528-79-0Relevant academic research and scientific papers
Chemical profile of lippia thymoides, evaluation of the acetylcholinesterase inhibitory activity of its essential oil, and molecular docking and molecular dynamics simulations
Silva, Sebasti?o Gomes,Da Costa, Renato Araujo,Figueiredo, Pablo Luis B.,Do Socorro Barros Brasil, Davi,De Aguiar Andrade, Eloisa Helena,De Oliveira, Mozaniel Santana,De Carvalho, Raul Nunes,Da Cruz, Jorddy Neves,De Jesus Chaves Neto, Antonio Maia,Nascimento, Lidiane Diniz
, (2019)
The essential oils of the fresh and dry flowers, leaves, branches, and roots of Lippia thymoides were obtained by hydrodistillation and analyzed using gas chromatography (GC) and GC-mass spectrometry (MS). The acetylcholinesterase inhibitory activity of the essential oil of fresh leaves was investigated on silica gel plates. The interactions of the key compounds with acetylcholinesterase were simulated by molecular docking and molecular dynamics studies. In total, 75 compounds were identified, and oxygenated monoterpenes were the dominant components of all the plant parts, ranging from 19.48% to 84.99%. In the roots, the main compounds were saturated and unsaturated fatty acids, having contents varying from 39.5% to 32.17%, respectively. In the evaluation of the anticholinesterase activity, the essential oils (detection limit (DL) = 0.1 ng/spot) were found to be about ten times less active than that of physostigmine (DL = 0.01ng/spot), whereas thymol and thymol acetate presented DL values each of 0.01 ng/spot, equivalent to that of the positive control. Based on the docking and molecular dynamics studies, thymol and thymol acetate interact with the catalytic residues Ser203 and His447 of the active site of acetylcholinesterase. The binding free energies (ΔGbind) for these ligands were -18.49 and -26.88 kcal/mol, demonstrating that the ligands are able to interact with the protein and inhibit their catalytic activity.
Biotechnological Potential of Eugenol and Thymol Derivatives Against Staphylococcus aureus from Bovine Mastitis
Nunes, Daiana O. S.,Vinturelle, Rafaelle,Martins, Francislene J.,dos Santos, Thiago F.,Valverde, Alessandra Leda,Ribeiro, Carlos Magno R.,Castro, Helena C.,Folly, Evelize
, p. 1846 - 1855 (2021/04/29)
Bovine mastitis is an infectious disease that affects the mammary gland of dairy cattle with considerable economic losses. Staphylococcus aureus is the main microorganism involved in this highly contagious process, and the treatment is only using antibiotics. Currently, the search for new treatment and/or compounds is still in need due to microbial resistance. In this work, we evaluated the potential of eugenol and thymol derivatives against S. aureus strains from bovine mastitis. On that purpose, nine derivatives were synthesized from eugenol and thymol (1–9), and tested against 15 strains of S. aureus from subclinical bovine mastitis. Initially, the strains were evaluated for the biofilm production profile, and those with strong adherence were selected to the antimicrobial sensitivity determination in the Minimum Inhibitory Concentration (MIC) assays. Herein the compounds toxicity was also evaluated by in silico analysis using Osiris DataWarrior software. The results showed that 60% of the strains were considered strongly adherent and three strains (S. aureus 4271, 4745 and 4746) were selected for the MIC tests. Among the nine eugenol and thymol derivatives tested, four were active against the evaluated strains (MIC = 32?μg?mL?1) within CLSI standard values. In silico analysis showed that all derivatives had cLopP ??4 and TPSA 140 ?2, and similar theoretical toxicity parameters to some antibiotics currently on the market. These molecules also showed negative drug-likeness values, pointing to the originality of these structures and theoretical feasibility on escaping of resistance mechanism and act against resistant strains. Thus, these eugenol derivatives may be considered as promising for the development of new treatments against bovine mastitis and future exploring on this purpose.
Environmentally benign decarboxylative: N-, O-, and S-Acetylations and acylations
Ghosh, Santanu,Purkait, Anisha,Jana, Chandan K.
supporting information, p. 8721 - 8727 (2020/12/30)
An operationally simple and general method for acetylation and acylation of a wide variety of substrates (amines, alcohols, phenols, thiols, and hydrazones) has been reported. Meldrum's acid and its derivatives have been used as an air-stable, non-volatile, cost-effective, and easy to handle acetylating/acylating agent. Easily separable byproducts (CO2 and acetone) allowed the isolation of analytically pure acetylated products without the requirement of work-up and any chromatography. This journal is
Structure-Odor Activity Studies on Derivatives of Aromatic and Oxygenated Monoterpenoids Synthesized by Modifying p-Cymene
Schreiner, Linda,Bauer, Johannes,Ortner, Eva,Buettner, Andrea
supporting information, p. 834 - 842 (2020/03/30)
Thymoquinone was recently reported as having a unique pencil-like odor and being the impact compound for the cedar-like and cedar wood-based product smell such as pencils. The compounds thymol and carvacrol are structurally related odorants commonly found in plants and foods such as thyme and oregano, also having a significant contribution to their overall aroma. However, a systematic elucidation of the sensory properties in this class of oxygenated, aromatic monoterpenoids has not been carried out. To close this gap and gain new insights into structure-odor relationships leading to pencil-like and woody odors, 19 structurally related derivatives of p-cymene starting from thymol and carvacrol were synthesized and characterized. The compounds had odor thresholds ranging from 2.0 ng/L air to 388.8 ng/L air, being lowest for thymol and carvacrol and highest for thymohydroquinone. The compounds smelled mostly thyme-like, oregano-like, and pencil-like with phenolic, earthy, and medicinal variations in their odor character, which could be successfully linked to structural motifs.
INSECTICIDAL COMPOSITION
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Paragraph 0063-0064, (2020/10/27)
PROBLEM TO BE SOLVED: To provide a composition that can exhibit effective insecticidal action on insect pests. SOLUTION: An insecticidal composition comprises, e.g., a compound represented by general formula (1) in the figure. [R1 is a C1-10 alkyl group or the like, where the alkyl group and the like may be substituted with a halogen atom or the like; R2 is a hydrogen atom or the like, or R2 may bind a methoxy group binding a carbon atom adjacent to a carbon atom which R2 binds, to form a -O-CH2-O- group.] SELECTED DRAWING: None COPYRIGHT: (C)2021,JPO&INPIT
Unprecedented acetylation of phenols using a catalytic amount of magnesium powder
Bajracharya, Gan B.,Shrestha, Suryaman Sama
supporting information, p. 1688 - 1693 (2018/06/15)
The acetylation of phenols with acetic anhydride was achieved using a catalytic amount of magnesium metal powder under air and solvent-free conditions to afford corresponding phenyl acetates in excellent yield (up to 98%).
Antifungal activity of phenolic monoterpenes and structure-related compounds against plant pathogenic fungi
Wang, Kaibo,Jiang, Shanshan,Pu, Te,Fan, Liming,Su, Fawu,Ye, Min
, p. 1 - 8 (2018/02/06)
The aim of this work is to explore the possibility of using the phenolic monoterpenes (PMs) as leading compounds with antifungal activity against plant disease. The in vitro antifungal activities of carvacrol and thymol against seven kinds of plant pathogenic fungi were evaluated on mycelium growth rate method, and the results showed that carvacrol and thymol exhibited broad spectrum antifungal activity. Structure requirement for the antifungal activity of PMs was also investigated. The preliminary conclusion was that phenolic hydroxyl and monoterpene were basic structures for the antifungal activity of PMs, and the position of phenolic hydroxyl showed less effect. Ester derivatives of carvacrol and thymol were more effective than carvacrol and thymol against plant pathogenic fungi. We suggested that carvacrol, thymol and their ester derivatives could potentially be used as new fungicide leading compounds.
Synthesis, antimicrobial activity and in silico studies on thymol esters
Lazarevi?, Jelena,Kolarevi?, Ana,Dordevi?, Aleksandra,Stojanovi?, Gordana,?melcerovi?, Andrija,Ciuffreda, Pierangela,Santaniello, Enzo
, p. 603 - 612 (2017/09/11)
Derivatisation of parent structure in terpenoids often results in enhancement of biological activity of newly obtained compounds. Thymol, a naturally occurring phenol biosynthesized through the terpene pathway, is a well known biocide with strong antimicrobial attributes and diverse therapeutic activities. We have aimed our study on a single modification of phenolic functionality in thymol in order to obtain a small focused library of twenty thymyl esters, ten of which were new compounds. All compounds were involved in in vitro antimicrobial testing. Another important aspect of current study was implementation of in silico calculation of physico-chemical, pharmacokinetic and toxicological properties, which could be helpful by giving an additional guidance in further research.
INSECTICIDAL COMPOSITION
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Paragraph 0063, (2017/09/29)
PROBLEM TO BE SOLVED: To provide a composition that can exhibit effective insecticidal action on pests. SOLUTION: An insecticidal composition comprises a compound represented by general formula (1) [R1 is a C1-10 alkyl group or the like, where the alkyl group and the like may be substituted with a halogen atom and the like; R2 is a hydrogen atom and the like, or R2 may bind a methoxy group binding a carbon atom adjacent to a carbon atom which R2 binds, to form a -O-CH2-O- group]. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT
Thymol and eugenol derivatives as potential antileishmanial agents
De Morais, Selene Maia,Vila-Nova, Nadja Soares,Bevilaqua, Claudia Maria Leal,Rondon, Fernanda Cristina,Lobo, Carlos Henrique,De Alencar Araripe Noronha Moura, Arlindo,Sales, Antnia Dbora,Rodrigues, Ana Paula Ribeiro,De Figuereido, Jos Ricardo,Campello, Claudio Cabral,Wilson, Mary E.,De Andrade, Heitor Franco
, p. 6250 - 6255 (2015/02/02)
In Northeastern Brazil visceral leishmaniasis is endemic with lethal cases among humans and dogs. Treatment is toxic and 5-10% of humans die despite treatment. The aim of this work was to survey natural active compounds to find new molecules with high activity and low toxicity against Leishmania infantum chagasi. The compounds thymol and eugenol were chosen to be starting compounds to synthesize acetyl and benzoyl derivatives and to test their antileishmanial activity in vitro and in vivo against L. i. chagasi. A screening assay using luciferase-expressing promastigotes was used to measure the growth inhibition of promastigotes, and an ELISA in situ was performed to evaluate the growth inhibition of amastigote. For the in vivo assay, thymol and eugenol derivatives were given IP to BALB/c mice at 100 mg/kg/day for 30 days. The thymol derivatives demonstrated the greater activity than the eugenol derivatives, and benzoyl-thymol was the best inhibitor (8.67 ± 0.28 μg/mL). All compounds demonstrated similar activity against amastigotes, and acetyl-thymol was more active than thymol and the positive control drug amphotericin B. Immunohistochemistry demonstrated the presence of Leishmania amastigote only in the spleen but not the liver of mice treated with acetyl-thymol. Thus, these synthesized derivatives demonstrated anti-leishmanial activity both in vitro and in vivo. These may constitute useful compounds to generate new agents for treatment of leishmaniasis.
