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Bioactive Natural Compounds: Isolation, Analysis and Evaluation

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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 (30 July 2022) | Viewed by 19570

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Prof. Dr. Vassya Bankova

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Chemistry of Natural Products Laboratory, Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Sofia, Bulgaria
Interests: natural products chemistry; medicinal plants; phytochemical analysis; bioactive natural products; bee products; propolis
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Prof. Dr. Milena Popova

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Chemistry of Natural Products Laboratory, Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Sofia, Bulgaria
Interests: natural products chemistry; bee products; propolis; medicinal plants; metabolic profiling; phytochemical analysis

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Dear Colleagues,

Biologically active natural compounds have been used by humanity for millennia, and nowadays 60% of human population relies on natural medicines, mostly of plant origin, for treatment and prevention of diseases. Plants, mushrooms, marine organisms, microorganisms produce secondary metabolites of unprecedented structural diversity, which provide valuable leads for drug discovery. Their isolation and analysis, and the evaluation of their biological properties are attracting growing attention in the fields of pharmaceutical and food industry, medicine, nutrition, and biotechnology. In recent years, numerous innovative methods for isolation of natural products have been developed, such as ultrasound and microwave-assisted extraction, high pressure methods, natural deep eutectic solvents, etc., while in the area of analysis, the metabolomics approach and the wide application of chemometrics caused a dramatical change. With regard to evaluation of the biological and pharmacological properties of natural products, in silico studies provide powerful tools for exploring the pharmacological profiles of natural products.

This Special Issue “Bioactive Natural Compounds: Isolation, Analysis and Evaluation” is intended to highlight the most recent developments and emerging trends in the field of natural products research. We cordially invite researchers form all over the world to submit Original full research articles as well as review articles, sharing their most recent findings and ideas in this exciting field of science.

Prof. Dr. Vassya Bankova
Prof. Dr. Milena Popova
Guest Editors

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Keywords

natural compounds
bioactivity
isolation of bioactive natural compounds
analysis of natural compounds
bioactivity evaluation

Published Papers (9 papers)

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Research

11 pages, 1041 KiB

Open AccessArticle

Amaryllidaceae-Type Alkaloids from Pancratium maritimum: Apoptosis-Inducing Effect and Cell Cycle Arrest on Triple-Negative Breast Cancer Cells

by Shirley A. R. Sancha, Adriana V. Gomes, Joana B. Loureiro, Lucília Saraiva and Maria José U. Ferreira

Molecules 2022, 27(18), 5759; https://doi.org/10.3390/molecules27185759 - 06 Sep 2022

Cited by 9 | Viewed by 1880

Abstract

Aiming to find Amaryllidaceae alkaloids against breast cancer, including the highly aggressive triple-negative breast cancer, the phytochemical study of Pancratium maritimum was carried out. Several Amaryllidaceae-type alkaloids, bearing scaffolds of the haemanthamine-, homolycorine-, lycorine-, galanthamine-, and tazettine-type were isolated (3–11), along with one alkamide (2) and a phenolic compound (1). The antiproliferative effect of compounds (1–11) was evaluated by the sulforhodamine B assay against triple-negative breast cancer cell lines MDA-MB-231 and MDA-MB-468, breast cancer cells MCF-7, and the non-malignant fibroblast (HFF-1) and breast (MCF12A) cell lines. The alkaloids 3, 5, 7, and 11 showed significant growth inhibitory effects against all breast cancer cell lines, with IC₅₀ (half-maximal inhibitory concentration) values ranging from 0.73 to 16.3 µM. The homolycorine-type alkaloid 7 was selected for further investigation in MDA-MB-231 cells. In the annexin-V assay, compound 7 increased cell death by apoptosis, which was substantiated, in western blot analyses, by the increased expression of the pro-apoptotic protein Bax, and the decreased expression of the anti-apoptotic protein Bcl-xL. Consistently, it further stimulated mitochondrial reactive oxygen species (ROS) generation. The antiproliferative effect of compound 7 was also associated with G2/M cell cycle arrest, which was supported by an increase in the p21 protein expression levels. In MDA-MB-231 cells, compound 7 also exhibited synergistic effects with conventional chemotherapeutic drugs such as etoposide. Full article

(This article belongs to the Special Issue Bioactive Natural Compounds: Isolation, Analysis and Evaluation)

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10 pages, 1989 KiB

Open AccessArticle

Betuletol, a Propolis Component, Suppresses IL-33 Gene Expression and Effective against Eosinophilia

by Aurpita Shaha, Rezwanul Islam, Naonobu Tanaka, Yoshiki Kashiwada, Hiroyuki Fukui, Noriaki Takeda, Yoshiaki Kitamura and Hiroyuki Mizuguchi

Molecules 2022, 27(17), 5459; https://doi.org/10.3390/molecules27175459 - 25 Aug 2022

Cited by 2 | Viewed by 1628

Abstract

Propolis, a resinous substance produced by honeybees, has been used in folk medicine since ancient times due to its many biological benefits such as antitumor, antioxidant, antimicrobial, anti-inflammatory, and immunomodulatory effects. Propolis contains flavonoids, terpenoids, aromatic aldehydes, and alcohols, which vary with different climate and environmental conditions. In our study, we examined the antiallergic activity of Brazilian green propolis (BGP) and isolated the active compound that can suppress an allergy-sensitive gene, IL-33, expression and eosinophilia. Ethanolic extract of BGP freeze-dried powder was fractionated with several solvent systems, and the active fractions were collected based on activity measurement. The single active compound was found by thin-layer chromatography. Using column chromatography and NMR, the active compound was isolated and identified as 3,5,7-trihydroxy-6,4’-dimethoxyflavone, also known as betuletol. Further, the antiallergic activity of that has been examined in PMA-induced up-regulation of IL-33 gene expression in Swiss 3T3 cells. Our data showed the IL-33 gene suppression both by BGP and the isolated active compound, betuletol. We also found that betuletol suppressed ERK phosphorylation, suggesting it could be effective in suppressing IL-33 mediated eosinophilic chronic inflammation and will provide new insights to develop potent therapeutics against allergic inflammations. Full article

(This article belongs to the Special Issue Bioactive Natural Compounds: Isolation, Analysis and Evaluation)

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21 pages, 1801 KiB

Open AccessArticle

Phytochemical Screening, Anti-Inflammatory, and Antidiabetic Activities of Different Extracts from Caralluma edulis Plant

by Maria Khan, Zahid Manzoor, Muhammad Rafiq, Shaukat Hussain Munawar, Muhammad Yasir Waqas, Hamid Majeed, Syed Zahid Ali Shah, Riaz Hussain, Hafiz Iftikhar Hussain, Tehreem Tahir, Katarzyna Kotwica-Mojzych and Mariusz Mojzych

Molecules 2022, 27(16), 5346; https://doi.org/10.3390/molecules27165346 - 22 Aug 2022

Cited by 3 | Viewed by 2433

Abstract

The plant Caralluma edulis is traditionally used against diabetes and inflammatory conditions in Pakistan. This study was designed to provide scientific validation of the traditional use of Caralluma edulis. Phytochemicals were extracted from the plant by different solvents (distilled water, methanol, ethanol, and acetone) using the Soxhlet’s extraction method. Bioactive compounds were detected by gas chromatography–mass spectrometry (GC-MS). The in vitro anti-inflammatory activities (albumin denaturation, membrane stabilization, and proteinase inhibition) and antioxidant capacity (DPPH scavenging activity, FRAP reducing activity) of different extracts from Caralluma edulis were assessed. The antidiabetic potential of Caralluma edulis plant extracts was determined in acute and subacute diabetic rabbit models. Oxidative stress and enzymatic antioxidant status were also estimated in MDA, CAT, and SOD levels. Results showed that the methanol extract yielded the highest contents of phenolics, flavonoids, alkaloids, and terpenoids. The in vitro anti-inflammatory activity and antioxidant potential of the methanol extract were the highest among the tested solvents. The tested extracts did not show any remarkable antidiabetic activity in the acute diabetic model. However, all tested extracts demonstrated antidiabetic potential in the subacute diabetic model. No adverse effect was observed at the tested dose (200 mg/kg) of Caralluma edulis extracts in experimental animals. It is concluded that methanol is the key solvent for extracting bioactive compounds from Caralluma edulis. The plant can be used against inflammatory disorders and may prove a potential candidate for drug development. Long-term use of Caralluma edulis at the tested dose (200 mg/kg) showed antidiabetic properties in the animal model. Full article

(This article belongs to the Special Issue Bioactive Natural Compounds: Isolation, Analysis and Evaluation)

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11 pages, 921 KiB

Open AccessArticle

Microwave-Assisted and Conventional Extractions of Volatile Compounds from Rosa x damascena Mill. Fresh Petals for Cosmetic Applications

by Carla Villa, Francesco Saverio Robustelli Della Cuna, Eleonora Russo, Mohammed Farhad Ibrahim, Elena Grignani and Stefania Preda

Molecules 2022, 27(12), 3963; https://doi.org/10.3390/molecules27123963 - 20 Jun 2022

Cited by 7 | Viewed by 2208

Abstract

Rosa x damascena Mill. essential oil is mainly used in the cosmetics and perfumery industry, but it also finds application in the food industry as a flavoring agent. The chemical composition of essential oils is affected by environment, soil, harvesting technique, storage condition, and extraction methods. Nowadays, the study and design of greener, more efficient, and sustainable extractive procedures is the main and strategic focus in the chemical research and development of botanical derivatives, especially as regards fragrances and essential oils. Several technologies are available, and the best method to use depends on the desired chemicals, but conventional extractive processes are often laborious and time-consuming, involve large amounts of solvents, and may cause the partial loss of volatiles, affecting the quality of the final product. In the last decade, microwave irradiation has been successfully applied to classical techniques, often improving the general extractive efficiency and extract quality. In the present paper, as a preliminary analytical screening approach, two microwave-mediated techniques, Solvent-Free Microwave Extraction (SFME) and Microwave Hydrodiffusion and Gravity (MHG), and two conventional procedures, Hydrodistillation (HD) and Steam Distillation (SD), were applied and compared for the extraction of volatile compounds from R. x damascena fresh petals to highlight differences and advantages of the selected procedure and of the obtained extracts useful in a cosmetic context as fragrances or active ingredients. The chemical composition of the extracts was investigated by GC-MS and GC-FID. Sixty-one components, distributed in the four techniques, were identified. SD and HD are dominated by oxygenated terpenes (59.01% and 50.06%, respectively), while MHG and SFME extracts are dominated by alcohols (61.67% and 46.81%, respectively). A relevant variability in the composition of the extracts relating to the extraction techniques used was observed. To point out the correlation between the process and composition of the obtained natural products, principal component analysis (PCA) of the data extracted from GC-FID was used. Taking into account a cosmetic application, SFME shows several advantages when compared with the other procedures. The extract (obtained in a significantly higher amount) contains a meaningful lower level of potential fragrance allergenic compounds and quite a double amount of benzyl alcohol and 2-phenyl ethanol that can also enhance the preservative action in personal care products. Full article

(This article belongs to the Special Issue Bioactive Natural Compounds: Isolation, Analysis and Evaluation)

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17 pages, 3214 KiB

Open AccessArticle

Targeted and Untargeted Mass Spectrometry-Based Metabolomics for Chemical Profiling of Three Coffee Species

by Andrea Montis, Florence Souard, Cédric Delporte, Piet Stoffelen, Caroline Stévigny and Pierre Van Antwerpen

Molecules 2022, 27(10), 3152; https://doi.org/10.3390/molecules27103152 - 14 May 2022

Cited by 6 | Viewed by 2006

Abstract

While coffee beans have been studied for many years, researchers are showing a growing interest in coffee leaves and by-products, but little information is currently available on coffee species other than Coffea arabica and Coffea canephora. The aim of this work was to perform a targeted and untargeted metabolomics study on Coffea arabica, Coffea canephora and Coffea anthonyi. The application of the recent high-resolution mass spectrometry-based metabolomics tools allowed us to gain a clear overview of the main differences among the coffee species. The results showed that the leaves and fruits of Coffea anthonyi had a different metabolite profile when compared to the two other species. In Coffea anthonyi, caffeine levels were found in lower concentrations while caffeoylquinic acid and mangiferin-related compounds were found in higher concentrations. A large number of specialized metabolites can be found in Coffea anthonyi tissues, making this species a valid candidate for innovative healthcare products made with coffee extracts. Full article

(This article belongs to the Special Issue Bioactive Natural Compounds: Isolation, Analysis and Evaluation)

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17 pages, 1989 KiB

Open AccessArticle

Antimicrobial Triterpenoids and Ingol Diterpenes from Propolis of Semi-Arid Region of Morocco

by Ralitsa Chimshirova, Milena Popova, Amina Chakir, Violeta Valcheva, Simeon Dimitrov, Boryana Trusheva, Abderrahmane Romane and Vassya Bankova

Molecules 2022, 27(7), 2206; https://doi.org/10.3390/molecules27072206 - 28 Mar 2022

Cited by 6 | Viewed by 2000

Abstract

The chemical composition and antimicrobial activity of propolis from a semi-arid region of Morocco were investigated. Fifteen compounds, including triterpenoids (1, 2, 7–12), macrocyclic diterpenes of ingol type (3–6) and aromatic derivatives (13–15), were isolated by various chromatographic methods. Their structures were elucidated by a combination of spectroscopic and chiroptical methods. Compounds 1 and 3 are new natural compounds, and 2, 4–6, and 9–11 are newly isolated from propolis. Moreover, the full nuclear magnetic resonance (NMR) assignments of three of the known compounds (2, 4 and 5) were reported for the first time. Most of the compounds tested, especially the diterpenes 3, 4, and 6, exhibited very good activity against different strains of bacteria and fungi. Compound 3 showed the strongest activity with minimum inhibitory concentrations (MICs) in the range of 4–64 µg/mL. The combination of isolated triterpenoids and ingol diterpenes was found to be characteristic for Euphorbia spp., and Euphorbia officinarum subsp. echinus could be suggested as a probable and new plant source of propolis. Full article

(This article belongs to the Special Issue Bioactive Natural Compounds: Isolation, Analysis and Evaluation)

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14 pages, 1737 KiB

Open AccessArticle

Effect of Kaempferol and Its Glycoside Derivatives on Antioxidant Status of HL-60 Cells Treated with Etoposide

by Magdalena Kluska, Michał Juszczak, Jerzy Żuchowski, Anna Stochmal and Katarzyna Woźniak

Molecules 2022, 27(2), 333; https://doi.org/10.3390/molecules27020333 - 06 Jan 2022

Cited by 16 | Viewed by 2067

Abstract

Kaempferol is a well-known antioxidant found in many plants and plant-based foods. In plants, kaempferol is present mainly in the form of glycoside derivatives. In this work, we focused on determining the effect of kaempferol and its glycoside derivatives on the expression level of genes related to the reduction of oxidative stress—NFE2L2, NQO1, SOD1, SOD2, and HO-1; the enzymatic activity of superoxide dismutases; and the level of glutathione. We used HL-60 acute promyelocytic leukemia cells, which were incubated with the anticancer drug etoposide and kaempferol or one of its three glycoside derivatives isolated from the aerial parts of Lens culinaris Medik.—kaempferol 3-O-[(6-O-E-caffeoyl)-β-d-glucopyranosyl-(1→2)]-β-d-galactopyranoside-7-O-β-d-glucuropyranoside (P2), kaempferol 3-O-[(6-O-E-p-coumaroyl)-β-d-glucopyranosyl-(1→2)]-β-d-galactopyranoside-7-O-β-d-glucuropyranoside (P5), and kaempferol 3-O-[(6-O-E-feruloyl)-β-d-glucopyranosyl-(1→2)]-β-d-galactopyranoside-7-O-β-d-glucuropyranoside (P7). We showed that none of the tested compounds affected NFE2L2 gene expression. Co-incubation with etoposide (1 µM) and kaempferol (10 and 50 µg/mL) leads to an increase in the expression of the HO-1 (9.49 and 9.33-fold at 10 µg/mL and 50 µg/mL, respectively), SOD1 (1.68-fold at 10 µg/mL), SOD2 (1.72-fold at 10–50 µg/mL), and NQO1 (1.84-fold at 50 µg/mL) genes in comparison to cells treated only with etoposide. The effect of kaempferol derivatives on gene expression differs depending on the derivative. All tested polyphenols increased the SOD activity in cells co-incubated with etoposide. We observed that the co-incubation of HL-60 cells with etoposide and kaempferol or derivative P7 increases the level of total glutathione in these cells. Taken together, our observations suggest that the antioxidant activity of kaempferol is related to the activation of antioxidant genes and proteins. Moreover, we observed that glycoside derivatives can have a different effect on the antioxidant cellular systems than kaempferol. Full article

(This article belongs to the Special Issue Bioactive Natural Compounds: Isolation, Analysis and Evaluation)

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8 pages, 513 KiB

Open AccessArticle

New Kendomycin Derivative Isolated from Streptomyces sp. Cl 58-27

by Constanze Paulus, Oleksandr Gromyko and Andriy Luzhetskyy

Molecules 2021, 26(22), 6834; https://doi.org/10.3390/molecules26226834 - 12 Nov 2021

Cited by 3 | Viewed by 1984

Abstract

In the course of screening new streptomycete strains, the strain Streptomyces sp. Cl 58-27 caught our attention due to its interesting secondary metabolite production profile. Here, we report the isolation and characterization of an ansamycin natural product that belongs structurally to the already known kendomycins. The structure of the new kendomycin E was elucidated using NMR spectroscopy, and the corresponding biosynthetic gene cluster was identified by sequencing the genome of Streptomyces sp. Cl 58-27 and conducting a detailed analysis of secondary metabolism gene clusters using bioinformatic tools. Full article

(This article belongs to the Special Issue Bioactive Natural Compounds: Isolation, Analysis and Evaluation)

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12 pages, 7579 KiB

Open AccessArticle

Composition of Algerian Propolis, Plant Origin, and Its Antiangiogenic Activity In Vitro

by Takahiro Hosoya, Ikumi Tsuchiya, Toshiro Ohta, Mokhtar Benhanifia and Shigenori Kumazawa

Molecules 2021, 26(21), 6510; https://doi.org/10.3390/molecules26216510 - 28 Oct 2021

Cited by 1 | Viewed by 1624

Abstract

The antiangiogenic activity of the ethanol extract of propolis collected from different regions in western Algeria was investigated using in vitro human umbilical vein endothelial cells (HUVECs). The ethanol extract with the strongest activity, i.e., Algerian propolis 1 (EEPA1), inhibited the formation of capillary networks in a dose-dependent manner (6.25–50 μg/mL) within 12 h and induced cell fragmentation of HUVECs at 50 μg/mL after treatment for 24 h. To identify the active compounds in EEAP1, a high-performance liquid chromatography (HPLC) analysis was performed, revealing that EEAP1 contains two major compounds. Both compounds were isolated by repeated column chromatography and identified as ω-hydroxyferulenol (1) and ferulenol (2), which have a coumarin structure conjugated with a farnesyl group according to NMR, high-resolution electrospray ionization mass spectroscopy, and chemical modification. Compounds 1 and 2 inhibited the tube-forming activity of HUVECs, especially 2, which exhibited a stronger antiangiogenic effect even at a low concentration of 3.31 μg/mL. Moreover, 2 suppressed the elongation and induced cell fragmentation at the same dose. The molecular changes in tube-forming HUVECs induced by 2 were found to be related to the activation of the caspase signals. To confirm the plant origin of propolis, an HPLC comparative analysis of the ethanol extracts of some plants near beekeeping areas and that of Algerian propolis (EEAP1) was performed, and similar chromatographic patterns were observed. This result suggests that the plant origin of this Algerian propolis is the resin of Ferula communis. Full article

(This article belongs to the Special Issue Bioactive Natural Compounds: Isolation, Analysis and Evaluation)

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