CONTEXT: 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 (1)H and (13)C 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.
CONTEXT: 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 (1)H and (13)C 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.
Authors: Francisco Valmor Macedo Cunha; Bruno de Sousa Gomes; Benedito de Sousa Neto; Alana Rodrigues Ferreira; Damião Pergentino de Sousa; Maria do Carmo de Carvalho e Martins; Francisco de Assis Oliveira Journal: Naunyn Schmiedebergs Arch Pharmacol Date: 2015-10-24 Impact factor: 3.000
Authors: Rita de Cássia da Silveira E Sá; Luciana Nalone Andrade; Rafael Dos Reis Barreto de Oliveira; Damião Pergentino de Sousa Journal: Molecules Date: 2014-01-27 Impact factor: 4.411
Authors: I Gusti Agung Ayu Kartika; In Jae Bang; Catur Riani; Muhamad Insanu; Jong Hwan Kwak; Kyu Hyuck Chung; I Ketut Adnyana Journal: Molecules Date: 2020-10-23 Impact factor: 4.411
Authors: Nayara Sabrina Freitas Alves; Suzana G Kaory Inoue; Adriana Ribeiro Carneiro; Ulisses Brigatto Albino; William N Setzer; José Guilherme Maia; Eloisa Helena Andrade; Joyce Kelly R da Silva Journal: PLoS One Date: 2022-01-21 Impact factor: 3.240