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Natural Products from the Amazon Region as Potential Antimicrobials
Published in Mahendra Rai, Chistiane M. Feitosa, Eco-Friendly Biobased Products Used in Microbial Diseases, 2022
Josiane E. A. Silva, Iasmin L. D. Paranatinga, Elaine C. P. Oliveira, Silvia K. S. Escher, Ananda S. Antonio, Leandro S. Nascimento, Patricia P. Orlandi, Valdir F. Veiga-Júnior
As an antimicrobial, eugenol had demonstrated activity against Gram-positive and Gram-negative bacteria such as, Escherichia coli, Pseudomonas fluorescens, Staphylococcus aureus, Bacillus cereus and Listeria monocytogenes. The mechanism of action of eugenol against microorganism is mainly through the increase of cellular membrane permeability, disruption of the cytoplasmic membrane and downregulation of gene transcription. By this mechanism, eugenol is also able to inhibit and disrupt the structure of Acinetobacter baumannii biofilms. In addition, eugenol also demonstrates synergic activity with penicillin and ampicillin against Streptococcus pneumoniae and Streptococcus pyogenes (Mak et al. 2019).
Monographs of fragrance chemicals and extracts that have caused contact allergy / allergic contact dermatitis
Published in Anton C. de Groot, Monographs in Contact Allergy, 2021
In dentistry, eugenol may be present in a variety of dental materials such as impression materials, filling materials, dental cements, endodontic sealers, periodontal dressing materials and dry socket dressings (94). Oral soft tissue reactions have been classified as follows (94): Eugenol is generally cytotoxic at high concentrations and has an adverse effect on fibroblasts and osteoblast-like cells. Thus, at high concentrations it produces necrosis and reduced healing. This effect is dose-related and will potentially affect all patients.In lower concentrations, eugenol can act as a contact allergen evoking a delayed hypersensitivity reaction (94,95,96,97,99,100,110).Rarely, eugenol when placed in the mouth, can cause a more significant generalised response including urticaria and anaphylactic shock (92,103).
Croton zehntneri: Essential Oils and Inclusion Complex
Published in Mahendra Rai, Shandesh Bhattarai, Chistiane M. Feitosa, Ethnopharmacology of Wild Plants, 2021
Lorenna Fonseca, Mahendra Rai, Sidney Gonçalo de Lima
Eugenol, as shown in Figure 16.2, is a phenylpropanoid derivative known for its characteristic flavor and aroma and for its antimicrobial and antioxidant properties, and is used as an agent of food flavor and fragrance. In addition, eugenol is a food additive approved by the U.S. Food and Drug Administration, with an LD50 of 3000 mg kg–1 for oral rats (Gong et al. 2016, Piletti et al. 2017). It is present in the essential oil of several plants, including Ocimum tenuiflorum (Raina et al. 2013), Ocimum basilicum(Bhuvaneshwari et al. 2016) and Syzygium aromaticum (Sebaaly et al. 2015); it can also be found in nutmeg, cinnamon, among others (Kim et al. 1997).
Application of the Mannich reaction in the structural modification of natural products
Published in Journal of Enzyme Inhibition and Medicinal Chemistry, 2023
Miao-Xia Pu, Hong-Yan Guo, Zhe-Shan Quan, Xiaoting Li, Qing-Kun Shen
Eugenol is a natural allyl phenol that has a simple structure, is easy to modify, and has a wide range of biological activities. Mannich base derivatives contain nitrogen-containing groups, which improve the water solubility of compounds and also protonate nitrogen atoms under physiological conditions to strengthen the interaction between ligands and receptors2. The structures of linezolid, eprazolid, and itraconazole antibacterial drugs suggest that the bioisosteric ring of piperazine or morpholine plays a vital role in their antibacterial activity. Pedro Henrique Oliveira Abrão et al.73 introduced a morpholino group into the lead compound eugenol through the Mannich reaction, synthesised a series of eugenol Mannich base derivatives, and evaluated their inhibitory activities against C. albicans ATCC10231 and Candida krusei ATCC 6258 (Table 3). In addition, they explored the effect of the phenolic hydroxyl groups of these compounds, being freed or masked as esters of different polarities and volumes, on their anticandidal activity. The results showed that compound 59 (Figure 4) exhibited the strongest antifungal activity, with IC50 values ranging 0.63–10.2 µg/mL. C. albicans and C. krusei were the most sensitive to compound 59 with an IC50 value of 0.63 µg/mL, which was much higher than that of the positive control drug fluconazole, of which the IC50 values were 3.27 and 104.5 µg/mL, respectively.
In vitro enzyme inhibition and in vivo anti-hyperuricemic potential of eugenol: an experimental approach
Published in Drug Development and Industrial Pharmacy, 2021
V. Vijeesh, A. Vysakh, Ninan Jisha, M. S. Latha
The natural molecules with unexplored biological potential might be beneficial for the treatment of various diseases. Eugenol is a natural phenolic compound commonly found in clove, cinnamon, etc. [7]. It is an unavoidable component in the pharmaceutical, cosmetical, and food industries [8]. As per the Food and Drug Administration guidelines, consuming the unburned form of eugenol is listed as ‘Generally Regarded As Safe’ [9]. Eugenol possesses remarkable biological activities such as antioxidant, anti-inflammatory, anti-cancer, anti-diabetic, hepatoprotective activities [10,11]. The anti-hyperuricemic effect of eugenol is not yet been discovered. The multi-spectroscopic binding and in silico docking studies of eugenol with XO was reported previously from our laboratory [12]. In this view, the current study was designed to evaluate the anti-hyperuricemic effect of eugenol in in vitro and in vivo models.
Relevant essential oil components: a minireview on increasing applications and potential toxicity
Published in Toxicology Mechanisms and Methods, 2021
Cristina Fuentes, Ana Fuentes, José Manuel Barat, María José Ruiz
Besides its antimicrobial role, and its analgesic and anesthetic action, eugenol exhibits anti-oxidant and anti-inflammatory effects at low concentrations (Fujisawa et al. 2002). Eugenol has been demonstrated to exert a beneficial action on both related properties through the inhibition of enzymes and oxidative processes (Barboza et al. 2018). Importantly, it has been found to inhibit lipid peroxidation at initial levels, by blocking secondary radicals derived from endoplasmic reticulum lipids (Nagababu et al. 2010). In line with this, the pharmacological properties of eugenol have been described for the treatment of diseases associated with oxidative stress and inflammatory responses. This compound exhibits a neuroprotective potential and offers hypolipidemic and anti-diabetic effectiveness. Moreover, eugenol has demonstrated anti-cancer activity by inhibiting the propagation of different cancer cell types, an anti-mutagenic potential against different genotoxic compounds, and its use in regenerative medicine has been proposed since the proliferation and migration promotion of stem cells in vitro has been demonstrated (Khalil et al. 2017; Sisakhtnezhad et al. 2018).