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A special issue of Metabolites (ISSN 2218-1989). This special issue belongs to the section "Plant Metabolism".

Deadline for manuscript submissions: closed (30 June 2023) | Viewed by 23059

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Dr. Alberto Jorge Oliveira Lopes

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Graduate Program in Chemistry, Federal Institute of Education, Science, and Technology of Maranhão, São Luis 65030-005, MA, Brazil
Interests: medicinal chemistry; natural products; bioinformatics; biological activity
Special Issues, Collections and Topics in MDPI journals

Dr. Adalberto Alves Pereira-Filho

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Laboratório de Fisiologia de Insetos Hematófagos, Departamento de Parasitologia/ICB, Universidade Federal de Minas Gerais, Belo Horizonte, Brazil
Interests: plant extracts; essential oils; natural products; PCR; medical entomology; protozoans; mollusks

Special Issue Information

Dear Colleagues,

Since the early days of human civilization, human beings have sought relief and cures for their ailments from natural products (NPs). Currently, the metabolites present in NP are still the main source of discovery and development of new drugs for the treatment of various human and animal diseases.

It is estimated that about 35% of all known drugs are directly or indirectly derived from natural products and that 60% to 75% of the drugs currently used for the treatment of neoplasms and infectious diseases are derived from natural products.

Many NPs are reported to have medicinal properties; however, scientific evidence about the efficacy of most of these is limited, despite their widespread use. The scientific evaluation of NP efficacy and the assessment of possible side effects are required prior to their adoption as a new definitive method of treatment. For most NPs with bioactive properties, little is known about which compounds are involved, because, in general, their chemical composition is complex, which makes it difficult to fully identify these metabolites. Thus, studies on this subject are essential.

This Special Issue accepts unpublished experimental studies that explore natural products (which may be of vegetable, marine, animal, or microbial origin), with a complete chemical characterization, as well as studies on isolated/synthetic metabolites evaluated as an alternative for the prevention and/or treatment of diseases, whether inflammatory, metabolic, infectious, parasitic or neoplasms. It is recommended that authors provide as much scientific evidence as possible to support the use of the proposed NP, indicating the proposed mode of action. Studies on the biological activity of NP without a proper chemical characterization or those with only theoretical data and no experimental evaluation will not be considered. However, review manuscripts are welcome.

Dr. Alberto Jorge Oliveira Lopes
Dr. Adalberto Alves Pereira-Filho
Guest Editors

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Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Metabolites is an international peer-reviewed open access monthly journal published by MDPI.

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Keywords

natural products
bioactive molecules
disease treatment, prevention and prophylaxis
metabolites
molecular and physiological mechanism
new drugs agents
human and animal health
drug discovery
therapeutic properties
medicinal chemistry

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Published Papers (9 papers)

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Research

12 pages, 318 KiB

Open AccessArticle

Thymoquinone Antifungal Activity against Candida glabrata Oral Isolates from Patients in Intensive Care Units—An In Vitro Study

by Noura Nouri, Shahla Roudbar Mohammadi, Justin Beardsley, Peyman Aslani, Fatemeh Ghaffarifar, Maryam Roudbary and Célia Fortuna Rodrigues

Metabolites 2023, 13(4), 580; https://doi.org/10.3390/metabo13040580 - 21 Apr 2023

Cited by 6 | Viewed by 2402

Abstract

The number of Candida spp. infections and drug resistance are dramatically increasing worldwide, particularly among immunosuppressed patients, and it is urgent to find novel compounds with antifungal activity. In this work, the antifungal and antibiofilm activity of thymoquinone (TQ), a key bioactive constituent of black cumin seed Nigella sativa L., was evaluated against Candida glabrata, a WHO ‘high-priority’ pathogen. Then, its effect on the expression of C. glabrata EPA6 and EPA7 genes (related to biofilm adhesion and development, respectively) were analyzed. Swab samples were taken from the oral cavity of 90 hospitalized patients in ICU wards, transferred to sterile falcon tubes, and cultured on Sabouraud Dextrose Agar (SDA) and Chromagar Candida for presumptive identification. Next, a 21-plex PCR was carried out for the confirmation of species level. C. glabrata isolates underwent antifungal drug susceptibility testing against fluconazole (FLZ), itraconazole (ITZ), amphotericin B (AMB), and TQ according to the CLSI microdilution method (M27, A3/S4). Biofilm formation was measured by an MTT assay. EPA6 and EPA7 gene expression was assessed by real-time PCR. From the 90 swab samples, 40 isolates were identified as C. glabrata with the 21-plex PCR. Most isolates were resistant to FLZ (n = 29, 72.5%), whereas 12.5% and 5% were ITZ and AMB resistant, respectively. The minimum inhibitory concentration (MIC₅₀) of TQ against C. glabrata was 50 µg/mL. Importantly, TQ significantly inhibited the biofilm formation of C. glabrata isolates, and EPA6 gene expression was reduced significantly at MIC₅₀ concentration of TQ. TQ seems to have some antifungal, antibiofilm (adhesion) effect on C. glabrata isolates, showing that this plant secondary metabolite is a promising agent to overcome Candida infections, especially oral candidiasis. Full article

(This article belongs to the Special Issue The Natural Products in the Treatment and Prevention of Diseases)

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16 pages, 3093 KiB

Open AccessArticle

Cuminaldehyde Effects in a MIA-Induced Experimental Model Osteoarthritis in Rat Knees

by Sebastião Vieira de Morais, Priscylla Gouveia Mendonça, Cleydlenne Costa Vasconcelos, Paloma Larissa Arruda Lopes, João Batista Santos Garcia, Natalia Tabosa Machado Calzerra, Thyago Moreira de Queiroz, Silvia Tereza de Jesus Rodrigues Moreira Lima, Gyl Eanes Barros Silva, Alberto Jorge Oliveira Lopes, Maria do Socorro de Sousa Cartágenes and Gerson Ricardo de Souza Domingues

Metabolites 2023, 13(3), 397; https://doi.org/10.3390/metabo13030397 - 8 Mar 2023

Cited by 1 | Viewed by 2439

Abstract

Osteoarthritis (OA) is a chronic degenerative disease that has a significant global impact. It is associated with aging and characterized by widespread joint destruction. Cuminaldehyde is a biologically active component of essential oils that has shown promise in the treatment of nociceptive and inflammatory diseases. This study investigated the effects of cuminaldehyde on an experimental model of osteoarthritis induced in rat knees. Cuminaldehyde was found to be as effective as indomethacin in reducing pain in all evaluated tests, including forced walking, functional disability of weight distribution on the legs, and spontaneous pain in animals with osteoarthritis. The knees of animals treated with cuminaldehyde had significantly higher radiographic and histopathological scores than those of animals that did not receive the treatment. Cuminaldehyde also modulated the production of pro-inflammatory cytokines. In vitro assays showed that cuminaldehyde preferentially inhibits COX-2 enzyme activity. In silico studies demonstrated that cuminaldehyde has satisfactory energy affinity parameters with opioid receptors and COX-2. These findings suggest that cuminaldehyde’s anti-inflammatory activity is multifactorial, acting through multiple pathways. Its nociceptive activity occurs via central and peripheral mechanisms. Cuminaldehyde modulates the immune response of the inflammatory process and may be considered a leading compound for the development of new anti-inflammatory and analgesic drugs. Full article

(This article belongs to the Special Issue The Natural Products in the Treatment and Prevention of Diseases)

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16 pages, 1861 KiB

Open AccessArticle

Chemical Characterization and Leishmanicidal Activity In Vitro and In Silico of Natural Products Obtained from Leaves of Vernonanthura brasiliana (L.) H. Rob (Asteraceae)

by Yuri Nascimento Fróes, João Guilherme Nantes Araújo, Joyce Resende dos Santos Gonçalves, Milena de Jesus Marinho Garcia de Oliveira, Gustavo Oliveira Everton, Victor Elias Mouchrek Filho, Maria Raimunda Chagas Silva, Luís Douglas Miranda Silva, Lucilene Amorim Silva, Lídio Gonçalves Lima Neto, Renata Mondêgo de Oliveira, Mylena Andréa Oliveira Torres, Luís Cláudio Nascimento da Silva, Alberto Jorge Oliveira Lopes, Amanda Silva dos Santos Aliança, Cláudia Quintino da Rocha and Joicy Cortez de Sá Sousa

Metabolites 2023, 13(2), 285; https://doi.org/10.3390/metabo13020285 - 16 Feb 2023

Cited by 2 | Viewed by 2051

Abstract

Vernonanthura brasiliana (L.) H. Rob is a medicinal plant used for the treatment of several infections. This study aimed to evaluate the antileishmanial activity of V. brasiliana leaves using in vitro and in silico approaches. The chemical composition of V. brasiliana leaf extract was determined through liquid chromatography-mass spectrometry (LC-MS). The inhibitory activity against Leishmania amazonensis promastigote was evaluated by the MTT method. In silico analysis was performed using Lanosterol 14alpha-demethylase (CYP51) as the target. The toxicity analysis was performed in RAW 264.7 cells and Tenebrio molitor larvae. LC-MS revealed the presence of 14 compounds in V. brasiliana crude extract, including flavonoids, flavones, sesquiterpene lactones, and quinic acids. Eriodictol (ΔGbind = −9.0), luteolin (ΔGbind = −8.7), and apigenin (ΔGbind = −8.6) obtained greater strength of molecular interaction with lanosterol demethylase in the molecular docking study. The hexane fraction of V. brasiliana showed the best leishmanicidal activity against L. amazonensis in vitro (IC₅₀ 12.44 ± 0.875 µg·mL⁻¹) and low cytotoxicity in RAW 264.7 cells (CC₅₀ 314.89 µg·mL⁻¹, SI = 25.30) and T. molitor larvae. However, the hexane fraction and Amphotericin-B had antagonistic interaction (FICI index ≥ 4.0). This study revealed that V. brasiliana and its metabolites are potential sources of lead compounds for drugs for leishmaniasis treatment. Full article

(This article belongs to the Special Issue The Natural Products in the Treatment and Prevention of Diseases)

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10 pages, 2223 KiB

Open AccessArticle

In Vitro Activity of Essential Oils from Piper Species (Piperaceae) against Tachyzoites of Toxoplasma gondii

by Adalberto Alves Pereira Filho, Mariana Maciel Cunha, Mariana Alves Stanton, Lydia Fumiko Yamaguchi, Massuo Jorge Kato and Érica S. Martins-Duarte

Metabolites 2023, 13(1), 95; https://doi.org/10.3390/metabo13010095 - 6 Jan 2023

Cited by 4 | Viewed by 2388

Abstract

Toxoplasmosis is a tropical and neglected disease caused by the parasitic protozoa Toxplasma gondii. Conventional treatment with sulfadiazine and pyrimethamine plus folinic acid, has some drawbacks, such as inefficacy in the chronic phase, toxic side effects, and potential cases of resistance have been observed. In this study, the activity of essential oils (EOs) from three Piper species and their main constituents, including α-Pinene (Piper lindbergii and P. cernuum), β-Pinene (P. cernuum), and dillapiole (P. aduncum), were evaluated against tachyzoites of T. gondii. α-Pinene was more active [(IC₅₀ 0.3265 (0.2958 to 0.3604) μg/mL)] against tachyzoites than P. lindbergii EO [0.8387 (0.6492 to 1.084) μg/mL]. Both α-Pinene and P. lindbergii EO exhibited low cytotoxicity against NHDF cells, with CC₅₀ 41.37 (37.64 to 45.09) µg/mL and 83.80 (75.42 to 91.34) µg/mL, respectively, suggesting they could be of potential use against toxoplasmosis. Full article

(This article belongs to the Special Issue The Natural Products in the Treatment and Prevention of Diseases)

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18 pages, 3054 KiB

Open AccessArticle

Curcumin Decreases Viability and Inhibits Proliferation of Imatinib-Sensitive and Imatinib-Resistant Chronic Myeloid Leukemia Cell Lines

by Esma Bilajac, Lejla Mahmutović, Una Glamočlija, Amar Osmanović, Altijana Hromić-Jahjefendić, Murtaza M. Tambuwala and Mirza Suljagić

Metabolites 2023, 13(1), 58; https://doi.org/10.3390/metabo13010058 - 30 Dec 2022

Cited by 8 | Viewed by 2380

Abstract

Chronic myeloid leukemia (CML) is a myeloproliferative haematological malignancy characterized by constitutive activation of BCR-ABL1 tyrosine kinase in the majority of patients. BCR-ABL1 expression activates signaling pathways involved in cell proliferation and survival. Current treatment options for CML include tyrosine kinase inhibitors (TKI) with resistance as a major issue. Various treatment options for overcoming resistance are being investigated. Among them, phytochemical curcumin could play an important role. Curcumin has been found to exhibit anti-cancerous effects in various models, including CML, through regulation of multiple molecular signaling pathways contributing to tumorigenesis. We have evaluated curcumin’s effects on imatinib-sensitive LAMA84S and K562, as well as imatinib-resistant LAMA84R cell lines. Our results indicate a significant dose-dependent decrease in cell viability and proliferation of imatinib-sensitive and imatinib-resistant cell lines after curcumin treatment. Suppression of key signaling molecules regulating metabolic and proliferative events, such as Akt, P70S6K and NF-kB, was observed. Increased expression of caspase-3 suggests the potential pro-apoptotic effect of curcumin in the imatinib-resistant CML model. Additional in silico molecular docking studies revealed binding modes and affinities of curcumin with different targets and the results are in accordance with in vitro findings. Altogether, these results indicate the potential role of curcumin in the treatment of CML. Full article

(This article belongs to the Special Issue The Natural Products in the Treatment and Prevention of Diseases)

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21 pages, 4266 KiB

Open AccessArticle

Investigation of the Therapeutic Effect of Total Alkaloids of Corydalis saxicola Bunting on CCl₄-Induced Liver Fibrosis in Rats by LC/MS-Based Metabolomics Analysis and Network Pharmacology

by Qianyi Wang, Zhuo Luo, Danfeng Li, Jinghua Qin, Ziping Pan, Bingjian Guo, Lijun Deng, Yunyuan Nong, Zheng Huang, Ying He, Hongwei Guo, Dan Zhu, Yonghong Liang and Zhiheng Su

Metabolites 2023, 13(1), 9; https://doi.org/10.3390/metabo13010009 - 21 Dec 2022

Cited by 16 | Viewed by 2686

Abstract

Liver fibrosis is a pathological result of liver injury that usually leads to a pathophysiological wound healing response. The total alkaloids of Corydalis saxicola Bunting (TACS) have been used for hepatoprotective effects on the liver. However, its exact therapeutic mechanisms of liver fibrosis are not yet well understood. To explore the potential anti-fibrosis mechanism of TACS, metabolomics coupled with network pharmacology were applied to reveal the underlying mechanisms. Ultra-performance liquid chromatography quadrupole time-of-flight mass spectrometry (UPLC-Q-TOF/MS) combined with multivariate statistical analyses were performed to estimate changes in metabolic profiles. As a result, a total of 23 metabolites in rats with liver fibrosis were altered; of these, 11 had been downregulated and 12 had been upregulated compared with the control group. After TACS treatment, the levels of 13 metabolites were significantly restored compared with the CCl₄-treated group, of which 4 metabolites were up-regulated and 9 metabolites were down-regulated. Many of these metabolites are involved in the bile acid metabolism, glutathione metabolism, tryptophan metabolism and purine metabolism. Then, three key targets, including cytochrome P450 family1 subfamily A member 1 (CYP1A1), ornithine decarboxylase 1 (OCD1) and monoamine oxidase Type B (MAOB) were predicted as potential therapeutic targets of TACS against liver fibrosis through network pharmacology analysis. Finally, palmatine, tetrahydropalmatine and dehydrocavidine were screened as potential active compounds responsible for the anti-fibrosis effect of TACS by molecular docking analysis. This study reveals that TACS exerted anti-fibrosis effects by regulating the liver metabolic pathway with multiple components and multiple targets, which is helpful to further clarify the hepatoprotective mechanisms of natural plant extracts. Full article

(This article belongs to the Special Issue The Natural Products in the Treatment and Prevention of Diseases)

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16 pages, 2871 KiB

Open AccessArticle

Antibacterial and Antibiofilm Activity of Carvacrol against Oral Pathogenic Bacteria

by Irene Fernández-Babiano, María Luisa Navarro-Pérez, Ciro Pérez-Giraldo and María Coronada Fernández-Calderón

Metabolites 2022, 12(12), 1255; https://doi.org/10.3390/metabo12121255 - 13 Dec 2022

Cited by 5 | Viewed by 2761

Abstract

Faced with the current situation of high rates of microbial resistance, together with the scarcity of new antibiotics, it is necessary to search for and identify new antimicrobials, preferably natural, to alleviate this situation. The aim of this work was to evaluate the antibacterial activity of carvacrol (CAR), a phenolic compound of essential oils, against pathogenic microorganisms causing oral infections, such as Streptococcus mutans and S. sanguinis, never evaluated before. The minimum inhibitory and the minimum bactericidal concentration were 93.4 μg/mL and 373.6 μg/mL, respectively, for the two strains. The growth kinetics under different concentrations of CAR, as well as the bactericidal power were determined. The subinhibitory concentrations delayed and decreased bacterial growth. Its efficacy on mature biofilms was also tested. Finally, the possible hemolytic effect of CAR, not observable at the bactericidal concentrations under study, was evaluated. Findings obtained point to CAR as an excellent alternative agent to safely prevent periodontal diseases. In addition, it is important to highlight the use of an experimental methodology that includes dual-species biofilm and subinhibitory concentration models to determine optimal CAR treatment concentrations. Thus, CAR could be used preventively in mouthwashes or biomaterials, or in treatments to avoid existing antibiotic resistance. Full article

(This article belongs to the Special Issue The Natural Products in the Treatment and Prevention of Diseases)

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20 pages, 2760 KiB

Open AccessArticle

Anti-Candida albicans Activity of Ononin and Other Secondary Metabolites from Platonia Insignis MART

by Anderson França da Silva, Josivan Regis Farias, Danielle Cristine Gomes Franco, Andrea Araruna Galiza, Elizangela Pestana Motta, Aluísio da Silva Oliveira, Cleydlenne Costa Vasconcelos, Maria do Socorro de Sousa Cartágenes, Claudia Quintino da Rocha, Mayara Cristina Pinto da Silva, Alberto Jorge Oliveira Lopes, Flavia Raquel Fernandes do Nascimento, Cristina Andrade Monteiro and Rosane Nassar Meireles Guerra

Metabolites 2022, 12(11), 1014; https://doi.org/10.3390/metabo12111014 - 24 Oct 2022

Cited by 8 | Viewed by 2220

Abstract

Candida albicans is a human pathogen that is part of the healthy microbiome. However, it is often associated with opportunistic fungal infections. The treatment of these infections is challenging because prolonged exposure to antifungal drugs can culminate in fungal resistance during therapy, and there is a limited number of available drugs. Therefore, this study investigated the antifungal activity of ononin by in silico and in vitro assays, and in Tenebrio molitor as an alternative in vivo model of infection caused by C. albicans. Ononin is an isoflavone glycoside derived from formononetin that has various biological activities. According in silico evaluation, ononin showed the best electron affinity in molecular docking with CaCYP51, with a binding free energy of −10.89 kcal/mol, superior to that of the antifungal drugs fluconazole and posaconazole. The ononin + CaCYP51 complex formed hydrogen bonds with Tyr132, Ser378, Phe380, and Met508, as well as hydrophobic connections with Tyr118, Leu121, Phe126, Leu131, Ile304, and Leu309, and interactions with the heme group. Ononin exerted anti-Candida albicans activity, with MIC between 3.9 and 7.8 µg/mL, and inhibited young and mature biofilms, with a reduction in cell density and metabolic activity of 50 to 80%. The compound was not cytotoxic to sheep red blood cells at concentrations up to 1000 µg/mL. Larvae of the mealworm T. molitor were used as an alternative in vivo model of C. albicans infection. Ononin was able to prolong larval survival at concentrations of 0.5, 1, and 5 mg/kg, and was not toxic up to a concentration of 20 mg/kg. Moreover, ononin reduced the fungal charge in treated animals. In conclusion, our results suggest that ononin has anti-Candida albicans activity and is a potential candidate for the development of new therapeutic alternatives. Full article

(This article belongs to the Special Issue The Natural Products in the Treatment and Prevention of Diseases)

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15 pages, 6390 KiB

Open AccessArticle

Mechanisms of Ardisia japonica in the Treatment of Hepatic Injury in Rats Based on LC-MS Metabolomics

by Tian Fu, Shuiling Qin, Huajuan He, Kefeng Zhang, Wei Zhang, Xin Tang and Wei Wu

Metabolites 2022, 12(10), 981; https://doi.org/10.3390/metabo12100981 - 17 Oct 2022

Cited by 4 | Viewed by 2371

Abstract

The mechanism of action of Ardisia japonica in the treatment of immune liver injury was systematically analyzed from the perspective of the biological metabolic network by using non-targeted metabolomics combined with biological network analysis tools. A rat model of acute immune hepatic injury was established by Concanavalin A (Con A) and the efficacy of the treatment of acute immune liver injury was judged by gavage of A. japonica. Liquid chromatography-mass spectrometry (LC-MS)-based plasma metabolomics was used to identify the key metabolites and metabolic pathways for the hepatoprotective effects of A. japonica. The results demonstrated that A. japonica reduced the levels of inflammatory parameters, decreased hepatic malondialdehyde levels, and enhanced hepatic antioxidant enzyme activity in animal experiments. The clustering of metabolomic samples showed significant separation in principal component analysis plots and the three groups in PLS-DA and OPLS-DA models could be clearly distinguished in multivariate statistical analysis. Among the 937 total metabolites, 445 metabolites were significantly different between the control and model groups, while 144 metabolites were identified as metabolites with differences between the model and administration groups, and a total of 39 differential metabolites were identified to affect the metabolic levels of the three groups. The differential metabolites were principally involved in the citric acid cycle, glutathione metabolism, vitamin B6 metabolism, and steroid hormone biosynthesis. This study found that A. japonica can significantly inhibit acute liver injury in rats, and exert a hepatoprotective effect through anti-inflammatory effect, inhibition of lipid peroxidation, improvement of the antioxidant defense system, and regulation of metabolites and related metabolic pathways. This study will provide a theoretical basis for the application of A. japonica in the treatment of the liver injury. Full article

(This article belongs to the Special Issue The Natural Products in the Treatment and Prevention of Diseases)

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