The anti-inflammatory activity of dillapiole and some semisynthetic analogues

Página do item simplificado
dc.contributor.authorParise-Filho R.
dc.contributor.authorPastrello M.
dc.contributor.authorPereira Camerlingo C.E.
dc.contributor.authorSilva G.J.
dc.contributor.authorAgostinho L.A.
dc.contributor.authorDe Souza T.
dc.contributor.authorMotter Magri F.M.
dc.contributor.authorRibeiro R.R.
dc.contributor.authorBrandt C.A.
dc.contributor.authorCarneiro Polli M.
dc.date.accessioned2024-03-13T01:10:17Z
dc.date.available2024-03-13T01:10:17Z
dc.date.issued2011
dc.description.abstractContext: Piper aduncum L. (Piperaceae) produces an essential oil (dillapiole) with great exploitative potential and it has proven effects against traditional cultures of phytopathogens, such as fungi, bacteria and mollusks, as well as analgesic action with low levels of toxicity. Objective: This study investigated the in vivo anti-inflammatory activity of dillapiole. Furthermore, in order to elucidate its structure-anti-inflammatory activity relationship (SAR), semisynthetic analogues were proposed by using the molecular simplification strategy. Materials and methods: Dillapiole and safrole were isolated and purified using column chromatography. The semisynthetic analogues were obtained by using simple organic reactions, such as catalytic reduction and isomerization. All the analogues were purified by column chromatography and characterized by 1H and 13C NMR. The anti-inflammatory activities of dillapiole and its analogues were studied in carrageenan-induced rat paw edema model. Results: Dillapiole and di-hydrodillapiole significantly (p<0.05) inhibited rat paw edema. All the other substances tested, including safrole, were less powerful inhibitors with activities inferior to that of indomethacin. Discussion and conclusion: These findings showed that dillapiole and di-hydrodillapiole have moderate anti-phlogistic properties, indicating that they can be used as prototypes for newer anti-inflammatory compounds. Structure-activity relationship studies revealed that the benzodioxole ring is important for biological activity as well as the alkyl groups in the side chain and the methoxy groups in the aromatic ring. © 2011 Informa Healthcare USA, Inc.
dc.description.firstpage1173
dc.description.issuenumber11
dc.description.lastpage1179
dc.description.volume49
dc.identifier.doi10.3109/13880209.2011.575793
dc.identifier.issn1744-5116
dc.identifier.urihttps://dspace.mackenzie.br/handle/10899/36933
dc.relation.ispartofPharmaceutical Biology
dc.rightsAcesso Restrito
dc.subject.otherlanguageMolecular modification
dc.subject.otherlanguagePhenylpropanoids
dc.subject.otherlanguagePiper aduncum
dc.subject.otherlanguagePiperaceae
dc.subject.otherlanguageStructure-activity relationship
dc.titleThe anti-inflammatory activity of dillapiole and some semisynthetic analogues
dc.typeArtigo
local.scopus.citations48
local.scopus.eid2-s2.0-80054901281
local.scopus.updated2024-05-01
local.scopus.urlhttps://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=80054901281&origin=inward
Arquivos
Coleções
Artigos de periódico