors. Moreover, the latest research progress of SFC applications in medicinal plant analyses is illuminated, with a focus on herbal medicine-related SFC papers at the analytical and preparative scale that were published during the period of 2012 to December 2018. The most relevant applications were ordered by the constitutes to be analysed. As for the respective research cases, analytical protocol and data processing strategies were offered, as well as the indicated restrictions or superiority of the method; thus, the current status of SFC in medicinal plant analysis was presented.
... HSCCC, HPCCC and CPC have also been successfully applied in the separation of volatile oil, which is difficult to separate via conventional column chromatography. Six volatile compounds (curdione (95), curcumol (96), germacrone (97), curzerene (98), 1,8-cineole (99) and β-elemene (100)) were isolated by CPC from the essential oil of Curcuma wenyujin using a nonaqueous two-phase solvent system consisting of petroleum etheracetonitrile-acetone (4:3:1 v/v/v) [69]. Four major sesquiterpenoids (ar-turmerone (101), α-turmerone (102), β-turmerone (103), and E-atlantone (104)) with similar structures were separated from the essential oil of Curcuma longa in a single HSCCC run using a two-phase solvent system composed of n-heptane-ethyl acetateacetonitrile-water (9.5/0.5/9/1, ...
... (R,S)-goitrin (141-142) is the active ingredient of TCM Isatidis Radix. The chiral separation of (R) and (S) goitrins was successfully achieved by prep-SFC on a Chiralpak IC column using acetonitrile as the organic modifier [95]. ...
Natural medicines were the only option for the prevention and treatment of human diseases for thousands of years. Natural products are important sources for drug development. The amounts of bioactive natural products in natural medicines are always fairly low. Today, it is very crucial to develop effective and selective methods for the extraction and isolation of those bioactive natural products. This paper intends to provide a comprehensive view of a variety of methods used in the extraction and isolation of natural products. This paper also presents the advantage, disadvantage and practical examples of conventional and modern techniques involved in natural products research.
... The variety of possibilities is now making natural products the first application domain for analytical SFC (Fig. 5). Natural products have also been a significantly growing field at the preparative scale [35, 37, [153][154][155][156][157][158][159][160][161][162], not only at the analytical scale. In addition to the above examples of structural families, purification of lignans [14] and polyphenols [163] with preparative SFC has been demonstrated. ...
Supercritical fluid chromatography (SFC), which employs pressurized carbon dioxide as the major component of the mobile phase, has been known for several decades but has faced a significant resurgence of interest in the recent years, thanks to the development of modern instruments to comply with current expectations in terms of robustness and sensitivity. This review is focused on the recent literature, specifically since the introduction of modern systems but in relation to older literature, to identify the changing trends in application domains. Typically, natural products, bioanalysis, food science, and environmental analyses are all strongly increasing. Together with reduced extra-column volumes in the instruments, the advent of sub-2-μm particles and superficially porous particles in the stationary phases is favoring ultra-high-performance SFC (UHPSFC) allowing for improved resolution and faster analyses, but without the constraints of viscous liquids encountered in ultra-high-performance liquid chromatography (UHPLC). Hyphenation to mass spectrometry is also more frequent and opened the way to new application domains, and raises different issues from liquid chromatography mobile phases, especially due to decompression of carbon dioxide. It is also shown that the frontiers between SFC and HPLC are fading, as switching from one method to the other, even within the course of a single analysis, is facilitated my modern instruments. The present review is not intended to be exhaustive but rather giving a snapshot of recent trends in supercritical fluid chromatography, based on the observation of about 500 papers published in English-written peer-reviewed journals from 2014 to 2018. Graphical abstractᅟ ᅟ
... To date, X-ray crystallography, NMR, vibrational circular dichroism (VCD) and enantioselective chromatography have been frequently adopted to determine the chiral components of TCMs [1,2]. Several enantioselective chromatography such as reversed-phase high-performance liquid chromatography (RP-HPLC) coupled with the type of Chrialpak®IC chiral column [19,20] and supercritical fluid chromatography (SFC) have been used for chiral separation of R,S-goitrin in R. Isatidis [21,22]. However, these methods were limited owing to the complex operation, high cost, and lack of simultaneous quantification of other chiral glucosinolates. ...
... Compared to previous published methods [19][20][21][22], glucosinolates profiles of crude drug, decoction pieces, and granules of R. Isatidis were performed using HPLC-UV-CD, which improved the limitation of high-cost chiral columns, complex operation of sample preparation, and simultaneous quantification of the characteristic glucosinolates. In the typical UV and CD chromatograms of R. Isatidis samples (Figure 1), R-goitrin and S-goitrin showed the same retention time, UV absorption feature, and overlapping peak. ...
As chemical drugs, separation and quantification of the specific enantiomer from the chiral compounds in herbal medicines are becoming more important. To clarify the chemical characterization of chiral glucosinolates—the antiviral active ingredients of Radix Isatidis, an optimized efficient method of HPLC-UV-CD was developed to simultaneously separate and quantify the four main chiral glucosinolates: progoitrin, epiprogoitrin, and R,S-goitrin. The first step was to determine progoitrin, epiprogoitrin, and R,S-goitrin using HPLC-UV, and then determine the R-goitrin and S-goitrin by coupling with CD detection. Subsequently, through the linear relations between anisotropy factor (g factor) and the percent optical purity of R-goitrin, the contents of R-goitrin and S-goitrin from the R,S-goitrin mixture were calculated separately. Furthermore, the chemical composition features of the four chiral glucosinolates in 37 samples from crude drugs, decoction pieces, and granules of R. Isatidis were conducted. The total content of the four glucosinolates was obviously higher in crude drugs, and the variance character of each glucosinolate contents was different. In summary, the accurate measurement method reported here allows for better control of the internal quality of R. Isatidis and its granules and provides a powerful approach for the analysis of other chiral components in traditional Chinese medicines.
In the second part of this review article, the recent progress in supercritical fluid chromatography (SFC) for enantiomeric separations is evaluated. With the substantial developments carried out over the past years in instrumentation, columns, and detector hyphenation, the interest in chiral SFC has been steadily growing in various fields. In combination with novel developments in chiral stationary phase chemistries, the enantioselective analysis range has been significantly extended. Several applications reported on the enantioselective separation of drugs and pharmaceutical compounds using chiral SFC are discussed, including pharmaceutical applications, clinical research, forensic toxicology, and environmental sciences.
Complexity and variability in composition are major challenges associated with the analysis of natural products in biological matrices like plant extracts. To indicate and confirm that SFC is an excellent analytical technique to investigate such samples, is the aim of this review. It is shown that in recently published manuscripts the range of successfully assessed compounds was very wide, including compounds of variable polarity (lipids, flavonoids, saponins, terpenes) or acidity/alkalinity (phenolic acids, alkaloids), not to forget chiral separations required for a meaningful characterisation of e.g. cannabinoids. This versatility in target analytes is possible because of the flexible nature of SFC, being compatible with different stationary phase chemistries (silica, reversed phase or chiral materials, HILIC) and detection modes (DAD, MS, ELSD, ECD). The online coupling to SFE, allowing simultaneous extraction and analysis of a sample, is a relatively new technical option and addressed as well. Divided by different compound classes, this review reports on the range of separation and detection conditions that have been described for natural product analysis by SFC from 2015 till date; limitations and advantages of individual assays are discussed and compared to related studies. By considering both, “standard” as well as innovative/uncommon applications, the current status and future perspectives of this emerging separation technique are highlighted.
