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Chromatographic Science of Natural Products

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

Deadline for manuscript submissions: closed (31 August 2020) | Viewed by 61160

Special Issue Editors


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Guest Editor
Department of Inorganic Chemistry, Medical University of Lublin, Lublin, Poland
Interests: liquid chromatography; phytochemistry; drug analysis
Special Issues, Collections and Topics in MDPI journals

E-Mail Website
Guest Editor
Department of Inorganic Chemistry, Medical University of Lublin, Lublin, Poland
Interests: liquid chromatography; TLC; phytochemistry; chemometry
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Phytochemistry is a crucial area that encompasses the confirmation of plant material identity as well as the qualitative and quantitative analysis of natural products and mixtures in the quality control of plant drugs and food and cosmetic products. The use of chromatographic analysis is able to fulfill most of the goals of phytochemistry, and can be applied in various forms. TLC offers a quick and cheap method for the parallel separation of several samples on one plate, and is the perfect method for comparison of extracts and/or standards in the same chromatographic run. Various detection methods and derivatizations allow for verification of the composition of complex samples, and the determination of properties. Preliminary information connected with the pharmacological activity of plant material components can be obtained from the biodetection of different activities, including antioxidant, antibiotic, as well as of selected enzymes. Gas chromatography is a perfect tool for the determination of volatile active compounds of plant origin, such as essential oils or flavor compounds in food products including wines, fruit products, and spices, among others. High-performance liquid chromatography can be widely used for the identification of particular plant components, for example, markers and other active compounds in plants and plant products. Various chromatographic methods, including counter current chromatography, can be applied in the isolation of compounds of interest from extracts. This Special Issue of Molecules aims to publish papers which will provide new and interesting information regarding the application of chromatographic methods in the area of plant chemistry.

Prof. Dr. Monika Waksmundzka-Hajnos
Dr. Miroslaw Hawryl
Guest Editors

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Keywords

  • TLC-bioautography
  • HPLC, TLC, and GC in phytochemistry and food analysis
  • chemometry in fingerprinting
  • examination of biological activity of plant components and food
  • isolation and identification of natural compounds

Published Papers (16 papers)

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Research

14 pages, 1390 KiB  
Article
Highly Efficient Extraction Procedures Based on Natural Deep Eutectic Solvents or Ionic Liquids for Determination of 20-Hydroxyecdysone in Spinach
by Sylwia Bajkacz, Kornelia Rusin, Anna Wolny, Jakub Adamek, Karol Erfurt and Anna Chrobok
Molecules 2020, 25(20), 4736; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25204736 - 15 Oct 2020
Cited by 17 | Viewed by 2486
Abstract
A novel, efficient extraction procedure based on natural deep eutectic solvents (NADES) and ionic liquids (ILs) for determination of 20-hydroxyecdysone (20-E) in spinach has been developed. NADES, the first green extraction agent, with different hydrogen bond donors and acceptors are screened in order [...] Read more.
A novel, efficient extraction procedure based on natural deep eutectic solvents (NADES) and ionic liquids (ILs) for determination of 20-hydroxyecdysone (20-E) in spinach has been developed. NADES, the first green extraction agent, with different hydrogen bond donors and acceptors are screened in order to determine extraction efficiencies. NADES consisting of lactic acid and levulinic acid at a molar ratio of 1:1 exhibits the highest yields. ILs, the second green extraction agent, with various cations and anions are also investigated, where [TEA] [OAc]·AcOH, χAcOH = 0.75 displays the highest recovery. Moreover, NADES-SLE and IL-SLE (SLE, solid-liquid extraction) parameters are investigated. Using the obtained optimized method, the recoveries of the target compound in spinach are above 93% and 88% for NADES-SLE and IL-SLE procedure, respectively. The methods display good linearity within the range of 0.5–30 μg/g and LODs of 0.17 µg/g. The proposed NADES-SLE-UHPLC-UV and IL-SLE-UHPLC-UV procedures can be applied to the analysis of 20-E in real spinach samples, making it a potentially promising technique for food matrix. The main advantage of this study is the superior efficiency of the new, green extraction solvents, which results in a significant reduction of extraction time and solvents as compared to those in the literature. Full article
(This article belongs to the Special Issue Chromatographic Science of Natural Products)
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11 pages, 760 KiB  
Communication
Polyphenol Composition and Antioxidant Potential of Instant Gruels Enriched with Lycium barbarum L. Fruit
by Marta Olech, Kamila Kasprzak, Agnieszka Wójtowicz, Tomasz Oniszczuk, Renata Nowak, Monika Waksmundzka-Hajnos, Maciej Combrzyński, Marek Gancarz, Iwona Kowalska, Anna Krajewska and Anna Oniszczuk
Molecules 2020, 25(19), 4538; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25194538 - 03 Oct 2020
Cited by 19 | Viewed by 2520
Abstract
Goji fruit (Lycium barbarum L.) has been identified as a polyphenolic compound plant source of noted richness. It also contains polysaccharides, carotenoids, vitamins and minerals, fatty and organic acids. The purpose of the presented research was to produce innovative instant corn gruels [...] Read more.
Goji fruit (Lycium barbarum L.) has been identified as a polyphenolic compound plant source of noted richness. It also contains polysaccharides, carotenoids, vitamins and minerals, fatty and organic acids. The purpose of the presented research was to produce innovative instant corn gruels with various dry goji berry contents (1, 3 and 5%), to determine the level of included polyphenolic compounds (including individual free phenolic acids) and to assess the antioxidant properties of these functional-food products. A further objective was to identify the optimum value of one of the most important production parameter, the rotational speed of the extruder’s screw during gruel processing. The undertaken chromatographic analysis (LC-ESI-MS/MS) showed a wide variety of available phenolic acids. In the samples with 5% addition of fruit, eight phenolic acids were detected, whereas in the corn gruel without additives, only five were noted. The antioxidant activity, the content of free phenolic acids and the sum of polyphenols increased with increase of the functional additive. For all goji content, screw speeds of 100 and 120 rpm rather than 80 rpm resulted in higher polyphenol amounts and greater Trolox equivalent antioxidant capacity, as well as higher ability to scavenge DPPH. Full article
(This article belongs to the Special Issue Chromatographic Science of Natural Products)
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22 pages, 1505 KiB  
Article
HPLC Fingerprint Analysis with the Antioxidant and Cytotoxic Activities of Selected Lichens Combined with the Chemometric Calculations
by Anna Hawrył, Mirosław Hawrył, Agnieszka Hajnos-Stolarz, Jagoda Abramek, Anna Bogucka-Kocka and Łukasz Komsta
Molecules 2020, 25(18), 4301; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25184301 - 19 Sep 2020
Cited by 17 | Viewed by 3436
Abstract
The aim of this study was to evaluate the ability of multivariate techniques to predict antioxidant and cytotoxic activity of the selected lichens from the chromatographic data. A simple and reproducible HPLC-DAD technique has been used to obtain the chromatographic fingerprint profiles. Reversed [...] Read more.
The aim of this study was to evaluate the ability of multivariate techniques to predict antioxidant and cytotoxic activity of the selected lichens from the chromatographic data. A simple and reproducible HPLC-DAD technique has been used to obtain the chromatographic fingerprint profiles. Reversed phase high performance liquid chromatography (RP-HPLC) linear gradient system with methanol, water and phosphoric acid (V) (pH 2.3) as the mobile phase was used (50 min). Principal Component Analysis (PCA) has been applied to the evaluation of the phytochemical similarity between studied samples, especially between the same species collected in various places of Poland (Cetraria islandica (L.) Ach., CI, Cladina mitis Sandst., CM, Hypogymnia physodes (L.) Nyl., HP). The ability to scavenge free radicals was evaluated using 2,2-diphenyl-1-picrylhydrazyl (DPPH) and ferric reducing antioxidant power (FRAP) methods and the total phenolic content was determined by Folin-Ciocalteu (F-C) test. In the case of DPPH % of inhibition was higher for selected species (Pseudevernia furfuracea (L.) Zopf, H. physodes in comparison to the literature data. The FRAP test showed that the H. physodes extract had higher ability to scavenge free radical in comparison to Cladonia furcata (Huds.) Schrader and Evernia prunastri (L.) Ach., whereas P. furfuracea extract showed higher ability than C. islandica. The high content of phenolics in P. furfuracea and H. physodes confirms their high antioxidant activity. The cytotoxic activity of studied extracts was tested by cell culture method using the human HL-60 / MX2 acute CKL-22 (CRL-2257) promyelocytic leukemia tumor cell line. The lowest values of IC50 [µg∙mL−1] were obtained for: H. physodes (HP1)—99.4; C. digitate—122.6; H. physodes (HP)—136.5, C. subulata—142.6; C. mitis—180.2. Full article
(This article belongs to the Special Issue Chromatographic Science of Natural Products)
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17 pages, 2763 KiB  
Article
Application of Super Absorbent Polymer and Plant Mucilage Improved Essential Oil Quantity and Quality of Ocimum basilicum var. Keshkeni Luvelou
by Somaye Beigi, Majid Azizi and Marcello Iriti
Molecules 2020, 25(11), 2503; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25112503 - 28 May 2020
Cited by 8 | Viewed by 3095
Abstract
One of the major factors limiting the production of medicinal plants in arid and semi-arid areas is water deficit or drought stress. One-third of the land in the world is arid and semi-arid and is inhabited by nearly 4 × 108 people. [...] Read more.
One of the major factors limiting the production of medicinal plants in arid and semi-arid areas is water deficit or drought stress. One-third of the land in the world is arid and semi-arid and is inhabited by nearly 4 × 108 people. Ocimum basilicum (sweet basil) is a valuable medicinal plant that is sensitive to water deficit, and water shortage negatively affects sweet basil yield and quality. Water availability in the root zone of basil could ameliorate the negative effects of water shortage. To the best of our knowledge, although the effects of hydrophilic polymers (HPs) have been studied in different agricultural crops, the effects of HP application in medicinal plants have not been previously investigated. This investigation was conducted to explore the effects on water use efficiency when using Stockosorb® (STS) and psyllium seed mucilage (PSM) as hydrophilic polymers (HPs) and the effects of these HPs on essential oil quality, quantity, and yield. The research was set up in a factorial experiment on the basis of completely randomized block design with three replications. We used two HPs, STS (industrial) and PSM (herbal), with two methods of application (mixed with soil, mixed with soil + root) at four concentrations (0%, 0.1%, 0.2%, and 0.3% (w/w)). Results showed that the STS and PSM significantly increased the dry herb yield (both shoot and root) in comparison to the control, and the improving effect was higher when these HPs were mixed with soil + root. The highest dry herb yield (6.74 and 3.68 g/plant for shoot and root, respectively) was detected in the PSM at 0.1% mixed with soil + root. There was not any significant difference in dry herb yield among PSM (0.1%), PSM (0.2%), and STS (0.2%) when mixed with soil + root. Soil application of PSM and soil + root application of STS at a concentration of 0.3% increased the Essential Oil (EO) content almost three-fold in comparison to the control (0.5% and 0.52% to 0.18% v/w, respectively). The maximum essential oil yield was recorded in plants treated with STS (0.2% in) or PSM (0.1%) by soil + root application (0.21 and 0.19 mL/plant, respectively). PSM at concentrations of 0.1% and 0.2% (mixed with soil + root) showed the highest water use efficiency (1.91 and 1.82 g dry weight (DW)/L H2O, respectively). STS mixed with soil also significantly improved water use efficiency (WUE) in comparison to the control. The application of these HPs improved the quality of sweet basil essential oil by increasing the linalool and decreasing the eugenol, epi-α-cadinol, and trans-α-bergamotene content. Full article
(This article belongs to the Special Issue Chromatographic Science of Natural Products)
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11 pages, 4300 KiB  
Article
Extraction and Quantification of Sulforaphane and Indole-3-Carbinol from Rapeseed Tissues Using QuEChERS Coupled with UHPLC-MS/MS
by Xu Yu, Fei Ma, Liangxiao Zhang and Peiwu Li
Molecules 2020, 25(9), 2149; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25092149 - 04 May 2020
Cited by 11 | Viewed by 3138
Abstract
Rapeseed (Brassica napus L.) is rich in phenols, vitamins, carotenoids, and mineral elements, such as selenium. Additionally, it contains the active ingredients sulforaphane and indole-3-carbinol, which have been demonstrated to have pharmacological effects. In this study, sulforaphane and indole-3-carbinol were extracted and [...] Read more.
Rapeseed (Brassica napus L.) is rich in phenols, vitamins, carotenoids, and mineral elements, such as selenium. Additionally, it contains the active ingredients sulforaphane and indole-3-carbinol, which have been demonstrated to have pharmacological effects. In this study, sulforaphane and indole-3-carbinol were extracted and quantified from rapeseeds using quick, easy, cheap, effective, rugged and safe (QuEChERS) method coupled with ultra high performance liquid chromarography tandem mass spectrometry (UHPLC-MS/MS). The major parameters for extraction and purification efficiency were optimized, including the hydrolysis reaction, extraction condition and type and amount of purification adsorbents. The limit of detection (LOD) and the limit of quantification (LOQ) for sulforaphane were 0.05 μg/kg and 0.15 μg/kg, and for indole-3-carbinol were 5 μg/kg and 15 μg/kg, respectively. The developed method was used to successfully analyze fifty rapeseed samples. The QuEChERS coupled with UHPLC-MS/MS simultaneously detect sulforaphane and indole-3-carbinol in vegetable matrix and evaluate the quality and nutrition of rapeseed samples. Full article
(This article belongs to the Special Issue Chromatographic Science of Natural Products)
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11 pages, 1215 KiB  
Communication
Stability Evaluation of DMT and Harmala Alkaloids in Ayahuasca Tea Samples
by Gabriela de Oliveira Silveira, Rafael Guimarães dos Santos, Felipe Rebello Lourenço, Giordano Novak Rossi, Jaime E. C. Hallak and Mauricio Yonamine
Molecules 2020, 25(9), 2072; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25092072 - 29 Apr 2020
Cited by 17 | Viewed by 8162
Abstract
Ayahuasca tea is a hallucinogenic beverage used for religious purposes in Brazil and many other countries that has therapeutic potential in the treatment of some mental health disorders. In the context of psychedelic research, quantification of the tea’s main alkaloids prior to its [...] Read more.
Ayahuasca tea is a hallucinogenic beverage used for religious purposes in Brazil and many other countries that has therapeutic potential in the treatment of some mental health disorders. In the context of psychedelic research, quantification of the tea’s main alkaloids prior to its administration in animal or human studies is essential. For this reason, this study aims to provide information regarding the stability of the main ayahuasca alkaloids (dimethyltryptamine, DMT; harmine, HRM; tetrahydroharmine, THH; harmaline, HRL) in three different conditions: (1) A year stored in a refrigerator either in plastic or glass containers, (2) seven days at 37 °C to reproduce usual mail transportation, and (3) after three freeze–thaw cycles. Samples were quantified after a dilute-and-shoot procedure using liquid chromatography tandem mass spectrometry (LC-ESI-MS/MS). There was no significant degradation of DMT concentration over time in all tested conditions. Harmala alkaloids (THH, HRL, and HRM) showed important variations after long-term and high-temperature storages. Although DMT has proven to be stable in all studied conditions, the harmala alkaloids revealed intense degradation and even concentration increment. This may be caused by degradation, alkaloid inter-conversion, and leaching from tea precipitate material. Therefore, ayahuasca quantification before administration in controlled sets is mandatory. Full article
(This article belongs to the Special Issue Chromatographic Science of Natural Products)
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19 pages, 606 KiB  
Article
Characterization of Free and Bound Phenolic Acids and Flavonoid Aglycones in Rosa rugosa Thunb. Leaves and Achenes Using LC–ESI–MS/MS–MRM Methods
by Marta Olech, Wioleta Pietrzak and Renata Nowak
Molecules 2020, 25(8), 1804; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25081804 - 15 Apr 2020
Cited by 25 | Viewed by 4237
Abstract
Fast and reliable determination of polyphenols is a quite common goal during investigation of new plant materials and herbal products, their standardization, quality control, or chemo-taxonomical studies. The aim of this study was to develop and validate methods based on the application of [...] Read more.
Fast and reliable determination of polyphenols is a quite common goal during investigation of new plant materials and herbal products, their standardization, quality control, or chemo-taxonomical studies. The aim of this study was to develop and validate methods based on the application of reversed phase liquid chromatography/electrospray ionization triple quadrupole mass spectrometry (LC-ESI-MS/MS) using multiple reaction monitoring (MRM) for comprehensive quantitative and qualitative analysis of phenolic acids and flavonoid aglycones. LC-MS/MS-MRM protocols were applied for the determination of free and bound phenolics in a series of plant samples prepared from leaves and achenes (true fruits) of Japanese rose (Rosa rugosa Thunb.). The presence of large amount of phenolic compounds was detected in rose leaves (786.44 µg/g and 14.46 µg/g of phenolic acids and flavonoid aglycones, respectively). Isoferulic acid and five aglycones were revealed for the first time in this plant material. Moreover, 15 phenolic acids and six aglycones were found in the rose achenes, including eight phenolic acids and four aglycones that had not been previously reported in this rose organ. It was shown that leaves and achenes may constitute an industrially relevant source of phenolic compounds for potential commercial use in pharmaceutical, food, or cosmetic industry. Full article
(This article belongs to the Special Issue Chromatographic Science of Natural Products)
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14 pages, 4137 KiB  
Article
Isolation and Identification of Anthocyanin Component in the Fruits of Acanthopanax Sessiliflorus (Rupr. & Maxim.) Seem. by Means of High Speed Counter Current Chromatography and Evaluation of Its Antioxidant Activity
by Liang Chen, Xiulan Xin, Hui Feng, Shuangshi Li, Qiguang Cao, Xinying Wang and Frank Vriesekoop
Molecules 2020, 25(8), 1781; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25081781 - 13 Apr 2020
Cited by 12 | Viewed by 3113
Abstract
Acanthopanax sessiliflorus (Rupr. & Maxim.) Seem. (Araliaceae) is one of the most abundant species of genus Acanthopanax. The fruits of A. sessiliflorus are used in traditional medical protocols as an analgesic, tonic, antidiabetic, antihypertensive, anti-inflammatory, antitumor, and immune-stimulating agent. In [...] Read more.
Acanthopanax sessiliflorus (Rupr. & Maxim.) Seem. (Araliaceae) is one of the most abundant species of genus Acanthopanax. The fruits of A. sessiliflorus are used in traditional medical protocols as an analgesic, tonic, antidiabetic, antihypertensive, anti-inflammatory, antitumor, and immune-stimulating agent. In this work, we carried out a comprehensive investigation into the anthocyanin components in the fruits of A. sessiliflorus. The anthocyanin content in the fresh fruits of A. sessiliflorus was determined by high performance liquid chromatography-diode array detection (HPLC/DAD), and the anthocyanin component was isolated from these using high-speed counter-current chromatography (HSCCC) and elucidated by electro-spray ionization-mass spectrometry (ESI/MS), 1H- and 13C-NMR. Its antioxidant activity was evaluated by ferric-reducing antioxidant power (FRAP) and 2,2-diphenyl-1-picrylhydrazyl (DPPH). We found that A. sessiliflorus contained a gross anthocyanin content of 121.35 mg/100 g. HSCCC was successfully used for separation and purification of the primary anthocyanin component, cyanidin 3-xylosyl-galactoside. The antioxidant and radical scavenging tests indicated that cyanidin 3-xylosyl-galactoside is a potent antioxidant. Full article
(This article belongs to the Special Issue Chromatographic Science of Natural Products)
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15 pages, 756 KiB  
Article
Phenolic Composition of the Leaves of Pyrola rotundifolia L. and Their Antioxidant and Cytotoxic Activity
by Katarzyna Szewczyk, Anna Bogucka-Kocka, Natalia Vorobets, Anna Grzywa-Celińska and Sebastian Granica
Molecules 2020, 25(7), 1749; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25071749 - 10 Apr 2020
Cited by 14 | Viewed by 3107
Abstract
The leaves of Pyrola rotundifolia L. were extracted in the mixed solvent of methanol/acetone/water (2:2:1, v/v/v) and investigated for their phytochemical analysis and biological activity. Total phenolic and flavonoid contents were determined spectrophotometrically. A high content of phenols [...] Read more.
The leaves of Pyrola rotundifolia L. were extracted in the mixed solvent of methanol/acetone/water (2:2:1, v/v/v) and investigated for their phytochemical analysis and biological activity. Total phenolic and flavonoid contents were determined spectrophotometrically. A high content of phenols (208.35 mg GAE/g of dry extract), flavonoids (38.90 mg QE/g of dry extract) and gallotannins (722.91 GAE/g of dry extract) was obtained. Ultra-high performance liquid chromatography diode array detector tandem mass spectrometry (UHPLC–DAD–MS) allowed for the detection of 23 major peaks at 254 nm. The extract was analyzed for its antioxidant capacity using 2,2-diphenyl-1-picryl-hydrazyl (DPPH) and 2,2′-azinobis[3-ethylbenzthiazoline]-6-sulfonic acid (ABTS•+) radical scavenging, metal chelating power and β-carotene-linoleic acid bleaching assays. The examined extract showed moderate radical scavenging and chelating activity, and good inhibiting ability of linoleic acid oxidation (EC50 = 0.05 mg/mL) in comparison to standards. The cytotoxic effect in increasing concentration on five types of leukemic cell lines was also investigated using trypan blue vital staining. It was found that the analyzed extract induced the apoptosis of all the tested cell lines. Our findings suggest that the leaves of P. rotundifolia are a source of valuable compounds providing protection against oxidative damage, hence their use in traditional medicine is justified. Full article
(This article belongs to the Special Issue Chromatographic Science of Natural Products)
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16 pages, 3929 KiB  
Article
Ionic Liquid-Based Ultrasonic-Assisted Extraction Coupled with HPLC and Artificial Neural Network Analysis for Ganoderma lucidum
by Changqin Li, Yiping Cui, Jie Lu, Cunyu Liu, Sitan Chen, Changyang Ma, Zhenhua Liu, Jinmei Wang and Wenyi Kang
Molecules 2020, 25(6), 1309; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25061309 - 13 Mar 2020
Cited by 13 | Viewed by 4052
Abstract
Ganoderma lucidum is widely used in traditional Chinese medicine (TCM). Ganoderic acid A and D are the main bioactive components with anticancer effects in G. lucidum. To obtain the maximum content of two compounds from G. lucidum, a novel extraction method, [...] Read more.
Ganoderma lucidum is widely used in traditional Chinese medicine (TCM). Ganoderic acid A and D are the main bioactive components with anticancer effects in G. lucidum. To obtain the maximum content of two compounds from G. lucidum, a novel extraction method, an ionic liquid-based ultrasonic-assisted method (ILUAE) was established. Ionic liquids (ILs) of different types and parameters, including the concentration of ILs, ultrasonic power, ultrasonic time, rotational speed, solid–liquid ratio, were optimized by the orthogonal experiment and variance analysis. Under these optimal conditions, the total extraction yield of the two compounds in G. lucidum was 3.31 mg/g, which is 36.21% higher than that of the traditional solvent extraction method. Subsequently, an artificial neural network (ANN) was developed to model the performance of the total extraction yield. The Levenberg–Marquardt back propagation algorithm with the sigmoid transfer function (logsig) at the hidden layer and a linear transfer function (purelin) at the output layer were used. Results showed that single hidden layer with 9 neurons presented the best values for the mean squared error (MSE) and the correlation coefficient (R), with respectively corresponding values of 0.09622 and 0.93332. Full article
(This article belongs to the Special Issue Chromatographic Science of Natural Products)
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18 pages, 2061 KiB  
Article
Composition, Antifungal, Phytotoxic, and Insecticidal Activities of Thymus kotschyanus Essential Oil
by Ghader Ghasemi, Abolfazl Alirezalu, Youbert Ghosta, Azadeh Jarrahi, Seyed Ali Safavi, Mahdi Abbas-Mohammadi, Francisco J. Barba, Paulo E. S. Munekata, Rubén Domínguez and José M. Lorenzo
Molecules 2020, 25(5), 1152; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25051152 - 04 Mar 2020
Cited by 35 | Viewed by 4055
Abstract
Essential oils (EOs) are some of the outstanding compounds found in Thymus that can exert antifungal, phytotoxic, and insecticidal activities, which encourage their exploration and potential use for agricultural and food purposes. The essential oils (EO) obtained from Thymus kotschyanus collected in the [...] Read more.
Essential oils (EOs) are some of the outstanding compounds found in Thymus that can exert antifungal, phytotoxic, and insecticidal activities, which encourage their exploration and potential use for agricultural and food purposes. The essential oils (EO) obtained from Thymus kotschyanus collected in the East Azerbaijan Province (Iran) were characterized using a gas chromatography-mass spectrometry (GC-MS) analysis. Thymol was the most important compound (60.48%), although 35 other active compounds were identified in the EO. Significant amounts of carvacrol (3.08%), p-cymene (5.56%), and γ-terpinene (6.67%) were found in the EO. The T. kotschyanus EO was tested against important phytopathogenic fungi (Botrytis cinerea, Aspergillus niger, and Penicillium expansum). The antifungal assay showed that the use of ≥500 ppm of EO resulted in a fungicidal effect against all funguses tested. In a similar way, the use of ≥500 ppm of EO inhibited the germination of all crop weed seeds (Amaranthus retroflexus L. and Panicum miliaceum L.) and their subsequent growth, which demonstrated its herbicidal effect. Finally, the insecticidal capacity of T. kotschyanus EO was also observed against selected insects (Oryzaephilus surinamensis and Sitophilus oryzae). O. surinamensis was more susceptible to the effect of EO (LC50 = 4.78 µL/L air) than S. oryzae (LC50 = 13.20 µL/L air). The obtained results of the present study can provide new safe resources to the development of new products for the food, agriculture, and pharmaceutical industries. Full article
(This article belongs to the Special Issue Chromatographic Science of Natural Products)
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12 pages, 1775 KiB  
Article
Extraction and Determination of Vitamin K1 in Foods by Ultrasound-Assisted Extraction, SPE, and LC-MS/MS
by Yueqing Xu, Liangxiao Zhang, Ruinan Yang, Xu Yu, Li Yu, Fei Ma, Hui Li, Xiupin Wang and Peiwu Li
Molecules 2020, 25(4), 839; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25040839 - 14 Feb 2020
Cited by 8 | Viewed by 4387
Abstract
Vitamin K1 is one of the important hydrophobic vitamins in fat-containing foods. Traditionally, lipase is employed in the determination of vitamin K1 to remove the lipids, which makes the detection complex, time-consuming, and insensitive. In this study, the determination of vitamin [...] Read more.
Vitamin K1 is one of the important hydrophobic vitamins in fat-containing foods. Traditionally, lipase is employed in the determination of vitamin K1 to remove the lipids, which makes the detection complex, time-consuming, and insensitive. In this study, the determination of vitamin K1 in fat-containing foods was developed based on ultrasound-assisted extraction (UAE), solid-phase extraction (SPE) combined with liquid chromatography–tandem mass spectrometry (LC-MS/MS). The optimal conditions for extraction of vitamin K1 were material–liquid ratio of 1:70 (g/mL), extraction temperature of 50 °C, extraction power of 700 W, extraction time of 50 min, material-wash fluid ratio of 1:60 (g/mL), and 8 mL of hexane/anhydrous ether (97:3, v/v) as the elution solvent. Then, vitamin K1 was analyzed on a ZORBAX SB-C18 column (50 mm × 2.1 mm, 1.8 μm) by gradient elution with water (0.01% formic acid) and methanol (0.01 formic acid + 2.5 mmol/L ammonium formate) as the mobile phase. The limit of detection (LOD) and limit of quantification (LOQ) were 0.05 and 0.16 μg/kg, respectively. Calibration curve was linear over the range of 10–500 ng/mL (R2 > 0.9988). The recoveries at three spiked levels were between 80.9% and 119.1%. The validation and application indicated that the proposed method was simple and sensitive in determination of vitamin K1 in fat-containing foods. Full article
(This article belongs to the Special Issue Chromatographic Science of Natural Products)
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16 pages, 858 KiB  
Article
Phenolic Profile, Antioxidant and Anti-Proliferative Activities of Methanolic Extracts from Asclepias linaria Cav. Leaves
by José Alejandro Sánchez-Gutiérrez, Dafné Moreno-Lorenzana, Dioselina Álvarez-Bernal, Jacobo Rodríguez-Campos and José Roberto Medina-Medrano
Molecules 2020, 25(1), 54; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25010054 - 23 Dec 2019
Cited by 7 | Viewed by 3085
Abstract
Asclepias linaria Cav. (Apocynaceae) is a shrubby plant endemic of Mexico which has been used in traditional medicine. However, the bioactive potential of this plant remains unexplored. In this study, the phenolic composition, antioxidant, and cytotoxic activities of A. linaria leaves were determined. [...] Read more.
Asclepias linaria Cav. (Apocynaceae) is a shrubby plant endemic of Mexico which has been used in traditional medicine. However, the bioactive potential of this plant remains unexplored. In this study, the phenolic composition, antioxidant, and cytotoxic activities of A. linaria leaves were determined. In order to estimate the phenolic composition of the leaves, the total phenolic, flavonoid, and condensed tannins contents were determined. Furthermore, the antioxidant activity was measured by the scavenging activity of the 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2′-azino-bis[3-ethylbenzothiazoline-6-sulphonic acid] (ABTS•+) radicals and the total antioxidant capacity. The phenolic compounds identified in the A. linaria leaves by ultra-performance liquid chromatography coupled to mass spectrometry (UPLC-MS) include phenolic acids, such as p-coumaric and ferulic acid, as well as flavonoids, such as rutin and quercetin. The leaves’ extracts of A. linaria showed a high scavenging activity of DPPH and ABTS•+ radicals (IC50 0.12 ± 0.001 and 0.51 ± 0.003 µg/mL, respectively), high total antioxidant capacity values (99.77 ± 4.32 mg of ascorbic acid equivalents/g of dry tissue), and had a cytotoxic effect against K562 and HL60 hematologic neoplasia cells lines, but no toxicity towards the normal mononuclear cell line was observed. These results highlight the potential of A. linaria and could be considered as a possible alternative source of anticancer compounds. Full article
(This article belongs to the Special Issue Chromatographic Science of Natural Products)
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10 pages, 26079 KiB  
Article
Applicability of a Monolithic Column for Separation of Isoquinoline Alkalodis from Chelidonium majus Extract
by Michał Staniak, Magdalena Wójciak-Kosior, Ireneusz Sowa, Maciej Strzemski, Jan Sawicki, Sławomir Dresler and Katarzyna Tyszczuk-Rotko
Molecules 2019, 24(19), 3612; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules24193612 - 07 Oct 2019
Cited by 4 | Viewed by 2537
Abstract
Isoquinoline alkaloids are the main group of secondary metabolites present in Chelidonium majus extracts, and they are still the object of interest of many researchers. Therefore, the development of methods for the investigation and separation of the alkaloids is still an important task. [...] Read more.
Isoquinoline alkaloids are the main group of secondary metabolites present in Chelidonium majus extracts, and they are still the object of interest of many researchers. Therefore, the development of methods for the investigation and separation of the alkaloids is still an important task. In this work, the application potential of a silica-based monolithic column for the separation of alkaloids was assessed. The influence of the organic modifier, temperature, salt concentration, and pH of the eluent on basic chromatographic parameters such as retention, resolution between neighboring peaks, chromatographic plate numbers, and peak asymmetry were investigated. Based on the obtained results, a gradient elution program was developed and used to separate and quantitatively determine the main alkaloids in a Chelidonium majus root extract. Full article
(This article belongs to the Special Issue Chromatographic Science of Natural Products)
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16 pages, 3199 KiB  
Article
Preparative Purification of Total Flavonoids from Sophora tonkinensis Gagnep. by Macroporous Resin Column Chromatography and Comparative Analysis of Flavonoid Profiles by HPLC-PAD
by Mengyang Hou, Wenzhong Hu, Zhilong Xiu, Aili Jiang, Lei Men, Kexin Hao, Xingsheng Sun and Duo Cao
Molecules 2019, 24(17), 3200; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules24173200 - 03 Sep 2019
Cited by 27 | Viewed by 4166
Abstract
For the full development and utilization of Sophora tonkinensis Gagnep., this study was primarily intended to established a simple and efficient approach for the preparative purification of total flavonoids from S. tonkinensis by macroporous resin column chromatography (MRCC). The adsorption and desorption characteristics [...] Read more.
For the full development and utilization of Sophora tonkinensis Gagnep., this study was primarily intended to established a simple and efficient approach for the preparative purification of total flavonoids from S. tonkinensis by macroporous resin column chromatography (MRCC). The adsorption and desorption characteristics of the total flavonoids on ten macroporous resins were first studied, and AB-8 resin was chosen as the most suitable, and the adsorption data were best fitted to the pseudo-second-order kinetics model and Langmuir isotherm model. Furthermore, the technological parameters for the purification of the total flavonoids were optimized using column chromatography. After a sample one-step purification procedure, the content of the total flavonoids increased by about 4.76-fold from 12.14% to 57.82%, with a recovery yield of 84.93%. In addition, the comparative analysis of the flavonoid extracts before and after purification was performed by high-performance liquid chromatography coupled with photodiode-array detection (HPLC-PAD). The results showed that the contents of six major flavonoids in the purified product were all higher than before the purification. Therefore, the AB-8 MRCC established in this work was a promising method for the industrial-scale purification of the total flavonoids from S. tonkinensis. Full article
(This article belongs to the Special Issue Chromatographic Science of Natural Products)
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18 pages, 1735 KiB  
Article
Comparative Analysis of Phytochemical Composition of Gamma-Irradiated Mutant Cultivars of Chrysanthemum morifolium
by Jaihyunk Ryu, Bomi Nam, Bo-Ram Kim, Sang Hoon Kim, Yeong Deuk Jo, Joon-Woo Ahn, Jin-Baek Kim, Chang Hyun Jin and Ah-Reum Han
Molecules 2019, 24(16), 3003; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules24163003 - 19 Aug 2019
Cited by 24 | Viewed by 4698
Abstract
The flowers of chrysanthemum species are used as a herbal tea and in traditional medicine. In addition, members of the genus have been selected to develop horticultural cultivars of diverse floral colors and capitulum forms. In this research, we investigated the phytochemical composition [...] Read more.
The flowers of chrysanthemum species are used as a herbal tea and in traditional medicine. In addition, members of the genus have been selected to develop horticultural cultivars of diverse floral colors and capitulum forms. In this research, we investigated the phytochemical composition of eight gamma-irradiation mutant cultivars of Chrysanthemum morifolium and their original cultivars. The mutant chrysanthemum cultivars were generated by treatment with various doses of 60Co gamma irradiation of stem cuttings of three commercial chrysanthemum cultivars as follows: ‘ARTI-Dark Chocolate’ (50Gy), ‘ARTI-Purple Lady’ (30 Gy), and ‘ARTI-Yellow Star’ (50 Gy) derived from ‘Noble Wine’; ‘ARTI-Red Star’ (50 Gy) and ‘ARTI-Rising Sun’ (30 Gy) from ‘Pinky’; ‘ARTI-Purple’ (40 Gy) and ‘ARTI-Queen’ (30 Gy) from ‘Argus’; and ‘ARTI-Rollypop’ (70 Gy) from ‘Plaisir d’amour’. Quantitative analysis of flavonoids, phenolic acids, anthocyanins, and carotenoids in the flowers of the 12 chrysanthemum cultivars was performed using high performance liquid chromatography-diode array detector-electrospray ionization mass spectrometry (HPLC-DAD-ESIMS). Essential oils from the flowers of these cultivars were analyzed by gas chromatography–mass spectrometry (GC-MS). The mutant cultivars, ‘ARTI-Dark Chocolate’, ‘ARTI-Purple Lady’, ‘ARTI-Purple’, and ‘ARTI-Queen’ showed higher total amounts of flavonoid and phenolic acid compared with those of the respective original cultivars. The mutant cultivars, ‘ARTI-Dark Chocolate’, ‘ARTI-Purple Lady’ and ‘ARTI-Purple’, which produce purple to pink petals, contained more than two-times higher amounts of anthocyanins compared with those of their original cultivars. Of the mutant cultivars, ‘ARTI-Yellow Star’ in which petal color was changed to yellow, showed the greatest accumulation of carotenoids. Ninety-nine volatile compounds were detected, of which hydrocarbons and terpenoids were abundant in all cultivars analyzed. This is the first report that demonstrated the phytochemical analysis of novel chrysanthemum cultivars derived from C. morifolium hydrid using HPLC-DAD-ESIMS and GC-MS. These findings suggest that the selected mutant chrysanthemum cultivars show potential as a functional source of phytochemicals associated with the abundance of health-beneficial components, as well as good source for horticulture and pigment industries. Full article
(This article belongs to the Special Issue Chromatographic Science of Natural Products)
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