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Bioactive Molecules of Natural Origin: Mechanisms of Action Related to Health Risks and Benefits 2.0

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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 (30 April 2023) | Viewed by 25754

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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
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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
Guest Editor

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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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Related Special Issue

Bioactive Molecules of Natural Origin: Mechanisms of Action Related to Health Risks and Benefits—3rd Edition in International Journal of Molecular Sciences (3 articles)

Published Papers (11 papers)

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Research

Jump to: Review

19 pages, 3992 KiB

Open AccessArticle

Tannic Acid Mitigates Rotenone-Induced Dopaminergic Neurodegeneration by Inhibiting Inflammation, Oxidative Stress, Apoptosis, and Glutamate Toxicity in Rats

by Sheikh Azimullah, Mohamed Fizur Nagoor Meeran, Khatija Ayoob, Seenipandi Arunachalam, Shreesh Ojha and Rami Beiram

Int. J. Mol. Sci. 2023, 24(12), 9876; https://doi.org/10.3390/ijms24129876 - 8 Jun 2023

Cited by 6 | Viewed by 2213

Abstract

Parkinson’s disease (PD), a movement disorder, is a neurodegenerative disease characterized by the degeneration of dopaminergic neurons in the substantia nigra pars compacta (SNpc) region of the brain. The etiopathogenesis of PD involves increased oxidative stress, augmented inflammation, impaired autophagy, accumulation of α-synuclein, and α-Glutamate neurotoxicity. The treatment of PD is limited and there is a lack of agents to prevent the disease/delay its progression and inhibit the onset of pathogenic events. Many agents of natural and synthetic origin have been investigated employing experimental models of PD, mimicking human PD. In the present study, we assessed the effect of tannic acid (TA) in a rodent model of PD induced by rotenone (ROT), a pesticide and an environmental toxin of natural origin reported to cause PD in agricultural workers and farmers. Rotenone (2.5 mg/kg/day, i.p.) was administered for 28 days, and TA (50 mg/kg, orally) was administered 30 min before ROT injections. The study results showed an increase in oxidative stress, as evidenced by the depletion of endogenous antioxidants and enhanced formation of lipid peroxidation products, along with the onset of inflammation following a rise in inflammatory mediators and proinflammatory cytokines. ROT injections have also augmented apoptosis, impaired autophagy, promoted synaptic loss, and perturbed α-Glutamate hyperpolarization in rats. ROT injections also induced the loss of dopaminergic neurons subsequent to the activation of microglia and astrocytes. However, TA treatment was observed to reduce lipid peroxidation, prevent loss of endogenous antioxidants, and inhibit the release and synthesis of proinflammatory cytokines, in addition to the favorable modulation of apoptosis and autophagic pathways. Treatment with TA also attenuated the activation of microglia and astrocytes along with preservation of dopaminergic neurons following reduced loss of dopaminergic neurodegeneration and inhibition of synaptic loss and α-Glutamate cytotoxicity. The effects of TA in ROT-induced PD were attributed to the antioxidant, anti-inflammatory, antiapoptotic, and neurogenesis properties. Based on the present study findings, it can be concluded that TA may be a promising novel therapeutic candidate for pharmaceutical as well as nutraceutical development owing to its neuroprotective properties in PD. Further regulatory toxicology and translational studies are suggested for future clinical usage in PD. Full article

(This article belongs to the Special Issue Bioactive Molecules of Natural Origin: Mechanisms of Action Related to Health Risks and Benefits 2.0)

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15 pages, 4367 KiB

Open AccessArticle

Digested Cinnamon (Cinnamomum verum J. Presl) Bark Extract Modulates Claudin-2 Gene Expression and Protein Levels under TNFα/IL-1β Inflammatory Stimulus

by Elena Lonati, Gessica Sala, Paolo Corbetta, Stefania Pagliari, Emanuela Cazzaniga, Laura Botto, Pierangela Rovellini, Ilaria Bruni, Paola Palestini and Alessandra Bulbarelli

Int. J. Mol. Sci. 2023, 24(11), 9201; https://doi.org/10.3390/ijms24119201 - 24 May 2023

Cited by 7 | Viewed by 2018

Abstract

Epigenetic changes, host–gut microbiota interactions, and environmental factors contribute to inflammatory bowel disease (IBD) onset and progression. A healthy lifestyle may help to slow down the chronic or remitting/relapsing intestinal tract inflammation characteristic of IBD. In this scenario, the employment of a nutritional strategy to prevent the onset or supplement disease therapies included functional food consumption. Its formulation consists of the addition of a phytoextract enriched in bioactive molecules. A good candidate as an ingredient is the Cinnamon verum aqueous extract. Indeed, this extract, subjected to a process of gastrointestinal digestion simulation (INFOGEST), exhibits beneficial antioxidant and anti-inflammatory properties in an in vitro model of the inflamed intestinal barrier. Here, we deepen the study of the mechanisms related to the effect of digested cinnamon extract pre-treatment, showing a correlation between transepithelial electrical resistance (TEER) decrement and alterations in claudin-2 expression under Tumor necrosis factor-α/Interleukin-1β (TNF-α/IL-1) β cytokine administration. Our results show that pre-treatment with cinnamon extract prevents TEER loss by claudin-2 protein level regulation, influencing both gene transcription and autophagy-mediated degradation. Hence, cinnamon polyphenols and their metabolites probably work as mediators in gene regulation and receptor/pathway activation, leading to an adaptive response against renewed insults. Full article

(This article belongs to the Special Issue Bioactive Molecules of Natural Origin: Mechanisms of Action Related to Health Risks and Benefits 2.0)

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18 pages, 3835 KiB

Open AccessArticle

The Effect of Epimedium Isopentenyl Flavonoids on the Broiler Gut Health Using Microbiomic and Metabolomic Analyses

by Jiaqi Zhang, Qingyu Zhao, Yuchang Qin, Wei Si, Huiyan Zhang and Junmin Zhang

Int. J. Mol. Sci. 2023, 24(8), 7646; https://doi.org/10.3390/ijms24087646 - 21 Apr 2023

Cited by 4 | Viewed by 2277

Abstract

Epimedium (EM), also known as barrenwort, is a traditional medicinal plant rich in isopentenyl flavonols, which have beneficial biological activities and can improve human and animal health, but its mechanism is still unclear. In this study, ultra-high-performance liquid chromatography/quadrupole-time-of-flight-mass spectrometry (UHPLC-Q-TOF/MS) and ultra-high-performance liquid chromatography triple-quadrupole mass spectrometry (UHPLC-QqQ-MS/MS) were used to analyse the main components of EM, and isopentenyl flavonols such as Epimedin A, B, and C as well as Icariin were the major components of EM. Meanwhile, broilers were selected as model animals to illuminate the mechanism of Epimedium isopentenyl flavonols (EMIE) on gut health. The results showed that supplementation with 200 mg/kg EM improved the immune response, increased cecum short-chain fatty acids (SCFAs) and lactate concentrations, and improved nutrient digestibility in broilers. In addition, 16S rRNA sequencing showed that EMIE altered the composition of cecal microbiome, increasing the relative abundance of beneficial bacteria (Candidatus Soleaferrea and Lachbospiraceae NC2004 group and Butyricioccus) and reducing that of harmful bacteria (UBA1819, Negativibacillus, and Eisenbergiella). Metabolomic analysis identified 48 differential metabolites, of which Erosnin and Tyrosyl-Tryptophan were identified as core biomarkers. Erosnin and tyrosyl-tryptophan are potential biomarkers to evaluate the effects of EMIE. This shows that EMIE may regulate the cecum microbiota through Butyricicoccus, with changes in the relative abundance of the genera Eisenbergiella and Un. Peptostreptococcaceae affecting the serum metabolite levels of the host. EMIE is an excellent health product, and dietary isopentenyl flavonols, as bioactive components, can improve health by altering the microbiota structure and the plasma metabolite profiles. This study provides the scientific basis for the future application of EM in diets. Full article

(This article belongs to the Special Issue Bioactive Molecules of Natural Origin: Mechanisms of Action Related to Health Risks and Benefits 2.0)

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17 pages, 10397 KiB

Open AccessArticle

Preliminary Approaches to Cosmeceuticals Emulsions Based on N-ProlylPalmitoyl Tripeptide-56 Acetat-Bakuchiol Complex Intended to Combat Skin Oxidative Stress

by Ana Simona Barna, Claudia Maxim, Adriana Trifan, Alexandra Cristina Blaga, Ramona Cimpoesu, Delia Turcov and Daniela Suteu

Int. J. Mol. Sci. 2023, 24(8), 7004; https://doi.org/10.3390/ijms24087004 - 10 Apr 2023

Cited by 3 | Viewed by 2253

Abstract

This study focuses on the development of a performant formulation for O/W dermato-cosmetic emulsions, which can be incorporated into novel dermato-cosmetic products or used as such. The O/W dermato-cosmetic emulsions contain an active complex based on a plant-derived monoterpene phenol, bakuchiol (BAK) and a signaling peptide named n-prolyl palmitoyl tripeptide-56 acetate (TPA). As a dispersed phase, we used a mix of vegetable oils, and as a continuous phase, Rosa damascena hydrosol was employed. Three emulsions containing different concentrations of the active complex were formulated (0.5% BAK + 0.5% TPA = E.1.1., 1% BAK + 1%TPA = E.1.2., 1% BAK + 2% TPA = E.1.3.). Stability testing was performed through sensory analysis, stability after centrifugation, conductivity and optical microscopy. A preliminary in vitro study regarding the diffusion ability of antioxidants through chicken skin was also undertaken. DPPH and ABTS assays were used to highlight the optimal concentration and combination in the formulation in terms of antioxidant properties and safety level of the active complex (BAK/TPA). Our results showed that the active complex used for preparing emulsions with BAK and TPA showed good antioxidant activity and is suitable for obtaining topical products with potential antiaging effects. Full article

(This article belongs to the Special Issue Bioactive Molecules of Natural Origin: Mechanisms of Action Related to Health Risks and Benefits 2.0)

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9 pages, 1273 KiB

Open AccessCommunication

Collagen-Derived Dipeptides and Amino Acids Have Immunomodulatory Effects in M1-Differentiated RAW264.7 Cells and PBMC

by Takaki Tominaga, Jiapeng Huang, Shuo Wang, Miwa Noguchi, Yishan Tong, Momoko Asano-Oritani and Katsuhiko Suzuki

Int. J. Mol. Sci. 2023, 24(8), 6925; https://doi.org/10.3390/ijms24086925 - 8 Apr 2023

Cited by 2 | Viewed by 1833

Abstract

A number of food components, such as polyphenols and phytonutrients, have immunomodulatory effects. Collagen has various bioactivities, such as antioxidative effects, the promotion of wound healing, and relieving symptoms of bone/joint disease. Collagen is digested into dipeptides and amino acids in the gastrointestinal tract and subsequently absorbed. However, the difference in immunomodulatory effects between collagen-derived dipeptides and amino acids is unknown. To investigate such differences, we incubated M1 macrophages or peripheral blood mononuclear cells (PBMC) with collagen-derived dipeptides (hydroxyproline-glycine (Hyp-Gly) and proline-hydroxyproline (Pro-Hyp)) and amino acids (proline (Pro), hydroxyproline (Hyp), and glycine (Gly)). We first investigated the dose dependency of Hyp-Gly on cytokine secretion. Hyp-Gly modulates cytokine secretion from M1 macrophages at 100 µM, but not at 10 µM and 1 µM. We then compared immunomodulatory effects between dipeptides and mixtures of amino acids on M1 macrophages and PBMC. There was, however, no difference in cytokine secretion between dipeptides and their respective amino acids. We conclude that collagen-derived dipeptides and amino acids have immunomodulatory effects on M1-differentiated RAW264.7 cells and PBMC and that there is no difference in the immunomodulatory effects between dipeptides and amino acids. Full article

(This article belongs to the Special Issue Bioactive Molecules of Natural Origin: Mechanisms of Action Related to Health Risks and Benefits 2.0)

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18 pages, 5156 KiB

Open AccessArticle

Anti-Melanogenesis Effects of a Cyclic Peptide Derived from Flaxseed via Inhibition of CREB Pathway

by Ji Hye Yoon, Won Young Jang, Sang Hee Park, Han Gyung Kim, Youn Young Shim, Martin J. T. Reaney and Jae Youl Cho

Int. J. Mol. Sci. 2023, 24(1), 536; https://doi.org/10.3390/ijms24010536 - 28 Dec 2022

Cited by 2 | Viewed by 2716

Abstract

Linosorbs (Los) are cyclic peptides from flaxseed oil composed of the LO mixture (LOMIX). The activity of LO has been reported as being anti-cancer and anti-inflammatory. However, the study of skin protection has still not proceeded. In particular, there are poorly understood mechanisms of melanogenesis to LO. Therefore, we investigated the anti-melanogenesis effects of LOMIX and LO, and its activity was examined in mouse melanoma cell lines. The treatment of LOMIX (50 and 100 μg/mL) and LO (6.25–50 μM) suppressed melanin secretion and synthesis, which were 3-fold increased, in a dose-dependent manner, up to 95%. In particular, [1–9-NαC]-linusorb B3 (LO1) and [1-9-NαC]-linusorb B2 (LO2) treatment (12.5 and 25 μM) highly suppressed the synthesis of melanin in B16F10 cell lines up to 90%, without toxicity. LOMIX and LOs decreased the 2- or 3-fold increased mRNA levels, including the microphthalmia-associated transcription factor (MITF), Tyrosinase, tyrosinase-related protein 1 (TYRP1), and tyrosinase-related protein 2 (TYRP2) at the highest concentration (25 μM). Moreover, the treatment of 25 μM LO1 and LO2 inhibited the expression of MITF and phosphorylation of upper regulatory proteins such as CREB and PKA. Taken together, these results suggested that LOMIX and its individual LO could inhibit melanin synthesis via downregulating the CREB-dependent signaling pathways, and it could be used for novel therapeutic materials in hyperpigmentation. Full article

(This article belongs to the Special Issue Bioactive Molecules of Natural Origin: Mechanisms of Action Related to Health Risks and Benefits 2.0)

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17 pages, 5458 KiB

Open AccessArticle

Prunus spinosa Extract Sensitized HCT116 Spheroids to 5-Fluorouracil Toxicity, Inhibiting Autophagy

by Maria Condello, Rosa Vona and Stefania Meschini

Int. J. Mol. Sci. 2022, 23(24), 16098; https://doi.org/10.3390/ijms232416098 - 17 Dec 2022

Cited by 1 | Viewed by 1912

Abstract

Autophagy is a lysosomal degradation and recycling process involved in tumor progression and drug resistance. The aim of this work was to inhibit autophagy and increase apoptosis in a 3D model of human colorectal cancer by combined treatment with our patented natural product Prunus spinosa + nutraceutical activator complex (PsT + NAC^®) and 5-fluorouracil (5-FU). By means of cytotoxic evaluation (MTT assay), cytofluorimetric analysis, light and fluorescence microscopy investigation and Western blotting evaluation of the molecular pathway PI3/AKT/mTOR, Caspase-9, Caspase-3, Beclin1, p62 and LC3, we demonstrated that the combination PsT + NAC^® and 5-FU significantly reduces autophagy by increasing the apoptotic phenomenon. These results demonstrate the importance of using non-toxic natural compounds to improve the therapeutic efficacy and reduce the side effects induced by conventional drugs in human colon cancer. Full article

(This article belongs to the Special Issue Bioactive Molecules of Natural Origin: Mechanisms of Action Related to Health Risks and Benefits 2.0)

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24 pages, 1916 KiB

Open AccessArticle

Molecular Characterization of Thymus capitellatus Extracts and Their Antioxidant, Neuroprotective and Anti-Proliferative Activities

by Carlos Martins-Gomes, Jan Steck, Judith Keller, Mirko Bunzel, Fernando M. Nunes and Amélia M. Silva

Int. J. Mol. Sci. 2022, 23(23), 15187; https://doi.org/10.3390/ijms232315187 - 2 Dec 2022

Cited by 4 | Viewed by 1969

Abstract

Thymus capitellatus Hoffmanns & Link is an endemic species of the Iberian Peninsula listed as near-threatened, due to its restricted geographical distribution, occurring mainly in Portugal’s mainland. In this work, we detail for the first time T. capitellatus extracts’ phytochemical composition, as well as an evaluation of bioactivities to point out potential health benefits. Aqueous decoction (AD) and hydroethanolic (HE) extracts were obtained, both rich in flavonoids. However, quercetin-(?)-O-hexoside was identified as the main compound in T. capitellatus HE extract, while the phenolic acid rosmarinic acid was the main component of AD extracts. In addition, HE extract presents significant amounts of salvianolic acids and of the terpenoids oleanolic and ursolic acid. Both extracts showed antioxidant activity, evaluated by their capacity to scavenge ABTS and superoxide radicals, as well as an ability to prevent lipid peroxidation. AD extracts were also effective in scavenging hydroxyl and nitric oxide radicals. As potential functional foods, T. capitellatus extracts presented neuroprotective and anti-diabetic activity, in addition to time- and dose-dependent anti-proliferative activity against Caco-2 (colorectal adenocarcinoma) and HepG2 (hepatic carcinoma) cells. HE extract presented higher cytotoxicity than AD extract, and HepG2 cells were more resistant than Caco-2 cells. After 24 h exposure to HE extract, the IC₅₀ values were 330 μg/mL and 447 μg/mL for Caco-2 and HepG2 cells, respectively. T. capitellatus has potential as a functional food or as a source of bioactive molecules. These results also highlight the need to preserve species with as yet unknown molecular compositions and potential medicinal applications. Full article

(This article belongs to the Special Issue Bioactive Molecules of Natural Origin: Mechanisms of Action Related to Health Risks and Benefits 2.0)

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11 pages, 1061 KiB

Open AccessCommunication

Ex Vivo Antioxidant and Cholinesterase Inhibiting Effects of a Novel Galantamine–Curcumin Hybrid on Scopolamine-Induced Neurotoxicity in Mice

by Rumyana Simeonova, Mariyana Atanasova, Georgi Stavrakov, Irena Philipova and Irini Doytchinova

Int. J. Mol. Sci. 2022, 23(23), 14843; https://doi.org/10.3390/ijms232314843 - 27 Nov 2022

Cited by 5 | Viewed by 1524

Abstract

Oxidative stress is an essential factor in the development and progression of Alzheimer’s disease (AD). An excessive amount of reactive oxygen species (ROS) induces the peroxidation of lipid membranes, reduces the activity of antioxidant enzymes and causes neurotoxicity. In this study, we investigated the antioxidant and cholinesterase inhibitory potential of a novel galantamine–curcumin hybrid, named 4b, administered orally in two doses (2.5 mg/kg and 5 mg/kg) in scopolamine (SC)-induced neurotoxicity in mice. To evaluate the effects of 4b, we used galantamine (GAL) (3 mg/kg) and curcumin (CCN) (25 mg/kg) as positive controls. Ex vivo experiments on mouse brains showed that the higher dose of 4b (5 mg/kg) increased reduced glutathione (GSH) levels by 46%, catalase (CAT) and superoxide dismutase (SOD) activity by 57%, and glutathione peroxidase (GPx) activity by 108%, compared with the SC-treated group. At the same time, 4b (5 mg/kg) significantly reduced the brain malondialdehyde (MDA) level by 31% and acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) activities by 40% and 30%, respectively, relative to the SC-impaired group. The results showed that 4b acted as an antioxidant agent and brain protector, making it promising for further experimental research in the field of neurodegenerative diseases. Full article

(This article belongs to the Special Issue Bioactive Molecules of Natural Origin: Mechanisms of Action Related to Health Risks and Benefits 2.0)

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Review

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24 pages, 941 KiB

Open AccessReview

Impact of Volatile Organic Compounds on the Growth of Aspergillus flavus and Related Aflatoxin B1 Production: A Review

by Laurie Josselin, Caroline De Clerck, Marthe De Boevre, Antonio Moretti and Marie-Laure Fauconnier

Int. J. Mol. Sci. 2022, 23(24), 15557; https://doi.org/10.3390/ijms232415557 - 8 Dec 2022

Cited by 8 | Viewed by 2785

Abstract

Volatile organic compounds (VOCs) are secondary metabolites of varied chemical nature that are emitted by living beings and participate in their interactions. In addition, some VOCs called bioactive VOCs cause changes in the metabolism of other living species that share the same environment. In recent years, knowledge on VOCs emitted by Aspergillus flavus, the main species producing aflatoxin B1 (AFB1), a highly harmful mycotoxin, has increased. This review presents an overview of all VOCs identified as a result of A. flavus toxigenic (AFB1-producing) and non-toxigenic (non AFB1-producing) strains growth on different substrates, and the factors influencing their emissions. We also included all bioactive VOCs, mixes of VOCs or volatolomes of microbial species that impact A. flavus growth and/or related AFB1 production. The modes of action of VOCs impacting the fungus development are presented. Finally, the potential applications of VOCs as biocontrol agents in the context of mycotoxin control are discussed. Full article

(This article belongs to the Special Issue Bioactive Molecules of Natural Origin: Mechanisms of Action Related to Health Risks and Benefits 2.0)

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28 pages, 8462 KiB

Open AccessReview

Impact of Reactive Species on Amino Acids—Biological Relevance in Proteins and Induced Pathologies

by Celia María Curieses Andrés, José Manuel Pérez de la Lastra, Celia Andrés Juan, Francisco J. Plou and Eduardo Pérez-Lebeña

Int. J. Mol. Sci. 2022, 23(22), 14049; https://doi.org/10.3390/ijms232214049 - 14 Nov 2022

Cited by 25 | Viewed by 3042

Abstract

This review examines the impact of reactive species RS (of oxygen ROS, nitrogen RNS and halogens RHS) on various amino acids, analyzed from a reactive point of view of how during these reactions, the molecules are hydroxylated, nitrated, or halogenated such that they can lose their capacity to form part of the proteins or peptides, and can lose their function. The reactions of the RS with several amino acids are described, and an attempt was made to review and explain the chemical mechanisms of the formation of the hydroxylated, nitrated, and halogenated derivatives. One aim of this work is to provide a theoretical analysis of the amino acids and derivatives compounds in the possible positions. Tyrosine, methionine, cysteine, and tryptophan can react with the harmful peroxynitrite or ^•OH and ^•NO₂ radicals and glycine, serine, alanine, valine, arginine, lysine, tyrosine, histidine, cysteine, methionine, cystine, tryptophan, glutamine and asparagine can react with hypochlorous acid HOCl. These theoretical results may help to explain the loss of function of proteins subjected to these three types of reactive stresses. We hope that this work can help to assess the potential damage that reactive species can cause to free amino acids or the corresponding residues when they are part of peptides and proteins. Full article

(This article belongs to the Special Issue Bioactive Molecules of Natural Origin: Mechanisms of Action Related to Health Risks and Benefits 2.0)

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