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Natural Molecules in Drug Discovery and Pharmacology

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A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Medicinal Chemistry".

Deadline for manuscript submissions: closed (30 November 2022) | Viewed by 51400

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Dr. Steve Peigneur

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Toxicology and Pharmacology, Department Pharmaceutical Sciences, Catholic University Leuven, Herestraat 49 Box 922, 3000 Leuven, Belgium
Interests: peptide toxin; small molecules; voltage-gated ion channel; electrophysiology; pharmacology; venom; drug discovery
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Special Issue Information

Dear Colleagues,

Both plants and venomous animals (cone snails, scorpions, spiders, snakes, centipedes, cnidarian, etc.) are still largely unexplored sources of natural, biologically active compounds. These molecules are being increasingly recognized as new emerging source of therapeutics. Plant-based drug discovery continues to provide new and important leads against various pharmacological targets. At the same time, venomous animals are considered to be specialized predators that have evolved the most sophisticated peptide chemistry and neuropharmacology for their own biological purposes, by producing venom that contains a structural and functional diversity of neurotoxins.

Both plant molecules and venom-derived neurotoxins have been shown to be highly selective ligands for a wide range of ion channels and receptors. Therefore, they represent interesting lead compounds for the development of, for example, analgesics, anti-cancer drugs, and drugs for neurological disorders such as multiple sclerosis, Parkinson disease, Alzheimer disease, and so on.

This Special Issue of Molecules aims to provide a comprehensive look at the natural molecules in drug discovery and pharmacology, and will focus on the isolation and structure elucidation of new natural products, the mechanism of action, and the structure–function of natural products and their analogues, including but not limited to, the recent developments related to the emergence of natural molecules as an underutilized source of bioactive compounds with a clinical potential.

Dr. Steve Peigneur
Guest Editor

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Keywords

neurotoxins
natural compounds
antibiotics
antimicrobial molecules
plant molecules
sodium channels
potassium channels
calcium channels
chloride ion channels
TRP channels
ASIC channels
opiate receptors
acetylcholine receptors
NMDA receptor
cone snail venom
spider venom
amphibian molecules
sea anemone toxins
scorpion toxins
snake toxins
centipede toxins

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Published Papers (11 papers)

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Research

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13 pages, 4163 KiB

Open AccessArticle

Purification and Characterization of Bot33: A Non-Toxic Peptide from the Venom of Buthus occitanus tunetanus Scorpion

by Rym ElFessi, Oussema Khamessi, Najet Srairi-Abid, Jean-Marc Sabatier, Jan Tytgat, Steve Peigneur and Riadh Kharrat

Molecules 2022, 27(21), 7278; https://doi.org/10.3390/molecules27217278 - 26 Oct 2022

Cited by 5 | Viewed by 2235

Abstract

Scorpion venom is a rich source of promising therapeutic compounds, such as highly selective ion channel ligands with potent pharmacological effects. Bot33 is a new short polypeptide of 38 amino acid residues with six cysteines purified from the venom of the Buthus occitanus tunetanus scorpion. Bot33 has revealed less than 40% identity with other known alpha-KTx families. This peptide displayed a neutral amino acid (Leucine), in the position equivalent to lysine 27, described as essential for the interaction with Kv channels. Bot33 did not show any toxicity following i.c.v. injection until 2 µg/kg mouse body weight. Due to its very low venom concentration (0.24%), Bot33 was chemically synthesized. Unexpectedly, this peptide has been subjected to a screening on ion channels expressed in Xenopus laevis oocytes, and it was found that Bot33 has no effect on seven Kv channel subtypes. Interestingly, an in silico molecular docking study shows that the Leu27 prevents the interaction of Bot33 with the Kv1.3 channel. All our results indicate that Bot33 may have a different mode of action from other scorpion toxins, which will be interesting to elucidate. Full article

(This article belongs to the Special Issue Natural Molecules in Drug Discovery and Pharmacology)

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19 pages, 5784 KiB

Open AccessArticle

Discovery of Leptulipin, a New Anticancer Protein from theIranian Scorpion, Hemiscorpius lepturus

by Ali Rezaei, Saeme Asgari, Samira Komijani, Seyedeh Narjes Sadat, Jean-Marc Sabatier, Davood Nasrabadi, Kamran Pooshang Bagheri, Delavar Shahbazzadeh, Mohammad Reza Akbari Eidgahi, Michel De Waard and Hasan Mirzahoseini

Molecules 2022, 27(7), 2056; https://doi.org/10.3390/molecules27072056 - 22 Mar 2022

Cited by 7 | Viewed by 2906

Abstract

Cancer is one of the leading causes of mortality in the world. Unfortunately, the present anticancer chemotherapeutics display high cytotoxicity. Accordingly, the discovery of new anticancer agents with lower side effects is highly necessitated. This study aimed to discover an anticancer compound from Hemiscorpius lepturus scorpion venom. Bioactivity-guided chromatography was performed to isolate an active compound against colon and breast cancer cell lines. 2D electrophoresis and MALDI-TOF were performed to identify the molecule. A partial protein sequence was obtained by mass spectrometry, while the full-length was deciphered using a cDNA library of the venom gland by bioinformatics analyses and was designated as leptulipin. The gene was cloned in pET-26b, expressed, and purified. The anticancer effect and mechanism action of leptulipin were evaluated by MTT, apoptosis, and cell cycle assays, as well as by gene expression analysis of apoptosis-related genes. The treated cells displayed inhibition of cell proliferation, altered morphology, DNA fragmentation, and cell cycle arrest. Furthermore, the treated cells showed a decrease in BCL-2 expression and an increase in Bax and Caspase 9 genes. In this study, we discovered a new anticancer protein from H. lepturus scorpion venom. Leptulipin showed significant anticancer activity against breast and colon cancer cell lines. Full article

(This article belongs to the Special Issue Natural Molecules in Drug Discovery and Pharmacology)

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9 pages, 1107 KiB

Open AccessArticle

Efficacy and Limitations of Chemically Diverse Small-Molecule Enzyme-Inhibitors against the Synergistic Coagulotoxic Activities of Bitis Viper Venoms

by Nicholas J. Youngman, Matthew R. Lewin, Rebecca Carter, Arno Naude and Bryan G. Fry

Molecules 2022, 27(5), 1733; https://doi.org/10.3390/molecules27051733 - 7 Mar 2022

Cited by 4 | Viewed by 2419

Abstract

Snakebite remains a significant public health burden globally, disproportionately affecting low-income and impoverished regions of the world. Recently, researchers have begun to focus on the use of small-molecule inhibitors as potential candidates for the neutralisation of key snake venom toxins and as potential field therapies. Bitis vipers represent some of the most medically important as well as frequently encountered snake species in Africa, with a number of species possessing anticoagulant phospholipase A₂ (PLA₂) toxins that prevent the prothrombinase complex from inducing clot formation. Additionally, species within the genus are known to exert pseudo-procoagulant activity, whereby kallikrein enzymatic toxins cleave fibrinogen to form a weak fibrin clot that rapidly degrades, thereby depleting fibrinogen levels and contributing to the net anticoagulant state. Utilising well-validated coagulation assays measuring time until clot formation, this study addresses the in vitro efficacy of three small molecule enzyme inhibitors (marimastat, prinomastat and varespladib) in neutralising these aforementioned activities. The PLA₂ inhibitor varespladib showed the greatest efficacy for the neutralisation of PLA₂-driven anticoagulant venom activity, with the metalloproteinase inhibitors prinomastat and marimastat both showing low and highly variable degrees of cross-neutralisation with PLA₂ anticoagulant toxicity. However, none of the inhibitors showed efficacy in neutralising the pseudo-procoagulant venom activity exerted by the venom of B. caudalis. Our results highlight the complex nature of snake venoms, for which single-compound treatments will not be universally effective, but combinations might prove highly effective. Despite the limitations of these inhibitors with regards to in vitro kallikrein enzyme pseudo-procoagulant venom activity, our results further support the growing body of literature indicating the potential use of small molecule inhibitors to enhance first-aid treatment of snakebite envenoming, particularly in cases where hospital and thus antivenom treatment is either unavailable or far away. Full article

(This article belongs to the Special Issue Natural Molecules in Drug Discovery and Pharmacology)

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22 pages, 6818 KiB

Open AccessArticle

De Novo Transcriptome Analysis of the Venom of Latrodectus geometricus with the Discovery of an Insect-Selective Na Channel Modulator

by Pornsawan Khamtorn, Steve Peigneur, Fernanda Gobbi Amorim, Loïc Quinton, Jan Tytgat and Sakda Daduang

Molecules 2022, 27(1), 47; https://doi.org/10.3390/molecules27010047 - 22 Dec 2021

Cited by 9 | Viewed by 4113

Abstract

The brown widow spider, Latrodectus geometricus, is a predator of a variety of agricultural insects and is also hazardous for humans. Its venom is a true pharmacopeia representing neurotoxic peptides targeting the ion channels and/or receptors of both vertebrates and invertebrates. The lack of transcriptomic information, however, limits our knowledge of the diversity of components present in its venom. The purpose of this study was two-fold: (1) carry out a transcriptomic analysis of the venom, and (2) investigate the bioactivity of the venom using an electrophysiological bioassay. From 32,505 assembled transcripts, 8 toxin families were classified, and the ankyrin repeats (ANK), agatoxin, centipede toxin, ctenitoxin, lycotoxin, scorpion toxin-like, and SCP families were reported in the L. geometricus venom gland. The diversity of L. geometricus venom was also uncovered by the transcriptomics approach with the presence of defensins, chitinases, translationally controlled tumor proteins (TCTPs), leucine-rich proteins, serine proteases, and other important venom components. The venom was also chromatographically purified, and the activity contained in the fractions was investigated using an electrophysiological bioassay with the use of a voltage clamp on ion channels in order to find if the neurotoxic effects of the spider venom could be linked to a particular molecular target. The findings show that U24-ctenitoxin-Pn1a involves the inhibition of the insect sodium (Na_v) channels, BgNa_v and DmNa_v. This study provides an overview of the molecular diversity of L. geometricus venom, which can be used as a reference for the venom of other spider species. The venom composition profile also increases our knowledge for the development of novel insecticides targeting voltage-gated sodium channels. Full article

(This article belongs to the Special Issue Natural Molecules in Drug Discovery and Pharmacology)

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9 pages, 752 KiB

Open AccessArticle

The Cytotoxic Effect of Apis mellifera Venom with a Synergistic Potential of Its Two Main Components—Melittin and PLA2—On Colon Cancer HCT116 Cell Lines

by Carole Yaacoub, Mariam Rifi, Dany El-Obeid, Hiba Mawlawi, Jean-Marc Sabatier, Bruno Coutard and Ziad Fajloun

Molecules 2021, 26(8), 2264; https://doi.org/10.3390/molecules26082264 - 14 Apr 2021

Cited by 30 | Viewed by 4066

Abstract

Colon carcinogenesis is ranked second globally among human diseases after cardiovascular failures. Bee venom (BV) has been shown to possess in vitro anticancer effects against several types of cancer cells. The two main biopeptides of Apis mellifera BV, namely, melittin (MEL) and phospholipase A2 (PLA2), are suspected to be the biomolecules responsible for the anticancer activity. The present work aims to evaluate the cytotoxic effect of the A. mellifera venom on human colon carcinoma cells (HCT116), and to assess the synergistic effect of MEL and PLA2 on these cells. After analyzing, through high-pressure liquid chromatography, the proportions of MEL and PLA2 on BV, we have established a cell viability assay to evaluate the effect of BV, MEL, PLA2, and a mixture of MEL and PLA2 on the HCT116 cells. Results obtained showed a strong cytotoxicity effect induced by the A. mellifera venom and to a lower extent MEL or PLA2 alone. Remarkably, when MEL and PLA2 were added together, their cytotoxic effect was greatly improved, suggesting a synergistic activity on HCT116 cells. These findings confirm the cytotoxic effect of the A. mellifera venom and highlight the presence of synergistic potential activities between MEL and PLA2, possibly inducing membrane disruption of HCT116 cancer cells. Altogether, these results could serve as a basis for the development of new anticancer treatments. Full article

(This article belongs to the Special Issue Natural Molecules in Drug Discovery and Pharmacology)

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13 pages, 5400 KiB

Open AccessArticle

Proposed Mechanism for the Antitrypanosomal Activity of Quercetin and Myricetin Isolated from Hypericum afrum Lam.: Phytochemistry, In Vitro Testing and Modeling Studies

by Farida Larit, Khaled M. Elokely, Manal A. Nael, Samira Benyahia, Francisco León, Stephen J. Cutler and Mohammed M. Ghoneim

Molecules 2021, 26(4), 1009; https://doi.org/10.3390/molecules26041009 - 14 Feb 2021

Cited by 14 | Viewed by 3034

Abstract

The in vitro activity of L. donovani (promastigotes, axenic amastigotes and intracellular amastigotes in THP1 cells) and T. brucei, from the fractions obtained from the hydroalcoholic extract of the aerial part of Hypericum afrum and the isolated compounds, has been evaluated. The chloroform, ethyl acetate and n-butanol extracts showed significant antitrypanosomal activity towards T. brucei, with IC₅₀ values of 12.35, 13.53 and 12.93 µg/mL and with IC₉₀ values of 14.94, 19.31 and 18.67 µg/mL, respectively. The phytochemical investigation of the fractions led to the isolation and identification of quercetin (1), myricitrin (2), biapigenin (3), myricetin (4), hyperoside (5), myricetin-3-O-β-d-galactopyranoside (6) and myricetin-3’-O-β-d-glucopyranoside (7). Myricetin-3’-O-β-d-glucopyranoside (7) has been isolated for the first time from this genus. The chemical structures were elucidated by using comprehensive one- and two-dimensional nuclear magnetic resonance (1D and 2D NMR) spectroscopic data, as well as high-resolution electrospray ionization mass spectrometry (HR-ESI–MS). These compounds have also been evaluated for their antiprotozoal activity. Quercetin (1) and myricetin (4) showed noteworthy activity against T. brucei, with IC₅₀ and IC₉₀ values of 7.52 and 5.71 µM, and 9.76 and 7.97 µM, respectively. The T. brucei hexokinase (TbHK1) enzyme was further explored as a potential target of quercetin and myricetin, using molecular modeling studies. This proposed mechanism assists in the exploration of new candidates for novel antitrypanosomal drugs. Full article

(This article belongs to the Special Issue Natural Molecules in Drug Discovery and Pharmacology)

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15 pages, 3533 KiB

Open AccessArticle

Role of β-Caryophyllene in the Antinociceptive and Anti-Inflammatory Effects of Tagetes lucida Cav. Essential Oil

by Alberto Hernandez-Leon, María Eva González-Trujano, Fernando Narváez-González, Gimena Pérez-Ortega, Fausto Rivero-Cruz and María Isabel Aguilar

Molecules 2020, 25(3), 675; https://doi.org/10.3390/molecules25030675 - 5 Feb 2020

Cited by 35 | Viewed by 4673

Abstract

Tagetes lucida Cav. (Asteraceae) is an ancient medicinal plant commonly used to alleviate pain. Nevertheless, scientific studies validating this property are lacking in the literature. Animal models of pain were used to evaluate the antinociceptive and anti-inflammatory activities of T. lucida essential oil (TLEO) and a bioactive metabolite. The chemical constitution and possible toxicity of the extract and the mechanism of action of β-caryophyllene were also explored. Temporal course curves and dose–response graphics were generated using TLEO (0.1–10 mg/kg or 3.16–31.62 mg/kg) and β-caryophyllene (3.16–10 mg/kg). Metamizole (80 mg/kg) and indomethacin (20 mg/kg) were used as reference drugs in the formalin assay and writhing test in rats and mice, respectively. The β-caryophyllene mechanism of action was explored in the presence of naloxone (1 mg/kg), flumazenil (10 mg/kg), WAY100635 (0.16 mg/kg), or nitro-l-arginine methyl ester (L-NAME) (20 mg/kg) in the formalin test in rats. GC/MS analysis demonstrated the presence of geranyl acetate (49.89%), geraniol (7.92%), and β-caryophyllene (6.27%). Significant and dose-dependent antinociceptive response was produced by TLEO and β-caryophyllene without the presence of gastric damage. In conclusion, β-caryophyllene was confirmed as a bioactive compound in the T. lucida analgesic properties by involving the participation of receptors like opioids, benzodiazepines, and Serotonin 1A receptor (5-HT_1A), as well as nitric oxide. Full article

(This article belongs to the Special Issue Natural Molecules in Drug Discovery and Pharmacology)

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Review

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15 pages, 1786 KiB

Open AccessReview

Anti-Alphaviral Alkaloids: Focus on Some Isoquinolines, Indoles and Quinolizidines

by Anne-Laure Sandenon Seteyen, Emmanuelle Girard-Valenciennes, Axelle Septembre-Malaterre, Philippe Gasque, Pascale Guiraud and Jimmy Sélambarom

Molecules 2022, 27(16), 5080; https://doi.org/10.3390/molecules27165080 - 10 Aug 2022

Cited by 5 | Viewed by 2441

Abstract

The discovery and the development of safe and efficient therapeutics against arthritogenic alphaviruses (e.g., chikungunya virus) remain a continuous challenge. Alkaloids are structurally diverse and naturally occurring compounds in plants, with a wide range of biological activities including beneficial effects against prominent pathogenic viruses and inflammation. In this short review, we discuss the effects of some alkaloids of three biologically relevant structural classes (isoquinolines, indoles and quinolizidines). Based on various experimental models (viral infections and chronic diseases), we highlight the immunomodulatory effects of these alkaloids. The data established the capacity of these alkaloids to interfere in host antiviral and inflammatory responses through key components (antiviral interferon response, ROS production, inflammatory signaling pathways and pro- and anti-inflammatory cytokines production) also involved in alphavirus infection and resulting inflammation. Thus, these data may provide a convincing perspective of research for the use of alkaloids as immunomodulators against arthritogenic alphavirus infection and induced inflammation. Full article

(This article belongs to the Special Issue Natural Molecules in Drug Discovery and Pharmacology)

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14 pages, 4385 KiB

Open AccessFeature PaperReview

Snake Venom Components: Tools and Cures to Target Cardiovascular Diseases

by Jacinthe Frangieh, Mohamad Rima, Ziad Fajloun, Daniel Henrion, Jean-Marc Sabatier, Christian Legros and César Mattei

Molecules 2021, 26(8), 2223; https://doi.org/10.3390/molecules26082223 - 12 Apr 2021

Cited by 28 | Viewed by 9377

Abstract

Cardiovascular diseases (CVDs) are considered as a major cause of death worldwide. Therefore, identifying and developing therapeutic strategies to treat and reduce the prevalence of CVDs is a major medical challenge. Several drugs used for the treatment of CVDs, such as captopril, emerged from natural products, namely snake venoms. These venoms are complex mixtures of bioactive molecules, which, among other physiological networks, target the cardiovascular system, leading to them being considered in the development and design of new drugs. In this review, we describe some snake venom molecules targeting the cardiovascular system such as phospholipase A2 (PLA2), natriuretic peptides (NPs), bradykinin-potentiating peptides (BPPs), cysteine-rich secretory proteins (CRISPs), disintegrins, fibrinolytic enzymes, and three-finger toxins (3FTXs). In addition, their molecular targets, and mechanisms of action—vasorelaxation, inhibition of platelet aggregation, cardioprotective activities—are discussed. The dissection of their biological effects at the molecular scale give insights for the development of future snake venom-derived drugs. Full article

(This article belongs to the Special Issue Natural Molecules in Drug Discovery and Pharmacology)

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22 pages, 975 KiB

Open AccessReview

Anticancer and Antiviral Properties of Cardiac Glycosides: A Review to Explore the Mechanism of Actions

by Dhanasekhar Reddy, Ranjith Kumavath, Debmalya Barh, Vasco Azevedo and Preetam Ghosh

Molecules 2020, 25(16), 3596; https://doi.org/10.3390/molecules25163596 - 7 Aug 2020

Cited by 55 | Viewed by 8153

Abstract

Cardiac glycosides (CGs) have a long history of treating cardiac diseases. However, recent reports have suggested that CGs also possess anticancer and antiviral activities. The primary mechanism of action of these anticancer agents is by suppressing the Na⁺/k⁺-ATPase by decreasing the intracellular K⁺ and increasing the Na⁺ and Ca²⁺. Additionally, CGs were known to act as inhibitors of IL8 production, DNA topoisomerase I and II, anoikis prevention and suppression of several target genes responsible for the inhibition of cancer cell proliferation. Moreover, CGs were reported to be effective against several DNA and RNA viral species such as influenza, human cytomegalovirus, herpes simplex virus, coronavirus, tick-borne encephalitis (TBE) virus and Ebola virus. CGs were reported to suppress the HIV-1 gene expression, viral protein translation and alters viral pre-mRNA splicing to inhibit the viral replication. To date, four CGs (Anvirzel, UNBS1450, PBI05204 and digoxin) were in clinical trials for their anticancer activity. This review encapsulates the current knowledge about CGs as anticancer and antiviral drugs in isolation and in combination with some other drugs to enhance their efficiency. Further studies of this class of biomolecules are necessary to determine their possible inhibitory role in cancer and viral diseases. Full article

(This article belongs to the Special Issue Natural Molecules in Drug Discovery and Pharmacology)

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33 pages, 9392 KiB

Open AccessFeature PaperReview

Pharmacological Potential of Small Molecules for Treating Corneal Neovascularization

by Zachary Barry, Bomina Park and Timothy W. Corson

Molecules 2020, 25(15), 3468; https://doi.org/10.3390/molecules25153468 - 30 Jul 2020

Cited by 19 | Viewed by 6442

Abstract

Under healthy conditions, the cornea is an avascular structure which allows for transparency and optimal visual acuity. Its avascular nature is maintained by a balance of proangiogenic and antiangiogenic factors. An imbalance of these factors can result in abnormal blood vessel proliferation into the cornea. This corneal neovascularization (CoNV) can stem from a variety of insults including hypoxia and ocular surface inflammation caused by trauma, infection, chemical burns, and immunological diseases. CoNV threatens corneal transparency, resulting in permanent vision loss. Mainstay treatments of CoNV have partial efficacy and associated side effects, revealing the need for novel treatments. Numerous natural products and synthetic small molecules have shown potential in preclinical studies in vivo as antiangiogenic therapies for CoNV. Such small molecules include synthetic inhibitors of the vascular endothelial growth factor (VEGF) receptor and other tyrosine kinases, plus repurposed antimicrobials, as well as natural source-derived flavonoid and non-flavonoid phytochemicals, immunosuppressants, vitamins, and histone deacetylase inhibitors. They induce antiangiogenic and anti-inflammatory effects through inhibition of VEGF, NF-κB, and other growth factor receptor pathways. Here, we review the potential of small molecules, both synthetics and natural products, targeting these and other molecular mechanisms, as antiangiogenic agents in the treatment of CoNV. Full article

(This article belongs to the Special Issue Natural Molecules in Drug Discovery and Pharmacology)

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