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Chiral Chromatography Analysis of Natural and Bioactive Compounds
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Chiral Chromatography Analysis of Natural and Bioactive Compounds

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

Deadline for manuscript submissions: closed (31 March 2024) | Viewed by 11692

Special Issue Editors

Dr. Marcelo Andrés Muñoz

E-Mail Website
Guest Editor
Instituto de Ciencias Químicas, Facultad de Ciencias, Universidad Austral de Chile, Casilla 567, Valdivia, Chile
Interests: stereochemistry; vibrational circular dichroism; chiral chromatography; natural products; computational chemistry
Dr. Mario Juan Simirgiotis Aguero

E-Mail Website
Guest Editor
Instituto de Farmacia, Facultad de Ciencias, Universidad Austral de Chile, Casilla 567, Valdivia, Chile
Interests: stereochemistry; natural products; computational chemistry; HPLC-MS; NMR
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Chromatography has become an essential tool in the different areas of life sciences. This is due to its unsurpassed ability to separate and analyze complex mixtures, which are common in biological samples. On the other hand, the ability of modern gas and liquid chromatography to separate mixtures of stereoisomers, and in particular enantiomers, has led to the use of this technique in the different areas of science where this type of compounds is predominant. One of these areas is natural product chemistry, where the size and complexity of secondary metabolites, coupled with the inherent chirality of their biosynthetic pathways, often generate optical isomers that are difficult to isolate and identify. Likewise, the development of bioactive compounds, including their synthesis and stereochemical assignment, requires efficient and rapid separation methodologies, in both analytical and preparative scales. Therefore, chiral chromatography is today the technique of choice for isolating, characterizing, and quantifying chiral natural and bioactive compounds, not only in research laboratories but also in development and quality control laboratories in the food and pharmaceutical industries.

This Special Issue will address novel advances in the uses of Chiral Gas and Liquid Chromatography in the analysis of natural compounds and other bioactive compounds. Topics include both the development and application of GC and LC methods in plant extracts, bioactive compounds synthesis, pharmaceuticals, natural toxins, and other related samples and matrices. Original research articles, as well as reviews, are welcome.

Dr. Marcelo Andrés Muñoz
Dr. Mario Juan Simirgiotis Aguero
Guest Editors

Manuscript Submission Information

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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

  • chiral HPLC
  • chiral GC
  • chiral analysis
  • enantiomers
  • stereoisomers
  • plant extracts
  • organic synthesis
  • pharmaceuticals

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Published Papers (5 papers)

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Research

18 pages, 5042 KiB  
Article
Optimization of HS-SPME-GC/MS Analysis of Wine Volatiles Supported by Chemometrics for the Aroma Profiling of Trebbiano d’Abruzzo and Pecorino White Wines Produced in Abruzzo (Italy)
by Leucio Rossi, Martina Foschi, Alessandra Biancolillo, Maria Anna Maggi and Angelo Antonio D’Archivio
Molecules 2023, 28(4), 1534; https://doi.org/10.3390/molecules28041534 - 5 Feb 2023
Cited by 6 | Viewed by 2590
Abstract
Headspace Solid-Phase Microextraction coupled to Gas-Chromatography with Mass Spectrometry detection (HS-SPME/GC-MS) has been widely used to analyze the composition of wine aroma. This technique was here applied to investigate the volatile profile of Trebbiano d’Abruzzo and Pecorino white wines produced in Abruzzo (Italy). [...] Read more.
Headspace Solid-Phase Microextraction coupled to Gas-Chromatography with Mass Spectrometry detection (HS-SPME/GC-MS) has been widely used to analyze the composition of wine aroma. This technique was here applied to investigate the volatile profile of Trebbiano d’Abruzzo and Pecorino white wines produced in Abruzzo (Italy). Optimization of SPME conditions was conducted by Design of Experiments combined with Response Surface Methodology. We investigated the influence of the kind of sorbent, PDMS, CW/DVB, or PDMS/CAR/DVB, and the effect of the fiber exposure time, temperature, and salt concentration on the total area of the chromatogram and the extraction efficiency of ethyl decanoate and 3-methyl-1-butanol, representative of apolar and polar compounds, respectively. The PDMS/CAR/DVB sorbent allowed the extraction of about 70 compounds, whereas only a part of these substances could be extracted on the PDMS and CW/DVB fibers. Reliable response surfaces for the total area and peak areas of the selected volatiles collected on the PDMS and PDMS/CAR/DVB sorbents and, in the latter case, principal component analysis were evaluated to find the optimal conditions. The optimized extraction conditions were applied for a preliminary comparison of the volatile profile of the two wine varieties and in a successive varietal discrimination study based on data-fusion approaches. Full article
(This article belongs to the Special Issue Chiral Chromatography Analysis of Natural and Bioactive Compounds)
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14 pages, 1897 KiB  
Article
The Enantioselective Potential of NicoShell and TeicoShell Columns for Basic Pharmaceuticals and Forensic Drugs in Sub/Supercritical Fluid Chromatography
by Denisa Folprechtová, Martin G. Schmid, Daniel W. Armstrong and Květa Kalíková
Molecules 2023, 28(3), 1202; https://doi.org/10.3390/molecules28031202 - 26 Jan 2023
Cited by 2 | Viewed by 1900
Abstract
The enantioselective potential of two macrocyclic glycopeptide-based chiral stationary phases for analysis of 28 structurally diverse biologically active compounds such as derivatives of pyrovalerone, ketamine, cathinone, and other representatives of psychostimulants and antidepressants was evaluated in sub/supercritical fluid chromatography. The chiral selectors immobilized [...] Read more.
The enantioselective potential of two macrocyclic glycopeptide-based chiral stationary phases for analysis of 28 structurally diverse biologically active compounds such as derivatives of pyrovalerone, ketamine, cathinone, and other representatives of psychostimulants and antidepressants was evaluated in sub/supercritical fluid chromatography. The chiral selectors immobilized on 2.7 μm superficially porous particles were teicoplanin (TeicoShell column) and modified macrocyclic glycopeptide (NicoShell column). The influence of the organic modifier and different mobile phase additives on the retention and enantioresolution were investigated. The obtained results confirmed that the mobile phase additives, especially water as a single additive or in combination with basic and acidic additives, improve peak shape and enhance enantioresolution. In addition, the effect of temperature was evaluated to optimize the enantioseparation process. Both columns exhibited comparable enantioselectivity, approximately 90% of the compounds tested were enantioseparated, and 30% out of them were baseline enantioresolved under the tested conditions. The complementary enantioselectivity of the macrocyclic glycopeptide-based chiral stationary phases was emphasized. This work can be useful for the method development for the enantioseparation of basic biologically active compounds of interest. Full article
(This article belongs to the Special Issue Chiral Chromatography Analysis of Natural and Bioactive Compounds)
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11 pages, 1975 KiB  
Article
Chiral Separation, Configuration Confirmation and Bioactivity Determination of the Stereoisomers of Hesperidin and Narirutin in Citrus reticulata Blanco
by Bingtong Jiang, Sirong Cao, Jiayu Zhang and Zhaokun Wang
Molecules 2023, 28(2), 873; https://doi.org/10.3390/molecules28020873 - 15 Jan 2023
Cited by 3 | Viewed by 2131
Abstract
Hesperidin and narirutin are a class of flavanone glycosides, which are the main active constituents in Citrus reticulata Blanco. In the present study, a chiral HPLC-UV method with amylose tris(3,5-dimethylphenylcarbamate) as a stationary phase under a normal-phase mode was used to achieve the [...] Read more.
Hesperidin and narirutin are a class of flavanone glycosides, which are the main active constituents in Citrus reticulata Blanco. In the present study, a chiral HPLC-UV method with amylose tris(3,5-dimethylphenylcarbamate) as a stationary phase under a normal-phase mode was used to achieve the stereoselective separation of the C-2 diastereomers of hesperidin and narirutin simultaneously. The single epimer was then successfully prepared by applying semi-preparative chromatography, whose absolute configuration (R/S) was characterized by combining the experimental electronic circular dichroism (ECD) detection with time-dependent density functional theory (TDDFT) calculations. The epimer composition of these two chiral flavanone glycosides in Citrus reticulata Blanco was then determined, which was found to be slightly different in the herbs from different production regions. The anti-inflammatory activity of each prepared single epimer was further evaluated, and some differences between one pair of epimers of hesperidin and narirutin were observed, which suggested that the presence of different epimers should be considered in the quality evaluation and control of natural medicine. Full article
(This article belongs to the Special Issue Chiral Chromatography Analysis of Natural and Bioactive Compounds)
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16 pages, 1239 KiB  
Article
Environmentally Sustainable Achiral and Chiral Chromatographic Analysis of Amino Acids in Food Supplements
by Ina Varfaj, Andrea Carotti, Luciano Mangiapelo, Lina Cossignani, Agnese Taticchi, Antonio Macchiarulo, Federica Ianni and Roccaldo Sardella
Molecules 2022, 27(22), 7724; https://doi.org/10.3390/molecules27227724 - 9 Nov 2022
Cited by 6 | Viewed by 2341
Abstract
Two LC methods were developed for the achiral and chiral reversed-phase (RP) analysis of an amino acid (AA) pool in a food supplement, in compliance with the main paradigms of Green Chromatography. A direct achiral ion-pairing RP-HPLC method was optimized under gradient conditions [...] Read more.
Two LC methods were developed for the achiral and chiral reversed-phase (RP) analysis of an amino acid (AA) pool in a food supplement, in compliance with the main paradigms of Green Chromatography. A direct achiral ion-pairing RP-HPLC method was optimized under gradient conditions with a water-ethanol (EtOH) eluent containing heptafluorobutyric acid (0.1%, v/v), to quantify the eight essential AAs (Ile, Leu, Lys, Met, Phe, Thr, Trp, and Val) contained in the food supplement. Thus, the usually employed acetonitrile was profitably substituted with the less toxic and more benign EtOH. The method was validated for Leu and Phe. The chiral LC method performed with a teicoplanin chiral stationary phase was developed with a water-EtOH (60:40, v/v) eluent with 0.1%, v/v acetic acid. The enantioselective analysis was carried out without any prior derivatization step. Both developed methods performed highly for all eight AAs and revealed that: (i) the content of six out of eight AAs was consistent with the manufacturer declaration; (ii) only L-AAs were present. Furthermore, it was demonstrated that a two-dimensional achiral–chiral configuration is possible in practice, making it even more environmentally sustainable. A molecular modelling investigation revealed interesting insights into the enantiorecognition mechanism of Lys. Full article
(This article belongs to the Special Issue Chiral Chromatography Analysis of Natural and Bioactive Compounds)
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16 pages, 3233 KiB  
Article
A Box–Behnken Extraction Design and Hepatoprotective Effect of Isolated Eupalitin-3-O-β-D-Galactopyranoside from Boerhavia diffusa Linn.
by Kamal Y. Thajudeen, Yahya I. Asiri, Shahana Salam, Shabeer Ali Thorakkattil, Mohamed Rahamathulla and Ilyas Uoorakkottil
Molecules 2022, 27(19), 6444; https://doi.org/10.3390/molecules27196444 - 29 Sep 2022
Cited by 2 | Viewed by 1967
Abstract
The objectives of this study were to optimize and quantify the maximum percentage yield of eupalitin-3-O-β-D-galactopyranosidefrom Boerhavia diffusa leaves using response surface methodology (RSM), as well as to demonstrate the hepatoprotective benefits of the bioactive compound. The Box–Behnken experimental design was [...] Read more.
The objectives of this study were to optimize and quantify the maximum percentage yield of eupalitin-3-O-β-D-galactopyranosidefrom Boerhavia diffusa leaves using response surface methodology (RSM), as well as to demonstrate the hepatoprotective benefits of the bioactive compound. The Box–Behnken experimental design was utilized to optimize the eupalitin-3-O-β-D-galactopyranoside extraction procedure, which also looked at the extraction duration, temperature, and solvent concentration as independent variables. Boerhaviadiffusa leaves were extracted, and n-hexane, chloroform, ethyl acetate, and water were used to fractionate the dried extracts. The dried ethyl acetate fraction was thoroughly mixed in hot methanol and stored overnight in the refrigerator. The cold methanol was filtered, the solid was separated, and hot methanol was used many times to re-crystallize the solid to obtain pure eupalitin-3-O-β-D-galactopyranoside (0.1578% w/w). The proposed HPTLC method for the validation and quantification of eupalitin-3-O-β-D-galactopyranosidewassuccessfully validated and developed. The linearity (R2 = 0.994), detection limit (30 ng), and quantification limit (100 ng) of the method, as well as its range (100–5000 ng), inter and intraday precision (0.67% and 0.991% RSD), specificity, and accuracy (99.78% RSD), were all validated as satisfactory. The separation of the eupalitin-3-O-β-D-galactopyranoside band was achieved on an HPTLC plate using toluene:acetone:water (5:15:1 v/v) as a developing system. The Box–Behnken statistical design was used to determine the best optimization method, which was found to be extraction time (90 min), temperature (45 °C), and solvent ratio (80% methanol in water v/v) for eupalitin-3-O-β-D-galactopyranoside. Standard silymarin ranged from 80.2% at 100 µg/mL to 86.94% at 500 µg/mL in terms of significant high hepatoprotection (cell induced with carbon tetrachloride 0.1%), whereas isolated eupalitin-3-O-β-D-galactopyranoside ranged from 62.62% at 500 µg/mL to 70.23% at 1000 µg/mL. More recently, it is a source of structurally unique flavonoid compounds that may offer opportunities for developing novel semi-synthetic molecules. Full article
(This article belongs to the Special Issue Chiral Chromatography Analysis of Natural and Bioactive Compounds)
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