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Application of Liquid Chromatography in Food and Natural Products Extracts Analysis

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

Deadline for manuscript submissions: closed (31 January 2023) | Viewed by 20716

Special Issue Editor

Dr. Zeineb Aturki

E-Mail Website
Guest Editor
Institute for Biological Systems (ISB), Consiglio Nazionale delle Ricerche, Area della Ricerca di Roma I, Via Salaria Km 29.300, 00015 Rome, Italy
Interests: miniaturized separation techniques; liquid chromatography; mass spectrometry; food and natural products extracts characterization; bioactive compounds; polyphenols; contaminants
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Liquid chromatography (LC) is by far the most powerful and versatile separation technique for both preparative and analytical purposes. Because of the great separation efficiency, LC enables the resolution of complex mixtures allowing the simultaneous determination of each constituent. Food products, as well as natural product extracts, are very complex mixtures including naturally occurring compounds and other substances such as pesticides, mycotoxins, and veterinary drugs. Therefore, to guarantee the safety, quality, and authenticity of a food product or to assure the purity of extracted biomolecules used as potential new drug candidates, efficient methods are strongly required. Among the analytical techniques, LC combined with ultraviolet (UV) detection and/or coupled to mass spectrometry (MS) are the tools of choice to assess the safety and quality of food or natural products. Currently, ultra-high-performance liquid chromatography (UHPLC) is an increasingly used chromatographic technique because of its enhanced efficiency, resolution, and fast analysis.

This Special Issue will address novel advances in the application of Liquid Chromatography in the analysis of food and plant extracts. The topics include the development of LC methods for the analysis of bioactive compounds, additives, and contaminants, which can evaluate the nutritional properties, safety, and quality of the products. Original research articles as well as reviews are welcome.

Dr. Zeineb Aturki
Guest Editor

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Keywords

  • Liquid chromatography
  • Bioactive molecules
  • Contaminants
  • Nutritional properties
  • Mass spectrometry
  • UV-detection

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Published Papers (7 papers)

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Research

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15 pages, 2392 KiB  
Article
Isomers of the Tomato Glycoalkaloids α-Tomatine and Dehydrotomatine: Relationship to Health Benefits
by Nobuyuki Kozukue, Dong-Seok Kim, Suk-Hyun Choi, Masashi Mizuno and Mendel Friedman
Molecules 2023, 28(8), 3621; https://doi.org/10.3390/molecules28083621 - 21 Apr 2023
Cited by 4 | Viewed by 2848
Abstract
High-performance liquid chromatography (HPLC) analysis of three commercial tomatine samples and another isolated from green tomatoes revealed the presence of two small peaks in addition to those associated with the glycoalkaloids dehydrotomatine and α-tomatine. The present study investigated the possible structures of the [...] Read more.
High-performance liquid chromatography (HPLC) analysis of three commercial tomatine samples and another isolated from green tomatoes revealed the presence of two small peaks in addition to those associated with the glycoalkaloids dehydrotomatine and α-tomatine. The present study investigated the possible structures of the compounds associated with the two small peaks using HPLC–mass spectrophotometric (MS) methods. Although the two peaks elute much earlier on chromatographic columns than the elution times of the known tomato glycoalkaloids dehydrotomatine and α-tomatine, isolation of the two compounds by preparative chromatography and subsequent analysis by MS shows the two compounds have identical molecular weights, tetrasaccharide side chains, and MS and MS/MS fragmentation patterns to dehydrotomatine and α-tomatine. We suggest the two isolated compounds are isomeric forms of dehydrotomatine and α-tomatine. The analytical data indicate that widely used commercial tomatine preparations and those extracted from green tomatoes and tomato leaves consist of a mixture of α-tomatine, dehydrotomatine, an α-tomatine isomer, and a dehydrotomatine isomer in an approximate ratio of 81:15:4:1, respectively. The significance of the reported health benefits of tomatine and tomatidine is mentioned. Full article
(This article belongs to the Special Issue Application of Liquid Chromatography in Food and Natural Products Extracts Analysis)
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13 pages, 1337 KiB  
Article
Determination of Anthraquinone-Tagged Amines Using High-Performance Liquid Chromatography with Online UV Irradiation and Luminol Chemiluminescence Detection
by Naoya Kishikawa, Mahmoud El-Maghrabey, Ayaka Kawamoto, Kaname Ohyama and Naotaka Kuroda
Molecules 2023, 28(5), 2146; https://doi.org/10.3390/molecules28052146 - 24 Feb 2023
Cited by 2 | Viewed by 1699
Abstract
Quinones are frequently used as derivatization reagents in HPLC analysis to improve detection sensitivity. In the present study, a simple, sensitive, and selective chemiluminescence (CL) derivatization strategy for biogenic amines, prior to their HPLC-CL analysis, was developed. The novel CL derivatization strategy was [...] Read more.
Quinones are frequently used as derivatization reagents in HPLC analysis to improve detection sensitivity. In the present study, a simple, sensitive, and selective chemiluminescence (CL) derivatization strategy for biogenic amines, prior to their HPLC-CL analysis, was developed. The novel CL derivatization strategy was established based on using anthraquinone-2-carbonyl chloride as derivatizing agent for amines and then using the unique property of the quinones’ moiety to generate reactive oxygen species (ROS) in response to UV irradiation. Typical amines such as tryptamine and phenethylamine were derivatized with anthraquinone-2-carbonyl chloride and then injected into an HPLC system equipped with an online photoreactor. The anthraquinone-tagged amines are separated and then UV-irradiated when they pass through a photoreactor to generate ROS from the quinone moiety of the derivative. Tryptamine and phenethylamine can be determined by measuring the chemiluminescence intensity produced by the reaction of the generated ROS with luminol. The chemiluminescence disappears when the photoreactor is turned off, suggesting that ROS are no longer generated from the quinone moiety in the absence of UV irradiation. This result indicates that the generation of ROS could be controlled by turning the photoreactor on and off. Under the optimized conditions, the limits of detection for tryptamine and phenethylamine were 124 and 84 nM, respectively. The developed method is successfully applied to determine the concentrations of tryptamine and phenethylamine in wine samples. Full article
(This article belongs to the Special Issue Application of Liquid Chromatography in Food and Natural Products Extracts Analysis)
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10 pages, 1062 KiB  
Communication
Determination of d- and l-Amino Acids in Garlic Foodstuffs by Liquid Chromatography–Tandem Mass Spectrometry
by Mayu Onozato, Haruna Nakanoue, Tatsuya Sakamoto, Maho Umino and Takeshi Fukushima
Molecules 2023, 28(4), 1773; https://doi.org/10.3390/molecules28041773 - 13 Feb 2023
Cited by 8 | Viewed by 2286
Abstract
Black garlic is currently attracting interest as a health food and constituent of commercial supplements; however, no data regarding the d-amino acids within black garlic have been reported. Therefore, the amino acid compositions of methanol extracts from fresh and black garlic were [...] Read more.
Black garlic is currently attracting interest as a health food and constituent of commercial supplements; however, no data regarding the d-amino acids within black garlic have been reported. Therefore, the amino acid compositions of methanol extracts from fresh and black garlic were compared herein. We investigated the contents of the d- and l-forms of amino acids in commercial fresh, black, and freeze-dried garlic foodstuffs by liquid chromatography–tandem mass spectrometry (LC–MS/MS) using a pre-column chiral derivatization reagent, succinimidyl 2-(3-((benzyloxy)carbonyl)-1-methyl-5-oxoimidazolidin-4-yl) acetate. Several d-amino acids, namely, the d-forms of Asn, Ala, Ser, Thr, Glu, Asp, Pro, Arg, Phe, Orn, Lys, and Tyr, were observed in the methanol extract of black garlic, whereas only d-Ala was detected in that of fresh garlic foodstuffs. These data suggest that several d-amino acids can be produced during fermentation for preparing black garlic. Full article
(This article belongs to the Special Issue Application of Liquid Chromatography in Food and Natural Products Extracts Analysis)
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13 pages, 3229 KiB  
Article
Rapid Identification and Analysis of Ochratoxin-A in Food and Agricultural Soil Samples Using a Novel Semi-Automated In-Syringe Based Fast Mycotoxin Extraction (FaMEx) Technique Coupled with UHPLC-MS/MS
by Karthikeyan Prakasham, Swapnil Gurrani, Jen-Taie Shiea, Ming-Tsang Wu, Chia-Fang Wu, Yi-Jia Ku, Tseng-Yu Tsai, Hung-Ta Hua, Yu-Jia Lin, Po-Chin Huang, Gangadhar Andaluri and Vinoth Kumar Ponnusamy
Molecules 2023, 28(3), 1442; https://doi.org/10.3390/molecules28031442 - 2 Feb 2023
Cited by 2 | Viewed by 2728
Abstract
In this work, a fast mycotoxin extraction (FaMEx) technique was developed for the rapid identification and quantification of carcinogenic ochratoxin-A (OTA) in food (coffee and tea) and agricultural soil samples using ultra-high-performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS) detection. The FaMEx technique advancement is [...] Read more.
In this work, a fast mycotoxin extraction (FaMEx) technique was developed for the rapid identification and quantification of carcinogenic ochratoxin-A (OTA) in food (coffee and tea) and agricultural soil samples using ultra-high-performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS) detection. The FaMEx technique advancement is based on two plastic syringes integrated setup for rapid extraction and its subsequent controlled clean-up process. In the extraction process, a 0.25-g sample and extraction solvent were added to the first syringe barrel for the vortex-based extraction. Then, the extraction syringe was connected to a clean-up syringe (pre-packed with C18, activated carbon, and MgSO4) with a syringe filter. Afterward, the whole set-up was placed in an automated programmable mechanical set-up for controlled elution. To enhance FaMEx technology performance, the various influencing sample pretreatment parameters were optimized. Furthermore, the developed FaMEx method indicated excellent linearity (0.9998 and 0.9996 for coffee/tea and soil) with highly sensitive detection (0.30 and 0.29 ng/mL for coffee/tea and soil) and quantification limits (1.0 and 0.96 for coffee/tea and soil), which is lower than the toxicity limit compliant with the European Union regulation for OTA (5 ng/g). The method showed acceptable relative recovery (84.48 to 100.59%) with <7.34% of relative standard deviation for evaluated real samples, and the matrix effects were calculated as <−13.77% for coffee/tea and −9.7 for soil samples. The obtained results revealed that the developed semi-automated FaMEx/UHPLC-MS/MS technique is easy, fast, low-cost, sensitive, and precise for mycotoxin detection in food and environmental samples. Full article
(This article belongs to the Special Issue Application of Liquid Chromatography in Food and Natural Products Extracts Analysis)
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18 pages, 3207 KiB  
Article
Molecular Networking, Network Pharmacology, and Molecular Docking Approaches Employed to Investigate the Changes in Ephedrae Herba before and after Honey-Processing
by Hengyang Li, Long Guo, Xiaoying Ding, Qi An, Lei Wang, Shenghui Hao, Wenjie Li, Tao Wang, Zetong Gao, Yuguang Zheng and Dan Zhang
Molecules 2022, 27(13), 4057; https://doi.org/10.3390/molecules27134057 - 23 Jun 2022
Cited by 8 | Viewed by 2897
Abstract
Raw Ephedrae herba (REH) and honey-processed Ephedrae herba (HEH) were the different decoction pieces of Ephedrae herba (EH). Honey-processing that changes REH into HEH has been shown to relieve cough and asthma to a synergistic extent. However, the chemical markers and the synergistic [...] Read more.
Raw Ephedrae herba (REH) and honey-processed Ephedrae herba (HEH) were the different decoction pieces of Ephedrae herba (EH). Honey-processing that changes REH into HEH has been shown to relieve cough and asthma to a synergistic extent. However, the chemical markers and the synergistic mechanism of HEH need to be further studied. In this study, the ultra-high performance liquid chromatography coupled with hybrid quadrupole time of flight mass spectrometry (UPLC-Q-TOF-MS) and molecular networking (MN) were used to investigate the chemical composition of REH and HEH, which led to the identification of 92 compounds. A total of 38 differential chemical markers for REH and HEH were identified using principal component analysis (PCA) and orthogonal partial least squares discriminant analysis (OPLS-DA). Network pharmacology suggests that the synergistic effect of HEH in relieving cough and asthma may be due to 31 differential chemical markers acting through 111 biological targets. Among them, four compounds and two targets probably played an important role based on the results of molecular docking. This study enriched our knowledge about the chemical composition of REH and HEH, as well as the synergistic mechanism of HEH. Full article
(This article belongs to the Special Issue Application of Liquid Chromatography in Food and Natural Products Extracts Analysis)
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14 pages, 1491 KiB  
Article
Chemical Fingerprint Analysis and Quantitative Analysis of Saccharides in Morindae Officinalis Radix by HPLC-ELSD
by Hongmei Sun, Yini Cai, Jie Shen, Enyao Ma, Zhimin Zhao, Depo Yang, Xiuwei Yang and Xinjun Xu
Molecules 2021, 26(23), 7242; https://doi.org/10.3390/molecules26237242 - 29 Nov 2021
Cited by 6 | Viewed by 2553
Abstract
A method based on high performance liquid chromatography with evaporative light scattering detection (HPLC-ELSD) was developed for the quantitative analysis of three active compounds and chemical fingerprint analyses of saccharides in Morindae officinalis radix. Ten batches of Morindae officinalis radix were collected from [...] Read more.
A method based on high performance liquid chromatography with evaporative light scattering detection (HPLC-ELSD) was developed for the quantitative analysis of three active compounds and chemical fingerprint analyses of saccharides in Morindae officinalis radix. Ten batches of Morindae officinalis radix were collected from different plantations in the Guangdong region of China and used to establish the fingerprint. The samples were separated with a COSMOIL Sugar-D column (4.6 mm × 250 mm, 5 μm) by using gradient elution with water (A) and acetonitrile (B). In addition, Trapped-Ion-Mobility (tims) Time-Of-Flight (tims TOF) was used to identify saccharides of Morindae officinalis radix. Fingerprint chromatogram presented 26 common characteristic peaks in the roots of Morinda officinalis How, and the similarities were more than 0.926. In quantitative analysis, the three compounds showed good regression (r = 0.9995–0.9998) within the test ranges, and the recoveries of the method were in the range of 96.7–101.7%. The contents of sucrose, kestose and nystose in all samples were determined as 1.21–7.92%, 1.02–3.37%, and 2.38–6.55%, respectively. The developed HPLC fingerprint method is reliable and was validated for the quality control and identification of Morindae officinalis radix and can be successfully used to assess the quality of Morindae officinalis radix. Full article
(This article belongs to the Special Issue Application of Liquid Chromatography in Food and Natural Products Extracts Analysis)
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Review

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34 pages, 21979 KiB  
Review
Analysis of Chlorophylls/Chlorophyllins in Food Products Using HPLC and HPLC-MS Methods
by Badal Kumar Mandal and Yong-Chien Ling
Molecules 2023, 28(10), 4012; https://doi.org/10.3390/molecules28104012 - 10 May 2023
Cited by 2 | Viewed by 4490
Abstract
Of the different quality parameters of any food commodity or beverage, color is the most important, attractive and choice-affecting sensory factor to consumers and customers. Nowadays, food industries are interested in making the appearance of their food products attractive and interesting in order [...] Read more.
Of the different quality parameters of any food commodity or beverage, color is the most important, attractive and choice-affecting sensory factor to consumers and customers. Nowadays, food industries are interested in making the appearance of their food products attractive and interesting in order to appeal to consumers/customers. Natural green colorants have been accepted universally due to their natural appeal as well as their nontoxic nature to consumers. In addition, several food safety issues mean that natural green colorants are preferable to synthetic food colorants, which are mostly unsafe to the consumers but are less costly, more stable, and create more attractive color hues in food processing. Natural colorants are prone to degradation into numerous fragments during food processing, and thereafter, in storage. Although different hyphenated techniques (especially high-performance liquid chromatography (HPLC), LC-MS/HRMS, and LC/MS-MS are extensively used to characterize all these degradants and fragments, some of them are not responsive to any of these techniques, and some substituents in the tetrapyrrole skeleton are insensitive to these characterization tools. Such circumstances warrant an alternative tool to characterize them accurately for risk assessment and legislation purposes. This review summarizes the different degradants of chlorophylls and chlorophyllins under different conditions, their separation and identification using various hyphenated techniques, national legislation regarding them, and the challenges involved in their analysis. Finally, this review proposes that a non-targeted analysis method that combines HPLC and HR-MS assisted by powerful software tools and a large database could be an effective tool to analyze all possible chlorophyll and chlorophyllin-based colorants and degradants in food products in the future. Full article
(This article belongs to the Special Issue Application of Liquid Chromatography in Food and Natural Products Extracts Analysis)
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