Eugenol β-Amino/β-Alkoxy Alcohols with Selective Anticancer Activity

International Journal of Molecular Sciences, Journal Year: 2022, Volume and Issue: 23(7), P. 3759 - 3759

Published: March 29, 2022

Eugenol, 4-allyl-2-methoxyphenol, is the main constituent of clove essential oil and has demonstrated relevant biological activity, namely anticancer activity. Aiming to increase this we synthesized a series eugenol β-amino alcohol β-alkoxy derivatives, which were then tested against two human cancer cell lines, gastric adenocarcinoma cells (AGS) lung (A549). An initial screening was performed identify most cytotoxic compounds. The results that three derivatives had activity justified subsequent studies, having been shown trigger apoptosis. Importantly, potent molecules displayed no appreciable toxicity towards noncancer cells. Structure-activity relationships show changes in structure led enhanced can contribute future design more selective drugs.

Language: Английский

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Design and Synthesis of Eugenol Derivatives Bearing a 1,2,3-Triazole Moiety for Papaya Protection against Colletotrichum gloeosporioides

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: 72(22), P. 12459 - 12468

Published: May 21, 2024

A series of 19 novel eugenol derivatives containing a 1,2,3-triazole moiety was synthesized via two-step process, with the key step being copper(I)-catalyzed azide–alkyne cycloaddition reaction. The compounds were assessed for their antifungal activities against Colletotrichum gloeosporioides, causative agent papaya anthracnose. Triazoles 2k, 2m, 2l, and 2n, at 100 ppm, most effective, reducing mycelial growth by 88.3, 85.5, 82.4, 81.4%, respectively. Molecular docking calculations allowed us to elucidate binding mode these in catalytic pocket C. gloeosporioides CYP51. best-docked bind closely heme cofactor within channel access lanosterol (LAN) substrate, crucial interactions involving residues Tyr102, Ile355, Met485, Phe486. From such studies, activity is likely attributed prevention substrate LAN entry derivatives. triazoles derived from natural represent lead search environmentally safe agents controlling gloeosporioides.

Language: Английский

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Chemical Composition, Insecticidal and Mosquito Larvicidal Activities of Allspice (Pimenta dioica) Essential Oil

Molecules, Journal Year: 2021, Volume and Issue: 26(21), P. 6698 - 6698

Published: Nov. 5, 2021

Essential oils are biologically and environmentally safe pesticidal compounds yielded from aromatic plants. Spices important sources of essential oils, they widely used in the medicine, food, various other industries. Among different spices, Allspice (Pimenta dioica) is underexplored terms its biological efficacy a limited number studies available on chemical composition oil (AEO); thus, present study evaluated larvicidal property, repellency, fumigant toxicity against common pests stored products AEO. AEO was found to inhibit survival larvae such vectors as Aedis, Culex, Armigeres species. Further, exert repellant effects Sitophilus, Callosobruchus, Tribolium. Similarly, be high for these The contact Sitophilus Callosobruchus. Apart that, non-target organism (guppy fishes) non-genotoxic an Allium cepa model. Overall, results indicate that could biopesticidal compound.

Language: Английский

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Biological activities and gene expression of detoxifying enzymes in Tribolium castaneum induced by Moutan cortex essential oil

Journal of Toxicology and Environmental Health, Journal Year: 2022, Volume and Issue: 85(14), P. 591 - 602

Published: April 18, 2022

Tribolium castaneum is one of the most harmful storage pests in world. The aim this study was to determine chemical composition, repellent, and contact activities Moutan cortex essential oil against insect pest. In addition, effects were examined on expressions three major detoxifying enzyme genes T. castaneum. Four components identified by gas chromatography-mass spectrometry (GC-MS), which predominantly paeonol (99.13%). Paeonol exerted significant repellent activity castaneum, more potent than positive control N.N-diethyl-meta-toluamide (DEET). toxicity observed at 24 h after exposure paeonol. Further, quantitative real-time PCR (qRT-PCR) used assess expression changes detoxification including carboxylesterase (CarE), glutathione S-transferase (Gst) cytochrome P4506BQ8 (Cyp6bq8). Among these, Gst highly up-regulated treatment with highest level 4.9-fold (Rps18 as internal reference gene) greater following treatment. Data indicated that might play a critical role metabolic toxic xenobiotics. Taken together, our findings lay foundation for development potential natural or pesticide pests.

Language: Английский

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Synthesis and anticancer activity of novel Eugenol derivatives against breast cancer cells

Natural Product Research, Journal Year: 2022, Volume and Issue: 37(10), P. 1632 - 1640

Published: July 25, 2022

Eugenol chemically known as 4-allyl-2-methoxyphenol is a major phenolic component of Syzigium aromaticum and associated with significant biological activities. In the present work, new eugenol 1,2,3-triazole derivatives have been synthesized, characterized using NMR, mass spectrometry, IR, elemental analysis screened for their anticancer activity against breast cancer cells. Compound 9, namely 3-(4-((4-allyl-2-methoxyphenoxy)methyl)-1H-1,2,3-triazol-1-yl)-N'-(4-methylbenzoyl) benzohydrazide was found to be most potent candidate better than in exhibiting cytotoxicity IC50 6.91 3.15 μM, comparable Doxorubicin 6.58 3.21 μM MDA-MB-231 MCF-7 cells, respectively. Furthermore, compound 9 treated cells observed by propidium iodide staining significantly increased cell population S phase G2 43.64% 35.19%, respectively therefore arresting cycle at phase. These results indicate that linked ring could used leads treatment this deadly diseases.

Language: Английский

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Amino Alcohols from Eugenol as Potential Semisynthetic Insecticides: Chemical, Biological, and Computational Insights

Molecules, Journal Year: 2021, Volume and Issue: 26(21), P. 6616 - 6616

Published: Oct. 31, 2021

A series of β-amino alcohols were prepared by the reaction eugenol epoxide with aliphatic and aromatic amine nucleophiles. The synthesized compounds fully characterized evaluated as potential insecticides through assessment their biological activity against Sf9 insect cells, compared a commercial synthetic pesticide (chlorpyrifos, CHPY). Three derivatives bearing terminal benzene ring, either substituted or unsubstituted, identified most potent molecules, two them displaying higher toxicity to cells than CHPY. In addition, promising molecules able increase serine proteases (caspases) pivotal apoptosis more toxic human cells. Structure-based inverted virtual screening molecular dynamics simulations demonstrate that these likely target acetylcholinesterase and/or odorant-binding proteins are form stable complexes proteins. Encapsulation assays in liposomes DMPG DPPC/DMPG (1:1) performed for active compound, high encapsulation efficiencies obtained. thermosensitive formulation was achieved compound release being efficient at temperatures.

Language: Английский

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Cytotoxic Plant Extracts towards Insect Cells: Bioactivity and Nanoencapsulation Studies for Application as Biopesticides

Molecules, Journal Year: 2020, Volume and Issue: 25(24), P. 5855 - 5855

Published: Dec. 11, 2020

The potential of plant extracts as bioinsecticides has been described a promising field agricultural development. In this work, the Punica granatum (pomegranate), Phytolacca americana (American pokeweed), Glandora prostrata (shrubby gromwell), Ulex europaeus (gorce), Tagetes patula (French marigold), Camellia japonica red (camellia), Ruta graveolens (rue or herb-of-grace) were obtained, purified, and their activity against Spodoptera frugiperda (Sf9) insect cells was investigated. From pool over twenty comprising different polarities vegetable materials, less polar samples shown to be more toxic towards cell line Sf9. Among these, dichloromethane extract R. capable causing loss viability 50%, exceeding effect commercial insecticide chlorpyrifos. This elicited chromatin condensation fragmentation in treated cells. Nanoencapsulation assays cytotoxic soybean liposomes chitosan nanostructures carried out. nanosystems exhibited sizes lower around 200 nm, low polydispersity, generally high encapsulation efficiencies. Release showed that nanoemulsions provide fast total release, while liposome-based systems are suitable for delayed release. These results represent proof-of-concept future development bioinsecticide nanoformulations based on extracts.

Language: Английский

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The Application of Entomopathogenic Fungi Metarhizium anisopliae, Beauveria bassiana, and Trichoderma harzianum for Coptotermes curvignathus and Cryptotermes cynocephalus Termite Control in Indonesia

Journal of the Korean Wood Science and Technology, Journal Year: 2024, Volume and Issue: 52(3), P. 262 - 275

Published: May 1, 2024

In Indonesia, Coptotermes curvignathus Holmgren and Cryptotermes cyanocephalus Light termite attacks can damage wood causing losses of 8.7 trillion rupiah per year. Wood treatment soil barrier are very important to protect structures their components from infestation. The application synthetic chemicals that pose risks the environment human health. growing movement replace these with new termiticides safe for in place persistent organic pollutants. Efficacy performance entomopathogenic fungi spores such as produce decanoic acid, hexadecanoic palmitic octadecadienoic acid potential compounds provide ecofriendly control. Entomopathogenic fungal Metarhizium anisopliae, Trichoderma harzianum, Beauveria bassiana, active ingredient were formulated nanocellulose was added an inert which helped deliver ingredients on controlling target pest, enhance utility ability product control termites. mortality termites successively main cause death. higher concentrations being associated used affect increased number mortality. M. anisopliae paired 60% concentrate best percentage yielded greatest C. cynocephalus field testing, provided better, it showed finest result rather than B. bassiana T. harzianum. results research indicate be Pest Control Management subterranean drywood

Language: Английский

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Combinatorial Synthesis of Novel 1-sulfonyloxy/acyloxyeugenol Derivatives as Fungicidal Agents

Combinatorial Chemistry & High Throughput Screening, Journal Year: 2021, Volume and Issue: 25(9), P. 1545 - 1551

Published: Aug. 15, 2021

Background: Developing the high-efficiency and low-risk small-molecule greenfungicide is key to effective control of plant pathogenic oomycetes. Essential oils play a very important role in novel fungicide discovery for their unique sources potential target sites. Eugenol, kind essential oil, was mainly isolated from unopened dried flower buds Syzygium aromaticum Myrtaceae family. Due its structural skeleton, eugenol derivatives have exhibited wide range biological activities. However, study on synthesis 1-sulfonyloxy/acyloxyeugenol as fungicidal agents against Phytophthora capsici has not yet been reported. Methods: Twenty-six (3a-p 5a-j) were prepared structures well characterized by 1H NMR, HRMS, m.p. Their activity evaluated P. using mycelial growth rate method. Results: To find natural-product-based oomycetes, we herein designed synthesized two series Leonian, vitro. Results revealed that, among all compounds, especially compounds 3a, 3f, 3n displayed most potent anti-oomycete with EC50 values 79.05, 75.05, 70.80, respectively. Conclusion: The results that sulfonyloxy group higher than acyloxy group. It suggested can be improved introducing This will pave way further design, modification, development agents.

Language: Английский

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Larvicidal activity and chemical composition of essential oils against Aedes aegypti Linn (Diptera: Culicidae) and Aedes albopictus Skuse (Diptera: Culicidae)

Journal of Health & Biological Sciences, Journal Year: 2024, Volume and Issue: 12(1), P. 1 - 10

Published: Sept. 2, 2024

Introduction Aedes mosquitoes are the main vectors of dengue, chikungunya, and Zika viruses. Essential oils have been used in research as alternatives to synthetic insecticides traditionally programs control these diseases. Methods: leaves plants from Caatinga biome were obtain essential which for larvicide essays against aegypti albopictus larvae. Results: significant differences observed LC50 values C. zeylanicum, winterianus, E. citriodora, O. micranthum, T. erecta Ae. aegypti, while A. conyzoides, micranthum albopictus, at analyzed times. The 24 h revealed a larvicidal effect all tested samples, with emphasis on conyzoides L. gracilis gracilis, an < 100 ppm. It was predominance terpenes components oils, and, some them, representing major constituent (citronellal: 47.71% citriodora 47.63% winterianus; geraniol: 30.54% citronellol: 25.61% citriodora; carvacrol: 55.13% gracilis; cyclohexen-1-one, 2-isopropyl-5-methyl-: 69.94% erecta). other compounds precocene (chromene - 97.66% conyzoides), eugenol (phenylpropanoid 96.28% 73.21% zeylanicum respectively). Conclusions: findings this study potential control, alternative source traditional chemical controls populations vectors. Further studies effects non-target organisms combined action two or more evaluated under field conditions obtaining commercially efficient formulations extracts.

Language: Английский

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