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Separation and Quantitative Analysis of Natural Product Extracts

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A special issue of Separations (ISSN 2297-8739). This special issue belongs to the section "Analysis of Natural Products and Pharmaceuticals".

Deadline for manuscript submissions: closed (10 May 2023) | Viewed by 34927

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Prof. Dr. Wojciech Piekoszewski

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Department of Analytical Chemistry, Faculty of Chemistry, Jagiellonian University, 30-387 Krakow, Poland
Interests: plant drugs; natural products; analytical chemistry; extraction techniques; high separation methods; HPLC; LC-MS, GC-MS; capillary electrophoresis; method development; method optimization; method validation
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Dr. Katarzyna Madej

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Department of Analytical Chemistry, Jagiellonian University, Kraków, Poland
Interests: analysis of drugs in biological and environmental materials; analysis of pesticide residues in food and environmental samples; sample preparation techniques; chromatographic and related techniques
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Today, natural products are attracting significant attention from scientists, doctors, customers and producers alike. This is mainly due to the presence of healing and health-promoting compounds in them. These products include a variety of plants and animal organisms. Recently, products made from the Cannabis sativa family have also been very popular, which, due to the content of non-psychoactive cannabinoids, can constitute a great healing potential in the case of many diseases. The use of natural products in medicine, however, requires reliable quality control; i.e., purity and qualitative and quantitative composition. For this purpose, it is necessary to develop appropriate procedures for the isolation of active ingredients and methods of analyzing the obtained extracts. Thus, the development of efficient extraction methods as well as sensitive, selective and reliable methods for the determination of bioactive compounds, as well as the accompanying potentially harmful ingredients (e.g. pesticides), is a critical step in allowing extracts of natural products for consumption and sale.

This Special Issue encourages you to share your research findings on current developments in the development and application of extraction methods and analytical methods for the determination of analytes in this type of natural product.

Prof. Dr. Wojciech Piekoszewski
Dr. Katarzyna Madej
Guest Editors

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Keywords

Extraction methods
Analytical methods
Quantitative analysis
Natural product extracts
Chromatography
HPLC and related techniques
Mass spectrometry
Separation technology
Chemical analysis

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Published Papers (9 papers)

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Research

19 pages, 1466 KiB

Open AccessArticle

Moroccan Endemic Artemisia herba-alba Essential Oil: GC-MS Analysis and Antibacterial and Antifungal Investigation

by Habiba Houti, Mohamed Ghanmi, Badr Satrani, Fouad El Mansouri, Francesco Cacciola, Moulay Sadiki and Abdellatif Boukir

Separations 2023, 10(1), 59; https://doi.org/10.3390/separations10010059 - 16 Jan 2023

Cited by 17 | Viewed by 4167

Abstract

In Morocco, the endemic Artemisia herba-alba is well known by its traditional uses and health benefits. The search for natural, safe, and effective antibacterial and antifungal agents from plants is in high demand due to microbial and fungal resistance to conventional synthetic antibiotics and antifungal drugs. In this study, the A. herba-alba was collected from the region of Fez-Boulemane during the periods of March, June, and September. Essential oils (EOs) were extracted from the aerial part of the plant by the hydrodistillation method. The chemical constituents were determined using GC-MS as analytical tools. The antimicrobial activities of different oils were tested using the macrodilution method. The results showed the difference in the yields between the three EOs (0.49, 1.74, 1.30% (mL/100 g)), respectively, as well as in their corresponding chemical compositions. The main constituents revealed by GC-MS are higher contents of oxygenated monoterpenes (84.7, 84.4, 81%), such as cis chrysanthenyl acetate (30, 26.7, 27.6%), β-thujone (23.2, 12.9, 15.4%), camphor (9.76, 14.3, 15.8%), chrysanthenone (2.4, 1, 14%), 1,8-cineole (1.5, 11.7, 11.8%), trans β-dihydroterpineol (7.8, 7.2, 6.9%), α-thujone (4.8, 3, 5.4%), and sesquiterpenic davanone (3.9, 1.5, 1.4%), respectively. The three EOs biological activities’ results showed significant antimicrobial effects against four bacteria tested (E. coli, B. subtilis, S. aureus, M. luteus), with the MIC values ranging from 0.1 to 0.03% (v/v), as well as interesting antifungal effects on both wood rot fungi against four fungi examined (G. trabeum, P. placenta, C. puteana, C. versicolor) and molds against three microorganisms tested (A. niger, P. digitatum, P. expansum), with MIC values ranging from 0.2 to 0.03% (v/v) and 0.4 to 0.03% (v/v), respectively. The June and September EO samples showed more potent activities than those collected during March. Our research findings showed quantitative variability in both EO contents and chemical compositions, which could be due to the phenological stages, climatic conditions of growth, and harvesting periods. The potent results of the antimicrobial/antifungal activities were provided by the EOs of June and September and might be correlated to the contribution and synergism effect of all oxygenated monoterpenes. These results support the possible application of A. herba-alba EOs as natural and safe antibacterial agents, and an effective alternative to synthetic drugs, enabling the prevention and treatment of certain pathogenic infections in food and health, and the preservation of wood alteration against fungi. Full article

(This article belongs to the Special Issue Separation and Quantitative Analysis of Natural Product Extracts)

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13 pages, 1276 KiB

Open AccessArticle

The Essential Oil Composition of Helichrysum italicum (Roth) G. Don: Influence of Steam, Hydro and Microwave-Assisted Distillation

by Zvonimir Jažo, Mateo Glumac, Ivana Drventić, Ljilja Žilić, Tea Dujmović, Danica Bajić, Marko Vučemilo, Ena Ivić, Sanida Bektić, Goran T. Anačkov and Mila Radan

Separations 2022, 9(10), 280; https://doi.org/10.3390/separations9100280 - 1 Oct 2022

Cited by 7 | Viewed by 3024

Abstract

Helichrysum italicum (Roth) G. Don (Asteraceae), also known as immortelle, usually grows in the Mediterranean area. The composition of the essential oil (EO) of immortelle is a mixture of various aromatic substances, mainly monoterpenes and sesquiterpenes. Distillation is the most widely used method for extraction of EO immortelle, although the yield is very low (<1%). In this work, we aim to investigate how the use of different distillation methods affects the yield and chemical composition of immortelle EO. For this purpose, we applied two conventional methods: steam distillation (SD) and hydrodistillation (HD), and a modern (environmentally friendly) technique—microwave-assisted distillation (MAD). Wild immortelles from four different locations in Croatia were collected and carefully prepared for extraction. Each sample was then analyzed by gas chromatography–mass spectrometry (GC-MS). GraphPad Prisma statistical software was used to study the statistics between different groups of connections and analyze the data on the number of connections. The results show that HD gives a significantly higher yield (0.31 ± 0.09%) compared to MAD (0.15 ± 0.03%) and SD (0.12 ± 0.04%). On the other hand, the highest number of chemical compounds was identified with MAD (95.75 ± 15.31%), and most of them are subordinate compounds with complex structures. SD isolated EOs are rich in derived acyclic compounds with the highest percentage of ketones. The results show that the application of different distillation methods significantly affects the composition of the obtained immortelle EO, considering the yield of EO, the number of isolated, derived and non-derived compounds, chemotypes and compounds with simple (acyclic) and complex structures. Full article

(This article belongs to the Special Issue Separation and Quantitative Analysis of Natural Product Extracts)

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16 pages, 4662 KiB

Open AccessArticle

Purification, Identification and Neuroprotective Effects of Proteins from Bombyx batryticatus in Glu-Stimulated PC12 Cells

by Mei-Bian Hu, Xiang-Long Meng, Pu Wang, Shuo-Sheng Zhang, Chun-Jie Wu and Yu-Jie Liu

Separations 2022, 9(9), 236; https://doi.org/10.3390/separations9090236 - 1 Sep 2022

Cited by 2 | Viewed by 1850

Abstract

Bombyx batryticatus (BB) is one of the most commonly used Traditional Chinese Medicines (TCMs) in the treatment of convulsions and epilepsy. The antiepileptic effects of total proteins from BB (BBPs) have been proven in our previous research. In this study, BBPs were further purified, the neuroprotective effects were evaluated in Glu-stimulated PC12 cells, and the structure was identified by Matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF-MS). Six subfractions (PF-1 to PF-6) were obtained by DEAE-52 Sepharose FF ion-exchange chromatography. It was found that PF-1, PF-2, and PF-3, with similar protein compositions, possessed neuroprotective effects in Glu-stimulated PC12 cells by significantly increasing the GABA level, and decreasing the levels of IL-1β and TNF-α. The most active fraction (PF-2) was further separated by Sephadex G-75 gel filtration chromatography, and an effective protein component named PF-2-2 was obtained. Fluorescein isothiocyanate-labeled PF-2-2 (FITC-PF-2-2) was prepared, and the binding of FITC-F-2-2 to the PC12 cells was directly observed with a confocal microscope. PF-2-2 was found to first bind to the surface of PC12 cells and then internalize into the cells. The main band of PF-2-2 was then analyzed by MALDI-TOF/TOF-MS and searched in the MASCOT database; finally a protein named Low molecular mass 30 kDa lipoprotein 21G1 was identified. In conclusion, PF-2-2 and purified proteins isolated from BBPs have potential application prospects in the treatment of epilepsy. Full article

(This article belongs to the Special Issue Separation and Quantitative Analysis of Natural Product Extracts)

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15 pages, 3447 KiB

Open AccessArticle

Ultrasonic Extraction and Separation of Taxanes from Taxus cuspidata Optimized by Response Surface Methodology

by Yajing Zhang, Zirui Zhao, Huiwen Meng, Wenlong Li and Shujie Wang

Separations 2022, 9(8), 193; https://doi.org/10.3390/separations9080193 - 26 Jul 2022

Cited by 7 | Viewed by 2174

Abstract

Taxanes are natural compounds with strong antitumor activity. In this study, we first extracted taxanes from the needles of Taxus cuspidata using ultrasonic (US) extraction, and then assessed the effects of different extraction conditions on the yields of eight target compounds. Response surface methodology (RSM) was further used to optimize the extraction conditions: when the liquid-to-solid ratio was 20.88 times, ultrasonic power was 140.00 W, ultrasonic time was 47.63 min, and ethanol content in solvent was 83.50%, taxane yields reached the maximum value of 354.28 μg/g. Under these conditions, the actual extraction rate of taxanes from the needles was 342.27 μg/g. The scanning electron microscopy (SEM) results indicated that the morphology of the needles, suspension cells, and callus of Taxus cuspidata extracted by ultrasonic wave had changed, the pores of the sections of the needles extracted by ultrasonic wave had become relatively loose, and the pore diameter had obviously increased. The callus and overall structure of the suspension cells extracted by ultrasonic wave were destroyed, forming cell fragments. The components of Taxus cuspidata are complex; the high-performance liquid chromatography (HPLC) method established in this paper is suitable for the rapid and effective separation of taxanes in Taxus cuspidata. We systematically and comprehensively compared the yields of taxanes in needles, callus, and suspension cells of Taxus cuspidata, and the taxane yields were increased by the suspension cell culture. Full article

(This article belongs to the Special Issue Separation and Quantitative Analysis of Natural Product Extracts)

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19 pages, 4309 KiB

Open AccessArticle

Antioxidant and Antibacterial Activities of a Purified Polysaccharide Extracted from Ceratonia siliqua L. and Its Involvement in the Enhancement Performance of Whipped Cream

by Ameni Dammak, Sirine Ben Slima, Marco D. R. Gomes da Silva, Riadh Ben Salah, Awad M. Aljuaid, Wafik Hachicha and Mohamed Bouaziz

Separations 2022, 9(5), 117; https://doi.org/10.3390/separations9050117 - 10 May 2022

Cited by 8 | Viewed by 2801

Abstract

The main objective discussed in this research was to determine the structural characteristics of carob kibble water-soluble polysaccharide (KWSP), extracted from Ceratonia siliqua L., and to assess its in vitro antioxidant activities, as well as its effect on whipped cream. The results obtained through ¹³C, ¹H, and the hetero-nuclear single quantum coherence (HSQC) nuclear magnetic resonance (NMR) and Fourier transform infrared spectroscopy (FT-IR) analysis indicated that KWSP had the characteristic bands of polysaccharides. Thin layer chromatography (TLC) and high performance liquid chromatography (HPLC) suggested that KWSP is a hetero-polysaccharide composed of glucose and fructose, with an average molecular weight (Mw) amounting to 65 KDa. In addition, KWSP showed a good water holding capacity (WHC), a good oil holding capacity (OHC), and an emulsification stability, rated as 3.14 ± 0.05 g/g, 0.87 ± 0.02 g/g, and 71 ± 0.01%, respectively. The antioxidant activity of KWSP was investigated in vitro, demonstrating important DPPH and ABTS⋅+ radical scavenging activities and a good total antioxidant capacity. KWSP exhibited antibacterial activity against Listeria monocytogenes, Staphylococcus aureus, and Salmonella enterica. On the other hand, the incorporation of KWSP in whipped cream was investigated, to enhance its antioxidant capacity and consequently to extend its expiration date. Moreover, KWSP reduces the formation of conjugated dienes and trienes in cream fat. Full article

(This article belongs to the Special Issue Separation and Quantitative Analysis of Natural Product Extracts)

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13 pages, 885 KiB

Open AccessArticle

Simultaneous Quantification of 17 Cannabinoids in Cannabis Inflorescence by Liquid Chromatography-Mass Spectrometry

by Amitha K. Hewavitharana, Francine Gloerfelt-Tarp, Matthew Nolan, Bronwyn J. Barkla, Sarah Purdy and Tobias Kretzschmar

Separations 2022, 9(4), 85; https://doi.org/10.3390/separations9040085 - 28 Mar 2022

Cited by 7 | Viewed by 7522

Abstract

With an increasing appreciation for the unique pharmacological properties associated with distinct, individual cannabinoids of Cannabis sativa, there is demand for accurate and reliable quantification for a growing number of them. Although recent methods are based on highly selective chromatography-mass spectrometry technology, most are limited to a few cannabinoids, while relying on unnecessarily sophisticated and expensive ultra-high performance liquid chromatography and tandem mass spectrometry. Here we report an optimised, simple extraction method followed by a reliable and simple high performance liquid chromatography method for separation. The detection is performed using a time-of-flight mass spectrometer that is available in most natural products research laboratories. Due to the simplicity of instrumentation, and the robustness resulting from a high resolution in the chromatography of isobaric cannabinoids, the method is well suited for routine phytocannabinoid analysis for a range of applications. The method was validated in terms of detection and quantification limits, repeatability, and recoveries for a total of 17 cannabinoids: detection limits were in the range 11–520 pg when using a 1 µL sample injection volume, and the recovery percentages ranged from 85% to 108%. The validated method was subsequently applied to determine cannabinoid composition in the inflorescences of several medicinal Cannabis sativa varieties. Full article

(This article belongs to the Special Issue Separation and Quantitative Analysis of Natural Product Extracts)

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11 pages, 2367 KiB

Open AccessArticle

HPLC-DAD Analysis of Hemp Oil Supplements for Determination of Four Cannabinoids: Cannabidiol, Cannabidiolic Acid, Cannabinol and Delta 9-Tetrahydrocannabinol

by Katarzyna Madej, Aleksandra Chmiołek, Kamila Szlachta and Wojciech Piekoszewski

Separations 2021, 8(12), 227; https://doi.org/10.3390/separations8120227 - 23 Nov 2021

Cited by 10 | Viewed by 5133

Abstract

Growing consumer interest in hemp oilseed supplements requires quality control. Therefore, appropriate, effective and verified analytical methods are needed for the determination of some bioactive cannabinoids in them. The aim of the study is to present an extended (compared to our previous research) validated high performance liquid chromatography with diode array detection (HPLC-DAD) method for the determination of four cannabinoids (cannabidiol, cannabidiolic acid, cannabinol and delta-9-tetrahydrocannabinol) in an oil matrix, which was used to determine these cannabinoids in seven commercial hemp oil supplements. In our method, the isolation of the target compounds was based on liquid extraction with acetonitrile combined with the freezing (at −41 °C) of the oil phase. The results show that in some cases, the determined concentrations of cannabinoids in the tested supplements differ significantly from those declared by the manufacturers. As for the main medicinal cannabinoid (CBD) in hemp oil supplements, in two cases, the measured concentration was significantly lower (1.45 and 1.81%) than the declared (5 and 5%), and in the other supplements, the obtained results confirm the declared amount of CBD within the error range from 3.29 to 9.2%. Therefore, to ensure the safe and beneficial use of these supplements by consumers, it is necessary to monitor their cannabinoid composition. Full article

(This article belongs to the Special Issue Separation and Quantitative Analysis of Natural Product Extracts)

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9 pages, 478 KiB

Open AccessArticle

Nutritional Value of Sea Urchin Roe (Strongylocentrotidae)—Study of Composition and Storage Conditions

by Victoria A. Matveeva, Lidia V. Shulgina, Yury V. Prikhodko, Yury P. Shulgin, Katarzyna Madej and Wojciech Piekoszewski

Separations 2021, 8(10), 174; https://doi.org/10.3390/separations8100174 - 7 Oct 2021

Cited by 3 | Viewed by 4725

Abstract

Although the roe of sea urchins inhabiting the Far Eastern seas possesses many healing properties and may be used as a dietary product, a reduction and deterioration in its nutritional quality during storage occurs. Therefore, in order to make sea urchin products widely accessible to the world population, it is very important to have appropriate technology to keep the roe from spoiling. To store sea urchin roe for a long time, methods of pre-processing sea urchin gonads before freezing were tested. In terms of preserving organoleptic properties and nutritional quality, the most adequate procedure consists of a short period (20 or 30 s) of heat (boiling water) treatment of sea urchin roe after removal from the shell. This procedure results in an inactivation of enzymes that catalyze the hydrolytic processes of lipids and proteins during storage. After blanching and cooling, the roe was packed, frozen and kept at a temperature of −18 °C and −25 °C. The quality of sea urchin roe did not change during storage at the temperature of −18 °C for 6 months, and at the temperature of −25 °C for 10 months. Full article

(This article belongs to the Special Issue Separation and Quantitative Analysis of Natural Product Extracts)

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15 pages, 1610 KiB

Open AccessArticle

Characterization of Moravian Wines by Selected Chemical Parameters

by Jan Javorský, Martin Král, Marek Šnirc, Július Árvay, Bohuslava Tremlová and Dani Dordević

Separations 2021, 8(7), 89; https://doi.org/10.3390/separations8070089 - 22 Jun 2021

Cited by 1 | Viewed by 2282

Abstract

Knowledge of analytical values in wines is essential to ensure product safety and compliance with legislation, and it is also essential to understand the various technologies in wine production. The aim of this work was to evaluate the analytical parameters of bottled Moravian wines from the Znojmo sub-region, from harvests 2015 and 2016. Basic oenological parameters and biologically active substances were evaluated. Moreover, we evaluated conditions during bottle aging in wines from harvest 2016. The results of the basic analytical values such as total phenolic acid (TPA), total sulfur dioxide (SO₂), pH, actual alcohol content (EtOH), and titratable acidity (TA) were in accordance with generally known values in wines and met the legislative requirements within oenological practices. Biologically active substances, such as gallic acid, trans-caffeic acid (TCA), trans-p-coumaric acid (TPCA), rutin, ferulic acid (FA), myricetin, resveratrol, and quercetin were identified. Comparing the analytical values of individual types of wine leads to a better understanding of winemaking technology and the development of wine as such. The subject of the study was also the monitoring of produced grape pomace incurred during wine production harvest 2015 with the indication of possibilities of its further use. Full article

(This article belongs to the Special Issue Separation and Quantitative Analysis of Natural Product Extracts)

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