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Bioactive Molecules of Natural Origin: Mechanisms of Action Related to Health Risks and Benefits

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A special issue of International Journal of Molecular Sciences (ISSN 1422-0067). This special issue belongs to the section "Bioactives and Nutraceuticals".

Deadline for manuscript submissions: closed (31 July 2021) | Viewed by 71709

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Prof. Dr. Marie-Laure Fauconnier

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Laboratory of Chemistry of Natural Molecules, Gembloux Agro-Bio Tech, University of Liège, Passage des Déportés 2, 5030 Gembloux, Belgium
Interests: essential oil; VOCs; oxylipins for applications in agronomy and food science
Special Issues, Collections and Topics in MDPI journals

Prof. Dr. Laurence Lins

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Laboratory of Molecular Biophysics at Interfaces, Gembloux Agro-Bio Tech, University of Liège, Passage des déportés, B-5030 Gembloux, Belgium
Interests: molecular modelling; protein sequence analysis; protein and peptide–lipid interaction; membrane interaction; structure–activity reationships (SAR); molecular biophysics
Special Issues, Collections and Topics in MDPI journals

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Dear Colleagues,

Bioactive natural compounds (such as alkaloids, phenolics, terpenes, saponins, and volatile organic compounds) are increasingly used for their antioxidant, anti-inflammatory, bactericidal, fungicidal and virucidal properties for the benefit of human health. Moreover, they are found in a growing number of applications, such as cosmetics and wellness; but also in sectors where they were not traditionally used such as food preservation, household products and in the field of plant-protection products in agronomy. The number of publications treating bioactive natural compounds has increased significantly in recent years, but many publications are essentially descriptive.

The aim of this Special Issue is to study, at a molecular level, the mechanisms of action of bioactive natural compounds in their various beneficial properties to human health or to other domains and to carry out a rigorous assessment of the risks (toxicity, allergies, for example). This knowledge will contribute to a more rational and safer use of these compounds in the many sectors where they are employed.

Prof. Dr. Marie-Laure Fauconnier
Prof. Dr. Laurence Lins
Guest Editors

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Keywords

natural compounds
alkaloids
phenolics
terpenes
saponins
essential oils
volatile organic compounds
mechanisms of action
health risk
antioxidant
anti-inflammatory
bactericide
fungicide
virucidal properties
cosmetics
plant protection products

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Published Papers (12 papers)

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Research

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18 pages, 1239 KiB

Open AccessArticle

Antifungal Activity and DNA Topoisomerase Inhibition of Hydrolysable Tannins from Punica granatum L.

by Virginia Brighenti, Ramona Iseppi, Luca Pinzi, Annamaria Mincuzzi, Antonio Ippolito, Patrizia Messi, Simona Marianna Sanzani, Giulio Rastelli and Federica Pellati

Int. J. Mol. Sci. 2021, 22(8), 4175; https://doi.org/10.3390/ijms22084175 - 17 Apr 2021

Cited by 27 | Viewed by 3916

Abstract

Punica granatum L. (pomegranate) fruit is known to be an important source of bioactive phenolic compounds belonging to hydrolysable tannins. Pomegranate extracts have shown antifungal activity, but the compounds responsible for this activity and their mechanism/s of action have not been completely elucidated up to now. The aim of the present study was the investigation of the inhibition ability of a selection of pomegranate phenolic compounds (i.e., punicalagin, punicalin, ellagic acid, gallic acid) on both plant and human fungal pathogens. In addition, the biological target of punicalagin was identified here for the first time. The antifungal activity of pomegranate phenolics was evaluated by means of Agar Disk Diffusion Assay and minimum inhibitory concentration (MIC) evaluation. A chemoinformatic analysis predicted for the first time topoisomerases I and II as potential biological targets of punicalagin, and this prediction was confirmed by in vitro inhibition assays. Concerning phytopathogens, all the tested compounds were effective, often similarly to the fungicide imazalil at the label dose. Particularly, punicalagin showed the lowest MIC for Alternaria alternata and Botrytis cinerea, whereas punicalin was the most active compound in terms of growth control extent. As for human pathogens, punicalagin was the most active compound among the tested ones against Candida albicans reference strains, as well as against the clinically isolates. UHPLC coupled with HRMS indicated that C. albicans, similarly to the phytopathogen Coniella granati, is able to hydrolyze both punicalagin and punicalin as a response to the fungal attack. Punicalagin showed a strong inhibitory activity, with IC₅₀ values of 9.0 and 4.6 µM against C. albicans topoisomerases I and II, respectively. Altogether, the results provide evidence that punicalagin is a valuable candidate to be further exploited as an antifungal agent in particular against human fungal infections. Full article

(This article belongs to the Special Issue Bioactive Molecules of Natural Origin: Mechanisms of Action Related to Health Risks and Benefits)

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13 pages, 1122 KiB

Open AccessArticle

Bioprospecting of Natural Compounds from Brazilian Cerrado Biome Plants in Human Cervical Cancer Cell Lines

by Marcela N. Rosa, Larissa R. V. e Silva, Giovanna B. Longato, Adriane F. Evangelista, Izabela N. F. Gomes, Ana Laura V. Alves, Bruno G. de Oliveira, Fernanda E. Pinto, Wanderson Romão, Allisson R. de Rezende, Arali A. C. Araújo, Lohanna S. F. M. Oliveira, Alessandra A. de M. Souza, Stephanie C. Oliveira, Rosy Iara M. de A. Ribeiro, Viviane A. O. Silva and Rui M. Reis

Int. J. Mol. Sci. 2021, 22(7), 3383; https://doi.org/10.3390/ijms22073383 - 25 Mar 2021

Cited by 11 | Viewed by 3878

Abstract

Cervical cancer is the third most common in Brazilian women. The chemotherapy used for the treatment of this disease can cause many side effects; then, to overcome this problem, new treatment options are necessary. Natural compounds represent one of the most promising sources for the development of new drugs. In this study, 13 different species of 6 families from the Brazilian Cerrado vegetation biome were screened against human cervical cancer cell lines (CCC). Some of these species were also evaluated in one normal keratinocyte cell line (HaCaT). The effect of crude extracts on cell viability was evaluated by a colorimetric method (MTS assay). Extracts from Annona crassiflora, Miconia albicans, Miconia chamissois, Stryphnodendron adstringens, Tapirira guianensis, Xylopia aromatica, and Achyrocline alata showed half-maximal inhibitory concentration (IC₅₀) values < 30 μg/mL for at least one CCC. A. crassiflora and S. adstringens extracts were selective for CCC. Mass spectrometry (Electrospray Ionization Fourier Transform Ion Cyclotron Resonance Mass Spectrometer (ESI FT-ICR MS)) of A. crassiflora identified fatty acids and flavonols as secondary compounds. One of the A. crassiflora fractions, 7C24 (from chloroform partition), increased H2AX phosphorylation (suggesting DNA damage), PARP cleavage, and cell cycle arrest in CCC. Kaempferol-3-O-rhamnoside and oleic acid were bioactive molecules identified in 7C24 fraction. These findings emphasize the importance of investigating bioactive molecules from natural sources for developing new anti-cancer drugs. Full article

(This article belongs to the Special Issue Bioactive Molecules of Natural Origin: Mechanisms of Action Related to Health Risks and Benefits)

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17 pages, 1847 KiB

Open AccessArticle

Is the Membrane Lipid Matrix a Key Target for Action of Pharmacologically Active Plant Saponins?

by Svetlana S. Efimova and Olga S. Ostroumova

Int. J. Mol. Sci. 2021, 22(6), 3167; https://doi.org/10.3390/ijms22063167 - 20 Mar 2021

Cited by 14 | Viewed by 2392

Abstract

This study was focused on the molecular mechanisms of action of saponins and related compounds (sapogenins and alkaloids) on model lipid membranes. Steroids and triterpenes were tested. A systematic analysis of the effects of these chemicals on the physicochemical properties of the lipid bilayers and on the formation and functionality of the reconstituted ion channels induced by antimicrobial agents was performed. It was found that digitonin, tribulosin, and dioscin substantially reduced the boundary potential of the phosphatidylcholine membranes. We concluded that saponins might affect the membrane boundary potential by restructuring the membrane hydration layer. Moreover, an increase in the conductance and lifetime of gramicidin A channels in the presence of tribulosin was due to an alteration in the membrane dipole potential. Differential scanning microcalorimetry data indicated the key role of the sapogenin core structure (steroid or triterpenic) in affecting lipid melting and disordering. We showed that an alteration in pore forming activity of syringomycin E by dioscin might be due to amendments in the lipid packing. We also found that the ability of saponins to disengage the fluorescent marker calcein from lipid vesicles might be also determined by their ability to induce a positive curvature stress. Full article

(This article belongs to the Special Issue Bioactive Molecules of Natural Origin: Mechanisms of Action Related to Health Risks and Benefits)

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13 pages, 3510 KiB

Open AccessArticle

Antiosteoarthritic Effect of Morroniside in Chondrocyte Inflammation and Destabilization of Medial Meniscus-Induced Mouse Model

by Eunkuk Park, Chang Gun Lee, Seong Jae Han, Seung Hee Yun, Seokjin Hwang, Hyoju Jeon, Jeonghyun Kim, Chun Whan Choi, Siyoung Yang and Seon-Yong Jeong

Int. J. Mol. Sci. 2021, 22(6), 2987; https://doi.org/10.3390/ijms22062987 - 15 Mar 2021

Cited by 24 | Viewed by 3604

Abstract

Osteoarthritis (OA) is a common degenerative disease that results in joint inflammation as well as pain and stiffness. A previous study has reported that Cornus officinalis (CO) extract inhibits oxidant activities and oxidative stress in RAW 264.7 cells. In the present study, we isolated bioactive compound(s) by fractionating the CO extract to elucidate its antiosteoarthritic effects. A single bioactive component, morroniside, was identified as a potential candidate. The CO extract and morroniside exhibited antiosteoarthritic effects by downregulating factors associated with cartilage degradation, including cyclooxygenase-2 (Cox-2), matrix metalloproteinase 3 (Mmp-3), and matrix metalloproteinase 13 (Mmp-13), in interleukin-1 beta (IL-1β)-induced chondrocytes. Furthermore, morroniside prevented prostaglandin E2 (PGE2) and collagenase secretion in IL-1β-induced chondrocytes. In the destabilization of the medial meniscus (DMM)-induced mouse osteoarthritic model, morroniside administration attenuated cartilage destruction by decreasing expression of inflammatory mediators, such as Cox-2, Mmp3, and Mmp13, in the articular cartilage. Transverse microcomputed tomography analysis revealed that morroniside reduced DMM-induced sclerosis in the subchondral bone plate. These findings suggest that morroniside may be a potential protective bioactive compound against OA pathogenesis. Full article

(This article belongs to the Special Issue Bioactive Molecules of Natural Origin: Mechanisms of Action Related to Health Risks and Benefits)

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17 pages, 1627 KiB

Open AccessArticle

Effects of Physiological Doses of Resveratrol and Quercetin on Glucose Metabolism in Primary Myotubes

by Itziar Eseberri, Claire Laurens, Jonatan Miranda, Katie Louche, Arrate Lasa, Cedric Moro and Maria P. Portillo

Int. J. Mol. Sci. 2021, 22(3), 1384; https://doi.org/10.3390/ijms22031384 - 30 Jan 2021

Cited by 11 | Viewed by 2739

Abstract

Phenolic compounds have emerged in recent years as an option to face insulin resistance and diabetes. The central aim of this study was: (1) to demonstrate that physiological doses of resveratrol (RSV) or quercetin (Q) can influence glucose metabolism in human myotubes, (2) to establish whether AMP-activated protein kinase (AMPK) and protein kinase B –PKB- (Akt) pathways are involved in this effect. In addition, the effects of these polyphenols on mitochondrial biogenesis and fatty acid oxidation were analysed. Myotubes from healthy donors were cultured for 24 h with either 0.1 μM of RSV or with 10 μM of Q. Glucose metabolism, such as glycogen synthesis, glucose oxidation, and lactate production, were measured with D[U-¹⁴C]glucose. β-oxidation using [1–¹⁴C]palmitate as well as the expression of key metabolic genes and proteins by Real Time PCR and Western blot were also assessed. Although RSV and Q increased pgc1α expression, they did not significantly change either glucose oxidation or β-oxidation. Q increased AMPK, insulin receptor substrate 1 (IRS-1), and AS160 phosphorylation in basal conditions and glycogen synthase kinase 3 (GSK3β) in insulin-stimulated conditions. RSV tended to increase the phosphorylation rates of AMPK and GSK3β. Both of the polyphenols increased insulin-stimulated glycogen synthesis and reduced lactate production in human myotubes. Thus, physiological doses of RSV or Q may exhibit anti-diabetic actions in human myotubes. Full article

(This article belongs to the Special Issue Bioactive Molecules of Natural Origin: Mechanisms of Action Related to Health Risks and Benefits)

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Review

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12 pages, 616 KiB

Open AccessReview

Essential Oil-Based Bioherbicides: Human Health Risks Analysis

by Chloë Maes, Jeroen Meersmans, Laurence Lins, Sandrine Bouquillon and Marie-Laure Fauconnier

Int. J. Mol. Sci. 2021, 22(17), 9396; https://doi.org/10.3390/ijms22179396 - 30 Aug 2021

Cited by 18 | Viewed by 3909

Abstract

In recent years, the development of new bio-based products for biocontrol has been gaining importance as it contributes to reducing the use of synthetic herbicides in agriculture. Conventional herbicides (i.e., the ones with synthetic molecules) can lead to adverse effects such as human diseases (cancers, neurodegenerative diseases, reproductive perturbations, etc.) but also to disturbing the environment because of their drift in the air, transport throughout aquatic systems and persistence across different environments. The use of natural molecules seems to be a very good alternative for maintaining productive agriculture but without the negative side effects of synthetic herbicides. In this context, essential oils and their components are increasingly studied in order to produce several categories of biopesticides thanks to their well-known biocidal activities. However, these molecules can also be potentially hazardous to humans and the environment. This article reviews the state of the literature and regulations with regard to the potential risks related to the use of essential oils as bioherbicides in agricultural and horticultural applications. Full article

(This article belongs to the Special Issue Bioactive Molecules of Natural Origin: Mechanisms of Action Related to Health Risks and Benefits)

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33 pages, 8456 KiB

Open AccessReview

Current Perspectives on the Physiological Activities of Fermented Soybean-Derived Cheonggukjang

by Il-Sup Kim, Cher-Won Hwang, Woong-Suk Yang and Cheorl-Ho Kim

Int. J. Mol. Sci. 2021, 22(11), 5746; https://doi.org/10.3390/ijms22115746 - 27 May 2021

Cited by 40 | Viewed by 6319

Abstract

Cheonggukjang (CGJ, fermented soybean paste), a traditional Korean fermented dish, has recently emerged as a functional food that improves blood circulation and intestinal regulation. Considering that excessive consumption of refined salt is associated with increased incidence of gastric cancer, high blood pressure, and stroke in Koreans, consuming CGJ may be desirable, as it can be made without salt, unlike other pastes. Soybeans in CGJ are fermented by Bacillus strains (B. subtilis or B. licheniformis), Lactobacillus spp., Leuconostoc spp., and Enterococcus faecium, which weaken the activity of putrefactive bacteria in the intestines, act as antibacterial agents against pathogens, and facilitate the excretion of harmful substances. Studies on CGJ have either focused on improving product quality or evaluating the bioactive substances contained in CGJ. The fermentation process of CGJ results in the production of enzymes and various physiologically active substances that are not found in raw soybeans, including dietary fiber, phospholipids, isoflavones (e.g., genistein and daidzein), phenolic acids, saponins, trypsin inhibitors, and phytic acids. These components prevent atherosclerosis, oxidative stress-mediated heart disease and inflammation, obesity, diabetes, senile dementia, cancer (e.g., breast and lung), and osteoporosis. They have also been shown to have thrombolytic, blood pressure-lowering, lipid-lowering, antimutagenic, immunostimulatory, anti-allergic, antibacterial, anti-atopic dermatitis, anti-androgenetic alopecia, and anti-asthmatic activities, as well as skin improvement properties. In this review, we examined the physiological activities of CGJ and confirmed its potential as a functional food. Full article

(This article belongs to the Special Issue Bioactive Molecules of Natural Origin: Mechanisms of Action Related to Health Risks and Benefits)

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28 pages, 1050 KiB

Open AccessReview

Influence of Trace Elements on Neurodegenerative Diseases of The Eye—The Glaucoma Model

by Agnieszka Kamińska, Giovanni Luca Romano, Robert Rejdak, Sandrine Zweifel, Michal Fiedorowicz, Magdalena Rejdak, Anahita Bajka, Rosario Amato, Claudio Bucolo, Teresio Avitabile, Filippo Drago and Mario Damiano Toro

Int. J. Mol. Sci. 2021, 22(9), 4323; https://doi.org/10.3390/ijms22094323 - 21 Apr 2021

Cited by 38 | Viewed by 4806

Abstract

Glaucoma is a heterogeneous group of chronic neurodegenerative disorders characterized by a relatively selective, progressive damage to the retinal ganglion cells (RGCs) and their axons, which leads to axon loss and visual field alterations. To date, many studies have shown the role of various elements, mainly metals, in maintaining the balance of prooxidative and antioxidative processes, regulation of fluid and ion flow through cell membranes of the ocular tissues. Based on the earlier and current research results, their relationship with the development and progression of glaucoma seems obvious and is increasingly appreciated. In this review, we aimed to summarize the current evidence on the role of trace elements in the pathogenesis and prevention of glaucomatous diseases. Special attention is also paid to the genetic background associated with glaucoma-related abnormalities of physiological processes that regulate or involve the ions of elements considered as trace elements necessary for the functioning of the cells. Full article

(This article belongs to the Special Issue Bioactive Molecules of Natural Origin: Mechanisms of Action Related to Health Risks and Benefits)

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31 pages, 1376 KiB

Open AccessReview

Maternal Reproductive Toxicity of Some Essential Oils and Their Constituents

by Noura S. Dosoky and William N. Setzer

Int. J. Mol. Sci. 2021, 22(5), 2380; https://doi.org/10.3390/ijms22052380 - 27 Feb 2021

Cited by 53 | Viewed by 16481

Abstract

Even though several plants can improve the female reproductive function, the use of herbs, herbal preparations, or essential oils during pregnancy is questionable. This review is focused on the effects of some essential oils and their constituents on the female reproductive system during pregnancy and on the development of the fetus. The major concerns include causing abortion, reproductive hormone modulation, maternal toxicity, teratogenicity, and embryo-fetotoxicity. This work summarizes the important studies on the reproductive effects of essential oil constituents anethole, apiole, citral, camphor, thymoquinone, trans-sabinyl acetate, methyl salicylate, thujone, pulegone, β-elemene, β-eudesmol, and costus lactone, among others. Full article

(This article belongs to the Special Issue Bioactive Molecules of Natural Origin: Mechanisms of Action Related to Health Risks and Benefits)

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16 pages, 712 KiB

Open AccessReview

Adjunctive Nutraceutical Therapies for COVID-19

by Lalita Subedi, Stephanie Tchen, Bhakta Prasad Gaire, Bingren Hu and Kurt Hu

Int. J. Mol. Sci. 2021, 22(4), 1963; https://doi.org/10.3390/ijms22041963 - 16 Feb 2021

Cited by 41 | Viewed by 5592

Abstract

The novel coronavirus, severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2/COVID-19), is a worldwide pandemic, as declared by the World Health Organization (WHO). It is a respiratory virus that infects people of all ages. Although it may present with mild to no symptoms in most patients, those who are older, immunocompromised, or with multiple comorbidities may present with severe and life-threatening infections. Throughout history, nutraceuticals, such as a variety of phytochemicals from medicinal plants and dietary supplements, have been used as adjunct therapies for many disease conditions, including viral infections. Appropriate use of these adjunct therapies with antiviral proprieties may be beneficial in the treatment and/or prophylaxis of COVID-19. In this review, we provide a comprehensive summary of nutraceuticals, such as vitamins C, D, E, zinc, melatonin, and other phytochemicals and function foods. These nutraceuticals may have potential therapeutic efficacies in fighting the threat of the SARS-CoV-2/COVID-19 pandemic. Full article

(This article belongs to the Special Issue Bioactive Molecules of Natural Origin: Mechanisms of Action Related to Health Risks and Benefits)

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23 pages, 4433 KiB

Open AccessReview

Bioactive Alkaloids from Genus Aspergillus: Mechanistic Interpretation of Their Antimicrobial and Potential SARS-CoV-2 Inhibitory Activity Using Molecular Modelling

by Fadia S. Youssef, Elham Alshammari and Mohamed L. Ashour

Int. J. Mol. Sci. 2021, 22(4), 1866; https://doi.org/10.3390/ijms22041866 - 13 Feb 2021

Cited by 39 | Viewed by 3576

Abstract

Genus Aspergillus represents a widely spread genus of fungi that is highly popular for possessing potent medicinal potential comprising mainly antimicrobial, cytotoxic and antioxidant properties. They are highly attributed to its richness by alkaloids, terpenes, steroids and polyketons. This review aimed to comprehensively explore the diverse alkaloids isolated and identified from different species of genus Aspergillus that were found to be associated with different marine organisms regarding their chemistry and biology. Around 174 alkaloid metabolites were reported, 66 of which showed important biological activities with respect to the tested biological activities mainly comprising antiviral, antibacterial, antifungal, cytotoxic, antioxidant and antifouling activities. Besides, in silico studies on different microbial proteins comprising DNA-gyrase, topoisomerase IV, dihydrofolate reductase, transcriptional regulator TcaR (protein), and aminoglycoside nucleotidyl transferase were done for sixteen alkaloids that showed anti-infective potential for better mechanistic interpretation of their probable mode of action. The inhibitory potential of compounds vs. Angiotensin-Converting Enzyme 2 (ACE2) as an important therapeutic target combating COVID-19 infection and its complication was also examined using molecular docking. Fumigatoside E showed the best fitting within the active sites of all the examined proteins. Thus, Aspergillus species isolated from marine organisms could afford bioactive entities combating infectious diseases. Full article

(This article belongs to the Special Issue Bioactive Molecules of Natural Origin: Mechanisms of Action Related to Health Risks and Benefits)

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27 pages, 1788 KiB

Open AccessReview

A Recent Insight Regarding the Phytochemistry and Bioactivity of Origanum vulgare L. Essential Oil

by Adelina Lombrea, Diana Antal, Florina Ardelean, Stefana Avram, Ioana Zinuca Pavel, Lavinia Vlaia, Ana-Maria Mut, Zorita Diaconeasa, Cristina Adriana Dehelean, Codruta Soica and Corina Danciu

Int. J. Mol. Sci. 2020, 21(24), 9653; https://doi.org/10.3390/ijms21249653 - 17 Dec 2020

Cited by 86 | Viewed by 13049

Abstract

Origanum vulgare L. is a widely used aromatic plant, especially due to its content in essential oil, mainly rich in carvacrol and thymol. The ethnopharmacological uses of Origanum vulgare L. essential oil (OEO) comprise digestive, respiratory, or dermatological disorders. The review focuses on the increasing number of recent studies investigating several biological activities of OEO. The bioactivities are in tight relation to the phytochemical profile of the essential oil, and also depend on taxonomic, climatic, and geographical characteristics of the plant material. The antibacterial, antifungal, antiparasitic, antioxidant, anti-inflammatory, antitumor, skin disorders beneficial effects, next to antihyperglycemic and anti-Alzheimer activities were reported and confirmed in multiple studies. Moreover, recent studies indicate a positive impact on skin disorders of OEO formulated as nanocarrier systems in order to improve its bioavailability and, thus, enhancing its therapeutic benefits. The review brings an up to date regarding the phytochemistry and bioactivity of Origanum vulgare L. essential oil, underlining also the most successful pharmaceutical formulation used for skin disorders. Full article

(This article belongs to the Special Issue Bioactive Molecules of Natural Origin: Mechanisms of Action Related to Health Risks and Benefits)

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