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Chromatographic Science of Natural Products III

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

Deadline for manuscript submissions: closed (31 December 2022) | Viewed by 17221

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Prof. Dr. Monika Waksmundzka-Hajnos

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Department of Inorganic Chemistry, Medical University of Lublin, Lublin, Poland
Interests: liquid chromatography; phytochemistry; drug analysis
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Dr. Miroslaw Hawryl

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Department of Inorganic Chemistry, Medical University of Lublin, Lublin, Poland
Interests: liquid chromatography; TLC; phytochemistry; chemometry
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Dear Colleagues,

Natural products are most often botanicals, e.g., substances obtained from plants, algae, fungi and lichens, including fresh and dried botanic entities and parts or components thereof isolated through extraction with water or various organic solvents, as well as oils, essential oils and oleoresins obtained through different isolation techniques. Botanicals are typically used in dietary, medicinal or cosmetic products available for purchase in pharmacies, supermarkets, specialist shops and online via the internet. Prior to being included in dietary, cosmetic and especially medicinal preparations, botanicals need authentication, followed by a thorough quality control for safety reasons. General information addressing the general public regarding what quality demands are expected of botanicals is provided in documentation issued by the Department of Health and Human Services in various countries, including pharmacopoeias. In 2011, the World Health Organization (WHO) published guidelines on a wide spectrum of quality control methods for herbal materials, all accompanied by a growing sophistication of analytical tools employed in the respective quality control methods. There is no doubt that an important role in these methodologies is played by gas chromatography (GC), high-performance liquid chromatography (HPLC) and ultra-performance liquid chromatography (UPLC), all equipped with versatile detection systems. There is, however, a cozy but broad enough space left for instrumental thin-layer chromatography in its standard (TLC) and high-performance (HPTLC) modes.

Fingerprinting through chromatographic profiling is a very effective and convenient method for the quality assessment of herbs. By definition, a chromatographic fingerprint is a chromatographic profile or image that represents the chemical characteristics of herbal material. A herbal sample fingerprint can also be defined as a set of characteristic chromatographic or spectroscopic signals, whose comparison leads to a sample recognition. All separation techniques can be applied to construct fingerprints. HPLC is the fingerprinting method of choice due to its specificity, good separability and having the possibility to derive a lot of chemical information. However, HPTLC offers a number of unique features that can outperform the other separation techniques used for fingerprinting. Identification is one of the leading targets of HPTLC, including the possibility of the detection of pharmacologically active compounds, such as antioxidants, inhibitors of selected enzymes and antibiotics. TLC it is the only chromatographic method that allows the presentation of results in the form of an image, also being the only chromatographic technique allowing the parallel separation of samples.

However, one problem associated with classic fingerprinting through the use of various chromatographic methods is the difficulty in indicating with 100% certainty which signals (peaks, bands, etc.) should be present in the obtained chromatographic image or profile (chromatogram) to confirm a sample’s identity, with some methods existing to solve this problem. The first method relies on a comparison of the analyzed sample with a defined botanical reference material (BRM) or a set of standard compounds; the other is a concept of multiple fingerprint construction and multidimensional fingerprinting, having gained much attention as a large amount of chromatographic and/or spectroscopic signals enable more comprehensive data analyses. Other than chemical detection, one method of performing multidimensional fingerprinting is also the use of biological detection. The chemometric approach of chromatograms or profiles, although more difficult, is based only on objective mathematical methods. Fingerprinting is also a method of choice in chemotaxonomy.

This Special Issue of Molecules aims to publish papers providing new and interesting information regarding the application of chromatographic methods in the area of plant chemistry and the construction of plant fingerprints. Due to the wide interest of the first Molecules Special Issue, “Chromatographic Science of Natural Products I” and “Chromatographic Science of Natural Products II”, we have decided to continue the consideration of this subject. We look forward to gathering and presenting further advances in this Special Issue entitled “Chromatographic Science of Natural Products III”.

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

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Keywords

TLC bioautography
HPLC, TLC and GC in phytochemistry, phytopharmaceuticals and food analysis
fingerprinting and chemometrics
examination of biological activity of plant components and food
chromatography in chemotaxonomy
isolation and identification of natural compounds

Related Special Issue

Chromatographic Science of Natural Products IV in Molecules

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10 pages, 473 KiB

Open AccessArticle

Flavonoid Composition and Antibacterial Properties of Crocus sativus L. Petal Extracts

by Nadia Naim, Aziz Bouymajane, Yassine Oulad El Majdoub, Said Ezrari, Rachid Lahlali, Abdessalem Tahiri, Said Ennahli, Roberto Laganà Vinci, Francesco Cacciola, Luigi Mondello and Ilham Madani

Molecules 2023, 28(1), 186; https://doi.org/10.3390/molecules28010186 - 26 Dec 2022

Cited by 9 | Viewed by 2376

Abstract

Saffron petals, which are the main by-products of Crocus sativus L. (Iridaceae family), are produced in large quantities and are known for their many beneficial properties. In this regard, this study aims to investigate the phenolic composition and antibacterial properties of hydroethanolic extracts from Crocus sativus L. petals collected from Serghina (province of Boulmane) in Morocco. The phenolic profiles were characterized using high-performance liquid chromatography coupled to a photodiode array and electrospray ionization mass spectrometry (HPLC-PDA-ESI/MS). The antibacterial potential was evaluated against four bacterial strains potentially causing food-borne disease (Staphylococcus aureus, Salmonella typhimurium, Escherichia coli, and Listeria monocytogenes) using disc diffusion and broth micro-dilution assays. Results showed that a total of 27 phenolic compounds was detected in the Crocus sativus L. petal extracts, which were assigned to flavonoids (kaempferol, quercetin, isorhamnetin, and myricetin derivatives). The most abundant compound was represented by kaempferol-sophoroside isomer (20.82 mg/g ± 0.152), followed by kaempferol-sophoroside-hexoside (2.63 mg/g ± 0.001). The hydroethanolic extracts of Crocus sativus L. petals demonstrated bactericidal effects against Staphylococcus aureus and Listeria monocetogenes and bacteriostatic effects against Escherichia coli and Salmonella typhimurium. Therefore, the by-product Crocus sativus L. petal extracts might be considered as valuable sources of natural antibacterial agents with potential applications in the food and pharmaceutical industries. Full article

(This article belongs to the Special Issue Chromatographic Science of Natural Products III)

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21 pages, 2976 KiB

Open AccessArticle

SPME-GC-MS and PTR-ToF-MS Techniques for the Profiling of the Metabolomic Pattern of VOCs and GC-MS for the Determination of the Cannabinoid Content of Three Cultivars of Cannabis sativa L. Pollen

by Cosimo Taiti, Elisa Masi, Vittoria Cicaloni, Vittorio Vinciguerra, Laura Salvini and Stefania Garzoli

Molecules 2022, 27(24), 8739; https://doi.org/10.3390/molecules27248739 - 09 Dec 2022

Cited by 4 | Viewed by 1222

Abstract

Considering the large number of volatile molecules that characterize Cannabis sativa L., adequate investigation supported by the application of robust and effective analytical methods is essential to better understand the impact of these low- and medium-molecular-weight molecules on the entire phytocomplex. This work aimed to characterize the volatile fraction of the chemical profile of three different cultivars of Cannabis sativa L. pollen, grown in Italy, which were thoroughly investigated by the application of two complementary techniques: SPME-GC-MS and PTR-ToF-MS. Furthermore, in order to provide more information on the chemical profile of the matrices under study, the cannabinoid content of the hexane extracts was also measured by GC-MS. Until now, no similar study, in terms of survey techniques applied, has been performed on C. sativa pollen. The obtained results showed a high content of volatile molecules, which differentiated the three matrices. The data relating to the content of cannabinoids were also interesting as they showed that one of the three cultivars was richer than the others. Finally, an in-depth statistical survey was performed to better compare the investigated samples and identify the molecules that most contribute to differentiating them. The findings of this study may be useful for integrating the compositional information on C. sativa L. Full article

(This article belongs to the Special Issue Chromatographic Science of Natural Products III)

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11 pages, 2867 KiB

Open AccessArticle

Qualitative and Quantitative Evaluation of Rosavin, Salidroside, and p-Tyrosol in Artic Root Products via TLC-Screening, HPLC-DAD, and NMR Spectroscopy

by Hanna Nikolaichuk, Marek Studziński, Marek Stankevič and Irena M. Choma

Molecules 2022, 27(23), 8299; https://doi.org/10.3390/molecules27238299 - 28 Nov 2022

Cited by 3 | Viewed by 1406

Abstract

Artic root is a well-known plant adaptogen with multipotential pharmacological properties. Thin-layer chromatography (TLC)—screening followed by diode-array high-performance liquid chromatography and nuclear magnetic resonance spectroscopy proved to be a reliable and convenient method for the simultaneous determination of the quality of various herbal raw materials and supplements. This combination allowed for comparing and differentiating arctic root samples as well as defining their authenticity. The study provided information on the chemical and biological properties of the seven chosen samples as well as qualitative and quantitative evaluation of the quality markers: rosavin, salidroside, and p-tyrosol. The absence of rosavin, salidroside, and p-tyrosol in three samples was detected using TLC screening and confirmed by HPLC-DAD and NMR. The paper highlighted the importance of quality control and strict regulation for herbal medicine supplements and preparations. Full article

(This article belongs to the Special Issue Chromatographic Science of Natural Products III)

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20 pages, 883 KiB

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New Insight on Phenolic Composition and Evaluation of the Vitamin C and Nutritional Value of Smoothies Sold on the Spanish Market

by María del Carmen Razola-Díaz, Eduardo Jesús Guerra-Hernández, Belén García-Villanova and Vito Verardo

Molecules 2022, 27(23), 8229; https://doi.org/10.3390/molecules27238229 - 25 Nov 2022

Cited by 2 | Viewed by 1507

Abstract

Fruits and vegetables are a source of a wide range of nutrients, including bioactive compounds. These compounds have great biological activity and have been linked to the prevention of chronic non-communicable diseases. Currently, the food industry is developing new products to introduce these compounds, whereby smoothies are becoming more popular among consumers. The aim of this study was to evaluate the nutritional quality and the polyphenol and vitamin C content of smoothies available on the Spanish market. An evaluation of the nutritional information and ingredients was carried out. The phenolic compounds were determined by HPLC-ESI-TOF-MS; the vitamin C content was quantified using HPLC-UV/VIS; and the antioxidant activity was analyzed by DPPH and FRAP. Among all of the ingredients of the smoothies, coconut and banana have shown a negative impact on the polyphenol content of the smoothies. In contrast, ingredients such as orange, mango, and passion fruit had a positive correlation with the vitamin C content. Moreover, apple and red fruits showed the highest positive correlations with most of the phenolic acids, flavonoids, total phenolic compounds, and antioxidant activities. In addition, a clustering analysis was performed, and four groups were clearly defined according to the bioactive composition determined here. This research is a precious step for the formulation of new smoothies and to increase their polyphenol quality. Full article

(This article belongs to the Special Issue Chromatographic Science of Natural Products III)

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10 pages, 1551 KiB

Open AccessArticle

A GC-MS Protocol for the Identification of Polycyclic Aromatic Alkaloids from Annonaceae

by Ilya A. P. Jourjine, Carolin Bauernschmidt, Christoph Müller and Franz Bracher

Molecules 2022, 27(23), 8217; https://doi.org/10.3390/molecules27238217 - 25 Nov 2022

Cited by 3 | Viewed by 1250

Abstract

The Annonaceae are an old family of flowering plants belonging to the order Magnoliales, distributed mainly in tropical regions. Numerous Annonaceae species find ethnobotanical use for curing a broad range of diseases, among them cancer and infections by diverse pathogens. Hence, bioactive natural products from Annonaceae have received considerable interest in drug development. Beyond cytotoxic acetogenins, unique aporphine-derived polycyclic aromatic alkaloids are characteristic constituents of Annonaceae. Among them are unique tri- and tetracyclic aromatic alkaloids like azafluorenones, diazafluoranthenes, azaanthracenes, and azaoxoaporphines. The complex substitution pattern of these alkaloids represents a major challenge in structure elucidation of isolated natural products. Based on a broad spectrum of alkaloids available from our previous work, we present a GC-MS protocol for the identification of over 20 polycyclic aromatic alkaloids from Annonaceae. This collection of data will contribute to the future identification of the metabolite patterns of extracts from Annonaceae as an important source of novel bioactive secondary metabolites. Full article

(This article belongs to the Special Issue Chromatographic Science of Natural Products III)

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17 pages, 2208 KiB

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Volatile Organic Compound Profiles of Cystoseira corniculata (Turner) Zanardini 1841 and Ericaria amentacea (C.Agardh) Molinari and Guiry 2020 (ex. Cystoseira amentacea (C.Agardh) Bory de Saint-Vincent, 1832)

by Sanja Radman and Igor Jerković

Molecules 2022, 27(20), 7131; https://doi.org/10.3390/molecules27207131 - 21 Oct 2022

Cited by 3 | Viewed by 1091

Abstract

The volatile organic compounds (VOCs) of fresh (FrCC) and air-dried (DrCC) Cystoseria corniculata and fresh (FrEA) and air-dried (DrEA) Ericaria amentacea from the Adriatic Sea were investigated by headspace solid-phase microextraction (HS-SPME) and hydrodistillation (HD) and analysed by gas chromatography and mass spectrometry (GC-MS). In HS-FrCC and HS-DrCC, aliphatic compounds were dominant, with decan-5-ol as the most abundant in HS-FrCC, but in HS-DrCC pentadecane dominated. Monoterpenes (β-cyclocitral, β-citral, and β-cyclohomocitral) and sesquiterpenes (cubenol) were abundant in HS-FrCC. Notable differences between fresh and air-dried samples were found for benzene derivatives. Fatty acids and their derivatives were the most abundant in HD-FrCC and HD-DrCC. In HS-FrEA and HS-DrEA, saturated aliphatic compounds as well as unsaturated aliphatic compounds (particularly hexan-1-ol and (Z)-hex-3-en-1-ol) predominantly showed decrements after drying. Pentadecane, heptadecane, pentadecanal, and hexan-1-ol were predominant in HD-FrEA, and their percentage decreased in HD-DrEA. The percentage of monoterpenes decreased after drying, but the percentages of diterpenes and especially sesquiterpenes increased. δ-Selinene was the major terpene and the most abundant in HD-DrEA. A significant increment after drying could be noticed for fatty acids and their derivatives. The great diversity of identified VOCs among these two macroalgae supports their different botanical classifications. Full article

(This article belongs to the Special Issue Chromatographic Science of Natural Products III)

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20 pages, 3285 KiB

Open AccessArticle

Chemotaxonomic Markers for the Leaf Buds of Common Finnish Trees and Shrubs: A Rapid UHPLC MS Fingerprinting Tool for Species Identification

by Marianna Manninen, Maarit Karonen and Juha-Pekka Salminen

Molecules 2022, 27(20), 6810; https://doi.org/10.3390/molecules27206810 - 11 Oct 2022

Cited by 2 | Viewed by 1493

Abstract

In this study, a chemotaxonomic tool was created on the basis of ultra-high-performance liquid chromatography–mass spectrometry (UHPLC–MS) for the identification of 13 common Finnish deciduous trees and shrubs from their leaf bud metabolites. The bud extracts were screened with UHPLC–ESI–QqQ–MS and UHPLC–ESI–Q–Orbitrap–MS to discover suitable markers for each species. Two approaches were tested in the marker selection: (1) unique species-specific markers to obtain selective fingerprints per species and (2) major markers to maximise the sensitivity of the fingerprints. The markers were used to create two selected ion-recording-based fingerprinting tools with UHPLC–ESI–QqQ–MS. The methods were evaluated for their selectivity, repeatability, and robustness in plant species identification by analysing leaf buds from several replicates of each species. The created chemotaxonomic tools were shown to provide unique chromatographic profiles for the studied species in less than 6 min. A variety of plant metabolites, such as flavonoids, triterpenoids, and hydroxycinnamic acid derivatives, were found to serve as good chemotaxonomic markers for the studied species. In 10 out of 13 cases, species-specific markers were superior in creating selective and repeatable fingerprints. Full article

(This article belongs to the Special Issue Chromatographic Science of Natural Products III)

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19 pages, 4638 KiB

Open AccessArticle

Integrating Enhanced Profiling and Chemometrics to Unveil the Potential Markers for Differentiating among the Leaves of Panax ginseng, P. quinquefolius, and P. notoginseng by Ultra-High Performance Liquid Chromatography/Ion Mobility-Quadrupole Time-of-Flight Mass Spectrometry

by Feifei Yang, Boxue Chen, Meiting Jiang, Huimin Wang, Ying Hu, Hongda Wang, Xiaoyan Xu, Xiumei Gao and Wenzhi Yang

Molecules 2022, 27(17), 5549; https://doi.org/10.3390/molecules27175549 - 29 Aug 2022

Cited by 14 | Viewed by 1774

Abstract

The leaves of Panax species (e.g., Panax ginseng-PGL, P. quinquefolius-PQL, and P. notoginseng-PNL) can serve as a source for healthcare products. Comprehensive characterization and unveiling of the metabolomic difference among PGL, PQL, and PNL are critical to ensure their correct use. For this purpose, enhanced profiling and chemometrics were integrated to probe into the ginsenoside markers for PGL/PQL/PNL by ultra-high performance liquid chromatography/ion mobility-quadrupole time-of-flight mass spectrometry (UHPLC/IM-QTOF-MS). A hybrid scan approach (HDMS^E-HDDDA) was established achieving the dimension-enhanced metabolic profiling, with 342 saponins identified or tentatively characterized from PGL/PQL/PNL. Multivariate statistical analysis (33 batches of leaf samples) could unveil 42 marker saponins, and the characteristic ginsenosides diagnostic for differentiating among PGL/PQL/PNL were primarily established. Compared with the single DDA or DIA, the HDMS^E-HDDDA hybrid scan approach could balance between the metabolome coverage and spectral reliability, leading to high-definition MS spectra and the additional collision-cross section (CCS) useful to differentiate isomers. Full article

(This article belongs to the Special Issue Chromatographic Science of Natural Products III)

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19 pages, 2197 KiB

Open AccessArticle

Antimicrobial, Antigenotoxicity, and Characterization of Calotropis procera and Its Rhizosphere-Inhabiting Actinobacteria: In Vitro and In Vivo Studies

by Amna A. Saddiq, Hend M. Tag, Nada M. Doleib, Asmaa S. Salman and Nashwa Hagagy

Molecules 2022, 27(10), 3123; https://doi.org/10.3390/molecules27103123 - 13 May 2022

Cited by 7 | Viewed by 2089

Abstract

Calotropis procera (C. procera) is a wild shrub that is a medicinal plant found in abundance throughout Saudi Arabia. In this study, we investigated the phytochemical composition and antigenotoxic properties of the ethanolic extract of C. procera, in addition to the antimicrobial activity of the plant and its rhizospheric actinobacteria effects against pathogenic microorganisms. Soil-extract medium supplemented with glycerol as a carbon source and starch–casein agar medium was used for isolation of actinobacteria from rhizosphere. From the plant, a total of 31 compounds were identified using gas chromatography/mass spectrometry (GC–MS). The main components were α-amyrin (39.36%), lupeol acetate (17.94%), phytol (13.32%), hexadecanoic acid (5.55%), stigmasterol (3.16%), linolenic acid (3.04%), and gombasterol A (2.14%). C. procera plant extract’s antimicrobial activity was investigated using an agar well-diffusion assay and minimum inhibitory concentration (MIC) against six pathogenic microbial strains. The plant extract of C. procera was considered significantly active against Staphylococcus aureus, Klebsiella pneumonia, and Escherichia coli, with inhibition zones of 18.66 mm, 21.26 mm, and 21.93 mm, respectively. The plant extract was considered to be a moderate inhibitor against Bacillus subtilis, with MIC ranging from 0.60–1.50 mg/mL. On the other hand, the isolated actinobacteria were considered to be a moderate inhibitor against S. aureus (MIC of 86 µg/mL), and a potent inhibitor, strain CALT_2, against Candida albicans (MIC of 35 µg/mL). The 16S rRNA gene sequence analysis showed that the potential strains belonged to the genus Streptomyces. The effect of C. procera extract against cyclophosphamide (CP)-induced genotoxicity was examined by evaluating chromosome abnormalities in mouse somatic cells and DNA fragmentation assays. The current study revealed that oral pretreatment of C. procera (50, 100, and 200 mg/kg b.w.) for 1, 7, and 14 days to cyclophosphamide-treated animals significantly reduced chromosomal abnormalities as well as DNA fragmentation in a dose-dependent manner. Moreover, C. procera extract had antimicrobial and antigenotoxic effects against CP-induced genotoxicity. Full article

(This article belongs to the Special Issue Chromatographic Science of Natural Products III)

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Review

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46 pages, 2648 KiB

Open AccessReview

Marigold Metabolites: Diversity and Separation Methods of Calendula Genus Phytochemicals from 1891 to 2022

by Daniil N. Olennikov and Nina I. Kashchenko

Molecules 2022, 27(23), 8626; https://doi.org/10.3390/molecules27238626 - 06 Dec 2022

Cited by 5 | Viewed by 2134

Abstract

Marigold (Calendula), an important asteraceous genus, has a history of many centuries of therapeutic use in traditional and officinal medicines all over the world. The scientific study of Calendula metabolites was initiated at the end of the 18th century and has been successfully performed for more than a century. The result is an investigation of five species (i.e., C. officinalis, C. arvensis, C. suffruticosa, C. stellata, and C. tripterocarpa) and the discovery of 656 metabolites (i.e., mono-, sesqui-, di-, and triterpenes, phenols, coumarins, hydroxycinnamates, flavonoids, fatty acids, carbohydrates, etc.), which are discussed in this review. The identified compounds were analyzed by various separation techniques as gas chromatography and liquid chromatography which are summarized here. Thus, the genus Calendula is still a high-demand plant-based medicine and a valuable bioactive agent, and research on it will continue for a long time. Full article

(This article belongs to the Special Issue Chromatographic Science of Natural Products III)

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