D-limonene exhibits superior antihyperalgesic effects in a β-cyclodextrin-complexed form in chronic musculoskeletal pain reducing Fos protein expression on spinal cord in mice

Araújo-Filho, Heitor G.; Pereira, Erik Willyame Menezes; Rezende, Marilia M.; Menezes, Paula P.; Araújo, Adriano A. S.; Barreto, Rosana S.S.; Martins, Anita O.B.P.B.; Albuquerque, Thaís Rodrigues de; Silva, Bruno Anderson Fernandes da; Alcântara, Isabel Sousa; Coutinho, Henrique Douglas Melo; Menezes, Irwin Rose Alencar de; Quintans‐Júnior, Lucindo J.; Quintans, Jullyana S.S.

doi:10.1016/j.neuroscience.2017.06.037

Cited by 38 publications

(27 citation statements)

References 91 publications

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“…Besides the activities described above, monoterpenes also produce significant effects on the cardiovascular system, promoting, among other actions, vasorelaxation, decreased heart rate, and hypotension [ 30 ]. Constituents of the essential oil of P. heptaphyllum exhibit biological activities, as p -cymene presents anti-inflammatory property [ 31 ], D-limonene presents antihyperalgesic action [ 32 ], and α -terpineol induces gastric protection [ 33 ].…”

Section: Resultsmentioning

confidence: 99%

Gas Chromatography-Triple Quadrupole Mass Spectrometry Analysis and Vasorelaxant Effect of Essential Oil fromProtium heptaphyllum(Aubl.) March.

Mobin

Lima

Almeida

et al. 2017

BioMed Research International

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The Protium heptaphyllum species, also known as Almécega, produces an oily resin, used in folk medicine as an analgesic and anti-inflammatory agent, in healing, and as an expectorant, which is rich in pentacyclic triterpenes and essential oils. In this study, the essential oil obtained by hydrodistillation of Almécega's resin was analyzed by gas chromatography-triple quadrupole mass spectrometry and evaluated for chemical composition and vasorelaxant activity in rat superior mesenteric artery. The main constituents determined by gas chromatography-triple quadrupole mass spectrometry were limonene, p-cineole, and o-cymene. In intact rings precontracted with phenylephrine (Phe 1 μM), EOPh (3–750 μg/mL) induced relaxation, and the essential oil had a concentration-dependent vasorelaxant effect, without involvement of endothelial mediators.

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Section: Resultsmentioning

confidence: 99%

Gas Chromatography-Triple Quadrupole Mass Spectrometry Analysis and Vasorelaxant Effect of Essential Oil fromProtium heptaphyllum(Aubl.) March.

Mobin

Lima

Almeida

et al. 2017

BioMed Research International

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“…In some cases, complexation may improve the bioavailability without affecting the pharmacological effect of the transported molecule. However, for essential oils and terpenes, it has been observed that complexation optimizes the pharmacological effects, reducing the effective doses [91,101,102]. In this study, it was found that at smaller doses, the anti-inflammatory effects of the COEFC were better or similar to those of the free OEFC or 1,8-cineole [29].…”

Section: Discussionmentioning

confidence: 58%

Anti-Inflammatory and Physicochemical Characterization of the Croton rhamnifolioides Essential Oil Inclusion Complex in β-Cyclodextrin

Martins

Wanderley

Alcântara

et al. 2020

Biology

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Croton rhamnifolioides is used in popular medicine for the treatment of inflammatory diseases. The objective of this study was to characterize and evaluate the anti-inflammatory effect of C. rhamnifolioides essential oil complexed in β-cyclodextrin (COEFC). The physicochemical characterization of the complexes was performed using different physical methods. The anti-inflammatory activity was evaluated in vivo by ear edema, paw edema, cotton pellet-induced granuloma, and vascular permeability by Evans blue extravasation. The mechanism of action was validated by molecular docking of the major constituent into the cyclooxygenase-2 (COX-2 enzyme). All doses of the COEFC reduced acute paw edema induced by carrageenan and dextran, as well as vascular permeability. Our results suggest the lowest effective dose of all samples inhibited the response induced by histamine or arachidonic acid as well as the granuloma formation. The complexation process showed that the pharmacological effects were maintained, however, showing similar results using much lower doses. The results demonstrated an involvement of the inhibition of pathways dependent on eicosanoids and histamine. Complexation of β-cyclodextrin/Essential oil (β-CD/EO) may present an important tool in the study of new compounds for the development of anti-inflammatory drugs.

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“…Limonene also inhibited nociceptive behavior induced by intraperitoneal acetic acid injection and plantar formalin [109]. In a complementary way, combined administration of limonene and β-ciclodextrin inhibited hyperalgesia in a chronic musculoskeletal pain model by downregulation c-FOS expression in the spinal cord [84]. Reinforcing this information, treatment with Schinus terebinthifolius essential oil-which is highly-concentrated in limonene-showed anti-hyperalgesic and anti-depressive effects in a neuropathic pain animal model [110].…”

Section: D-limonenementioning

confidence: 96%

“…Booth and Bohlmann described the terpenes-and cannabinoid-rich resin as the most valuable cannabis products, with different psychoactive and medicinal properties [83]. Studies regarding terpenoid compounds (i.e., D-limonene, β-myrcene, α-pinene, α-terpineol, β-pinene, β-caryophyllene, and others) have been growing in the last decades due to their large number and extensive employability [71,84]. However, the presence of terpenoids has not been restricted to the Cannabis sativa plant.…”

Section: Terpenoids In and Beyond The Cannabis Plantmentioning

confidence: 99%

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Terpenoids, Cannabimimetic Ligands, beyond the Cannabis Plant

et al. 2020

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Medicinal use of Cannabis sativa L. has an extensive history and it was essential in the discovery of phytocannabinoids, including the Cannabis major psychoactive compound—Δ9-tetrahydrocannabinol (Δ9-THC)—as well as the G-protein-coupled cannabinoid receptors (CBR), named cannabinoid receptor type-1 (CB1R) and cannabinoid receptor type-2 (CB2R), both part of the now known endocannabinoid system (ECS). Cannabinoids is a vast term that defines several compounds that have been characterized in three categories: (i) endogenous, (ii) synthetic, and (iii) phytocannabinoids, and are able to modulate the CBR and ECS. Particularly, phytocannabinoids are natural terpenoids or phenolic compounds derived from Cannabis sativa. However, these terpenoids and phenolic compounds can also be derived from other plants (non-cannabinoids) and still induce cannabinoid-like properties. Cannabimimetic ligands, beyond the Cannabis plant, can act as CBR agonists or antagonists, or ECS enzyme inhibitors, besides being able of playing a role in immune-mediated inflammatory and infectious diseases, neuroinflammatory, neurological, and neurodegenerative diseases, as well as in cancer, and autoimmunity by itself. In this review, we summarize and critically highlight past, present, and future progress on the understanding of the role of cannabinoid-like molecules, mainly terpenes, as prospective therapeutics for different pathological conditions.

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D-limonene exhibits superior antihyperalgesic effects in a β-cyclodextrin-complexed form in chronic musculoskeletal pain reducing Fos protein expression on spinal cord in mice

Cited by 38 publications

References 91 publications

Gas Chromatography-Triple Quadrupole Mass Spectrometry Analysis and Vasorelaxant Effect of Essential Oil fromProtium heptaphyllum(Aubl.) March.

Gas Chromatography-Triple Quadrupole Mass Spectrometry Analysis and Vasorelaxant Effect of Essential Oil fromProtium heptaphyllum(Aubl.) March.

Anti-Inflammatory and Physicochemical Characterization of the Croton rhamnifolioides Essential Oil Inclusion Complex in β-Cyclodextrin

Terpenoids, Cannabimimetic Ligands, beyond the Cannabis Plant

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