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Bioactive Compounds from Natural Sources: Characterization and Biological 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 (28 February 2023) | Viewed by 27320

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Dr. Jolanta Mierzejewska

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Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, Warsaw, Poland
Interests: microbial biotechnology; natural compounds; antimicrobial activity; antioxidant activity; extraction; microbiology

Special Issue Information

Dear Colleagues,

Overuse of antibiotics has led to the rapidly spreading resistance of microorganisms to known drugs. It is estimated that currently around 1 million people die each year from multi-drug-resistant microorganisms, and this number could increase tenfold over the next three decades. Hence, there is an urgent need to search for new drugs with a broad antimicrobial activity, as only the implementation of such agents will be profitable for pharmaceutical companies. Futhermore, not only medicine but also organic farming is looking for new natural antimicrobial agents, especially those with fungicidal activity, which could replace synthetic fungicides necessary to protect, for example, grapes and other fruits.Most antimicrobial compounds are derived from plants and microorganisms. These natural sources are rich in as yet unexplored secondary metabolites that have the potential to be new antimicrobial agents. Currently, many interdisciplinary teams of chemists and microbiologists conduct intensive research in this area, so we believe that it is worth devoting a special issue of Molecules to it. Therefore, we welcome studies that present research outcomes on all aspects of searching of new antimicrobial agents, including but not limited to the following topics:
Natural compounds with antimicrobial activity;Methods of production, isolation and purification;Scope of activity;Mechanisms of action;Chemical characteristics.

Dr. Jolanta Mierzejewska
Guest Editor

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Keywords

natural compounds
chemical composition
plant extracts
secondary metabolites
biological activity
antibacterial
antifungal
cytotoxicity

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Published Papers (10 papers)

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Research

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21 pages, 2797 KiB

Open AccessArticle

Datura stramonium Flowers as a Potential Natural Resource of Bioactive Molecules: Identification of Anti-Inflammatory Agents and Molecular Docking Analysis

by Bilel Damergi, Rym Essid, Nadia Fares, Nadine Khadraoui, Lucía Ageitos, Ameni Ben Alaya, Dorra Gharbi, Islem Abid, Monerah Rashed Alothman, Ferid Limam, Jaime Rodríguez, Carlos Jiménez and Olfa Tabbene

Molecules 2023, 28(13), 5195; https://doi.org/10.3390/molecules28135195 - 4 Jul 2023

Cited by 4 | Viewed by 2584

Abstract

The present study investigated the antioxidant, antibacterial, antiviral and anti-inflammatory activities of different aerial parts (flowers, leaves and seeds) of Datura stramonium. The plant material was extracted with 80% methanol for about 24 h. The sensitivity to microorganisms analysis was performed by the microdilution technique. Antioxidant tests were performed by scavenging the DPPH and ABTS radicals, and by FRAP assay. Anti-inflammatory activity was evaluated through the inhibition of nitric oxide production in activated macrophage RAW 264.7 cells. Cell viability was assessed with an MTT assay. Results show that the flower extract revealed a powerful antimicrobial capacity against Gram-positive bacteria and strong antioxidant and anti-inflammatory activities. No significant cytotoxicity to activated macrophages was recorded. High resolution electrospray ionization mass spectrometry and nuclear magnetic resonance analysis identified two molecules with important anti-inflammatory effects: 12α-hydroxydaturametelin B and daturametelin B. Molecular docking analysis with both pro-inflammatory agents tumor necrosis factor alpha and interleukin-6 revealed that both compounds showed good binding features with the selected target proteins. Our results suggest that D. stramonium flower is a promising source of compounds with potential antioxidant, antibacterial, and anti-inflammatory activities. Isolated withanolide steroidal lactones from D. stramonium flower extract with promising anti-inflammatory activity have therapeutic potential against inflammatory disorders. Full article

(This article belongs to the Special Issue Bioactive Compounds from Natural Sources: Characterization and Biological Evaluation)

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15 pages, 5533 KiB

Open AccessArticle

Comprehensive Analysis of Secondary Metabolites of Four Medicinal Thyme Species Used in Folk Medicine and Their Antioxidant Activities In Vitro

by Rui Yang, Yanmei Dong, Fei Gao, Jingyi Li, Zora Dajic Stevanovic, Hui Li and Lei Shi

Molecules 2023, 28(6), 2582; https://doi.org/10.3390/molecules28062582 - 12 Mar 2023

Cited by 3 | Viewed by 2472

Abstract

Thyme is a colloquial term for number of aromatic species belonging to the genus Thymus L., known for their expressed biological activities and therefore used worldwide for seasoning and in folk medicine. In the present paper, the content of the total polyphenols (TP), total flavonoids (TF), and antioxidant capacity were assessed in the extracts of four traditionally used thyme species. Moreover, a comprehensive metabolomic study of thyme bioactive compounds was performed, and the obtained data were processed using multivariate statistical tests. The results clearly demonstrated the positive correlation between the content of the TP, TF, and antioxidant activity, and TF was more significant than TP. The findings revealed that four selected thyme species contained 528 secondary metabolites, including 289 flavonoids and 146 phenolic acids. Thymus marschallianus had a higher concentration of active ingredients, which improve its antioxidant capacity. Differentially accumulated metabolites were formed by complex pathways such as flavonoid, flavone, flavonol, isoflavonoid, and anthocyanin biosynthesis. Correlation analysis showed that 59 metabolites (including 28 flavonoids, 18 phenolic acids, and 7 terpenoid compounds) were significantly correlated with obtained values of the antioxidant capacity. The results suggested that selected thyme species exhibit a great diversity in antioxidant-related components, whereas flavonoids may be responsible for the high antioxidant capacity of all studied thyme species. The present study greatly expands our understanding of the complex phytochemical profiles and related applications of selected medicinal plants. Full article

(This article belongs to the Special Issue Bioactive Compounds from Natural Sources: Characterization and Biological Evaluation)

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16 pages, 26547 KiB

Open AccessArticle

The Effective Treatment of Purpurin on Inflammation and Adjuvant-Induced Arthritis

by Weiya Zeng, Caihong Shen, Suifen Mo, Chen Ni, Ying Lin, Yuan Fang, Huiling Yang, Guihua Luo, Luhua Xiao, Ruoting Zhan and Ping Yan

Molecules 2023, 28(1), 366; https://doi.org/10.3390/molecules28010366 - 2 Jan 2023

Cited by 9 | Viewed by 2456

Abstract

Rubia cordifolia L. (Rubiaceae), one of the traditional anti-rheumatic herbal medicines in China, has been used to treat rheumatoid arthritis (RA) since ancient times. Purpurin, an active compound of Rubia cordifolia L., has been identified in previous studies and exerts antibacterial, antigenotoxic, anticancer, and antioxidant effects. However, the efficacy and the underlying mechanism of purpurin to alleviate RA are unclear. In this study, the effect of purpurin on inflammation was investigated using macrophage RAW264.7 inflammatory cells, induced by lipopolysaccharide (LPS), and adjuvant-induced arthritis (AIA) rat was established to explore the effect of purpurin on joint damage and immune disorders; the network pharmacology and molecular docking were integrated to dig out the prospective target. Purpurin showed significantly anti-inflammatory effect by reducing the content of IL-6, TNF-α, and IL-1β and increasing IL-10. Besides, purpurin obviously improved joint injury and hypotoxicity in the liver and spleen and regulated the level of FOXP3 and CD4+/CD8+. Furthermore, purpurin reduced the MMP3 content of AIA rats. Network pharmacology and molecular docking also suggested that MMP3 may be the key target of purpurin against RA. The results of this study strongly indicated that purpurin has a potential effect on anti-RA. Full article

(This article belongs to the Special Issue Bioactive Compounds from Natural Sources: Characterization and Biological Evaluation)

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13 pages, 2697 KiB

Open AccessArticle

Farnesol Protects against Cardiotoxicity Caused by Doxorubicin-Induced Stress, Inflammation, and Cell Death: An In Vivo Study in Wistar Rats

by Abdulrab Ahmed M. Alkhanjaf, Md Tanwir Athar, Zabih Ullah, Abdullah Mohammed H. Alsayhab, Ahmad Umar and Ibrahim Ahmed Shaikh

Molecules 2022, 27(23), 8589; https://doi.org/10.3390/molecules27238589 - 6 Dec 2022

Cited by 7 | Viewed by 2162

Abstract

Doxorubicin (DOXO) is an antineoplastic drug that is used extensively in managing multiple cancer types. However, DOXO-induced cardiotoxicity is a limiting factor for its widespread use and considerably affects patients’ quality of life. Farnesol (FSN) is a sesquiterpene with antioxidant, anti-inflammatory, and anti-tumor properties. Thus, the current study explored the cardioprotective effect of FSN against DOXO-induced cardiotoxicity. In this study, male Wistar rats were randomly divided into five groups (n = 7) and treated for 14 days. Group I (Control): normal saline, p.o. daily for 14 days; Group II (TOXIC): DOXO 2.4 mg/kg, i.p, thrice weekly for 14 days; Group III: FSN 100 mg/kg, p.o. daily for 14 days + DOXO similar to Group II; Group IV: FSN 200 mg/kg, p.o. daily for 14 days + DOXO similar to Group II; Group V (Standard): nifedipine 10 mg/kg, p.o. daily for 14 days + DOXO similar to Group II. At the end of the study, animals were weighed, blood was collected, and heart-weight was measured. The cardiac tissue was used to estimate biochemical markers and for histopathological studies. The observed results revealed that the FSN-treated group rats showed decrease in heart weight and heart weight/body weight ratio, reversed the oxidative stress, cardiac-specific injury markers, proinflammatory and proapoptotic markers and histopathological aberrations towards normal, and showed cardioprotection. In summary, the FSN reduces cardiac injuries caused by DOXO via its antioxidant, anti-inflammatory, and anti-apoptotic potential. However, more detailed mechanism-based studies are needed to bring this drug into clinical use. Full article

(This article belongs to the Special Issue Bioactive Compounds from Natural Sources: Characterization and Biological Evaluation)

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19 pages, 3612 KiB

Open AccessArticle

Chemical Synthesis and Biological Activities of Amaryllidaceae Alkaloid Norbelladine Derivatives and Precursors

by Marie-Pierre Girard, Vahid Karimzadegan, Marianne Héneault, Francis Cloutier, Gervais Bérubé, Lionel Berthoux, Natacha Mérindol and Isabel Desgagné-Penix

Molecules 2022, 27(17), 5621; https://doi.org/10.3390/molecules27175621 - 31 Aug 2022

Cited by 7 | Viewed by 2733

Abstract

Amaryllidaceae alkaloids (AAs) are a structurally diverse family of alkaloids recognized for their many therapeutic properties, such as antiviral, anti-cholinesterase, and anticancer properties. Norbelladine and its derivatives, whose biological properties are poorly studied, are key intermediates required for the biosynthesis of all ~650 reported AAs. To gain insight into their therapeutic potential, we synthesized a series of O-methylated norbelladine-type alkaloids and evaluated their cytotoxic effects on two types of cancer cell lines, their antiviral effects against the dengue virus (DENV) and the human immunodeficiency virus 1 (HIV-1), and their anti-Alzheimer’s disease (anti-cholinesterase and -prolyl oligopeptidase) properties. In monocytic leukemia cells, norcraugsodine was highly cytotoxic (CC₅₀ = 27.0 μM), while norbelladine was the most cytotoxic to hepatocarcinoma cells (CC₅₀ = 72.6 μM). HIV-1 infection was impaired only at cytotoxic concentrations of the compounds. The 3,4-dihydroxybenzaldehyde (selectivity index (SI) = 7.2), 3′,4′-O-dimethylnorbelladine (SI = 4.8), 4′-O-methylnorbelladine (SI > 4.9), 3′-O-methylnorbelladine (SI > 4.5), and norcraugsodine (SI = 3.2) reduced the number of DENV-infected cells with EC₅₀ values ranging from 24.1 to 44.9 μM. The O-methylation of norcraugsodine abolished its anti-DENV potential. Norbelladine and its O-methylated forms also displayed butyrylcholinesterase-inhibition properties (IC₅₀ values ranging from 26.1 to 91.6 μM). Altogether, the results provided hints of the structure–activity relationship of norbelladine-type alkaloids, which is important knowledge for the development of new inhibitors of DENV and butyrylcholinesterase. Full article

(This article belongs to the Special Issue Bioactive Compounds from Natural Sources: Characterization and Biological Evaluation)

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13 pages, 992 KiB

Open AccessArticle

Polycyclic Phenol Derivatives from the Leaves of Spermacoce latifolia and Their Antibacterial and α-Glucosidase Inhibitory Activity

by Shao-Bo Liu, Lei Zeng, Qiao-Lin Xu, Ying-Le Chen, Tao Lou, Shan-Xuan Zhang and Jian-Wen Tan

Molecules 2022, 27(10), 3334; https://doi.org/10.3390/molecules27103334 - 22 May 2022

Cited by 6 | Viewed by 2500

Abstract

Three new polycyclic phenol derivatives, 2-acetyl-4-hydroxy-6H-furo [2,3-g]chromen-6-one (1), 2-(1′,2′-dihydroxypropan-2′-yl)-4-hydroxy-6H-furo [2,3-g][1]benzopyran-6-one (2) and 3,8,10-trihydroxy-4,9-dimethoxy-6H-benzo[c]chromen-6-one (8), along with seven known ones (3–7, 9 and 10) were isolated for the first time from the leaves of Spermacoce latifolia. Their structures were determined by spectroscopic analysis and comparison with literature-reported data. These compounds were tested for their in vitro antibacterial activity against four Gram-(+) bacteria: Staphyloccocus aureus (SA), methicillin-resistant Staphylococcus aureus (MRSA), Bacillus cereus (BC), Bacillus subtilis (BS), and the Gram-(−) bacterium Escherichia coli. Compounds 1, 2, 5 and 8 showed antibacterial activity toward SA, BC and BS with MIC values ranging from 7.8 to 62.5 µg/mL, but they were inactive to MRSA. Compound 4 not only showed the best antibacterial activity against SA, BC and BS, but it further displayed significant antibacterial activity against MRSA (MIC 1.95 µg/mL) even stronger than vancomycin (MIC 3.9 µg/mL). No compounds showed inhibitory activity toward E. coli. Further bioassay indicated that compounds 1, 4, 5, 6, 8 and 9 showed in vitro α-glucosidase inhibitory activity, among which compound 9 displayed the best α-glucosidase inhibitory activity with IC₅₀ value (0.026 mM) about 15-fold stronger than the reference compound acarbose (IC₅₀ 0.408 mM). These results suggested that compounds 4, 8 and 9 were potentially highly valuable compounds worthy of consideration to be further developed as an effective anti-MRSA agent or effective α-glucosidase inhibitors, respectively. In addition, the obtained data also supported that S. latifolia was rich in structurally diverse bioactive compounds worthy of further investigation, at least in searching for potential antibiotics and α-glucosidase inhibitors. Full article

(This article belongs to the Special Issue Bioactive Compounds from Natural Sources: Characterization and Biological Evaluation)

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9 pages, 1881 KiB

Open AccessArticle

Antifungal Activity of Soft Tissue Extract from the Garden Snail Helix aspersa (Gastropoda, Mollusca)

by Hoda H. Abd-El Azeem, Gamalat Y. Osman, Hesham R. El-Seedi, Ahmed M. Fallatah, Shaden A. M. Khalifa and Mohamed M. Gharib

Molecules 2022, 27(10), 3170; https://doi.org/10.3390/molecules27103170 - 16 May 2022

Cited by 7 | Viewed by 2952

Abstract

Gastropods comprise approximately 80% of molluscans, of which land snails are used variably as food and traditional medicines due to their high protein content. Moreover, different components from land snails exhibit antimicrobial activities. In this study, we evaluated the antifungal activity of soft tissue extracts from Helix aspersa against Candida albicans, Aspergillus flavus, and Aspergillus brasiliensis by identifying extract components using liquid chromatography-tandem mass spectrometry (LC-MS-MS). Two concentrations of three extracts (methanol, acetone, and acetic acid) showed antifungal activity. Both acetone (1 g/3 mL) and acetic acid extracts (1 g/mL) significantly inhibited C.albicans growth (p = 0.0001, 5.2 ± 0.2 mm and p = 0.02, 69.7 ± 0.6 mm, respectively). A. flavus and A. brasiliensis growth were inhibited by all extracts at 1 g/mL, while inhibition was observed for acetic acid extracts against A. brasiliensis (p = 0.02, 50.3 ± 3.5 mm). The highest growth inhibition was observed for A. flavus using acetic acid and acetone extracts (inhibition zones = 38 ± 1.7 mm and 3.1 ± 0.7 mm, respectively). LC-MS-MS studies on methanol and acetone extracts identified 11-α-acetoxyprogesterone with a parent mass of 372.50800 m/z and 287.43500 m/z for luteolin. Methanol extracts contained hesperidin with a parent mass of 611.25400 m/z, whereas linoleic acid and genistein (parent mass = 280.4 and 271.48900 m/z, respectively) were the main metabolites. Full article

(This article belongs to the Special Issue Bioactive Compounds from Natural Sources: Characterization and Biological Evaluation)

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17 pages, 5107 KiB

Open AccessArticle

The Main Structural Unit Elucidation and Immunomodulatory Activity In Vitro of a Selenium-Enriched Polysaccharide Produced by Pleurotus ostreatus

by De Wang, Jiahui Wang, Hui Liu, Meng Liu, Yanjing Yang and Shian Zhong

Molecules 2022, 27(8), 2591; https://doi.org/10.3390/molecules27082591 - 18 Apr 2022

Cited by 12 | Viewed by 2245

Abstract

In recent years, the structure of selenium-enriched polysaccharides and their application in immunomodulation have attracted much attention. In previous studies, we extracted and purified a novel selenium-enriched Pleurotus ostreatus polysaccharide called Se-POP-21, but its structure and immunomodulatory activity were still unclear. In this study, the main structural unit formula of Se-POP-21 was characterized by methylation analysis and an NMR experiment. The results showed that the backbone of Se-POP-21 was →[2,6)-α-D-Galp-(1→6)-α-D-Galp-(1]₄→2,4)-β-L-Arap-(1→[2,6)-α-D-Galp-(1→6)-α-D-Galp-(1]₄→, branched chain of β-D-Manp-(1→ and β-D-Manp-(1→4)-β-L-Arap-(1→ connected with →2,6)-α-D-Galp-(1→ and →2,4)-β-L-Arap-(1→,respectively, through the O-2 bond. In vitro cell experiments indicated that Se-POP-21 could significantly enhance the proliferation and phagocytosis of RAW264.7 cells, upregulate the expression of costimulatory molecules CD80/CD86, and promote RAW264.7 cells to secrete NO, ROS, TNF-α, IL-1β, and IL-6 by activating the NF-κB protein. The results of this study indicate that Se-POP-21 can effectively activate RAW264.7 cells. Thus, it has the potential to be used in immunomodulatory drugs or functional foods. Full article

(This article belongs to the Special Issue Bioactive Compounds from Natural Sources: Characterization and Biological Evaluation)

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Review

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15 pages, 2539 KiB

Open AccessReview

Polygonum capitatum, the Hmong Medicinal Flora: A Comprehensive Review of Its Phytochemical, Pharmacological and Pharmacokinetic Characteristics

by Yan Lin, Lei He, Xing-Jun Chen, Xu Zhang, Xue-Long Yan, Bo Tu, Zhu Zeng and Ming-Hui He

Molecules 2022, 27(19), 6407; https://doi.org/10.3390/molecules27196407 - 28 Sep 2022

Cited by 4 | Viewed by 2164

Abstract

Polygonum capitatum, known as “Tou Hua Liao” (Chinese name), is a crucial source of Hmong medicinal plants that has benefited human health for a long time. This folk-medicinal plant is widely distributed in the south-west of China for the treatment of various urologic disorders including urinary tract infections, pyelonephritis, and urinary calculus. The purpose of this paper was to provide a systematic and comprehensive overview of the traditional usages, botany, phytochemistry, pharmacology, pharmacokinetics and clinical applications of this flora. Up until the end of 2022, at least 91 compounds had been reported from P. capitatum, mainly covering the classes of flavonoids, lignanoids, phenols and other components. The compounds and extracts isolated from P. capitatum exhibit a wide range of pharmacological activities, such as anti-inflammatory, antioxidant, antimicrobial, anticancer, analgesic, hypothermic, diuretic and other pharmacological effects. Qualitative and quantitative chemical analyses were also covered. Furthermore, the possible development trends and perspectives for future research on this medicinal plant were also discussed. Full article

(This article belongs to the Special Issue Bioactive Compounds from Natural Sources: Characterization and Biological Evaluation)

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19 pages, 453 KiB

Open AccessReview

Biological Activities of Organic Extracts of the Genus Aristolochia: A Review from 2005 to 2021

by Martín A. Lerma-Herrera, Lidia Beiza-Granados, Alejandra Ochoa-Zarzosa, Joel E. López-Meza, Pedro Navarro-Santos, Rafael Herrera-Bucio, Judit Aviña-Verduzco and Hugo A. García-Gutiérrez

Molecules 2022, 27(12), 3937; https://doi.org/10.3390/molecules27123937 - 20 Jun 2022

Cited by 13 | Viewed by 3944

Abstract

Different ethnomedicinal studies have investigated the relationship between various phytochemicals as well as organic extracts and their bioactive aspects. Studies on biological effects are attributed to secondary metabolites such as alkaloids, phenolic compounds, and terpenes. Since there have been no reviews in the literature on the traditional, phytochemical, and ethnomedicinal uses of the genus Aristolochia so far, this article systematically reviews 141 published studies that analyze the associations between secondary metabolites present in organic extracts and their beneficial effects. Most studies found associations between individual secondary metabolites and beneficial effects such as anticancer activity, antibacterial, antioxidant activity, snake anti-venom and anti-inflammatory activity. The aim of this review was to analyze studies carried out in the period 2005–2021 to update the existing knowledge on different species of the genus Aristolochia for ethnomedicinal uses, as well as pharmacological aspects and therapeutic uses. Full article

(This article belongs to the Special Issue Bioactive Compounds from Natural Sources: Characterization and Biological Evaluation)

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