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Keywords = anticholinesterase enzyme activity

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18 pages, 3571 KiB  
Article
Synthesis of Novel 7-Phenyl-2,3-Dihydropyrrolo[2,1-b]Quinazolin-9(1H)-ones as Cholinesterase Inhibitors Targeting Alzheimer’s Disease Through Suzuki–Miyaura Cross-Coupling Reaction
by Davron Turgunov, Lifei Nie, Azizbek Nasrullaev, Zarifa Murtazaeva, Bianlin Wang, Dilafruz Kholmurodova, Rustamkhon Kuryazov, Jiangyu Zhao, Khurshed Bozorov and Haji Akber Aisa
Molecules 2025, 30(13), 2791; https://doi.org/10.3390/molecules30132791 - 28 Jun 2025
Cited by 1 | Viewed by 619
Abstract
An important field of research in medicinal and organic chemistry involves halogen-containing heterocyclic synthones, which form the backbone of more complex organic compounds. This study aimed to design and synthesize 28 novel derivatives of 7-aryl-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one. The derivatives were created [...] Read more.
An important field of research in medicinal and organic chemistry involves halogen-containing heterocyclic synthones, which form the backbone of more complex organic compounds. This study aimed to design and synthesize 28 novel derivatives of 7-aryl-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one. The derivatives were created from 7-bromoquinoline intermediates to evaluate their potential as cholinesterase inhibitors for treating neurodegenerative diseases such as Alzheimer’s disease. The conditions for the Suzuki–Miyaura cross-coupling reaction were optimized to improve yield and purity. The derivatives were evaluated for their anticholinesterase activity using Ellman’s method, revealing that it most effectively inhibited cholinesterase within the micromolar range. 7-(3-Chloro-4-fluorophenyl)-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one derivative exhibited the highest inhibitory potency, with an IC50 value of 6.084 ± 0.26 μM. Additionally, molecular dynamics simulations provided insight into how this lead compound interacts with the enzyme, suggesting its potential as a drug candidate for Alzheimer’s disease. Full article
(This article belongs to the Special Issue Synthesis and Derivatization of Heterocyclic Compounds)
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15 pages, 544 KiB  
Article
Chemical Profiling and In Vitro Evaluation of Bioactive Properties of Evernia prunastri Extract: Implications for Therapeutic Applications
by Dejan Stojković, Jelena Živković, Stefani Bolevich, Sergey Bolevich, Gokhan Zengin, Uroš Gašić and Marina Soković
Plants 2025, 14(4), 583; https://doi.org/10.3390/plants14040583 - 14 Feb 2025
Cited by 1 | Viewed by 952
Abstract
Evernia prunastri (L.) Ach. (Parmeliaceae), an edible lichen commonly known as oakmoss, was traditionally used by Egyptians to make bread. In this study, the ethyl-acetate (EtOAc) extract of E. prunastri was investigated for its potential therapeutic applications in diabetes mellitus, Alzheimer’s and [...] Read more.
Evernia prunastri (L.) Ach. (Parmeliaceae), an edible lichen commonly known as oakmoss, was traditionally used by Egyptians to make bread. In this study, the ethyl-acetate (EtOAc) extract of E. prunastri was investigated for its potential therapeutic applications in diabetes mellitus, Alzheimer’s and Parkinson’s diseases, oxidative stress, and bacterial infections. The extract exhibited significant in vitro enzyme inhibition activities, including anti-amylase and anti-glucosidase activities linked to diabetes and anti-cholinesterase and anti-tyrosinase activities associated with Alzheimer’s and Parkinson’s diseases. The antioxidant activity was evaluated through multiple assays, including free radical scavenging (DPPH and ABTS), reducing power (CUPRAC and FRAP), metal chelation, and phosphomolybdenum methods, demonstrating strong oxidative stress relief potential. The antibacterial properties were also confirmed through antibacterial testing, showing efficacy against a range of bacterial strains. Total phenolic and flavonoid contents were quantified, while the chemical profile of the EtOAc extract was determined by LC-HRMS/MS analysis. The chemical composition was predominantly characterized by depsides (evernic acid and atranorin), phenolic acids (orsellinic acid), and dibenzofurans, revealing a diverse array of bioactive secondary metabolites. The extract demonstrated a broad spectrum of biological activities, including enzyme inhibition, antioxidant effects, and antibacterial properties. This study highlights the potential of E. prunastri as a functional food, providing a rich source of bioactive compounds with numerous health-promoting effects, and it suggests its relevance in therapeutic applications for chronic diseases such as diabetes, Alzheimer’s, and bacterial infections. Full article
(This article belongs to the Special Issue Bioactive Compounds in Plants—2nd Edition)
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18 pages, 3485 KiB  
Article
Computational Insight of Oleracone L, Portulacatone B, and Portulacatal from Portulaca oleracea L. as Potential Anticholinesterase Inhibitors for Alzheimer’s
by Shifaa O. Alshammari
Processes 2024, 12(7), 1456; https://doi.org/10.3390/pr12071456 - 12 Jul 2024
Cited by 6 | Viewed by 1357
Abstract
Alzheimer’s disease, characterized by a decline in cognitive functions, is frequently associated with decreased levels of acetylcholine due to the overactivity of acetylcholinesterase (AChE). Inhibiting AChE has been a key therapeutic strategy in treating Alzheimer’s disease, yet the search for effective inhibitors, particularly [...] Read more.
Alzheimer’s disease, characterized by a decline in cognitive functions, is frequently associated with decreased levels of acetylcholine due to the overactivity of acetylcholinesterase (AChE). Inhibiting AChE has been a key therapeutic strategy in treating Alzheimer’s disease, yet the search for effective inhibitors, particularly from natural sources, continues due to their potential for fewer side effects. In this context, three new alkaloids—oleracone L, portulacatone B, and portulacatal—extracted from Portulaca oleracea L., have recently shown promising anticholinesterase activity in vitro. However, no experimental or computational studies have yet explored their binding potential. This study represents the first comprehensive in silico analysis of these compounds, employing ADME prediction, molecular docking, molecular dynamics simulations, and MM-PBSA calculations to assess their therapeutic potential. The drug-likeness was evaluated based on Lipinski, Pfizer, Golden Triangle, and GSK rules, with all three alkaloids meeting these criteria. The ADME profiles suggested that these alkaloids can effectively cross the blood–brain barrier, a critical requirement for Alzheimer’s treatment. Molecular docking studies revealed that oleracone L had the highest binding affinity (−10.75 kcal/mol) towards AChE, followed by portulacatal and portulacatone B, demonstrating significant interactions with crucial enzyme residues. Molecular dynamics simulations over 200 ns confirmed the stability of these interactions, with RMSD values below 2 Å for all complexes, indicating stable binding throughout the simulation period. RMSF and the radius of gyration analyses further corroborated the minimal impact of these alkaloids on the enzyme’s overall flexibility and compactness. Moreover, MM-PBSA calculations provided additional support for the binding efficacy, showing that oleracone L, with the most favorable binding energy, could be a superior inhibitor, potentially due to its stronger and more consistent hydrogen bonding and favorable electrostatic interactions compared to the other studied alkaloids. These computational findings highlight the binding efficiency and potential therapeutic viability of these alkaloids as AChE inhibitors, suggesting they could be promising candidates for Alzheimer’s disease treatment. The study underscores the importance of further validation through in vitro and in vivo experiments to confirm these predictions. Full article
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8 pages, 693 KiB  
Article
Vegan and Vegetarian Soups Are Excellent Sources of Cholinesterase Inhibitors
by Dorota Gajowniczek-Ałasa, Ewa Baranowska-Wójcik and Dominik Szwajgier
Nutrients 2024, 16(13), 2025; https://doi.org/10.3390/nu16132025 - 26 Jun 2024
Cited by 1 | Viewed by 2169
Abstract
Background: The cholinesterase theory stands as the most popular worldwide therapy for Alzheimer’s disease (AD). Given the absence of a cure for AD, a plant-based diet has been repeatedly shown as positive in the prevention of AD, including exploring ready-made products in stores [...] Read more.
Background: The cholinesterase theory stands as the most popular worldwide therapy for Alzheimer’s disease (AD). Given the absence of a cure for AD, a plant-based diet has been repeatedly shown as positive in the prevention of AD, including exploring ready-made products in stores and the development of new functional foods. Goal: This study compared the anti-acetyl- and butyrylcholinesterase activity of thirty-two Polish market soups and five newly formulated soups intended to be functional. Additionally, the research aimed to assess the significance of animal content, distinguishing between vegan and vegetarian options, in cholinesterase inhibition. Materials and methods: The anticholinesterase activity was investigated using a spectrophotometric method, and the inhibitory activity was expressed as % inhibition of the enzyme. The study categorized soups into three groups based on ingredients: those containing animal-derived components, vegetarian soups and vegan soups. Results: Soups exhibited varying levels of activity against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), indicating differences in their compositions. Composition appeared to be the primary factor influencing anticholinesterase activity, as soups within each group showed significant variability in activity levels. While some commercial soups demonstrated notable anticholinesterase activity, they did not surpass the effectiveness of the optimized soups developed in the laboratory. Certain ingredients were associated with higher anticholinesterase activity, such as coconut, potato, onion, garlic, parsley and various spices and herbs. Conclusions: Vegetarian and vegan soups exhibited comparable or even superior anticholinesterase activity compared to animal-derived soups, highlighting the importance of plant-based ingredients. The study underscores the need for further research to explore the mechanisms underlying the anticholinesterase activity of soups, including the impact of ingredient combinations and processing methods. Full article
(This article belongs to the Section Phytochemicals and Human Health)
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13 pages, 1165 KiB  
Article
A Comparison of Phenolic, Flavonoid, and Amino Acid Compositions and In Vitro Antioxidant and Neuroprotective Activities in Thai Plant Protein Extracts
by Pontapan Polyiam and Wipawee Thukhammee
Molecules 2024, 29(13), 2990; https://doi.org/10.3390/molecules29132990 - 23 Jun 2024
Cited by 6 | Viewed by 2728
Abstract
The leaves of mulberry, Azolla spp., sunflower sprouts, cashew nut, and mung bean are considered rich sources of plant protein with high levels of branched-chain amino acids. Furthermore, they contain beneficial phytochemicals such as antioxidants and anti-inflammatory agents. Additionally, there are reports suggesting [...] Read more.
The leaves of mulberry, Azolla spp., sunflower sprouts, cashew nut, and mung bean are considered rich sources of plant protein with high levels of branched-chain amino acids. Furthermore, they contain beneficial phytochemicals such as antioxidants and anti-inflammatory agents. Additionally, there are reports suggesting that an adequate consumption of amino acids can reduce nerve cell damage, delay the onset of memory impairment, and improve sleep quality. In this study, protein isolates were prepared from the leaves of mulberry, Azolla spp., sunflower sprouts, cashew nut, and mung bean. The amino acid profile, dietary fiber content, phenolic content, and flavonoid content were evaluated. Pharmacological properties, such as antioxidant, anticholinesterase, monoamine oxidase, and γ-aminobutyric acid transaminase (GABA-T) activities, were also assessed. This study found that concentrated protein from mung beans has a higher quantity of essential amino acids (52,161 mg/100 g protein) compared to concentrated protein from sunflower sprouts (47,386 mg/100 g protein), Azolla spp. (42,097 mg/100 g protein), cashew nut (26,710 mg/100 g protein), and mulberry leaves (8931 mg/100 g protein). The dietary fiber content ranged from 0.90% to 3.24%, while the phenolic content and flavonoid content ranged from 0.25 to 2.29 mg/g and 0.01 to 2.01 mg/g of sample, respectively. Sunflower sprout protein isolates exhibited the highest levels of dietary fiber (3.24%), phenolic content (2.292 ± 0.082 mg of GAE/g), and flavonoids (2.014 mg quercetin/g of sample). The biological efficacy evaluation found that concentrated protein extract from sunflower sprouts has the highest antioxidant activity; the percentages of inhibition of 1,1-diphenyl-2-picrylhydrazyl radical (DPPH) and 2,2′-azino-bis-(3-ethylbenzthiazoline-6-sulphonic acid) (ABTS) radical were 20.503 ± 0.288% and 18.496 ± 0.105%, respectively. Five plant-based proteins exhibited a potent inhibition of acetylcholinesterase (AChE) enzyme activity, monoamine oxidase (MAO) inhibition, and GABA-T ranging from 3.42% to 24.62%, 6.14% to 20.16%, and 2.03% to 21.99%, respectively. These findings suggest that these plant protein extracts can be used as natural resources for developing food supplements with neuroprotective activity. Full article
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19 pages, 3248 KiB  
Article
Tailored Melatonin- and Donepezil-Based Hybrids Targeting Pathognomonic Changes in Alzheimer’s Disease: An In Vitro and In Vivo Investigation
by Rositsa Mihaylova, Violina T. Angelova, Jana Tchekalarova, Dimitrinka Atanasova, Petja Ivanova and Rumyana Simeonova
Int. J. Mol. Sci. 2024, 25(11), 5969; https://doi.org/10.3390/ijms25115969 - 29 May 2024
Cited by 5 | Viewed by 1779
Abstract
A plethora of pathophysiological events have been shown to play a synergistic role in neurodegeneration, revealing multiple potential targets for the pharmacological modulation of Alzheimer’s disease (AD). In continuation to our previous work on new indole- and/or donepezil-based hybrids as neuroprotective agents, the [...] Read more.
A plethora of pathophysiological events have been shown to play a synergistic role in neurodegeneration, revealing multiple potential targets for the pharmacological modulation of Alzheimer’s disease (AD). In continuation to our previous work on new indole- and/or donepezil-based hybrids as neuroprotective agents, the present study reports on the beneficial effects of lead compounds of the series on key pathognomonic features of AD in both cellular and in vivo models. An enzyme-linked immunosorbent assay (ELISA) was used to evaluate the anti-fibrillogenic properties of 15 selected derivatives and identify quantitative changes in the formation of neurotoxic β-amyloid (Aβ42) species in human neuronal cells in response to treatment. Among the most promising compounds were 3a and 3c, which have recently shown excellent antioxidant and anticholinesterase activities, and, therefore, have been subjected to further in vivo investigation in mice. An acute toxicity study was performed after intraperitoneal (i.p.) administration of both compounds, and 1/10 of the LD50 (35 mg/kg) was selected for subacute treatment (14 days) with scopolamine in mice. Donepezil (DNPZ) and/or galantamine (GAL) were used as reference drugs, aiming to establish any pharmacological superiority of the multifaceted approach in battling hallmark features of neurodegeneration. Our promising results give first insights into emerging disease-modifying strategies to combine multiple synergistic activities in a single molecule. Full article
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39 pages, 2992 KiB  
Article
Phytochemical Analysis, Biological Activities, and Molecular Docking Studies of Root Extracts from Paeonia Species in Serbia
by Petar Batinić, Aleksandra Jovanović, Dejan Stojković, Gökhan Zengin, Ilija Cvijetić, Uroš Gašić, Natalija Čutović, Mirjana B. Pešić, Danijel D. Milinčić, Tamara Carević, Aleksandar Marinković, Branko Bugarski and Tatjana Marković
Pharmaceuticals 2024, 17(4), 518; https://doi.org/10.3390/ph17040518 - 17 Apr 2024
Cited by 4 | Viewed by 2768
Abstract
Without being aware of their chemical composition, many cultures have used herbaceous peony roots for medicinal purposes. Modern phytopreparations intended for use in human therapy require specific knowledge about the chemistry of peony roots and their biological activities. In this study, ethanol–water extracts [...] Read more.
Without being aware of their chemical composition, many cultures have used herbaceous peony roots for medicinal purposes. Modern phytopreparations intended for use in human therapy require specific knowledge about the chemistry of peony roots and their biological activities. In this study, ethanol–water extracts were prepared by maceration and microwave- and ultrasound-assisted extractions (MAE and UAE, respectively) in order to obtain bioactive molecules from the roots of Paeonia tenuifolia L., Paeonia peregrina Mill., and Paeonia officinalis L. wild growing in Serbia. Chemical characterization; polyphenol and flavonoid content; antioxidant, multianti-enzymatic, and antibacterial activities of extracts; and in vitro gastrointestinal digestion (GID) of hot water extracts were performed. The strongest anti-cholinesterase activity was observed in PT extracts. The highest anti-ABTS (2,2′-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) radical potential was observed in PP extracts, whereas against DPPH (2,2-diphenyl-1-picrylhydrazyl radicals), the best results were achieved with PO extracts. Regarding antibacterial activity, extracts were strongly potent against Bacillus cereus. A molecular docking simulation was conducted to gather insights into the binding affinity and interactions of polyphenols and other Paeonia-specific molecules in the active sites of tested enzymes. In vitro GID of Paeonia teas showed a different recovery and behavior of the individual bioactives, with an increased recovery of methyl gallate and digallate and a decreased recovery of paeoniflorin and its derivatives. PT (Gulenovci) and PP (Pirot) extracts obtained by UAE and M were more efficient in the majority of the bioactivity assays. This study represents an initial step toward the possible application of Paeonia root extracts in pharmacy, medicine, and food technologies. Full article
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18 pages, 4395 KiB  
Article
Anti-Cholinergic Effects of the Phenolic Extract from the Astragalus crenatus Plant: A Computational and Network Pharmacology Study
by Sabrina Lekmine, Ouided Benslama, Hichem Tahraoui, Mohammad Shamsul Ola, Aicha Laouani, Kenza Kadi, Antonio Ignacio Martín-García and Ahmad Ali
Pharmaceuticals 2024, 17(3), 348; https://doi.org/10.3390/ph17030348 - 7 Mar 2024
Cited by 13 | Viewed by 2514
Abstract
Investigations into cholinesterase inhibition have received attention from researchers in recent years for the treatment of Alzheimer’s disease. Cholinesterase enzymes, namely, acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), hold pivotal significance in Alzheimer’s disease (AD) treatment. In this study, we utilized the ethanolic extract of [...] Read more.
Investigations into cholinesterase inhibition have received attention from researchers in recent years for the treatment of Alzheimer’s disease. Cholinesterase enzymes, namely, acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), hold pivotal significance in Alzheimer’s disease (AD) treatment. In this study, we utilized the ethanolic extract of Astragalus crenatus followed by liquid chromatography–electrospray ionization tandem mass spectrometry (LC-ESI-MS/MS) to separate and identify at least 21 compounds in the extract. Rosmarinic acid exhibited the highest concentration (96.675 ± 1.3 mg/g extract), succeeded by hesperidin (79.613 ± 1.2 mg/g extract), hesperetin (75.102 ± 1.4 mg/g extract), rutin (68.156 ± 1.6 mg/g extract), chlorogenic acid (67.645 ± 1.5 mg/g extract), fisetin (66.647 ± 2.3 mg/g extract), and hyperoside (63.173 ± 1.5 mg/g extract). A. crenatus extract efficiently inhibited both AChE and BChE activities in a dosage-dependent manner. Molecular docking was employed to scrutinize the anticholinesterase mechanisms of the identified phytocompounds. Notably, a network pharmacology analysis was executed for the most efficacious compound. Based on binding energies, hesperidin emerged as the most potent inhibitor against both AChE and BChE, exhibiting scores of −10.5 Kcal/mol and −9.8 Kcal/mol, respectively. Due to its dual inhibition of AChE and BChE activities, hesperidin from Astragalus crenatus holds promise for the development of novel therapeutics aimed at neurological disorders, particularly AD. Full article
(This article belongs to the Section Natural Products)
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21 pages, 7224 KiB  
Article
African Under-Utilized Medicinal Leafy Vegetables Studied by Microtiter Plate Assays and High-Performance Thin-Layer Chromatography–Planar Assays
by Ibukun O. Oresanya, Ilkay Erdogan Orhan, Julia Heil and Gertrud E. Morlock
Molecules 2024, 29(3), 733; https://doi.org/10.3390/molecules29030733 - 5 Feb 2024
Cited by 3 | Viewed by 2294
Abstract
Biological activities of six under-utilized medicinal leafy vegetable plants indigenous to Africa, i.e., Basella alba, Crassocephalum rubens, Gnetum africanum, Launaea taraxacifolia, Solanecio biafrae, and Solanum macrocarpon, were investigated via two independent techniques. The total phenolic content (TPC) [...] Read more.
Biological activities of six under-utilized medicinal leafy vegetable plants indigenous to Africa, i.e., Basella alba, Crassocephalum rubens, Gnetum africanum, Launaea taraxacifolia, Solanecio biafrae, and Solanum macrocarpon, were investigated via two independent techniques. The total phenolic content (TPC) was determined, and six microtiter plate assays were applied after extraction and fractionation. Three were antioxidant in vitro assays, i.e., ferric reducing antioxidant power (FRAP), cupric reduction antioxidant capacity (CUPRAC), and 2,2-diphenyl-1-picrylhydrazyl (DPPH) scavenging, and the others were enzyme (acetylcholinesterase, butyrylcholinesterase, and tyrosinase) inhibition assays. The highest TPC and antioxidant activity from all the methods were obtained from polar and medium polar fractions of C. rubens, S. biafrae, and S. macrocarpon. The highest acetyl- and butyrylcholinesterase inhibition was exhibited by polar fractions of S. biafrae, C. rubens, and L. taraxacifolia, the latter comparable to galantamine. The highest tyrosinase inhibition was observed in the n-butanol fraction of C. rubens and ethyl acetate fraction of S. biafrae. In vitro assay results of the different extracts and fractions were mostly in agreement with the bioactivity profiling via high-performance thin-layer chromatography–multi-imaging–effect-directed analysis, exploiting nine different planar assays. Several separated compounds of the plant extracts showed antioxidant, α-glucosidase, α-amylase, acetyl- and butyrylcholinesterase-inhibiting, Gram-positive/-negative antimicrobial, cytotoxic, and genotoxic activities. A prominent apolar bioactive compound zone was tentatively assigned to fatty acids, in particular linolenic acid, via electrospray ionization high-resolution mass spectrometry. The detected antioxidant, antimicrobial, antidiabetic, anticholinesterase, cytotoxic, and genotoxic potentials of these vegetable plants, in particular C. rubens, S. biafrae, and S. macrocarpon, may validate some of their ethnomedicinal uses. Full article
(This article belongs to the Special Issue Discovery of New Functional Foods with Bioactive Compounds)
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18 pages, 2956 KiB  
Article
Furofuranoid-Type Lignans and Related Phenolics from Anisacanthus virgularis (Salisb.) Nees with Promising Anticholinesterase and Anti-Ageing Properties: A Study Supported by Molecular Modelling
by Mohamed A. A. Orabi, Reda A. Abdelhamid, Hanan Elimam, Yaseen A. M. M. Elshaier, Ahmed A. Ali, Nayef Aldabaan, Abdulaziz Hassan Alhasaniah and Mohamed S. Refaey
Plants 2024, 13(2), 150; https://doi.org/10.3390/plants13020150 - 5 Jan 2024
Cited by 4 | Viewed by 1902
Abstract
Lignan phytomolecules demonstrate promising anti-Alzheimer activity by alleviating dementia and preserving nerve cells. The purpose of this work is to characterize the lignans of Anisacanthus virgularis and explore their potential anti-acetylcholinesterase and anti-ageing effects. Phytochemical investigation of A. virgularis aerial parts afforded a [...] Read more.
Lignan phytomolecules demonstrate promising anti-Alzheimer activity by alleviating dementia and preserving nerve cells. The purpose of this work is to characterize the lignans of Anisacanthus virgularis and explore their potential anti-acetylcholinesterase and anti-ageing effects. Phytochemical investigation of A. virgularis aerial parts afforded a new furofuranoid-type lignan (1), four known structural analogues, namely pinoresinol (2), epipinoresinol (3), phillyrin (4), and pinoresinol 4-O-β-d-glucoside (5), in addition to p-methoxy-trans-methyl cinnamate (6) and 1H-indole-3-carboxaldehyde (7). The structures were established from thorough spectroscopic analyses and comparisons with the literature. Assessment of the anticholinesterase activity of the lignans 15 displayed noticeable enzyme inhibition of 1 (IC50 = 85.03 ± 4.26 nM) and 5 (64.47 ± 2.75 nM) but lower activity of compounds 24 as compared to the reference drug donepezil. These findings were further emphasized by molecular docking of 1 and 5 with acetylcholinesterase (AChE). Rapid overlay chemical similarity (ROCS) and structure–activity relationships (SAR) analysis highlighted and rationalized the anti-AD capability of these compounds. Telomerase activation testing of the same isolates revealed 1.64-, 1.66-, and 1.72-fold activations in cells treated with compounds 1, 5, and 4, respectively, compared to untreated cells. Our findings may pave the way for further investigations into the development of anti-Alzheimer and/or anti-ageing drugs from furofuranoid-type lignans. Full article
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13 pages, 2301 KiB  
Article
The Effects of Different Roasting Methods on the Phenolic Contents, Antioxidant Potential, and In Vitro Inhibitory Activities of Sacha Inchi Seeds
by Suwapat Kittibunchakul, Varongsiri Kemsawasd, Chatrapa Hudthagosol, Promluck Sanporkha, Suwimol Sapwarobol and Uthaiwan Suttisansanee
Foods 2023, 12(22), 4178; https://doi.org/10.3390/foods12224178 - 20 Nov 2023
Cited by 12 | Viewed by 3086
Abstract
Roasted sacha inchi seeds are now commercialized as a health food product, but the influence of roasting methods on their proclaimed health effects has yet to be explored. This study investigated the total phenolic contents (TPCs), antioxidant potential, and inhibitory activities of raw [...] Read more.
Roasted sacha inchi seeds are now commercialized as a health food product, but the influence of roasting methods on their proclaimed health effects has yet to be explored. This study investigated the total phenolic contents (TPCs), antioxidant potential, and inhibitory activities of raw and roasted sacha inchi seeds in vitro. Individual phenolics in raw seeds were also identified in an attempt to explain the bioactivities of the seeds. The results suggested that roasting in a cooking pan, vacuum oven, and tray dryer had distinct impact on TPC in sacha inchi seeds, and thus differentially altered their antioxidant and inhibitory properties. Seeds that underwent roasting exhibited 1.5–2.7-fold higher antioxidant potentials than raw seeds. Certain roasting methods provided the products with anti-α-amylase and anti-cholinesterase activities, while inhibitions of these enzymes were not detected in raw seeds. Roasted seeds also possessed superior anti-lipase and anti-glycation activities when compared with raw seeds (up to 1.7- and 4.8-fold, respectively). The inhibitory properties observed in the seed samples might be attributed to their p-coumaric acid, ferulic acid, and quercetin, as these potential enzyme inhibitors were predominant in raw seeds. The overall results showed that pan-roasting could be used to obtain relatively high health benefits from the antioxidant and inhibitory activities of sacha inchi seeds. The information obtained from this study may serve as the basis for the proper processing of sacha inchi seeds to optimize their functional food and nutraceutical applications. Full article
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11 pages, 1530 KiB  
Article
Chemical and Biological Aspects of Different Species of the Genus Clinanthus Herb. (Amaryllidaceae) from South America
by María Lenny Rodríguez-Escobar, Luciana R. Tallini, Julia Lisa-Molina, Strahil Berkov, Francesc Viladomat, Alan Meerow, Jaume Bastida and Laura Torras-Claveria
Molecules 2023, 28(14), 5408; https://doi.org/10.3390/molecules28145408 - 14 Jul 2023
Cited by 4 | Viewed by 1669
Abstract
The genus Clinanthus Herb. is found in the Andes Region (South America), mainly in Peru, Ecuador, and Bolivia. These plants belong to the Amaryllidaceae family, specifically the Amaryllidoideae subfamily, which presents an exclusive group of alkaloids known as Amaryllidaceae alkaloids that show important [...] Read more.
The genus Clinanthus Herb. is found in the Andes Region (South America), mainly in Peru, Ecuador, and Bolivia. These plants belong to the Amaryllidaceae family, specifically the Amaryllidoideae subfamily, which presents an exclusive group of alkaloids known as Amaryllidaceae alkaloids that show important structural diversity and pharmacological properties. It is possible to find some publications in the literature regarding the botanical aspects of Clinanthus species, although there is little information available about their chemical and biological activities. The aim of this work was to obtain the alkaloid profile and the anti-cholinesterase activity of four different samples of Clinanthus collected in South America: Clinanthus sp., Clinanthus incarnatus, and Clinanthus variegatus. The alkaloid extract of each sample was analyzed by gas chromatography coupled with mass spectrometry (GC-MS), and their potential against the enzymes acetyl- and butyrylcholinesterase were evaluated. Thirteen alkaloids have been identified among these species, while six unidentified structures have also been detected in these plants. The alkaloid extract of the C. variegatus samples showed the highest structural diversity as well as the best activity against AChE, which was likely due to the presence of the alkaloid sanguinine. The results suggest this genus as a possible interesting new source of Amaryllidaceae alkaloids, which could contribute to the development of new medicines. Full article
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17 pages, 2114 KiB  
Article
In Vitro and In Silico Evaluation of Anticholinesterase and Antidiabetic Effects of Furanolabdanes and Other Constituents from Graptophyllum pictum (Linn.) Griffith
by Nathalie Tanko Metiefeng, Alfred Ngenge Tamfu, Maurice Fotsing Tagatsing, Turibio Kuiate Tabopda, Selcuk Kucukaydin, Martin Noah Mbane, Alex de Theodore Atchade, Emmanuel Talla, Celine Henoumont, Sophie Laurent, El Hassane Anouar and Rodica Mihaela Dinica
Molecules 2023, 28(12), 4802; https://doi.org/10.3390/molecules28124802 - 16 Jun 2023
Cited by 7 | Viewed by 2396
Abstract
Graptophyllum pictum is a tropical plant noticeable for its variegated leaves and exploited for various medicinal purposes. In this study, seven compounds, including three furanolabdane diterpenoids, i.e., Hypopurin E, Hypopurin A and Hypopurin B, as well as with Lupeol, β-sitosterol 3-O-β- [...] Read more.
Graptophyllum pictum is a tropical plant noticeable for its variegated leaves and exploited for various medicinal purposes. In this study, seven compounds, including three furanolabdane diterpenoids, i.e., Hypopurin E, Hypopurin A and Hypopurin B, as well as with Lupeol, β-sitosterol 3-O-β-d-glucopyranoside, stigmasterol 3-O-β-d-glucopyranoside and a mixture of β-sitosterol and stigmasterol, were isolated from G. pictum, and their structures were deduced from ESI-TOF-MS, HR-ESI-TOF-MS, 1D and 2D NMR experiments. The compounds were evaluated for their anticholinesterase activities against acetylcholinesterase (AChE) and butyrylcholinesterase (BchE), as well as their antidiabetic potential through inhibition of α-glucosidase and α-amylase. For AChE inhibition, no sample had IC50 within tested concentrations, though the most potent was Hypopurin A, which had a percentage inhibition of 40.18 ± 0.75%, compared to 85.91 ± 0.58% for galantamine, at 100 µg/mL. BChE was more susceptible to the leaves extract (IC50 = 58.21 ± 0.65 µg/mL), stem extract (IC50 = 67.05 ± 0.82 µg/mL), Hypopurin A (IC50 = 58.00 ± 0.90 µg/mL), Hypopurin B (IC50 = 67.05 ± 0.92 µg/mL) and Hypopurin E (IC50 = 86.90 ± 0.76 µg/mL). In the antidiabetic assay, the furanolabdane diterpenoids, lupeol and the extracts had moderate to good activities. Against α-glucosidase, lupeol, Hypopurin E, Hypopurin A and Hypopurin B had appreciable activities but the leaves (IC50 = 48.90 ± 0.17 µg/mL) and stem (IC50 = 45.61 ± 0.56 µg/mL) extracts were more active than the pure compounds. In the α-amylase assay, stem extract (IC50 = 64.47 ± 0.78 µg/mL), Hypopurin A (IC50 = 60.68 ± 0.55 µg/mL) and Hypopurin B (IC50 = 69.51 ± 1.30 µg/mL) had moderate activities compared to the standard acarbose (IC50 = 32.25 ± 0.36 µg/mL). Molecular docking was performed to determine the binding modes and free binding energies of Hypopurin E, Hypopurin A and Hypopurin B in relation to the enzymes and decipher the structure–activity relationship. The results indicated that G. pictum and its compounds could, in general, be used in the development of therapies for Alzheimer’s disease and diabetes. Full article
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24 pages, 2322 KiB  
Article
Orbitrap Mass Spectrometry-Based Profiling of Secondary Metabolites in Two Unexplored Eminium Species and Bioactivity Potential
by Ebru Yuce Babacan, Dimitrina Zheleva-Dimitrova, Reneta Gevrenova, Abdelhakim Bouyahya, Mehmet Maruf Balos, Ugur Cakilcioglu, Kouadio Ibrahime Sinan and Gokhan Zengin
Plants 2023, 12(12), 2252; https://doi.org/10.3390/plants12122252 - 8 Jun 2023
Cited by 4 | Viewed by 2618
Abstract
The study aimed at the metabolite profiling and evaluation of antioxidant and enzyme inhibitory properties of methanol extracts from flowers, leaves, and tubers of unexplored Eminium intortum (Banks & Sol.) Kuntze and E. spiculatum (Blume) Schott (Araceae). A total of 83 metabolites, including [...] Read more.
The study aimed at the metabolite profiling and evaluation of antioxidant and enzyme inhibitory properties of methanol extracts from flowers, leaves, and tubers of unexplored Eminium intortum (Banks & Sol.) Kuntze and E. spiculatum (Blume) Schott (Araceae). A total of 83 metabolites, including 19 phenolic acids, 46 flavonoids, 11 amino, and 7 fatty acids were identified by UHPLC-HRMS in the studied extracts for the first time. E. intortum flower and leaf extracts had the highest total phenolic and flavonoid contents (50.82 ± 0.71 mg GAE/g and 65.08 ± 0.38 RE/g, respectively). Significant radical scavenging activity (32.20 ± 1.26 and 54.34 ± 0.53 mg TE/g for DPPH and ABTS) and reducing power (88.27 ± 1.49 and 33.13 ± 0.68 mg TE/g for CUPRAC and FRAP) were observed in leaf extracts. E. intortum flowers showed the maximum anticholinesterase activity (2.72 ± 0.03 mg GALAE/g). E. spiculatum leaves and tubers exhibited the highest inhibition towards α-glucosidase (0.99 ± 0.02 ACAE/g) and tirosinase (50.73 ± 2.29 mg KAE/g), respectively. A multivariate analysis revealed that O-hydroxycinnamoylglycosyl-C-flavonoid glycosides mostly accounted for the discrimination of both species. Thus, E. intortum and E. spiculatum can be considered as potential candidates for designing functional ingredients in the pharmaceutical and nutraceutical industries. Full article
(This article belongs to the Special Issue Phytochemical Analysis and Metabolic Profiling in Plants)
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12 pages, 600 KiB  
Article
Chemical Profiling, Anticholinesterase, Antioxidant, and Antibacterial Potential of the Essential Oil from Myrcianthes discolor (Kunth) McVaugh, an Aromatic Tree from Southern Ecuador
by Diana Romero, Luis Cartuche, Eduardo Valarezo, Nixon Cumbicus and Vladimir Morocho
Antibiotics 2023, 12(4), 677; https://doi.org/10.3390/antibiotics12040677 - 30 Mar 2023
Cited by 5 | Viewed by 2400
Abstract
Myrcianthes discolor, an aromatic native tree from southern Ecuador, was collected to determine the chemical composition and the biological activity of its essential oil (EO). The EO was obtained by steam-distillation and analyzed by gas chromatography coupled to a mass and a FID [...] Read more.
Myrcianthes discolor, an aromatic native tree from southern Ecuador, was collected to determine the chemical composition and the biological activity of its essential oil (EO). The EO was obtained by steam-distillation and analyzed by gas chromatography coupled to a mass and a FID detector (GC-MS and GC-FID) and a non-polar DB5-MS column. Enantioselective GC-MS analysis was performed in a chiral capillary column. The antimicrobial, antioxidant, and anticholinesterase potency of the EO was carried out by the broth microdilution method, radical scavenging assays using 2,2′-azino-bis-3-ethylbenzthiazoline-6-sulphonic acid (ABTS) and 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical, and by measuring the inhibition of the acetylcholinesterase (AChE) enzyme. A total of 58 chemical compounds were identified, corresponding to 94.80% of the EO composition. Sesquiterpenes hydrocarbons represented more than 75% of the composition. The main compounds detected were E-caryophyllene with 29.40 ± 0.21%, bicyclogermacrene with 7.45 ± 0.16%, β-elemene with 6.93 ± 0.499%, α-cubebene with 6.06 ± 0.053%, α-humulene with 3.96 ± 0.023%, and δ-cadinene with 3.02 ± 0.002%. The enantiomeric analysis revealed the occurrence of two pairs of pure enantiomers, (−)-β-pinene and (−)-α-phellandrene. The EO exerted a strong inhibitory effect against AChE with an IC50 value of 6.68 ± 1.07 µg/mL and a moderate antiradical effect with a SC50 value of 144.93 ± 0.17 µg/mL for the ABTS radical and a weak or null effect for DPPH (3599.6 ± 0.32 µg/mL). In addition, a strong antibacterial effect against Enterococcus faecium was observed with a MIC of 62.5 μg/mL and Enterococcus faecalis with a MIC of 125 μg/mL. To the best of our knowledge, this is the first report of the chemical composition and biological profile of the EO of M. discolor, and its strong inhibitory effect over AChE and against two Gram-positive pathogenic bacteria, which encourage us to propose further studies to validate its pharmacological potential. Full article
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