Constituintes Químicos dos Zoantídeos Palythoa caribaeorum (Duchassaing & Michelotti, 1860) e Protopalythoa Variabilis (Duerden, 1898)
Autor(a) principal: | |
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Data de Publicação: | 2011 |
Tipo de documento: | Tese |
Idioma: | por |
Título da fonte: | Repositório Institucional da Universidade Federal do Ceará (UFC) |
Texto Completo: | http://www.repositorio.ufc.br/handle/riufc/15677 |
Resumo: | This work describes the chemical composition of the marine species Palythoa caribaeorum and Protopalythoa variabilis, both collected at Paracuru beach, state of Ceará. The cromatographic fractionation of the hexane extract from P. caribaeorum resulted in the isolation of four tetracyclic sterols possessing the ergostan skeleton: 24(R)-ergost-5-en-3b-ol (P-1); 5 a,8a-epidioxy-24(R)-ergost-6-en-3b-ol (P-2); 24(R)- ergost-5-en-3b,7a-diol (P-4) and 24(R)-7a-hydroperoxy-ergost-5-en-3b-ol (P-7), a glycerol derivative, 1-O-hexadecylglycerol (P-3) and four ceramides: N- (2S,3R,4E,8E,1,3-dihydroxy-4,8-octadecadienyl)hexadecanamide (P-5); N- (2S,3R,4E,1,3-dihydroxy-4-octadecenyl)hexadecanamide (P-6); N-[2S,3R,4E,8E,1-(2”- methylamino-ethanosulfonyl)-3-hydroxy-4,8-octadecaenyl]hexadecanamide (P-8) and N-[2S,3R,4E,1-(2”-methylaminoethano-sulfonyl)-3-hydroxy-4-octadecenyl]hexadecanamide (P-9). The cromatographic fractionation of the ethanol extract permited the isolation of a steroid, 24(R)-ergost-7-en-3b,5a,6b-triol (P-10) and a nucleoside 2- methyltimidine (P-11). Column chromatography of the hexane extract of P. variabilis led to the isolation of nonyl hexadecanoate (P-12), the sterol 24(R)-B-norergostan-3b- 5b-diol-6b-carboxylic acid (P-13) and the same chemical constituents previously isolated from P. caribaeorum (P-1, P-2, P-3 e P-4) including the four ceramides (P-5, P-6, P-8 e P-9). The citotoxic and antifungal properties of all ceramides were evaluated, nevertheless none of them showed any activity. All compounds were isolated through adsorption column cromatography over silica gel followed by high performance liquid chromatography. The structures of the isolated compounds were elucidated using spectrometric techniques, such as: GC/MS, HRESIMS, IR and NMR (1H, 13C and 15N) through 1D and 2D pulse sequences and, whenever the case, comparison with literature data |
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Constituintes Químicos dos Zoantídeos Palythoa caribaeorum (Duchassaing & Michelotti, 1860) e Protopalythoa Variabilis (Duerden, 1898)Chemical Constituents of the zoanthids Palythoa caribaeorum (Duchassaing & Michelotti, 1860) and Protopalythoa variabilis (Duerden, 1898)Palythoa caribaeorumProtopalythoa variabilisThis work describes the chemical composition of the marine species Palythoa caribaeorum and Protopalythoa variabilis, both collected at Paracuru beach, state of Ceará. The cromatographic fractionation of the hexane extract from P. caribaeorum resulted in the isolation of four tetracyclic sterols possessing the ergostan skeleton: 24(R)-ergost-5-en-3b-ol (P-1); 5 a,8a-epidioxy-24(R)-ergost-6-en-3b-ol (P-2); 24(R)- ergost-5-en-3b,7a-diol (P-4) and 24(R)-7a-hydroperoxy-ergost-5-en-3b-ol (P-7), a glycerol derivative, 1-O-hexadecylglycerol (P-3) and four ceramides: N- (2S,3R,4E,8E,1,3-dihydroxy-4,8-octadecadienyl)hexadecanamide (P-5); N- (2S,3R,4E,1,3-dihydroxy-4-octadecenyl)hexadecanamide (P-6); N-[2S,3R,4E,8E,1-(2”- methylamino-ethanosulfonyl)-3-hydroxy-4,8-octadecaenyl]hexadecanamide (P-8) and N-[2S,3R,4E,1-(2”-methylaminoethano-sulfonyl)-3-hydroxy-4-octadecenyl]hexadecanamide (P-9). The cromatographic fractionation of the ethanol extract permited the isolation of a steroid, 24(R)-ergost-7-en-3b,5a,6b-triol (P-10) and a nucleoside 2- methyltimidine (P-11). Column chromatography of the hexane extract of P. variabilis led to the isolation of nonyl hexadecanoate (P-12), the sterol 24(R)-B-norergostan-3b- 5b-diol-6b-carboxylic acid (P-13) and the same chemical constituents previously isolated from P. caribaeorum (P-1, P-2, P-3 e P-4) including the four ceramides (P-5, P-6, P-8 e P-9). The citotoxic and antifungal properties of all ceramides were evaluated, nevertheless none of them showed any activity. All compounds were isolated through adsorption column cromatography over silica gel followed by high performance liquid chromatography. The structures of the isolated compounds were elucidated using spectrometric techniques, such as: GC/MS, HRESIMS, IR and NMR (1H, 13C and 15N) through 1D and 2D pulse sequences and, whenever the case, comparison with literature dataEste trabalho descreve a composição química das espécies marinha Palythoa caribaeorum e Protopalythoa variabilis, coletadas no município de Paracuru-CE. O fracionamento cromatográfico do extrato hexânico de P. caribaeorum, resultou no isolamento de quatro esteróides tetracíclico de esqueleto ergostano: 24(R)-ergost-5-en-3-ol (P-1); 5,8-epidioxi-24(R)-ergost-6-en-3-ol (P-2); 24(R)-ergost-5-en-3,7-diol (P-4) e 24(R)-7-hidroperoxi-ergost-5-en-3-ol (P-7), um derivado do glicerol, 1-O-hexadecilglicerol (P-3) e quatro ceramidas: N-(2S,3R,4E,8E,1,3-dihidroxi-4,8-octadecadieno)hexadecanamida (P-5); N-(2S,3R,4E,1,3-dihidroxi-4-octadeceno)-hexadecanamida (P-6), N-[2S,3R,4E,8E,1-(2”-metilamino-etanosulfonila)-3-hidroxi-4,8-octadeca¬dieno]hexadecanamida (P-8) e N-[2S,3R,4E,1-(2”-metilaminoetano-sulfonila)-3-hidroxi-4-octadeceno]hexadecanamida (P-9). Do fracionamento cromatográfico do extrato etanólico, foi possível isolar o esteróide 24(R)-ergost-7-en-3,56-triol (P-10) e o nucleosídeo 2-metil-timidina (P-11). Do estudo químico do extrato hexânico de P. variabilis obteve-se os mesmos constituintes químicos isolados de P. caribaeorum (P-1, P-2, P-3 e P-4) e as quatro ceramidas (P-5, P-6, P-8 e P-9). Além destes compostos foi isolado um éster de cadeia alifática, hexadecanoato de nonila (P-12) e o esteróide ácido 24(R)-B-norergostan-3-5-diol-6-carboxílico (P-13). O potencial citotóxico e antifúngico das ceramidas foi avaliado, entretanto, estas não apresentaram atividade. Os compostos foram isolados através de cromatografia de adsorção em gel de sílica e cromatografia líquida de alta eficiência. As estruturas dos compostos obtidos foram elucidadas utilizando técnicas espectroscópicas e espectrométricas, tais como: espectrometria de massa acoplada a cromatografia gasosa (CG/EM); espectrometria de massa de alta resolução (EMAR); espectroscopia na região do infravermelho (IV) e Ressonância Magnética Nuclear (RMN 1H, 13C e 15N) através de sequências de pulsos uni e bidimensionais e comparação com dados de RMN na literatura.Pessoa, Otília Deusdênia LoiolaAlmeida, José Gustavo Lima de2016-03-22T15:49:40Z2016-03-22T15:49:40Z2011info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisapplication/pdfALMEIDA, J. G. L. Constituintes Químicos dos Zoantídeos Palythoa caribaeorum (Duchassaing & Michelotti, 1860) e Protopalythoa Variabilis (Duerden, 1898). 2011. 217 f. Tese (Doutorado em Química) - Universidade Federal do Ceará, Fortaleza, 2011.http://www.repositorio.ufc.br/handle/riufc/15677porreponame:Repositório Institucional da Universidade Federal do Ceará (UFC)instname:Universidade Federal do Ceará (UFC)instacron:UFCinfo:eu-repo/semantics/openAccess2019-08-23T22:21:22Zoai:repositorio.ufc.br:riufc/15677Repositório InstitucionalPUBhttp://www.repositorio.ufc.br/ri-oai/requestbu@ufc.br || repositorio@ufc.bropendoar:2024-09-11T18:23:44.668537Repositório Institucional da Universidade Federal do Ceará (UFC) - Universidade Federal do Ceará (UFC)false |
dc.title.none.fl_str_mv |
Constituintes Químicos dos Zoantídeos Palythoa caribaeorum (Duchassaing & Michelotti, 1860) e Protopalythoa Variabilis (Duerden, 1898) Chemical Constituents of the zoanthids Palythoa caribaeorum (Duchassaing & Michelotti, 1860) and Protopalythoa variabilis (Duerden, 1898) |
title |
Constituintes Químicos dos Zoantídeos Palythoa caribaeorum (Duchassaing & Michelotti, 1860) e Protopalythoa Variabilis (Duerden, 1898) |
spellingShingle |
Constituintes Químicos dos Zoantídeos Palythoa caribaeorum (Duchassaing & Michelotti, 1860) e Protopalythoa Variabilis (Duerden, 1898) Almeida, José Gustavo Lima de Palythoa caribaeorum Protopalythoa variabilis |
title_short |
Constituintes Químicos dos Zoantídeos Palythoa caribaeorum (Duchassaing & Michelotti, 1860) e Protopalythoa Variabilis (Duerden, 1898) |
title_full |
Constituintes Químicos dos Zoantídeos Palythoa caribaeorum (Duchassaing & Michelotti, 1860) e Protopalythoa Variabilis (Duerden, 1898) |
title_fullStr |
Constituintes Químicos dos Zoantídeos Palythoa caribaeorum (Duchassaing & Michelotti, 1860) e Protopalythoa Variabilis (Duerden, 1898) |
title_full_unstemmed |
Constituintes Químicos dos Zoantídeos Palythoa caribaeorum (Duchassaing & Michelotti, 1860) e Protopalythoa Variabilis (Duerden, 1898) |
title_sort |
Constituintes Químicos dos Zoantídeos Palythoa caribaeorum (Duchassaing & Michelotti, 1860) e Protopalythoa Variabilis (Duerden, 1898) |
author |
Almeida, José Gustavo Lima de |
author_facet |
Almeida, José Gustavo Lima de |
author_role |
author |
dc.contributor.none.fl_str_mv |
Pessoa, Otília Deusdênia Loiola |
dc.contributor.author.fl_str_mv |
Almeida, José Gustavo Lima de |
dc.subject.por.fl_str_mv |
Palythoa caribaeorum Protopalythoa variabilis |
topic |
Palythoa caribaeorum Protopalythoa variabilis |
description |
This work describes the chemical composition of the marine species Palythoa caribaeorum and Protopalythoa variabilis, both collected at Paracuru beach, state of Ceará. The cromatographic fractionation of the hexane extract from P. caribaeorum resulted in the isolation of four tetracyclic sterols possessing the ergostan skeleton: 24(R)-ergost-5-en-3b-ol (P-1); 5 a,8a-epidioxy-24(R)-ergost-6-en-3b-ol (P-2); 24(R)- ergost-5-en-3b,7a-diol (P-4) and 24(R)-7a-hydroperoxy-ergost-5-en-3b-ol (P-7), a glycerol derivative, 1-O-hexadecylglycerol (P-3) and four ceramides: N- (2S,3R,4E,8E,1,3-dihydroxy-4,8-octadecadienyl)hexadecanamide (P-5); N- (2S,3R,4E,1,3-dihydroxy-4-octadecenyl)hexadecanamide (P-6); N-[2S,3R,4E,8E,1-(2”- methylamino-ethanosulfonyl)-3-hydroxy-4,8-octadecaenyl]hexadecanamide (P-8) and N-[2S,3R,4E,1-(2”-methylaminoethano-sulfonyl)-3-hydroxy-4-octadecenyl]hexadecanamide (P-9). The cromatographic fractionation of the ethanol extract permited the isolation of a steroid, 24(R)-ergost-7-en-3b,5a,6b-triol (P-10) and a nucleoside 2- methyltimidine (P-11). Column chromatography of the hexane extract of P. variabilis led to the isolation of nonyl hexadecanoate (P-12), the sterol 24(R)-B-norergostan-3b- 5b-diol-6b-carboxylic acid (P-13) and the same chemical constituents previously isolated from P. caribaeorum (P-1, P-2, P-3 e P-4) including the four ceramides (P-5, P-6, P-8 e P-9). The citotoxic and antifungal properties of all ceramides were evaluated, nevertheless none of them showed any activity. All compounds were isolated through adsorption column cromatography over silica gel followed by high performance liquid chromatography. The structures of the isolated compounds were elucidated using spectrometric techniques, such as: GC/MS, HRESIMS, IR and NMR (1H, 13C and 15N) through 1D and 2D pulse sequences and, whenever the case, comparison with literature data |
publishDate |
2011 |
dc.date.none.fl_str_mv |
2011 2016-03-22T15:49:40Z 2016-03-22T15:49:40Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/doctoralThesis |
format |
doctoralThesis |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
ALMEIDA, J. G. L. Constituintes Químicos dos Zoantídeos Palythoa caribaeorum (Duchassaing & Michelotti, 1860) e Protopalythoa Variabilis (Duerden, 1898). 2011. 217 f. Tese (Doutorado em Química) - Universidade Federal do Ceará, Fortaleza, 2011. http://www.repositorio.ufc.br/handle/riufc/15677 |
identifier_str_mv |
ALMEIDA, J. G. L. Constituintes Químicos dos Zoantídeos Palythoa caribaeorum (Duchassaing & Michelotti, 1860) e Protopalythoa Variabilis (Duerden, 1898). 2011. 217 f. Tese (Doutorado em Química) - Universidade Federal do Ceará, Fortaleza, 2011. |
url |
http://www.repositorio.ufc.br/handle/riufc/15677 |
dc.language.iso.fl_str_mv |
por |
language |
por |
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info:eu-repo/semantics/openAccess |
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openAccess |
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application/pdf |
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reponame:Repositório Institucional da Universidade Federal do Ceará (UFC) instname:Universidade Federal do Ceará (UFC) instacron:UFC |
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Universidade Federal do Ceará (UFC) |
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UFC |
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UFC |
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Repositório Institucional da Universidade Federal do Ceará (UFC) |
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Repositório Institucional da Universidade Federal do Ceará (UFC) |
repository.name.fl_str_mv |
Repositório Institucional da Universidade Federal do Ceará (UFC) - Universidade Federal do Ceará (UFC) |
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bu@ufc.br || repositorio@ufc.br |
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