Acidic and hepatic derivatives of bioactive clerodane diterpenes casearins J and O

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dc.contributor.authorOda, Fernando Bombarda [UNESP]
dc.contributor.authorCrevelin, Eduardo José
dc.contributor.authorCrotti, Antônio Eduardo Miller
dc.contributor.authorOrlando, Allan Botinhon [UNESP]
dc.contributor.authorde Medeiros, Alexandra Ivo [UNESP]
dc.contributor.authorNogueira, Flávia Aparecida Resende
dc.contributor.authordos Santos, André Gonzaga [UNESP]
dc.contributor.institutionUniversidade Estadual Paulista (Unesp)
dc.contributor.institutionUniversidade de São Paulo (USP)
dc.contributor.institutionUniversity of Araraquara
dc.date.accessioned2019-10-06T16:34:41Z
dc.date.available2019-10-06T16:34:41Z
dc.date.issued2019-09-01
dc.description.abstractClerodane diterpenes from Casearia sylvestris are antiulcerogenic and anti-inflammatory. The finding that they may undergo acid degradation or hepatic metabolization led to an investigation of their degradation products. Purified clerodane diterpenes (casearins J and O) were subjected to in vitro assays to simulate their oral administration. Resulting derivatives were identified using chromatographic and spectrometric techniques. Nitric oxide synthesis by LPS-stimulated macrophages was assayed to verify whether structural modifications alter the anti-inflammatory activity of diterpenes. Nine compounds (1–9) were identified after acid degradation remaining 5.05% of casearin J. Besides the remaining casearin O (13.1%), eight compounds (10–17) were identified. The dialdehydes from each casearin were the major constituents. S9 rat liver treatment of casearins J and O generated two compounds identical to some of those produced by acid degradation, which remained 36.8% and 36.5% intact, respectively. Both casearins and its derivatives were not cytotoxicity at concentrations lower than 0.312 μg/mL (0.555 μM for casearin J and 0.516 μM for casearin O) and did not inhibit the nitric oxide production in this concentration. Thus, the structural modifications conducted did not alter the activity of casearins and the anti-inflammatory pathway of diterpenes probably is not involved on nitric oxide modulation.en
dc.description.affiliationSão Paulo State University (Unesp) School of Pharmaceutical Sciences Department of Natural Principles and Toxicology
dc.description.affiliationUniversity of São Paulo (USP) Faculty of Philosophy Sciences and Letters Department of Chemistry
dc.description.affiliationSão Paulo State University (Unesp) School of Pharmaceutical Sciences Department of Biological Sciences
dc.description.affiliationUniversity of Araraquara Department of Health and Biological Sciences
dc.description.affiliationUnespSão Paulo State University (Unesp) School of Pharmaceutical Sciences Department of Natural Principles and Toxicology
dc.description.affiliationUnespSão Paulo State University (Unesp) School of Pharmaceutical Sciences Department of Biological Sciences
dc.identifierhttp://dx.doi.org/10.1016/j.fitote.2019.104197
dc.identifier.citationFitoterapia, v. 137.
dc.identifier.doi10.1016/j.fitote.2019.104197
dc.identifier.issn1873-6971
dc.identifier.issn0367-326X
dc.identifier.scopus2-s2.0-85067258537
dc.identifier.urihttp://hdl.handle.net/11449/189247
dc.language.isoeng
dc.relation.ispartofFitoterapia
dc.rights.accessRightsAcesso aberto
dc.sourceScopus
dc.subjectCasearia sylvestris
dc.subjectClerodane diterpene
dc.subjectCytotoxicity
dc.subjectNitric oxide inhibition
dc.subjectS9 rat liver fraction
dc.subjectSimulated gastric fluid
dc.titleAcidic and hepatic derivatives of bioactive clerodane diterpenes casearins J and Oen
dc.typeArtigo
unesp.author.lattes4000625974516852[7]
unesp.author.orcid0000-0002-4920-2506[7]

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Artigos - Princípios Ativos Naturais e Toxicologia - FCFAR
Artigos - Ciências Biológicas - FCFAR