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Improvements and Opportunities on Natural Products for Novel Drug Discovery

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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 (20 July 2023) | Viewed by 36578

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Prof. Dr. María Isabel Calvo

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Department of Pharmaceutical Technology & Chemistry, University of Navarra, Pamplona, Spain
Interests: ethnopharmacology; medicinal plants; phytochemistry; natural products

Prof. Dr. Maria Luisa Kennedy

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Department of Pharmacology, Faculty of Chemical Sciences, National University of Asunción, San Lorenzo, Paraguay
Interests: natural product biological activity, in vivo pharmacological evaluation; medicinal chemistry

Dr. Francisco Leon

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Department of Drug Discovery and Biomedical Sciences, College of Pharmacy, University of South Carolina, Columbia, SC 29208, USA
Interests: natural products chemistry; synthesis of natural products; medicinal chemistry; alkaloids
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Special Issue Information

Dear colleagues,

Natural products are produced in nature, so it is straightforward and rational to believe that all of them have biological roles and have naturally evolved to be more valuable and effective. The generation of diversity in natural products has occurred not only within the limitations of available biosynthetic reactions and precursors but also in the context of biological utility, as a tool to understand, in depth, the biosynthetic routes for different compounds in different types of organisms. These kinds of substances and their derivatives are crucial as a pharmacotherapeutic tool on human health.

This Special Issue is dedicated to contributions on several aspects of drug discovery as essential mainstays on the innovation of new therapeutic agents, and the necessity in obtaining novel natural compounds, as well as the current reuse of known natural/derivative drugs with new therapeutic patterns. Traditional natural product chemistry has evolved, connecting but not limited to several other areas—for example, improved analytical tools, bioinformatic, omics, data mining, computational tools, genome mining, synthetic biology, and advances in microbial cultures. These interdisciplinary relationships open new opportunities for drug discovery.

Prof. Dr. María Isabel Calvo
Prof. Dr. Maria Luisa Kennedy
Dr. Francisco Leon
Guest Editors

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Keywords

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Natural products
Repurpose drugs
Bioinformatics
Computational tools

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Published Papers (10 papers)

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23 pages, 3624 KiB

Open AccessArticle

Phytochemical Analysis and Antiproliferative Activity of Ulex gallii Planch. (Fabaceae), a Medicinal Plant from Galicia (Spain)

by Lucía Bada, Renato B. Pereira, David M. Pereira, Marta Lores, María Celeiro, Elías Quezada, Eugenio Uriarte, José Gil-Longo and Dolores Viña

Molecules 2023, 28(1), 351; https://doi.org/10.3390/molecules28010351 - 1 Jan 2023

Cited by 1 | Viewed by 2517

Abstract

The genus Ulex comprises thirteen accepted species of perennial shrubs in the family Fabaceae. In Galicia (Spain) many of these are considered spontaneous colonizing species, which are easy to establish and maintain. Among them, Ulex gallii Planch. is used in traditional medicine for the same anti-infective, hypotensive and diuretic purposes as Ulex europaeus L., which is the most studied species. Likewise, some studies have described the antitumoral properties of several species. However, there are few scientific studies that justify the use of Ulex gallii Planch. and nothing has been reported about its composition to date. In our study, the entire plant was extracted with methanol and the crude extract was subjected to liquid phase extraction with distinct solvents, yielding three fractions: hexane (H), dichloromethane (D) and methanol (M), which were subsequently fractionated. The dichloromethane (D5, D7 and D8) and methanol (M4) sub-fractions showed antiproliferative activity on A549 (lung cancer) and AGS (stomach cancer) cell lines, and caspase 3/7 activity assessment and DNA quantification were also performed. Targeted analysis via UHPLC-QToF, in combination with untargeted analysis via MS-Dial, MS-Finder and Global Natural Products Social Molecular Networking (GNPS), allowed us to tentatively identify different metabolites in these sub-fractions, mostly flavonoids, that might be involved in their antiproliferative activity. Full article

(This article belongs to the Special Issue Improvements and Opportunities on Natural Products for Novel Drug Discovery)

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21 pages, 3785 KiB

Open AccessArticle

Metabolomic Profiling, Antioxidant and Enzyme Inhibition Properties and Molecular Docking Analysis of Antarctic Lichens

by Alfredo Torres-Benítez, José Erick Ortega-Valencia, Marta Sanchez, Pradeep Kumar Divakar, Mario J. Simirgiotis and María Pilar Gómez-Serranillos

Molecules 2022, 27(22), 8086; https://doi.org/10.3390/molecules27228086 - 21 Nov 2022

Cited by 9 | Viewed by 2223

Abstract

The lichen species Lecania brialmontii, Pseudephebe pubescens, and Sphaerophorus globosus are part of the prominent lichenoflora of the Antarctic territory. In this work, we report the metabolomic identification of ethanolic extracts of these species, their antioxidant and cholinesterase enzyme inhibitory activity, and conduct a molecular docking analysis with typical compounds. Eighteen compounds were identified by UHPLC-ESI-QTOF-MS in L. brialmontii, 18 compounds in P. pubescens, and 14 compounds in S. globosus. The content of phenolic compounds was variable among the species, ranging from 0.279 to 2.821 mg AG/g, and all three species showed high inhibition potential on the cholinesterase enzymes. Molecular docking showed important interactions between AChE and BChE with the selected compounds. This study evidences the chemical fingerprint of three species of the order Lecanorales that support the continuation of the study of other biological activities and their potential for medical research. Full article

(This article belongs to the Special Issue Improvements and Opportunities on Natural Products for Novel Drug Discovery)

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16 pages, 1906 KiB

Open AccessArticle

Callus Culture of Scorzonera radiata as a New, Highly Productive and Stable Source of Caffeoylquinic Acids

by Olga V. Grishchenko, Valeria P. Grigorchuk, Galina K. Tchernoded, Olga G. Koren and Victor P. Bulgakov

Molecules 2022, 27(22), 7989; https://doi.org/10.3390/molecules27227989 - 17 Nov 2022

Cited by 2 | Viewed by 1748

Abstract

During our ongoing efforts to investigate biotechnological sources of caffeoylquinic acid (CQA) metabolites, we discovered the plant Scorzonera radiata Fisch. (Asteraceae), which is able to produce callus cultures with high yield and extremely high stability. An actively growing callus line, designated as Sr-L1, retained the ability to produce 11 CQAs during long-term cultivation (more than 20 years). A total of 29 polyphenolic compounds were identified in the leaves and Sr-L1 callus culture of S. radiata, including CQAs, lignol derivatives, flavonoids, and dihydrostilbenes. The composition of CQAs in the Sr-L1 culture was identical to that in the S. radiata leaves. Sr-L1 calli did not produce flavonoids and dihydrostilbenes, but produced lignol derivatives, which were absent in leaves. The HPLC-UV-HRMS determination showed the presence of monoacyl derivatives of CQAs such as 5-CQA, 4-CQA, cis-5-CQA, and 5-O-p-coumaroylquinic acid in the Sr-L1 culture. Among diacyl derivatives, 3,4-diCQA, 3,5-diCQA, cis-3,5-diCQA, 4,5-diCQA, 3-O-p-coumaroyl-5-O-CQA, and 3-O-caffeoyl-5-O-p-coumaroylquinic acid were found. The content of 5-CQA reached 7.54 mg/g dry weight and the content of 3,5-diCQA was as high as 18.52 mg/g dry weight. 3,5-diCQA has been reported to be of high nutritional and pharmacological value, as it alleviates inflammatory pain, reverses memory impairment by preventing neuronal apoptosis, and counteracts excessive adipose tissue expansion, serving as an attractive treatment option for obesity. The high content of 3,5-diCQA and the exceptional stability of biosynthesis make callus cultures of S. radiata a promising source for the development of drugs and nutraceuticals. Full article

(This article belongs to the Special Issue Improvements and Opportunities on Natural Products for Novel Drug Discovery)

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16 pages, 3634 KiB

Open AccessArticle

In Vivo Antidepressant-Like Effect Assessment of Two Aloysia Species in Mice and LCMS Chemical Characterization of Ethanol Extract

by Teresa Taboada, Nelson L. Alvarenga, Antonia K. Galeano, Wilfrido J. Arrúa, Miguel A. Campuzano-Bublitz and María L. Kennedy

Molecules 2022, 27(22), 7828; https://doi.org/10.3390/molecules27227828 - 13 Nov 2022

Cited by 5 | Viewed by 2526

Abstract

Medicinal plants belonging to the Verbenaceae family demonstrated antidepressant effects in preclinical studies. Depression is one of the largest contributors to the global health burden of all countries. Plants from the Aloysia genus are traditionally used for affective disorders, and some of them have proven anxiolytic and antidepressant activity. The aim of this work was to evaluate the antidepressant effect of the ethanolic extract of Aloysia gratissima var. gratissima (Agg) and Aloysia virgata var. platyphylla (Avp) in mice. A tail suspension test (TST) and forced swimming test (FST) were conducted after three doses in a period of 24 h and after 7 days of treatment. Imipramine was used as an antidepressant drug. The main results demonstrated that Agg extract reduced the immobility time in mice treated orally for 7 consecutive days when compared to the control group (reduced by about 77%, imipramine 70%). Animals treated with three doses of Avp in a 24-h period had reduced immobility time in the FST (60%), and after 7 days of treatment the reduction was greater (Avp 50, 100, and 200 about 85%; Avp 400, 96.5%; p < 0.0001, imipramine, 77%). LCMS analysis showed the presence of verbascoside, hoffmaniaketone, and hoffmaniaketone acetate in both, A. virgata var. platyphylla and A. gratissima var gratissima. The flavonoids nepetin and 6-hydroxyluteolin were also found in Agg. Both tested extracts demonstrated promising antidepressant-like activity in mice. Full article

(This article belongs to the Special Issue Improvements and Opportunities on Natural Products for Novel Drug Discovery)

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25 pages, 1882 KiB

Open AccessFeature PaperArticle

Anticholinesterase Activity of Selected Medicinal Plants from Navarra Region of Spain and a Detailed Phytochemical Investigation of Origanum vulgare L. ssp. vulgare

by María Pilar de Torre, Rita Yolanda Cavero and María Isabel Calvo

Molecules 2022, 27(20), 7100; https://doi.org/10.3390/molecules27207100 - 20 Oct 2022

Cited by 11 | Viewed by 2783

Abstract

Alzheimer’s disease is a neurodegenerative disease characterized by progressive memory loss and cognitive impairment due to a severe loss of cholinergic neurons in specific brain areas. It is the most common type of dementia in the aging population. Although many anti-acetylcholinesterase (AChE) drugs are already available on the market, their performance sometimes yields unexpected results. For this reason, research works are ongoing to find potential anti-AChE agents both from natural and synthetic sources. In this study, 90 extracts from 30 native and naturalized medicinal plants are tested by TLC and Ellman’s colorimetric assay at 250, 125 and 62.5 μg/mL in order to determine the inhibitory effect on AChE. In total, 21 out of 90 extracts show high anti-AChE activity (75–100% inhibition) in a dose-dependent manner. Among them, ethanolic extract from aerial parts of O. vulgare ssp. vulgare shows an IC50 value 7.7 times lower than galantamine. This research also establishes the chemical profile of oregano extract by TLC, HPLC-DAD and LC-MS, and twenty-three compounds are identified and quantified. Dihydroxycinnamic acids and flavonoids are the most abundant ones (56.90 and 25.94%, respectively). Finally, total phenolic compounds and antioxidant properties are quantified by colorimetric methods. The total phenolic content is 207.64 ± 0.69 µg/mg of extract. The antioxidant activity is measured against two radicals, DPPH and ABTS. In both assays, the oregano extract shows high activity. The Pearson correlation matrix shows the relationship between syringic acids, a type of dihydroxybenzoic acid, and anti-AChE (r² = −0.9864) and antioxidant activity (r² = 0.9409 and 0.9976). In conclusion, the results of this study demonstrate promising potential new uses of these medicinal herbs for the treatment of Alzheimer’s. Origanum vulgare ssp. vulgare and syringic acids, which have anti-AChE activity and beneficial antioxidant capacity, can be highlighted as potential candidates for the development of drugs for the treatment of Alzheimer’s disease and other diseases characterized by a cholinergic deficit. Full article

(This article belongs to the Special Issue Improvements and Opportunities on Natural Products for Novel Drug Discovery)

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14 pages, 672 KiB

Open AccessFeature PaperArticle

Identification, Quantification, and Characterization of the Phenolic Fraction of Brunfelsia grandiflora: In Vitro Antioxidant Capacity

by Raquel Mateos, Norma Ramos-Cevallos, Americo Castro-Luna, Mariella Ramos-Gonzalez, Zoyla-Mirella Clavo, Miguel Quispe-Solano, Luis Goya and José-Luis Rodríguez

Molecules 2022, 27(19), 6510; https://doi.org/10.3390/molecules27196510 - 2 Oct 2022

Cited by 3 | Viewed by 1951

Abstract

Brunfelsia grandiflora is an ancient plant widely used for its promising medicinal properties, although little explored scientifically. Despite being a rich source of phenolic compounds responsible in part for the proven anti-inflammatory activity, its characterization has not been carried out to date. The present work deals with the exhaustive identification and quantification of its phenolic fraction, along with its antioxidant activity. Decoction resulting from the bark as fine powder was filtered and lyophilized, and polyphenols were extracted from the resulting product by aqueous-organic solvents. Seventy-nine polyphenols were identified using LC-MSⁿ. Hydroxycinnamates was the most abundant group of compounds (up to 66.8%), followed by hydroxycoumarins (15.5%), lignans (6.1%), flavonols (5.7%), phenolic simples (3.1), gallates (2.3%), flavanols (0.3%), and flavanones (0.2%). About 64% of the characterized phenols were in their glycosylated forms. The quantification of these phytochemicals by LC-QToF showed that this medicinal plant contained 2014.71 mg of phenolic compounds in 100 g dry matter, which evidences a great antioxidant potency determined by ABTS and DPPH assays. Therefore, Brunfelsia grandiflora represents an important source of polyphenols which supports its therapeutic properties scientifically proven. Full article

(This article belongs to the Special Issue Improvements and Opportunities on Natural Products for Novel Drug Discovery)

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17 pages, 3789 KiB

Open AccessArticle

Antibacterial, Antioxidant, and Phytotoxic Potential of Phytosynthesized Silver Nanoparticles Using Elaeagnus umbellata Fruit Extract

by Hafsa Zulfiqar, Muhammad Shoaib Amjad, Ansar Mehmood, Ghazala Mustafa, Zakia Binish, Samiullah Khan, Huma Arshad, Jarosław Proćków and José Manuel Pérez de la Lastra

Molecules 2022, 27(18), 5847; https://doi.org/10.3390/molecules27185847 - 9 Sep 2022

Cited by 13 | Viewed by 3105

Abstract

Due to its eco-friendliness, cost-effectiveness, ability to be handled safely, and a wide variety of biological activities, the green plant-mediated synthesis of nanoparticles has become increasingly popular. The present work deals with the green synthesis and characterization of silver nanoparticles (AgNPs) using Elaeagnus umbellata (fruit) and the evaluation of its antibacterial, antioxidant, and phytotoxic activities. For the synthesis of AgNPs, fruit extract was treated with a 4 mM AgNO₃ solution at room temperature, and a color change was observed. In UV-Visible spectroscopy, an absorption peak formation at 456 nm was the sign that AgNPs were present in the reaction solution. Scanning electron microscopy and physicochemical X-ray diffraction were used to characterize AgNPs, which revealed that they were crystalline, spherical, and had an average size of 11.94 ± 7.325 nm. The synthesized AgNPs showed excellent antibacterial activity against Klebsiella pneumoniae (14 mm), Staphylococcus aureus (13.5 mm), Proteus mirabilis (13 mm), and Pseudomonas aeruginosa (12.5 mm), as well as considerable antioxidant activity against DPPH with 69% inhibition at an IC₅₀ value of 43.38 µg/mL. AgNPs also exhibited a concentration-dependent effect on rice plants. Root and shoot length were found to be positively impacted at all concentrations, i.e., 12.5 µg/mL, 25 µg/mL, 50 µg/mL, and 100 µg/mL. Among these concentrations, the 50 µg/mL concentration of AgNPs was found to be most effective. The plant biomass decreased at higher AgNP exposure levels (i.e., 100 µg/mL), whereas 50 µg/mL caused a significant increase in plant biomass as compared to the control. This study provides an eco-friendly method for the synthesis of AgNPs which can be used for their antibacterial and antioxidant activities and also as growth promoters of crop plants. Full article

(This article belongs to the Special Issue Improvements and Opportunities on Natural Products for Novel Drug Discovery)

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10 pages, 1425 KiB

Open AccessArticle

Screening of Natural Products Inhibitors of SARS-CoV-2 Entry

by Pamela González-Maldonado, Nelson Alvarenga, Alberto Burgos-Edwards, Ma. Eugenia Flores-Giubi, Javier E. Barúa, Ma. Cristina Romero-Rodríguez, Ricardo Soto-Rifo, Fernando Valiente-Echeverría, Patricia Langjahr, Guadalupe Cantero-González and Pablo H. Sotelo

Molecules 2022, 27(5), 1743; https://doi.org/10.3390/molecules27051743 - 7 Mar 2022

Cited by 25 | Viewed by 4127

Abstract

The COVID-19 pandemic has led to the search for new molecules with antiviral activity against SARS-CoV-2. The entry of the virus into the cell is one of the main targets for inhibiting SARS-CoV-2 infection. Natural products are an important source of new therapeutic alternatives against diseases. Pseudotyped viruses allow the study of SARS-CoV-2 viral entry inhibitors, and due to their simplicity, they allow the screening of a large number of antiviral candidates in Biosafety Level 2 facilities. We used pseudotyped HIV-1 with the D614G SARS-CoV-2 spike glycoprotein to test its ability to infect ACE2-expressing HEK 293T cells in the presence of diverse natural products, including 21 plant extracts, 7 essential oils, and 13 compounds from plants and fungi. The 50% cytotoxic concentration (CC₅₀) was evaluated using the resazurin method. From these analyses, we determined the inhibitory activity of the extract of Stachytarpheta cayennensis, which had a half-maximal inhibitory concentration (IC₅₀) of 91.65 µg/mL, a CC₅₀ of 693.5 µg/mL, and a selectivity index (SI) of 7.57, indicating its potential use as an inhibitor of SARS-CoV-2 entry. Moreover, our work indicates the usefulness of the pseudotyped-virus system in the screening of SARS-CoV-2 entry inhibitors. Full article

(This article belongs to the Special Issue Improvements and Opportunities on Natural Products for Novel Drug Discovery)

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26 pages, 2474 KiB

Open AccessReview

The Polypharmacological Effects of Cannabidiol

by Jorge Castillo-Arellano, Ana Canseco-Alba, Stephen J. Cutler and Francisco León

Molecules 2023, 28(7), 3271; https://doi.org/10.3390/molecules28073271 - 6 Apr 2023

Cited by 44 | Viewed by 10265

Abstract

Cannabidiol (CBD) is a major phytocannabinoid present in Cannabis sativa (Linneo, 1753). This naturally occurring secondary metabolite does not induce intoxication or exhibit the characteristic profile of drugs of abuse from cannabis like Δ⁹-tetrahydrocannabinol (∆⁹-THC) does. In contrast to ∆⁹-THC, our knowledge of the neuro-molecular mechanisms of CBD is limited, and its pharmacology, which appears to be complex, has not yet been fully elucidated. The study of the pharmacological effects of CBD has grown exponentially in recent years, making it necessary to generate frequently updated reports on this important metabolite. In this article, a rationalized integration of the mechanisms of action of CBD on molecular targets and pharmacological implications in animal models and human diseases, such as epilepsy, pain, neuropsychiatric disorders, Alzheimer’s disease, and inflammatory diseases, are presented. We identify around 56 different molecular targets for CBD, including enzymes and ion channels/metabotropic receptors involved in neurologic conditions. Herein, we compiled the knowledge found in the scientific literature on the multiple mechanisms of actions of CBD. The in vitro and in vivo findings are essential for fully understanding the polypharmacological nature of this natural product. Full article

(This article belongs to the Special Issue Improvements and Opportunities on Natural Products for Novel Drug Discovery)

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26 pages, 1192 KiB

Open AccessReview

The Genus Cetraria s. str.—A Review of Its Botany, Phytochemistry, Traditional Uses and Pharmacology

by Marta Sánchez, Isabel Ureña-Vacas, Elena González-Burgos, Pradeep Kumar Divakar and Maria Pilar Gómez-Serranillos

Molecules 2022, 27(15), 4990; https://doi.org/10.3390/molecules27154990 - 5 Aug 2022

Cited by 10 | Viewed by 3875

Abstract

The genus Cetraria s. str. (Parmeliaceae family, Cetrarioid clade) consists of 15 species of mostly erect brown or greenish yellow fruticose or subfoliose thallus. These Cetraria species have a cosmopolitan distribution, being primarily located in the Northern Hemisphere, in North America and in the Eurasia area. Phytochemical analysis has demonstrated the presence of dibenzofuran derivatives (usnic acid), depsidones (fumarprotocetraric and protocetraric acids) and fatty acids (lichesterinic and protolichesterinic acids). The species of Cetraria, and more particularly Cetraria islandica, has been widely employed in folk medicine for the treatment of digestive and respiratory diseases as decoctions, tinctures, aqueous extract, and infusions. Moreover, Cetraria islandica has had an important nutritional and cosmetic value. These traditional uses have been validated in in vitro and in vivo pharmacological studies. Additionally, new therapeutic activities are being investigated, such as antioxidant, immunomodulatory, cytotoxic, genotoxic and antigenotoxic. Among all Cetraria species, the most investigated by far has been Cetraria islandica, followed by Cetraria pinastri and Cetraria aculeata. The aim of the current review is to update all the knowledge about the genus Cetraria covering aspects that include taxonomy and phylogeny, morphology and distribution, ecological and environmental interest, phytochemistry, traditional uses and pharmacological properties. Full article

(This article belongs to the Special Issue Improvements and Opportunities on Natural Products for Novel Drug Discovery)

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