Enhancement of orofacial antinociceptive effect of carvacrol, a monoterpene present in oregano and thyme oils, by β-cyclodextrin inclusion complex in mice

Silva, Juliane C.; Almeida, Jackson R.G.S.; Quintans, Jullyana S.S.; Gopalsamy, Rajiv Gandhi; Saravanan, S.; Serafini, Mairim Russo; Oliveira, Maria Rayane Correia de; Silva, Bruno Anderson Fernandes da; Martins, Anita O.B.P.B.; Castro, Fyama Ferreira e; Menezes, Irwin Rose Alencar de; Coutinho, Henrique Douglas Melo; Oliveira, Rita C. M.; Thangaraj, Parimelazhagan; Araújo, Adriano A. S.

doi:10.1016/j.biopha.2016.09.065

Cited by 31 publications

(23 citation statements)

References 55 publications

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“…Orofacial pain is diagnosed in patients with chronic pain in the face, mouth, neck, and intraoral structures. Antinociceptive effects of carvacrol and its enhanced effects with β‐cyclodextrin in mice were also investigated in this regard (Silva et al, 2016). Mice were pre‐treated with vehicle (0.9% NaCl, p.o.…”

Section: Biological Activities (Preclinical In Vitro/in Vivo Studies)mentioning

confidence: 99%

Phytochemical constituents, biological activities, and health‐promoting effects of the genusOriganum

Sharifi‐Rad

Yılmaz

Antika

et al. 2020

Phytotherapy Research

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Origanum species are mostly distributed around the Mediterranean, Euro‐Siberian, and Iran‐Siberian regions. Since time immemorial, the genus has popularly been used in Southern Europe, as well as on the American continent as a spice now known all over the world under the name “oregano” or “pizza‐spice.” Origanum plants are also employed to prepare bitter tinctures, wines, vermouths, beer, and kvass. The major components of Origanum essential oil are various terpenes, phenols, phenolic acids, and flavonoids with predominant occurrence of carvacrol and thymol (with reasonable amounts of p‐cymen and ‐terpinene) or of terpinene‐4‐ol, linalool, and sabinene hydrate. Many species of Origanum genus are used to treat kidney, digestive, nervous, and respiratory disorders, spasms, sore throat, diabetes, lean menstruation, hypertension, cold, insomnia, toothache, headache, epilepsy, urinary tract infections, etc. Origanum essential oil showed potent bioactivities owing to its major constituents' carvacrol, thymol, and monoterpenes. Several preclinical studies evidenced its pharmacological potential as antiproliferative or anticancer, antidiabetic, antihyperlipidemic, anti‐obesity, renoprotective, antiinflammatory, vasoprotective, cardioprotective, antinociceptive, insecticidal, and hepatoprotective properties. Its nanotechnological applications as a promising pharmaceutical in order to enhance the solubility, physicochemical stability, and the accumulation rate of its essential oils have been investigated. However, Origanum has been reported causing angioedema, perioral dermatitis, allergic reaction, inhibition of platelet aggregation, hypoglycemia, and abortion. Conclusive evidences are still required for its clinical applications against human medical conditions. Toxicity analyses and risk assessment will aid to its safe and efficacious application. In addition, elaborate structure–activity studies are needed to explore the potential use of Origanum‐derived phytochemicals as promising drug candidates.

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Section: Biological Activities (Preclinical In Vitro/in Vivo Studies)mentioning

confidence: 99%

Phytochemical constituents, biological activities, and health‐promoting effects of the genusOriganum

Sharifi‐Rad

Yılmaz

Antika

et al. 2020

Phytotherapy Research

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“…Despite the known effects of isolated monoterpenes, the complexation of monoterpenes with b-cyclodextrin has The table summarizes the ligands and molecular targets used in molecular docking research, as well as the residues that showed interaction with the compounds. produced more promising results for treating pain and inflammation (Quintans-Junior et al, 2013;Nascimento et al, 2014;Silva et al, 2016). In a chronic non-inflammatory muscle pain model, chronic treatment using a citronellal/b-cyclodextrin complex at a dose of 50 mg/kg, p.o.…”

Section: Citronellalmentioning

confidence: 99%

Antinociceptive Activity of Chemical Components of Essential Oils That Involves Docking Studies: A Review

et al. 2020

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Introduction: Pain is considered an unpleasant sensory and emotional experience, being considered as one of the most important causes of human suffering. Computational chemistry associated with bioinformatics has stood out in the process of developing new drugs, through natural products, to manage this condition. Objective: To analyze, through literature data, recent molecular coupling studies on the antinociceptive activity of essential oils and monoterpenes. Data source: Systematic search of the literature considering the years of publications between 2005 and December 2019, in the electronic databases PubMed and Science Direct. Eligibility Criteria: Were considered as criteria of 1) Biological activity: non-clinical effects of an OE and/or monoterpenes on antinociceptive activity based on animal models and in silico analysis, 2) studies with plant material: chemically characterized essential oils and/or their constituents isolated, 3) clinical and non-clinical studies with in silico analysis to assess antinociceptive activity, 4) articles published in English. Exclusion criteria were literature review, report or case series, meta-analysis, theses, dissertations, and book chapter. Results: Of 16,006 articles, 16 articles fulfilled all the criteria. All selected studies were non-clinical. The most prominent plant families used were Asteraceae, Euphorbiaceae, Verbenaceae, Lamiaceae, and Lauraceae. Among the phytochemicals studied were a-Terpineol, 3-(5-substituted-1,3,4-oxadiazol-2-yl)-N′-[2-oxo-1,2-dihydro-3H-indol-3ylidene] propane hydrazide, b-cyclodextrin complexed with citronellal, (−)-a-bisabolol, b-cyclodextrin complexed with farnesol, and p-Cymene. The softwares used for docking studies were Molegro Virtual Docker, Sybyl ® X, Vlife MDS, AutoDock Vina, Hex Protein Docking, and AutoDock 4.2 in PyRx 0.9. The molecular targets/complexes used were Nitric Oxide Synthase, COX-2, GluR2-S1S2, TRPV1, b-CD complex, CaV 1 , CaV 2.1 , CaV 2.2 , and CaV 2.3 , 5-HT receptor, delta receptor, kappa receptor, and MU (m)

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“…The use of naloxone, an opposing receptor antagonist, was able to reverse the effect, suggesting possible action of this essential oil at the central and peripheral levels. 37 Similarly, the essential oil of Cymbopogon winterianus, which contains 40.06% geraniol, promoted formalininduced antinociception, as evidenced by the time of leg licking, in the first and second phases of the test when administered orally at doses of 50, 100 and 200 mg/kg. These results corroborate the findings of this study.…”

Section: Discussionmentioning

confidence: 96%

Orofacial antinociceptive activity and anchorage molecular mechanism in silico of geraniol

et al. 2020

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We aimed to evaluate the orofacial antinociceptive effect of geraniol in mice and its molecular anchorage mechanism. Seven mice per group (probabilistic sample) were treated with geraniol (12.5, 25 and 50 mg/kg, i.p.), morphine (6 mg/kg, i.p.) and vehicle (saline + Tween 80 at 0.2%, i.p.) 30 minutes prior to the beginning of the experiment. Injecting glutamate (25 μM), capsaicin (2.5 μg) and formalin (2%) into the right upper lip (perinasal) of the mouse induced nociception. Behavioral analysis of the animals considered the friction time (in seconds) of the mentioned region using hind or front paws by a researcher blinded to the treatment groups. The statistical analysis was performed blindly, considering α = 5%. The results showed that in the glutamate and capsaicin tests, concentrations of 25 mg/kg and 50 mg/ kg presented antinociceptive activity (p < 0.005, power> 80%). In the formalin test, geraniol was able to reduce nociception at a concentration of 50 mg/kg (p < 0.005, power> 80%). In the molecular anchorage study, high values of binding between the evaluated substance and receptors of glutamate were observed (metabotropic glutamate receptor,-87.8501 Kcal/mol; N-methyl-D-aspartate,-86.4451 Kcal/mol; α-amino-3hydroxy-5-methyl-4-isoxazole propionic acid,-85.6755 Kcal/mol). Geraniol presented orofacial antinociceptive activity, probably by interacting with glutamate-related receptors.

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Enhancement of orofacial antinociceptive effect of carvacrol, a monoterpene present in oregano and thyme oils, by β-cyclodextrin inclusion complex in mice

Cited by 31 publications

References 55 publications

Phytochemical constituents, biological activities, and health‐promoting effects of the genusOriganum

Phytochemical constituents, biological activities, and health‐promoting effects of the genusOriganum

Antinociceptive Activity of Chemical Components of Essential Oils That Involves Docking Studies: A Review

Orofacial antinociceptive activity and anchorage molecular mechanism in silico of geraniol

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