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Isolation and Structure Determination of Bioactive Natural Products

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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 2021) | Viewed by 38223

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Dr. Magdalena Ligor

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Department of Environmental Chemistry and Ecoanalytics, Faculty of Chemistry, Nicolaus Copernicus University, Gagarin 7, PL-87 100 Torun, Poland
Interests: chromatographic techniques (GC/MS, LC/MS, TLC-MS); sample preparation methods (SPME, SPE, LLE); analysis of plant materials; food and water; determination of VOCs; biomedical chemistry; trace analysis
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Prof. Dr. Aleksandra Szydłowska-Czerniak

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Faculty of Chemistry, Nicolaus Copernitus University in Toruń, Toruń, Poland
Interests: antioxidant capacity; new synthetic antioxidants; oilseeds; vegetable oils; emulsions; confectionery; biodegradable smart packaging; new analytical methods; spectroscopic techniques; chemometric tools
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Dear Colleagues,

Due to the presence of biologically active compounds, a lot of extracts obtained from natural products have various antioxidant, anti-inﬂammatory, antifungal, as well as other properties. These components are widely spread in herbs, fruits, and natural products. Their isolation, separation, and analysis are of great interest in several fields, such as the pharmaceutical and food industries, biochemistry, medical cell biology, nutrition, and biotechnology research. In recent years, the most frequently used approaches, including selective isolation, preconcentration, and separation of primary and secondary plant metabolites, especially sugars (including cyclitols), polyphenols, terpenes, carotenoids, nitrogen-containing alkaloids and saponins present in a range of complex matrices, have been subject to discussion. Various conventional and non-conventional sample preparation methods have been used for the extraction of the abovementioned compounds. Moreover, chromatographic techniques, which are characterized by high sensitivity, selectivity, and versatility, are widely applied for the determination of these compounds.

This Special Issue is dedicated to featuring the latest research that is ongoing in the field of bioactive natural products. It is expected that most submissions will focus on the methodology of isolation and determination of biologically active compounds, but structural analysis will also be considered. Original research (communications, full papers, and reviews) that discusses innovative methodologies for the research of bioactive natural products with potential application in various industries fields is therefore welcome.

Assoc. Prof. Dr. Magdalena Ligor
Prof. Aleksandra Szydłowska-Czerniak
Guest Editor

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Keywords

primary and secondary plant metabolites
sample preparation methods
hyphenated analytical methods
natural product research
measuring biological activity
structure–activity relationships

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Isolation and Structure Determination of Bioactive Natural Products (2nd Edition) in Molecules (4 articles)

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Research

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14 pages, 1654 KiB

Open AccessArticle

Imperatorin Influences Depressive-like Behaviors: A Preclinical Study on Behavioral and Neurochemical Sex Differences

by Joanna Kowalczyk, Modestos Nakos-Bimpos, Alexia Polissidis, Christina Dalla, Nikolaos Kokras, Krystyna Skalicka-Woźniak and Barbara Budzyńska

Molecules 2022, 27(4), 1179; https://doi.org/10.3390/molecules27041179 - 10 Feb 2022

Cited by 5 | Viewed by 2161

Abstract

Imperatorin, a naturally derived furanocoumarin, exerts promising neuropharmacological properties. Therefore, it might be applicable in the treatment of brain diseases such as depression. In the present project, we aimed to investigate the sex-dependent effects of imperatorin (1, 5, and 10 mg/kg) on behavior and neurochemistry associated with antidepressant effects. The depressive-like behaviors of male and female Swiss mice were investigated in a forced swim test (FST). Subsequently, High-Performance Liquid Chromatography (HPLC) was used to evaluate the level of serotonin, its metabolite, 5-HIAA, and noradrenaline, in mouse brains. The study revealed that only males responded to imperatorin (1 and 5 mg/kg) treatment and caused an antidepressant effect, such as with respect to depressive-like behaviors, lowering immobility time and increasing immobility latency. The HPLC analysis demonstrated that serotonin levels in the prefrontal cortex of females decreased with the middle dose of imperatorin (5 mg/kg), while in the male prefrontal cortex, the lower dose (1 mg/kg) boosted serotonin levels. There were no evident changes observed with respect to noradrenaline and serotonin metabolite levels in the male hippocampus. To conclude, we propose that imperatorin has antidepressant potential, seemingly only in males, influencing brain serotonin level, but the direct mechanism of action requires further investigation. Full article

(This article belongs to the Special Issue Isolation and Structure Determination of Bioactive Natural Products)

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14 pages, 3636 KiB

Open AccessArticle

Separation and Quantification of Selected Sapogenins Extracted from Nettle, White Dead-Nettle, Common Soapwort and Washnut

by Magdalena Ligor, Anna Kiełbasa, Ileana-Andreea Ratiu and Bogusław Buszewski

Molecules 2021, 26(24), 7705; https://doi.org/10.3390/molecules26247705 - 20 Dec 2021

Cited by 4 | Viewed by 3280

Abstract

Saponins are an important group of secondary metabolites naturally occurring in plants with important properties like: antibacterial, antiviral and antifungal. Moreover, they are widely used in the cosmetic industry and household chemistry. The sapogenins are saponin hydrolyses products, frequently used to facilitate saponin detection. In the present study, an improved methodology for isolation and separation of five sapogenins extracted from nettle (Urtica dioica L.), white dead-nettle (Lamium album L.), common soapwort (Saponaria officinalis L.) and washnut (Sapindus mukorossi Gaertn.) was developed using ultra-high-performance liquid chromatography with an evaporative light-scattering detector (UHPLC-ELSD). Based on quantitative analysis, the highest content of hederagenin (999.1 ± 6.3 µg/g) and oleanolic acid (386.5 ± 27.7 µg/g) was found in washnut extracts. Good recoveries (71% ± 6 up to 99% ± 8) were achieved for four investigated targets, while just 22.2% ± 0.5 was obtained for the fifth one. Moreover, hederagenin and oleanolic acid of whose highest amount was detected in washnut (999.1 ± 6.3 µg/g and 386.5 ± 27.7 µg/g, respectively) were subject to another approach. Consequently, liquid chromatography coupled mass spectrometry (LC/MS) with multiple reaction monitoring mode (MRM) was used as an additional technique for fast and simultaneous identification of the mentioned targets. Full article

(This article belongs to the Special Issue Isolation and Structure Determination of Bioactive Natural Products)

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23 pages, 30579 KiB

Open AccessArticle

AaTs-1: A Tetrapeptide from Androctonus australis Scorpion Venom, Inhibiting U87 Glioblastoma Cells Proliferation by p53 and FPRL-1 Up-Regulations

by Dorra Aissaoui-Zid, Mohamed-Chiheb Saada, Wassim Moslah, Marie Potier-Cartereau, Aude Lemettre, Houcemeddine Othman, Marc Gaysinski, Zaineb Abdelkafi-Koubaa, Soumaya Souid, Naziha Marrakchi, Christophe Vandier, Khadija Essafi-Benkhadir and Najet Srairi-Abid

Molecules 2021, 26(24), 7610; https://doi.org/10.3390/molecules26247610 - 15 Dec 2021

Cited by 11 | Viewed by 3069

Abstract

Glioblastoma is an aggressive cancer, against which medical professionals are still quite helpless, due to its resistance to current treatments. Scorpion toxins have been proposed as a promising alternative for the development of effective targeted glioblastoma therapy and diagnostic. However, the exploitation of the long peptides could present disadvantages. In this work, we identified and synthetized AaTs-1, the first tetrapeptide from Androctonus australis scorpion venom (Aa), which exhibited an antiproliferative effect specifically against human glioblastoma cells. Both the native and synthetic AaTs-1 were endowed with the same inhibiting effect on the proliferation of U87 cells with an IC₅₀ of 0.56 mM. Interestingly, AaTs-1 was about two times more active than the anti-glioblastoma conventional chemotherapeutic drug, temozolomide (TMZ), and enhanced its efficacy on U87 cells. AaTs-1 showed a significant similarity with the synthetic peptide WKYMVm, an agonist of a G-coupled formyl-peptide receptor, FPRL-1, known to be involved in the proliferation of glioma cells. Interestingly, the tetrapeptide triggered the dephosphorylation of ERK, p38, and JNK kinases. It also enhanced the expression of p53 and FPRL-1, likely leading to the inhibition of the store operated calcium entry. Overall, our work uncovered AaTs-1 as a first natural potential FPRL-1 antagonist, which could be proposed as a promising target to develop new generation of innovative molecules used alone or in combination with TMZ to improve glioblastoma treatment response. Its chemical synthesis in non-limiting quantity represents a valuable advantage to design and develop low-cost active analogues to treat glioblastoma cancer. Full article

(This article belongs to the Special Issue Isolation and Structure Determination of Bioactive Natural Products)

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10 pages, 14721 KiB

Open AccessArticle

Antimicrobial, Antioxidant and Antiproliferative Secondary Metabolites from Inonotus nidus-pici

by Zsófia Garádi, Miklós Dékány, Ágnes M. Móricz, Anikó Gaál, Viktor Papp, Szabolcs Béni and Attila Ványolós

Molecules 2021, 26(18), 5453; https://doi.org/10.3390/molecules26185453 - 7 Sep 2021

Cited by 7 | Viewed by 3734

Abstract

Inonotus nidus-pici is a sterile conk which produces macrofungus, a neglected Central-Eastern European relative of the prized Inonotus obliquus, also known as chaga. Investigation of the methanol extract of the poroid fungus I. nidus-pici resulted in the isolation of citropremide (1), 3,4-dihydroxybenzalacetone (2) , lanosterol (3), ergost-6,8,22-trien-3β-ol (4), and ergosterol peroxide (5). The structures of fungal compounds were determined on the basis of one- and two-dimensional NMR and MS spectroscopic analysis. Compounds 1–2 and 4–5 were evaluated for their antioxidant and antimicrobial properties against several bacterial and fungal strains. 3,4-dihydroxybenzalacetone (2) and ergost-6,8,22-trien-3β-ol (4) demonstrated moderate antimicrobial activity, while the former possessed notable antioxidant activity in DPPH assay. The antiproliferative examinations performed on three human cancer (MES-SA, MES-SA/Dx5, A431) cell lines demonstrated that compounds 4 and 5 have notable cytotoxic activity with IC values in micromolar range. The current study represents the first report on the chemical profile of I. nidus-pici, providing a comprehensive study on the isolation and structure determination of bioactive secondary metabolites of this macrofungus. Full article

(This article belongs to the Special Issue Isolation and Structure Determination of Bioactive Natural Products)

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14 pages, 1972 KiB

Open AccessArticle

Two Novel Lyso-Ornithine Lipids Isolated from an Arctic Marine Lacinutrix sp. Bacterium

by Venke Kristoffersen, Marte Jenssen, Heba Raid Jawad, Johan Isaksson, Espen H. Hansen, Teppo Rämä, Kine Ø. Hansen and Jeanette Hammer Andersen

Molecules 2021, 26(17), 5295; https://doi.org/10.3390/molecules26175295 - 31 Aug 2021

Cited by 8 | Viewed by 3695

Abstract

The Lacinutrix genus was discovered in 2005 and includes 12 Gram-negative bacterial species. To the best of our knowledge, the secondary metabolite production potential of this genus has not been explored before, and examination of Lacinutrix species may reveal novel chemistry. As part of a screening project of Arctic marine bacteria, the Lacinutrix sp. strain M09B143 was cultivated, extracted, fractionated and tested for antibacterial and cytotoxic activities. One fraction had antibacterial activity and was subjected to mass spectrometry analysis, which revealed two compounds with elemental composition that did not match any known compounds in databases. This resulted in the identification and isolation of two novel isobranched lyso-ornithine lipids, whose structures were elucidated by mass spectrometry and NMR spectroscopy. Lyso-ornithine lipids consist of a 3-hydroxy fatty acid linked to the alpha amino group of an ornithine amino acid through an amide bond. The fatty acid chains were determined to be iso-C15:0 (1) and iso-C16:0 (2). Compound 1 was active against the Gram-positive S. agalactiae, while 2 showed cytotoxic activity against A2058 human melanoma cells. Full article

(This article belongs to the Special Issue Isolation and Structure Determination of Bioactive Natural Products)

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17 pages, 3727 KiB

Open AccessArticle

Separation and Determination of Chemopreventive Phytochemicals of Flavonoids from Brassicaceae Plants

by Sylwia Bajkacz, Magdalena Ligor, Irena Baranowska and Bogusław Buszewski

Molecules 2021, 26(16), 4734; https://doi.org/10.3390/molecules26164734 - 5 Aug 2021

Cited by 14 | Viewed by 2880

Abstract

The main aim of this study was to develop a method for the isolation and determination of polyphenols—in particular, flavonoids present in various morphological parts of plants belonging to the cabbage family (Brassicaceae). Therefore, a procedure consisting of maceration, acid hydrolysis and measurement of the total antioxidant capacity of plant extracts (using DPPH assay) was conducted. Qualitative analysis was performed employing thin-layer chromatography (TLC), which was presented to be a suitable methodology for the separation and determination of chemopreventive phytochemicals from plants belonging to the cabbage family. The study involved the analysis of 25 vegetal samples, including radish, broccoli, Brussels sprouts, kale, canola, kohlrabi, cabbage, Chinese cabbage, red cabbage, pak choi and cauliflower. In addition, selected flavonoids content in free form and bonded to glycosides was determined by using an RP-UHPLC-ESI-MS/MS method. Full article

(This article belongs to the Special Issue Isolation and Structure Determination of Bioactive Natural Products)

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10 pages, 1941 KiB

Open AccessArticle

New Constituents from the Leaves of Date Palm (Phoenix dactylifera L.) of Saudi Origin

by Rami K. Suleiman, Wissam Iali, Bassam El Ali and Saviour A. Umoren

Molecules 2021, 26(14), 4192; https://doi.org/10.3390/molecules26144192 - 10 Jul 2021

Cited by 14 | Viewed by 3265

Abstract

The phytochemical analysis of the butanolic extract from the leaves of date palm of Saudi origin resulted in the isolation of three major constituents, oleanolic acid (1), vanillyl alcohol (2), and β-sitosterol-3-O-β-d-glucoside (3), which had not been isolated from this plant or previously reported. Together, compounds 1 and 2 account for 1.0% of the butanol extract, which represents 0.4% of the mass of the dried leaves. The isolation of other known compounds for this plant such as fatty acids, lutein, and sucrose was also achieved in this study. The characterization and identification of the isolated compounds were conducted on the basis of Fourier-transform infrared spectroscopy (FTIR), ¹H and ¹³C nuclear magnetic resonance (NMR), liquid chromatography–mass spectrometry (LC–MS), and gas chromatography–mass spectrometry (GC–MS) analyses. The findings of the current study will definitely increase the knowledge about the contribution of the constituents of this plant to its well-known nutrition, corrosion inhibition, and antimicrobial properties. Full article

(This article belongs to the Special Issue Isolation and Structure Determination of Bioactive Natural Products)

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11 pages, 1930 KiB

Open AccessArticle

Prenylated Flavonoid Glycosides with PCSK9 mRNA Expression Inhibitory Activity from the Aerial Parts of Epimedium koreanum

by Eeray Kim, Young-Mi Kim, Jongmin Ahn, Hee-Sung Chae, Young-Won Chin and Jinwoong Kim

Molecules 2021, 26(12), 3590; https://doi.org/10.3390/molecules26123590 - 11 Jun 2021

Cited by 8 | Viewed by 2818

Abstract

Phytochemical investigation on the n-BuOH-soluble fraction of the aerial parts of Epimedium koreanum using the PCSK9 mRNA monitoring assay led to the identification of four previously undescribed acylated flavonoid glycosides and 18 known compounds. The structures of new compounds were elucidated by NMR, MS, and other chemical methods. All isolated compounds were tested for their inhibitory activity against PCSK9 mRNA expression in HepG2 cells. Of the isolates, compounds 6, 7, 10, 15, and 17–22 were found to significantly inhibit PCSK9 mRNA expression. In particular, compound 7 was shown to increase LDLR mRNA expression. Thus, compound 7 may potentially increase LDL uptake and lower cholesterol levels in the blood. Full article

(This article belongs to the Special Issue Isolation and Structure Determination of Bioactive Natural Products)

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10 pages, 1026 KiB

Open AccessArticle

Antifungal Activity of New Diterpenoid Alkaloids Isolated by Different Chromatographic Methods from Delphinium peregrinum L. var. eriocarpum Boiss

by Mohammad Alhilal, Yaser A. M. Sulaiman, Suzan Alhilal, Sobhi M. Gomha and Salama A. Ouf

Molecules 2021, 26(5), 1375; https://doi.org/10.3390/molecules26051375 - 4 Mar 2021

Cited by 8 | Viewed by 3675

Abstract

This paper aimed to investigate the potential antifungal influences of new alkaloids from Delphinium peregrinum L. var. eriocarpum Boiss. New Diterpenoid alkaloids Delcarpum (1), Hydrodavisine (4) and known alkaloids Peregrine (2), Delphitisine (3) were isolated by different chromatographic methods from the aerial parts of D. Peregrinum eriocarpum Boiss, which grows in Syria. The structures of alkaloids were proposed based on 1D NMR spectroscopy ¹H-NMR, ¹³C-NMR, DEPT-135, DEPT-90, 2D NMR spectroscopy DQF-COSY, HMQC, EI-Ms mass spectrum, and IR spectroscopic measurements. The antifungal activity of the isolated alkaloids was evaluated against different dermatophyte fungal isolates compared with fluconazole. In the case of Peregrine (2) the minimum inhibitory concentrations(MICs) recorded 128–256, 32–64, and 32 for Epidermophyton floccosum, Microsporum canis, and Trichophyton rubrum, respectively, compared to 32–64, 16, and 32 μg/mL in the case of fluconazole, respectively. The MICs recorded on application of the four alkaloids mixture were 64, 32, and 16 in the case of E. floccosum, M. canis, and T. rubrum, respectively, which were significantly lower than that measured for each of the individual alkaloid and were compatible for fluconazole. In conclusion, MICs of the tested alkaloids showed a variable potential effect on the investigated fungal isolates. Peregrine (2) was the most effective alkaloid, however, the application of the mixture of alkaloids induced significant synergistic activity that was more pronounced than the application of individual ones. Full article

(This article belongs to the Special Issue Isolation and Structure Determination of Bioactive Natural Products)

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Review

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20 pages, 3581 KiB

Open AccessReview

Modern Methods of Pre-Treatment of Plant Material for the Extraction of Bioactive Compounds

by Aneta Krakowska-Sieprawska, Anna Kiełbasa, Katarzyna Rafińska, Magdalena Ligor and Bogusław Buszewski

Molecules 2022, 27(3), 730; https://doi.org/10.3390/molecules27030730 - 23 Jan 2022

Cited by 61 | Viewed by 8000

Abstract

In this review, recent advances in the methods of pre-treatment of plant material for the extraction of secondary metabolites with high biological activity are presented. The correct preparation of the material for extraction is as important as the selection of the extraction method. This step should prevent the degradation of bioactive compounds as well as the development of fungi and bacteria. Currently, the methods of preparation are expected to modify the particles of the plant material in such a way that will contribute to the release of bioactive compounds loosely bonded to cell wall polymers. This review presents a wide range of methods of preparing plant material, including drying, freeze-drying, convection drying, microwave vacuum drying, enzymatic processes, and fermentation. The influence of the particular methods on the structure of plant material particles, the level of preserved bioactive compounds, and the possibility of their release during the extraction were highlighted. The plant material pre-treatment techniques used were discussed with respect to the amount of compounds released during extraction as well their application in various industries interested in products with a high content of biologically active compounds, such as the pharmaceutical, cosmetics, and food industries. Full article

(This article belongs to the Special Issue Isolation and Structure Determination of Bioactive Natural Products)

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