Synthesis and Pharmacological Evaluation of Carvacrol Propionate

Santana, Marília T.; Silva, Viviane Barros; Brito, Renan Guedes de; Santos, Priscila L.; Cavalcanti, Sócrates Cabral de Holanda; Barreto, Emiliano; Ferro, Jamylle Nunes de Souza; Santos, Márcio Roberto Viana dos; Araújo, Adriano Antunes de Sousa; Quintans‐Júnior, Lucindo José

doi:10.1007/s10753-014-9884-3

Cited by 7 publications

(5 citation statements)

References 54 publications

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“…The results of this experiment are matched with the results published by Santana et al These authors have achieved an antinociceptive effect of carvacrolpropionate when this derivate of monoterpene administered to mice orally in the same dosage range (25, 50, 100 mg/kg) in the pre-treatment of hyperalgesia caused by formalin [11]. Also, Bonfi t et al showed that isoproxy-carvacrol administered intraperitoneally (10,30, 100 mg/kg) in the pre-treatment of formalin-induced hyperalgesia in mice and in the pre-treatment of carrageenan-induced hyperalgesia in rats (paw pressure tests), achieved a signifi cant antinociceptive effect only at the highest dose (100 mg/kg) [19].…”

Section: Discussionsupporting

confidence: 89%

“…It has been shown that carvacrol administered orally in mice reduces formalin-induced nociception, mechanical hyperalgesia and infl ammation in damaged tissues [11]. Also, Guimaraes et al [12] demonstrated that carvacrol administered orally in mice exhibits signifi cant antinociceptive and anti-edematous activity on hyperalgesia and edema caused by carrageenan and tumor necrosis factor-alpha (TNF-α).…”

Section: Introductionmentioning

confidence: 99%

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The Effect of Carvacrol on Inflammatory Pain and Motor Coordination in Rats

et al. 2016

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Carvacrol is a monoterpenic phenol and an active ingredient of the plant essential oils of the family Lamiaceae. We have investigated the analgesic effect of carvacrol, the possible dependence of the effect in relation to animal sex, and the impact of carvacrol on motor coordination in rats. Hyperalgesia was induced by formalin (1.5%), which was administered SC in the upper lip of rat. Hyperalgesia and effects of carvacrol and indomethacin were measured by using the orofacial formalin test. The infl uence on motor coordination in animals treated with carvacrol was investigated by using the rota-rod test. Carvacrol administered PO in pre-treatment (45 min. prior to formalin) at a single dose of 50, 75 and 100 mg /kg BW, in the male, 50 and 100 mg /kg BW, in female rats caused a dose-dependent antinociceptive effect. This effect of carvacrol was signifi cantly higher (P<0.01, P<0.001) in male rats. Compared with indomethacin administered during pre-treatment (2 mg/kg, PO), carvacrol (100 mg/kg) exhibits signifi cantly higher (P <0.05 and P <0.001) antinociceptive effect on formalininduced hyperalgesia in male rats. In the rota-rod test carvacrol did not disturb the motor coordination in male rats, nor the dose of carvacrol with clear antinociceptive properties exhibited depressive effect on the CNS of treated rats. Keeping in mind that the monoterpene carvacrol is of plant origin, with potentially less side effects and without residues, it is realistic to expect the possibility of its therapeutic use in the treatment of infl ammatory pain in animals.

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Section: Discussionsupporting

confidence: 89%

Section: Introductionmentioning

confidence: 99%

The Effect of Carvacrol on Inflammatory Pain and Motor Coordination in Rats

et al. 2016

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“…Related studies found that (a) carvacrol enhanced warmth and heat pain on the human tongue; , (b) synthetic carvacrol propionate attenuates nociception, mechanical hyperalgesia, and inflammation in male Swiss mice through inhibition of cytokines; (c) oral administration of carvacrol in mice models of pain resulted in significant inhibition of nociception without impairment of motor performance, suggesting that the antinociceptive activity might not act through the opioid system; (d) results of a study of orofacial analgesic-like activity of carvacrol in rodents suggest that the compound might represent an important tool for the treatment of orofacial pain; (e) carvacrol in drinking water was more effective than the steroidal drug dexamethasone in mitigating adverse effects in sensitized guinea pigs, suggesting the monoterpene could be used to treat asthma in humans; and (f) Guimarães et al . reviewed mechanisms that might govern analgesic aspects of structurally different monoterpenes.…”

Section: Additional Bioactivities and Health-promoting Properties Of ...mentioning

confidence: 99%

Chemistry and Multibeneficial Bioactivities of Carvacrol (4-Isopropyl-2-methylphenol), a Component of Essential Oils Produced by Aromatic Plants and Spices

Friedman

2014

J. Agric. Food Chem.

167

111

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Aromatic plants produce organic compounds that may be involved in the defense of plants against phytopathogenic insects, bacteria, fungi, and viruses. One of these compounds, called carvacrol, which is found in high concentrations in essential oils such as oregano, has been reported to exhibit numerous bioactivities in cells and animals. This integrated overview surveys and interprets our present knowledge of the chemistry and analysis of carvacrol and its beneficial bioactivities. These activities include its antioxidative properties in food (e.g., lard, sunflower oil) and in vivo and the inhibition of foodborne and human antibiotic-susceptible and antibiotic-resistant pathogenic bacteria, viruses, pathogenic fungi and parasites, and insects in vitro and in human foods (e.g., apple juice, eggs, leafy greens, meat and poultry products, milk, oysters) and food animal feeds and wastes. Also covered are inhibitions of microbial and fungal toxin production and the anti-inflammatory, analgesic, antiarthritic, antiallergic, anticarcinogenic, antidiabetic, cardioprotective, gastroprotective, hepatoprotective, and neuroprotective properties of carvacrol as well as metabolic, synergistic, and mechanistic aspects. Areas for future research are also suggested. The collated information and suggested research might contribute to a better understanding of agronomical, biosynthetic, chemical, physiological, and cellular mechanisms of the described health-promoting effects of carvacrol, and facilitate and guide further studies needed to optimize the use of carvacrol as a multifunctional food in pure and encapsulated forms, in edible antimicrobial films, and in combination with plant-derived and medical antibiotics to help prevent or treat animal and human diseases.

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“…Studies have shown that adding tannin to zein to prepare zein/tannin nerve conduit, can enhance the effect of zein nerve conduit and promote the regeneration of peripheral nerves [81]. Compared with carvacrol, carvacrol propionate formed by esterification of carvacrol with propionyl chloride in the presence of triethylamine (TEA) has stronger antiinflammatory, analgesic and antihyperalgesic functions [82], carvacrol esters and ethers with amino groups formed by functionalizing the phenolic group of carvacrol can be anchored to the gold surface to develop antibacterial coatings [83]. Thymol combined with nonsteroidal antiinflammatory drugs can reduce the production of reactive oxygen species and reduce the probability of adverse reactions such as gastric mucosal damage [84]，which may be a new application of nonsteroidal anti-inflammatory drugs.…”

Section: Drug Loadingmentioning

confidence: 99%

Polymers containing natural plant phenolic compounds for peripheral nerve injury

Zheng

Qiu

et al. 2022

BAB

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Peripheral nerve injury is a serious and disabling disease prevalent in the world. It caused by trauma is often accompanied with soft tissue injuries, fractures, infections, etc., and can cause permanent damage. The treatment methods of peripheral nerve injury mainly include traditional microsurgical repair, neurotrophic drug treatment, as well as cuttingedge nerve conduit treatment, nerve stimulation, cell therapy, etc. However, more than 30% of patients with peripheral nerve injury still have poor recovery, including partial loss or complete loss of motor and/or sensory function, muscle atrophy，chronic pain and severe disability, among can lead to permanent disease. Phenolic compounds are secondary metabolites which is the most abundant in plants, consisting of an aromatic ring and one or more hydroxyl substituents, the main groups including flavonoids, phenolic acids, tannins, stilbene and lignans. A lot of studies have shown that natural phenolic compounds have various properties, such as antioxidant, anti-infective, anticancer, anti-inflammatory, etc., and have broad applications in the prevention of heart disease, cancer, diabetes, oxidative stress-related diseases, and neuroprotection prospect. This review discusses the potential applications and molecular mechanisms of natural phenolic compounds its polymer derivatives in the treatment of peripheral nerve injury.

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Synthesis and Pharmacological Evaluation of Carvacrol Propionate

Cited by 7 publications

References 54 publications

The Effect of Carvacrol on Inflammatory Pain and Motor Coordination in Rats

The Effect of Carvacrol on Inflammatory Pain and Motor Coordination in Rats

Chemistry and Multibeneficial Bioactivities of Carvacrol (4-Isopropyl-2-methylphenol), a Component of Essential Oils Produced by Aromatic Plants and Spices

Polymers containing natural plant phenolic compounds for peripheral nerve injury

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