Synthesis and Antibacterial Study of Thymol Derivatives

Rahim, Nurul Hazwani Che Abdul; Asari, Asnuzilawati; Ismail, Normaz Wana; Abdullah, Fauziah; Osman, Hasnah; Tahier, Soraya Shafawati Mohamad

doi:10.14233/ajchem.2018.20933

Cited by 4 publications

(3 citation statements)

References 8 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[12] Eugenol esters EU12-16 were synthesized by reaction of eugenol 1 with the corresponding carboxylic acids in dichloromethane, at room temperature, in the presence of 4-dimethylaminopyridine (DMAP) and N,N′-dicyclohexylcarbodiimide (DCC). The synthesis of compounds EU12 and EU13 is unpublished in the literature; compounds EU14 [26,27] and EU16 [28] have already been obtained, but by different synthetic routes; synthesis of compound EU15 was previously published. [27] As a result, detail experimental procedure and full characterization of compounds EU12-14 and EU16 are described below.…”

Section: Discussionmentioning

confidence: 99%

“…The synthesis of compounds EU12 and EU13 is unpublished in the literature; compounds EU14 [26,27] and EU16 [28] have already been obtained, but by different synthetic routes; synthesis of compound EU15 was previously published. [27] As a result, detail experimental procedure and full characterization of compounds EU12-14 and EU16 are described below.…”

Section: Discussionmentioning

confidence: 99%

See 1 more Smart Citation

Structural modification of naturally occurring phenolics as a strategy for developing cytotoxic molecules towards cancer cells

Olim,

Pereira,

Fernandes

et al. 2023

Archiv der Pharmazie

View full text Add to dashboard Cite

Natural products belonging to different chemical classes have been established as a promising source of novel anticancer drugs. Several low‐molecular‐weight compounds from the classes of monoterpenes, phenylpropanoids, and flavonoids were shown to possess anticancer activities in previous studies. In this work, over 20 semisynthetic derivatives of molecules belonging to these classes, namely thymol, eugenol, and 6‐hydroxyflavanone were synthesized and tested for their cytotoxicity against two human cancer cell lines, namely AGS cells (gastric adenocarcinoma) and A549 cells (human lung carcinoma). An initial screening based on viability assessment was performed to identify the most cytotoxic compounds at 100 μM. The results evidenced that two 6‐hydroxyflavanone derivatives were the most cytotoxic among the compounds tested, being selected for further studies. These derivatives displayed enhanced toxicity when compared with their natural counterparts. Moreover, the lactate dehydrogenase (LDH) assay showed that the loss of cell viability was not accompanied by a loss of membrane integrity, thus ruling out a necrotic process. Morphological studies with AGS cells demonstrated chromatin condensation compatible with apoptosis, confirmed by the activation of caspase 3/7. Furthermore, a viability assay on a noncancer human embryonic lung fibroblast cell line (MRC‐5) confirmed that these two derivatives possess selective anticancer activity.

show abstract

Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Structural modification of naturally occurring phenolics as a strategy for developing cytotoxic molecules towards cancer cells

Olim,

Pereira,

Fernandes

et al. 2023

Archiv der Pharmazie

View full text Add to dashboard Cite

show abstract

“…The synthesis of oxiranes EU7-11 was performed by the reaction of compounds EU1-5 , respectively, with m -chloroperbenzoic acid in dichloromethane, at room temperature [12] Eugenol esters EU12-16 were synthesized by reaction of eugenol 1 with the corresponding carboxylic acids in dichloromethane, at room temperature, in the presence of 4-dimethylaminopyridine (DMAP) and N,N’-dicyclohexylcarbodiimide (DCC). The synthesis of compounds EU12 and EU13 is unpublished in the literature; compounds EU14 [13,14], and EU16 [15] have already been obtained, but by different synthetic routes; synthesis of compound EU15 was previously published [14]. As a result, detail experimental procedure and full characterisation of compounds EU12-14 and EU16 are described below.…”

Section: Methodsmentioning

confidence: 99%

Structural modification of naturally-occurring phenolics as a strategy for developing cytotoxic molecules towards cancer cells

Olim

Pereira

Fernandes

et al. 2023

Preprint

View full text Add to dashboard Cite

Natural products belonging to different chemical classes have been established as a promising source of novel anticancer drugs. Several low molecular weight compounds from the classes of monoterpenes, phenylpropanoids and flavonoids were shown to possess anticancer activities in previous studies. In this work, over 20 semisynthetic derivatives of molecules belonging to these classes, namely thymol, eugenol and 6-hydroxyflavanone were synthesized and tested for their cytotoxicity against two human cancer cell lines, namely gastric adenocarcinoma (AGS cells) and human lung carcinoma (A549 cells). An initial screening based on viability assessment was performed in order to identify the most cytotoxic compounds at 100 μM. The results evidenced that two 6-hydroxyflavanone derivatives were the most cytotoxic among the compounds tested, being selected for further studies. Noteworthy, in a general way some of the derivatives synthesized displayed enhanced toxicity when compared with their natural counterparts. Moreover, LDH assay showed that the loss of cell viability was not accompanied by a loss of membrane integrity, thus ruling out a necrotic process. Morphological studies with AGS cells demonstrated chromatin condensation compatible with apoptosis, confirmed by the activation of caspase 3/7. Furthermore, a viability assay on non-cancer human embryonic lung fibroblast cell line (MRC-5) confirmed these two derivatives possess selective anticancer activity.

show abstract

Purinergic system as a potential target for inflammation and toxicity induced by thymol in immune cells and tissues

et al. 2018

View full text Add to dashboard Cite

Thymol is a phytochemical component present in many plants used as food additive in order to promote animal growth due to its several biological properties. However, possible side effects of thymol remain poorly known limited to few reports. In this sense, we evaluated the enzymes of the purinergic signaling such as, ectonucleoside triphosphate diphosphohydrolase (NTPDase), 5'-nucleotidase and adenosine deaminase (ADA), that play an important role on toxicity induced by excessive adenosine triphosphate (ATP) content in the extracellular environment. Thus, the aim of this study was to evaluate whether purinergic signaling could be considered a potential target of thymol-induced inflammation, and the toxicity in tissues and immune cells of mice after thymol administration. NTPDase activity (ATP as substrate) in serum, spleen, and splenic lymphocytes was lower after 30 days of oral treatment at doses of 10, 20, and 40 mg/kg of thymol, while ADA activity was stimulated at 20 and 40 mg/kg. No differences were observed between groups regarding NTPDase (ADP as substrate) and 5'-nucleotidase activities in all evaluated tissues. Based on these evidences, adenine nucleotide hydrolysis is modified in serum, spleen, and splenic lymphocytes of mice treated with thymol, contributing to inflammation and toxicity by a reduction on ATP hydrolyses and its possible accumulation in the extracellular medium and increased Ado desamination and its possible reduction in the extracellular environment, leading to a self-sustained pro-inflammatory deleterious cycle. In summary, all tested thymol concentrations induced inflammation and toxicity in tissues and immune cells of treated mice.

show abstract

Synthesis and Antibacterial Study of Thymol Derivatives

Abstract: Five thymol derivatives (2-6) were synthesized and evaluated for their antibacterial activity against four bacterial strains i.e., Bacillus subtilis, Staphylococcus aureus, Staphylococcus epidermidis and Escherichia coli using standard well-diffusion method.

Cited by 4 publications

References 8 publications

Structural modification of naturally occurring phenolics as a strategy for developing cytotoxic molecules towards cancer cells

Structural modification of naturally occurring phenolics as a strategy for developing cytotoxic molecules towards cancer cells

Structural modification of naturally-occurring phenolics as a strategy for developing cytotoxic molecules towards cancer cells

Purinergic system as a potential target for inflammation and toxicity induced by thymol in immune cells and tissues

Contact Info

Product

Resources

About