Evaluation and Theoretical Study on the Anti-inflammatory Mechanism of 1-Nitro-2-phenylethane

Abstract

In this study, 1-nitro-2-phenylethane was evaluated with respect to its effects in edema models of acute inflammation induced with carrageenan, dextran, and croton oil. 1-Nitro-2-phenylethane produced inhibition of rat paw edema induced by carrageenan and dextran at the doses of 25 and 50 mg/kg. The same doses caused an inhibition of croton oil-induced ear edema in mice. Our results suggest that 1-nitro-2-phenylethane has anti-inflammatory activity, probably of peripheral origin, acting in the synthesis and/or release of inflammatory mediators. A conformational study of 1-nitro-2-phenylethane was carried out using density functional theory calculations, showing three different groups of conformers corresponding to energy minimum geometries. The stereoelectronic repulsions are responsible for conformational preferences and the one most stable conformer. The prostaglandin endoperoxide synthase mechanism is related more to electrophilic than nucleophilic properties.

Aniba canelilla (Kunth) Mez (Lauraceae): A Review of Ethnobotany, Phytochemical, Antioxidant, Anti-Inflammatory, Cardiovascular, and Neurological Properties

“…The screening proceeded also revealed that it modulates only peripheral components of nociception, despite apparently involving opioid receptors in its mechanism of action (Lima et al, 2009). In inflammatory context, the results indicate the reduction of edema induced by croton oil, carrageenan, and dextran, with oral doses of 25 and 50 mg/kg (Vale et al, 2013). A possible mechanism related to these effects was pointed out by a conformational study conducted by Vale et al (2013) who demonstrated that 1N2PE molecule had a favorable configuration for interaction with prostaglandin endoperoxide synthase.…”

“…In this context, A. canelilla has shown promise, since published studies have ratified, in murine models, its antinociceptive and anti-inflammatory properties referred in traditional use. The study initially conducted by Lima (2008), later expanded and published in two other articles (Lima et al, 2009;Vale et al, 2013), demonstrated antinociceptive and anti-inflammatory activity using a fraction of the AcEO containing 1N2PE with 97.5 to 99% purity. This product was therefore applied to classic models of antinociceptive activity (abdominal contortions, hot plaque, and formalin) and antiedematogency (croton oil ear edema, paw edema by carrageenan or dextran), in addition to performing a theoretical study of functional density calculations.…”

“…Its chemical composition has two main constituents, 1-nitro-2-phenylethane (1N2PE), the first known natural nitro derivative which is generally pointed as the major component and is responsible for the cinnamon-like odor characteristic of the species, and methyleneugenol (Gottlieb and Magalhães, 1959;Gottlieb and Magalhães, 1960a;Oger et al, 1994;Maia et al, 2001;Taveira et al, 2003;Lima et al, 2004;Da Silva et al, 2007;Maia and Andrade, 2009;Silva et al, 2009;Sousa, 2011;Manhães et al, 2012;Vale et al, 2013;Almeida et al, 2017;Farias et al, 2017;Giongo et al, 2017). These substances were identified both in the stem wood, bark, and leaves.…”

Anticonvulsant Essential Oils and Their Relationship with Oxidative Stress in Epilepsy

“…1-Nitro-2-phenylethane (NPH) is a volatile compound found in the EOs of Aniba canelilla and Dennettia tripetala [58], and was the first nitrocomponent isolated from plants [238,239]. Several pharmacological activities for NPH have been reported, including anti-inflammatory [240], antinociceptive [241], trypanocidal [242], cytoprotective [243], anxiolytic and hypnotic effects [58]. NPH also presents vasodilator activity via stimulation of soluble guanylil cyclase [244], and induces vagal-vagal bradycardia in normotensive rats [245].…”

Anti-Inflammatory Potential of 1-Nitro-2-Phenylethylene

“…NPE has been shown to exert antinociceptive [ 9 ] and, vasorelaxant [ 10 , 11 ] effects in vivo. Furthermore, a recent study has suggested that NPE also has anti-inflammatory activity, as demonstrated by its ability to inhibit paw edema induced by dextran and carrageenan in rats and by croton oil in mice [ 12 ].…”