{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,15]],"date-time":"2026-06-15T22:28:18Z","timestamp":1781562498816,"version":"3.54.5"},"reference-count":61,"publisher":"Wiley","license":[{"start":{"date-parts":[[2019,3,31]],"date-time":"2019-03-31T00:00:00Z","timestamp":1553990400000},"content-version":"unspecified","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100003593","name":"Conselho Nacional de Desenvolvimento Cient\u00edfico e Tecnol\u00f3gico","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100003593","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100002322","name":"Coordena\u00e7\u00e3o de Aperfei\u00e7oamento de Pessoal de N\u00edvel Superior","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100002322","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Oxidative Medicine and Cellular Longevity"],"published-print":{"date-parts":[[2019,3,31]]},"abstract":"<jats:p>2-Allylphenol (2-AP) is a synthetic phenylpropanoid, structurally related to cardanol, thymol, and ortho-eugenol. Phenylpropanoids are described in the literature as being capable of promoting biological activity. Due to the similarity between 2-AP and other bioactive phenylpropanoids, the present research aims at evaluating the antioxidant, antinociceptive, and anti-inflammatory potential of 2-AP in silico,<jats:italic>in vitro<\/jats:italic>, and<jats:italic>in vivo<\/jats:italic>. At 30\u2009min prior to the start of<jats:italic>in vivo<\/jats:italic>pharmacological testing, administration of 2-AP (25, 50, 75, and 100\u2009mg\/kg\u2009i.p.), morphine (6\u2009mg\/kg\u2009i.p.), dexamethasone (2\u2009mg\/kg\u2009s.c.), or vehicle alone was performed. In the acetic acid-induced abdominal writhing tests, pretreatment with 2-AP significantly reduced the number of abdominal writhes, as well as decreased licking times in the glutamate and formalin tests. Investigation of the mechanism of action using the formalin model led to the conclusion that the opioid system does not participate in its activity. However, the adenosinergic system is involved. In the peritonitis tests, 2-AP inhibited leukocyte migration and reduced releases of proinflammatory mediators TNF-<jats:italic>\u03b1<\/jats:italic>and IL-1<jats:italic>\u03b2<\/jats:italic>.<jats:italic>In vitro<\/jats:italic>antioxidant assays demonstrated that 2-AP presents significant ability to sequester superoxide radicals.<jats:italic>In silico<\/jats:italic>docking studies confirmed interaction between 2-AP and the adenosine A2a receptor through hydrogen bonds with the critical asparagine 253 residues present in the active site. Investigation of 2-AP demonstrated its nociception inhibition and ability to reduce reactive oxygen species. Its interaction with A2a receptors may well be related to proinflammatory cytokines TNF-<jats:italic>\u03b1<\/jats:italic>and IL-1<jats:italic>\u03b2<\/jats:italic>reduction activity, corroborating its antinociceptive effect.<\/jats:p>","DOI":"10.1155\/2019\/1346878","type":"journal-article","created":{"date-parts":[[2019,3,31]],"date-time":"2019-03-31T23:30:26Z","timestamp":1554075026000},"page":"1-14","source":"Crossref","is-referenced-by-count":6,"title":["2-Allylphenol Reduces IL-1<i>\u03b2<\/i>and TNF-<i>\u03b1<\/i>, Promoting Antinociception through Adenosinergic, Anti-Inflammatory, and Antioxidant Mechanisms"],"prefix":"10.1155","volume":"2019","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-2264-2966","authenticated-orcid":true,"given":"Humberto de Carvalho","family":"Arag\u00e3o Neto","sequence":"first","affiliation":[{"name":"Institute of Drugs and Medicines Research, Federal University of Para\u00edba, Jo\u00e3o Pessoa 58051-085, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Diogo Vilar","family":"da Fons\u00eaca","sequence":"additional","affiliation":[{"name":"Institute of Drugs and Medicines Research, Federal University of Para\u00edba, Jo\u00e3o Pessoa 58051-085, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Renan Marinho","family":"Braga","sequence":"additional","affiliation":[{"name":"Institute of Drugs and Medicines Research, Federal University of Para\u00edba, Jo\u00e3o Pessoa 58051-085, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4863-8057","authenticated-orcid":true,"given":"Marcus Tullius","family":"Scotti","sequence":"additional","affiliation":[{"name":"Institute of Drugs and Medicines Research, Federal University of Para\u00edba, Jo\u00e3o Pessoa 58051-085, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Terezinha Weyne Ara\u00fajo Borges","family":"do Nascimento","sequence":"additional","affiliation":[{"name":"Institute of Drugs and Medicines Research, Federal University of Para\u00edba, Jo\u00e3o Pessoa 58051-085, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Davidson Barbosa","family":"Assis","sequence":"additional","affiliation":[{"name":"Institute of Drugs and Medicines Research, Federal University of Para\u00edba, Jo\u00e3o Pessoa 58051-085, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4192-7382","authenticated-orcid":true,"given":"Sandra","family":"Rodrigues-Mascarenhas","sequence":"additional","affiliation":[{"name":"Institute of Drugs and Medicines Research, Federal University of Para\u00edba, Jo\u00e3o Pessoa 58051-085, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8445-5189","authenticated-orcid":true,"given":"Luiz Henrique Agra Cavalcante","family":"Silva","sequence":"additional","affiliation":[{"name":"Institute of Drugs and Medicines Research, Federal University of Para\u00edba, Jo\u00e3o Pessoa 58051-085, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jos\u00e9 Guilherme Ferreira Marques","family":"Galv\u00e3o","sequence":"additional","affiliation":[{"name":"Institute of Drugs and Medicines Research, Federal University of Para\u00edba, Jo\u00e3o Pessoa 58051-085, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2252-1221","authenticated-orcid":true,"given":"Hugo Alexandre Oliveira","family":"Rocha","sequence":"additional","affiliation":[{"name":"Department of Biochemistry, Federal University of Rio Grande do Norte, Natal 59072-970, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Arthur Antunes Jacome","family":"Vidal","sequence":"additional","affiliation":[{"name":"Department of Biochemistry, Federal University of Rio Grande do Norte, Natal 59072-970, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9567-4096","authenticated-orcid":true,"given":"Jos\u00e9 Maria Barbosa","family":"Filho","sequence":"additional","affiliation":[{"name":"Institute of Drugs and Medicines Research, Federal University of Para\u00edba, Jo\u00e3o Pessoa 58051-085, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4430-8202","authenticated-orcid":true,"given":"Reinaldo N\u00f3brega","family":"de Almeida","sequence":"additional","affiliation":[{"name":"Institute of Drugs and Medicines Research, Federal University of Para\u00edba, Jo\u00e3o Pessoa 58051-085, Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","reference":[{"key":"1","doi-asserted-by":"publisher","DOI":"10.1016\/j.intimp.2016.06.005"},{"key":"2","doi-asserted-by":"publisher","DOI":"10.3390\/molecules21101321"},{"key":"3","doi-asserted-by":"publisher","DOI":"10.1186\/s12906-015-0669-5"},{"key":"4","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.0409225102"},{"key":"5","doi-asserted-by":"publisher","DOI":"10.1111\/j.1478-3231.2007.01463.x"},{"key":"6","doi-asserted-by":"publisher","DOI":"10.1016\/j.phrs.2003.08.004"},{"key":"7","doi-asserted-by":"publisher","DOI":"10.1155\/2018\/1785614"},{"key":"8","doi-asserted-by":"publisher","DOI":"10.1055\/s-2006-951688"},{"key":"9","doi-asserted-by":"publisher","DOI":"10.1007\/s40009-016-0530-5"},{"key":"10","first-page":"1583","volume":"92","year":"2016","journal-title":"Journal of the Indian Chemical Society"},{"key":"11","doi-asserted-by":"publisher","DOI":"10.1016\/j.ijbiomac.2014.05.017"},{"key":"12","doi-asserted-by":"publisher","DOI":"10.1248\/bpb.35.127"},{"key":"13","doi-asserted-by":"publisher","DOI":"10.1016\/j.ecoenv.2014.01.025"},{"key":"14","doi-asserted-by":"publisher","DOI":"10.1016\/j.brainres.2009.12.060"},{"key":"15","doi-asserted-by":"publisher","DOI":"10.1016\/j.neuroscience.2015.10.031"},{"key":"16","doi-asserted-by":"publisher","DOI":"10.1021\/jf00018a005"},{"key":"17","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodchem.2004.01.036"},{"key":"18","doi-asserted-by":"publisher","DOI":"10.1006\/abio.1999.4019"},{"key":"19","doi-asserted-by":"publisher","DOI":"10.1016\/j.theochem.2003.08.013"},{"key":"20","doi-asserted-by":"publisher","DOI":"10.1038\/nature10136"},{"key":"21","doi-asserted-by":"publisher","DOI":"10.1126\/science.1202793"},{"key":"22","doi-asserted-by":"publisher","DOI":"10.1021\/jm051197e"},{"key":"23","doi-asserted-by":"publisher","DOI":"10.1016\/S0166-1280(99)00360-7"},{"key":"24","doi-asserted-by":"publisher","DOI":"10.1111\/j.1476-5381.1968.tb00973.x"},{"key":"25","first-page":"412","volume":"18","year":"1959","journal-title":"Federation Proceedings"},{"key":"26","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejpain.2009.01.007"},{"key":"27","doi-asserted-by":"publisher","DOI":"10.1155\/2013\/459530"},{"key":"28","doi-asserted-by":"publisher","DOI":"10.1016\/j.pbb.2009.06.003"},{"key":"29","doi-asserted-by":"publisher","DOI":"10.1016\/j.semcdb.2006.10.008"},{"key":"30","doi-asserted-by":"publisher","DOI":"10.1002\/ptr.3235"},{"key":"31","doi-asserted-by":"publisher","DOI":"10.1016\/0304-3959(92)90003-T"},{"key":"32","doi-asserted-by":"publisher","DOI":"10.1097\/00001756-199301000-00006"},{"key":"33","doi-asserted-by":"publisher","DOI":"10.1016\/0304-3959(87)90088-1"},{"key":"34","doi-asserted-by":"publisher","DOI":"10.1002\/ptr.4686"},{"key":"35","doi-asserted-by":"publisher","DOI":"10.1016\/j.neubiorev.2008.12.003"},{"key":"36","doi-asserted-by":"publisher","DOI":"10.1016\/j.pain.2004.11.020"},{"key":"37","doi-asserted-by":"publisher","DOI":"10.1159\/000094762"},{"key":"38","doi-asserted-by":"publisher","DOI":"10.1016\/j.pain.2007.01.013"},{"key":"39","doi-asserted-by":"publisher","DOI":"10.1016\/0306-4522(94)00632-F"},{"key":"40","doi-asserted-by":"publisher","DOI":"10.1007\/BF00180011"},{"key":"41","doi-asserted-by":"publisher","DOI":"10.1016\/S0006-8993(01)02844-X"},{"key":"42","doi-asserted-by":"publisher","DOI":"10.1016\/j.drudis.2014.02.010"},{"key":"43","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejca.2012.06.005"},{"key":"44","doi-asserted-by":"publisher","DOI":"10.1016\/j.jpain.2006.06.010"},{"key":"45","doi-asserted-by":"publisher","DOI":"10.1038\/nrn2533"},{"key":"46","doi-asserted-by":"publisher","DOI":"10.1016\/j.bbi.2013.06.004"},{"key":"47","doi-asserted-by":"publisher","DOI":"10.3390\/ijms18040697"},{"key":"48","doi-asserted-by":"publisher","DOI":"10.1016\/j.actatropica.2010.08.003"},{"key":"49","doi-asserted-by":"publisher","DOI":"10.1097\/AIA.0b013e318034194e"},{"key":"50","doi-asserted-by":"publisher","DOI":"10.1016\/j.sjpain.2017.08.002"},{"issue":"11","key":"51","doi-asserted-by":"crossref","first-page":"6855","DOI":"10.1016\/S0021-9258(18)32301-9","volume":"258","year":"1983","journal-title":"Journal of Biological Chemistry"},{"key":"52","doi-asserted-by":"publisher","DOI":"10.1211\/0022357991777083"},{"key":"53","doi-asserted-by":"publisher","DOI":"10.1016\/j.fct.2009.09.036"},{"key":"54","doi-asserted-by":"publisher","DOI":"10.3390\/md9060952"},{"key":"55","doi-asserted-by":"publisher","DOI":"10.3390\/md9010124"},{"key":"56","doi-asserted-by":"publisher","DOI":"10.1089\/jmf.2014.0084"},{"key":"57","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodres.2018.04.028"},{"key":"58","doi-asserted-by":"publisher","DOI":"10.1080\/03601234.2014.951578"},{"key":"59","doi-asserted-by":"publisher","DOI":"10.1016\/j.fct.2010.06.036"},{"issue":"2","key":"60","first-page":"367","volume":"12","year":"2013","journal-title":"Iranian Journal of Pharmaceutical Research"},{"key":"61","doi-asserted-by":"publisher","DOI":"10.1016\/j.ejmech.2011.07.041"}],"container-title":["Oxidative Medicine and Cellular Longevity"],"original-title":[],"language":"en","link":[{"URL":"http:\/\/downloads.hindawi.com\/journals\/omcl\/2019\/1346878.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"http:\/\/downloads.hindawi.com\/journals\/omcl\/2019\/1346878.xml","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"http:\/\/downloads.hindawi.com\/journals\/omcl\/2019\/1346878.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2022,9,14]],"date-time":"2022-09-14T22:47:26Z","timestamp":1663195646000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.hindawi.com\/journals\/omcl\/2019\/1346878\/"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2019,3,31]]},"references-count":61,"alternative-id":["1346878","1346878"],"URL":"https:\/\/doi.org\/10.1155\/2019\/1346878","relation":{},"ISSN":["1942-0900","1942-0994"],"issn-type":[{"value":"1942-0900","type":"print"},{"value":"1942-0994","type":"electronic"}],"subject":[],"published":{"date-parts":[[2019,3,31]]}}}