Metab?litos secund?rios e avalia??o de atividades biol?gicas de Siolmatra brasiliensis (Cogn.) Baill. (Cucurbitaceae) e esp?cie do g?nero Ziziphus Mill. (Rhamnaceae)
| Ano de defesa: | 2018 |
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| Autor(a) principal: |
Santos, Carlos Henrique Corr?a dos
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| Orientador(a): | |
| Banca de defesa: | , , , , |
| Tipo de documento: | Tese |
| Tipo de acesso: | Acesso aberto |
| Idioma: | por |
| Instituição de defesa: |
Universidade Federal Rural do Rio de Janeiro
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| Programa de Pós-Graduação: |
Programa de P?s-Gradua??o em Qu?mica
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| Departamento: |
Instituto de Qu?mica
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| País: |
Brasil
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| Palavras-chave em Português: | |
| Palavras-chave em Inglês: | |
| Área do conhecimento CNPq: | |
| Link de acesso: | https://tede.ufrrj.br/jspui/handle/jspui/5514 |
Resumo: | Twenty compounds were isolated from the crude hydroethanolic stem extract of Siolmatra brasiliensis, the structures were assigned by extensive NMR and HR-ESI-MS analyses. Five flavonoids, two lignans, one glycosylated phytosterol and seven nor-cucurbitacins already described in the literature were identified, along with a previously undescribed phenolic derivative and four dammarane-type saponins (siolmatrin and siolmatrosides II-V). The antinociceptive and in vitro antiglycation activities of the crude extract and fractions from the species were evaluated. It is suggested that the presence of dammarane-type saponins and nor-cucurbitacins are responsible for the observed antinociceptive activity of the extract and especially the ethyl acetate fraction, on the other hand, the identified phenolic compounds may be responsible for the anti-glycation activity observed specially in the chloroform fraction. Four species of Ziziphus were included in this project to evaluate biological activities, in which, Z. joazeiro and Z. glaziovii presented promising results of bacterial inhibition of Aliivibrio fischeri and Bacillus subtilis, and all extracts showed significant cytotoxic activities against PC- 3 and HT-29. Seventeen compounds were isolated from the chloroform fraction of Z. glaziovii stem extract, one xanthone, one lignan, two lupane-type triterpenes, four ceanothane-type triterpenes and one glycosylated phytosterol, besides seven previously undescribed dammarane-type saponins (ziziglaziovigenin, ziziglaziovigenin 3-O-?-L-arabinopyranoside, ziziglaziovigenin-3-O-?-L-arabinofuranosyl-(1-2)-?-L-arabinopyranoside, ziziglaziovigenin 3-O-?-D-glucopyranosyl-(1-3)-?-L-arabinopyranoside, 16,22:16,30-diepoxy-20-hydroxydammar-24-methylidene 3-O-?-D-apiofuranosyl-(1-3)-O-[6-(3-methoxy-4-hydroxybenzoate)-?-D-glucopyranosyl-(1-2)]-?-D-glucopyranosyl-(1-2)-?-D-glucopyranoside, 16,22-epoxy-15,16,20-trihydroxydammar-24-methylidene 3-O-?-D-apiofuranosyl-(1-3)-O-[6-(3-methoxy-4-hidroxybenzoate)-?-D-glucopyranosyl-(1-2)]-?-D-glucopyranosyl-(1-2)-?-D-glucopyranoside e 16,22:16,30-diepoxy-20-hydroxydammar-24-methylidene 3-O-?-L-arabinofuranosyl-(1-2)-O-[4-O-sodium-sulphate-?-D-glucopyranosyl-(1-3)]-?-L-arabinopyranoside. The compounds evaluated for antibacterial activity, where epigouanic acid and alphitolic acid showed good inhibition of B. subtilis (IC50 of 20 and 12 ?M, respectively). The isolated compounds presented up to a 10 ?M concentration, none or weak cytotoxic activity. UHPLC-MS-MS analysis of the alkaloidal fraction from the crude stem extract of Z. joazeiro stem allowed the identification of eight Ib-type cyclopeptide alkaloids, the structures were suggested by mass fragmentation proposals. |
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Carvalho, Mario Geraldo deCPF: 257.152.327-91Wessjohann, Ludger A.Carvalho, Mario Geraldo deLeit?o, Gilda Guimar?esDavid, Jorge Maur?cioValverde, Alessandra LedaSuzart, Luciano RamosCPF: 031.250.371-74http://lattes.cnpq.br/9106363444050625Santos, Carlos Henrique Corr?a dos2022-04-03T19:56:19Z2018-10-19SANTOS, Carlos Henrique Corr?a dos. Metab?litos secund?rios e avalia??o de atividades biol?gicas de Siolmatra brasiliensis (Cogn.) Baill. (Cucurbitaceae) e esp?cie do g?nero Ziziphus Mill. (Rhamnaceae) - Vol.1. 2018. 211 f. Tese (Doutorado em Qu?mica) - Instituto de Qu?mica, Universidade Federal Rural do Rio de Janeiro, Serop?dica, 2018.https://tede.ufrrj.br/jspui/handle/jspui/5514Twenty compounds were isolated from the crude hydroethanolic stem extract of Siolmatra brasiliensis, the structures were assigned by extensive NMR and HR-ESI-MS analyses. Five flavonoids, two lignans, one glycosylated phytosterol and seven nor-cucurbitacins already described in the literature were identified, along with a previously undescribed phenolic derivative and four dammarane-type saponins (siolmatrin and siolmatrosides II-V). The antinociceptive and in vitro antiglycation activities of the crude extract and fractions from the species were evaluated. It is suggested that the presence of dammarane-type saponins and nor-cucurbitacins are responsible for the observed antinociceptive activity of the extract and especially the ethyl acetate fraction, on the other hand, the identified phenolic compounds may be responsible for the anti-glycation activity observed specially in the chloroform fraction. Four species of Ziziphus were included in this project to evaluate biological activities, in which, Z. joazeiro and Z. glaziovii presented promising results of bacterial inhibition of Aliivibrio fischeri and Bacillus subtilis, and all extracts showed significant cytotoxic activities against PC- 3 and HT-29. Seventeen compounds were isolated from the chloroform fraction of Z. glaziovii stem extract, one xanthone, one lignan, two lupane-type triterpenes, four ceanothane-type triterpenes and one glycosylated phytosterol, besides seven previously undescribed dammarane-type saponins (ziziglaziovigenin, ziziglaziovigenin 3-O-?-L-arabinopyranoside, ziziglaziovigenin-3-O-?-L-arabinofuranosyl-(1-2)-?-L-arabinopyranoside, ziziglaziovigenin 3-O-?-D-glucopyranosyl-(1-3)-?-L-arabinopyranoside, 16,22:16,30-diepoxy-20-hydroxydammar-24-methylidene 3-O-?-D-apiofuranosyl-(1-3)-O-[6-(3-methoxy-4-hydroxybenzoate)-?-D-glucopyranosyl-(1-2)]-?-D-glucopyranosyl-(1-2)-?-D-glucopyranoside, 16,22-epoxy-15,16,20-trihydroxydammar-24-methylidene 3-O-?-D-apiofuranosyl-(1-3)-O-[6-(3-methoxy-4-hidroxybenzoate)-?-D-glucopyranosyl-(1-2)]-?-D-glucopyranosyl-(1-2)-?-D-glucopyranoside e 16,22:16,30-diepoxy-20-hydroxydammar-24-methylidene 3-O-?-L-arabinofuranosyl-(1-2)-O-[4-O-sodium-sulphate-?-D-glucopyranosyl-(1-3)]-?-L-arabinopyranoside. The compounds evaluated for antibacterial activity, where epigouanic acid and alphitolic acid showed good inhibition of B. subtilis (IC50 of 20 and 12 ?M, respectively). The isolated compounds presented up to a 10 ?M concentration, none or weak cytotoxic activity. UHPLC-MS-MS analysis of the alkaloidal fraction from the crude stem extract of Z. joazeiro stem allowed the identification of eight Ib-type cyclopeptide alkaloids, the structures were suggested by mass fragmentation proposals.Vinte subst?ncias foram isoladas do extrato bruto hidroetan?lico do caule de Siolmatra brasiliensis, suas estruturas foram determinadas por an?lises extensivas de RMN e EM-AR-ESI. Foram identificados cinco flavonoides, duas lignanas, um fitoesterol glicosilado e sete nor-cucurbitacinas j? descritas na literatura al?m de um derivado fen?lico e quatro saponinas de esqueleto do tipo damarano in?ditas na literatura cient?fica (siolmatrina e siolmatros?deos II-V, respectivamente). Foram avaliadas as atividades antinociceptiva e anti-glica??o in vitro do extrato bruto e fra??es da esp?cie. Sugere-se que a presen?a de saponinas do tipo damarano e nor-cucurbitacinas sejam respons?veis pela atividade antinociceptiva conferida ao extrato e especialmente fra??o em acetato de etila e que as subst?ncias fen?licas sejam respons?veis pela atividade anti-glica??o conferida especialmente a fra??o em clorof?rmio. Inclu?ram-se nesse trabalho quatro esp?cies do g?nero Ziziphus para avalia??o de atividades biol?gicas, onde Z. joazeiro e Z. glaziovii apresentaram resultados promissores de inibi??o bacteriana de Aliivibrio fischeri e Bacillus subtilis e todos os extratos apresentaram atividades citot?xicas significantes frente a linhagens celulares PC-3 e HT-29. Desessete subst?ncias foram isoladas da fra??o em clorof?rmio do extrato metan?lico do caule de Z. glaziovii, sendo uma xantona, uma lignana, dois triterpenos do tipo lupano, quatro do tipo ceanotano e um fitosterol glicosilado j? descritos na literatura al?m de sete saponinas do tipo damarano in?ditas na literatura cient?fica (ziziglaziovigenina, ziziglaziovigenina 3-O-?-L-arabinopiranos?deo, ziziglaziovigenina-3-O-?-L-arabinofuranosil-(1-2)-?-L-arabinopiranos?deo, ziziglaziovigenina 3-O-?-D-glicopiranosil-(1-3)-?-L-arabinopiranos?deo, 16,22:16,30-diep?xi-20-hidr?xidamar-24-metilideno 3-O-?-D-apiofuranosil-(1-3)-O-[6-(3-met?xi-4-hidr?xibenzoato)-?-D-glicopiranosil-(1-2)]-?-D-glicopiranosil-(1-2)-?-D-glicopiranos?deo, 16,22-ep?xi-15,16,20-trihidr?xidamar-24-metilideno-3-O-?-D-apiofuranosil-(1-3)-O-[6-(3-met?xi-4-hidr?xibenzoato)-?-D-glicopiranosil-(1-2)]-?-D-glicopiranosil-(1-2)-?-D-glicopiranos?deo e 16,22:16,30-diep?xi-20-hidr?xidamar-24-metilideno 3-O-?-L-arabinofuranosil-(1-2)-O-[4-O-s?dio-sulfato-?-D-glicopiranosil-(1-3)]-?-L-arabinopiranos?deo). As subt?ncias foram avaliadas quanto ? atividade antibacteriana, onde o ?cido epigou?nico e ?cido alfit?lico mostraram bons resultados frente a B. subtilis (IC50 de 20 e 12 ??M, respectivamente). As subst??ncias apresentaram pouca ou nenhuma atividade citot?xica nas concentra??es testadas (0,01 e 10 ?M). A an?lise de CLUE-EM-EM da fra??o alcalo?dica do extrato bruto do caule de Z. joazeiro possibilitou a identifica??o de oito alcaloides ciclopept?dicos do tipo Ib, onde as estruturas foram sugeridas por propostas de fragmenta??o de massas.Submitted by Jorge Silva (jorgelmsilva@ufrrj.br) on 2022-04-03T19:56:19Z No. of bitstreams: 2 2018 - Carlos Henrique Corr?a dos Santos (Vol 1).pdf: 6793229 bytes, checksum: b4c56e9a124d764bb822d5abfcdf3121 (MD5) 2018 - Carlos Henrique Corr?a dos Santos (Vol 2).pdf: 31281768 bytes, checksum: 2708335fcf9d05485438c7cf6f8dabee (MD5)Made available in DSpace on 2022-04-03T19:56:19Z (GMT). No. of bitstreams: 2 2018 - Carlos Henrique Corr?a dos Santos (Vol 1).pdf: 6793229 bytes, checksum: b4c56e9a124d764bb822d5abfcdf3121 (MD5) 2018 - Carlos Henrique Corr?a dos Santos (Vol 2).pdf: 31281768 bytes, checksum: 2708335fcf9d05485438c7cf6f8dabee (MD5) Previous issue date: 2018-10-19CAPES - Coordena??o de Aperfei?oamento de Pessoal de N?vel SuperiorCNPq - Conselho Nacional de Desenvolvimento Cient?fico e Tecnol?gicoFAPERJ - Funda??o Carlos Chagas Filho de Amparo ? Pesquisa do Estado do Rio de Janeiroapplication/pdfhttps://tede.ufrrj.br/retrieve/68741/2018%20-%20Carlos%20Henrique%20Corr%c3%aaa%20dos%20Santos%20%28Vol%201%29.pdf.jpghttps://tede.ufrrj.br/retrieve/68743/2018%20-%20Carlos%20Henrique%20Corr%c3%aaa%20dos%20Santos%20%28Vol%202%29.pdf.jpgporUniversidade Federal Rural do Rio de JaneiroPrograma de P?s-Gradua??o em Qu?micaUFRRJBrasilInstituto de Qu?micaAGRAWAL, P. K. Carbon-13 NMR of flavonoids. Studies in Organic Chemistry. v. 39, p. 95-182, 1989. 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Chemical and Pharmaceutical Bulletin. v. 45 (6), p. 1056- 1062, 1997.Siolmatra brasiliensisZiziphustriterpenoidesalcaloides ciclopept?dicosatividades biol?gicastriterpenoidscyclopeptide alkaloidsbiological activitiesQu?micaMetab?litos secund?rios e avalia??o de atividades biol?gicas de Siolmatra brasiliensis (Cogn.) Baill. (Cucurbitaceae) e esp?cie do g?nero Ziziphus Mill. (Rhamnaceae)Secondary metabolites and evaluation of biological activities of Siolmatra brasiliensis (Cogn.) Baill. 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| dc.title.por.fl_str_mv |
Metab?litos secund?rios e avalia??o de atividades biol?gicas de Siolmatra brasiliensis (Cogn.) Baill. (Cucurbitaceae) e esp?cie do g?nero Ziziphus Mill. (Rhamnaceae) |
| dc.title.alternative.eng.fl_str_mv |
Secondary metabolites and evaluation of biological activities of Siolmatra brasiliensis (Cogn.) Baill. (Cucurbitaceae) and species from Ziziphus Mill. genus (Rhamnaceae) |
| title |
Metab?litos secund?rios e avalia??o de atividades biol?gicas de Siolmatra brasiliensis (Cogn.) Baill. (Cucurbitaceae) e esp?cie do g?nero Ziziphus Mill. (Rhamnaceae) |
| spellingShingle |
Metab?litos secund?rios e avalia??o de atividades biol?gicas de Siolmatra brasiliensis (Cogn.) Baill. (Cucurbitaceae) e esp?cie do g?nero Ziziphus Mill. (Rhamnaceae) Santos, Carlos Henrique Corr?a dos Siolmatra brasiliensis Ziziphus triterpenoides alcaloides ciclopept?dicos atividades biol?gicas triterpenoids cyclopeptide alkaloids biological activities Qu?mica |
| title_short |
Metab?litos secund?rios e avalia??o de atividades biol?gicas de Siolmatra brasiliensis (Cogn.) Baill. (Cucurbitaceae) e esp?cie do g?nero Ziziphus Mill. (Rhamnaceae) |
| title_full |
Metab?litos secund?rios e avalia??o de atividades biol?gicas de Siolmatra brasiliensis (Cogn.) Baill. (Cucurbitaceae) e esp?cie do g?nero Ziziphus Mill. (Rhamnaceae) |
| title_fullStr |
Metab?litos secund?rios e avalia??o de atividades biol?gicas de Siolmatra brasiliensis (Cogn.) Baill. (Cucurbitaceae) e esp?cie do g?nero Ziziphus Mill. (Rhamnaceae) |
| title_full_unstemmed |
Metab?litos secund?rios e avalia??o de atividades biol?gicas de Siolmatra brasiliensis (Cogn.) Baill. (Cucurbitaceae) e esp?cie do g?nero Ziziphus Mill. (Rhamnaceae) |
| title_sort |
Metab?litos secund?rios e avalia??o de atividades biol?gicas de Siolmatra brasiliensis (Cogn.) Baill. (Cucurbitaceae) e esp?cie do g?nero Ziziphus Mill. (Rhamnaceae) |
| author |
Santos, Carlos Henrique Corr?a dos |
| author_facet |
Santos, Carlos Henrique Corr?a dos |
| author_role |
author |
| dc.contributor.advisor1.fl_str_mv |
Carvalho, Mario Geraldo de |
| dc.contributor.advisor1ID.fl_str_mv |
CPF: 257.152.327-91 |
| dc.contributor.advisor-co1.fl_str_mv |
Wessjohann, Ludger A. |
| dc.contributor.referee1.fl_str_mv |
Carvalho, Mario Geraldo de |
| dc.contributor.referee2.fl_str_mv |
Leit?o, Gilda Guimar?es |
| dc.contributor.referee3.fl_str_mv |
David, Jorge Maur?cio |
| dc.contributor.referee4.fl_str_mv |
Valverde, Alessandra Leda |
| dc.contributor.referee5.fl_str_mv |
Suzart, Luciano Ramos |
| dc.contributor.authorID.fl_str_mv |
CPF: 031.250.371-74 |
| dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/9106363444050625 |
| dc.contributor.author.fl_str_mv |
Santos, Carlos Henrique Corr?a dos |
| contributor_str_mv |
Carvalho, Mario Geraldo de Wessjohann, Ludger A. Carvalho, Mario Geraldo de Leit?o, Gilda Guimar?es David, Jorge Maur?cio Valverde, Alessandra Leda Suzart, Luciano Ramos |
| dc.subject.por.fl_str_mv |
Siolmatra brasiliensis Ziziphus triterpenoides alcaloides ciclopept?dicos atividades biol?gicas |
| topic |
Siolmatra brasiliensis Ziziphus triterpenoides alcaloides ciclopept?dicos atividades biol?gicas triterpenoids cyclopeptide alkaloids biological activities Qu?mica |
| dc.subject.eng.fl_str_mv |
triterpenoids cyclopeptide alkaloids biological activities |
| dc.subject.cnpq.fl_str_mv |
Qu?mica |
| description |
Twenty compounds were isolated from the crude hydroethanolic stem extract of Siolmatra brasiliensis, the structures were assigned by extensive NMR and HR-ESI-MS analyses. Five flavonoids, two lignans, one glycosylated phytosterol and seven nor-cucurbitacins already described in the literature were identified, along with a previously undescribed phenolic derivative and four dammarane-type saponins (siolmatrin and siolmatrosides II-V). The antinociceptive and in vitro antiglycation activities of the crude extract and fractions from the species were evaluated. It is suggested that the presence of dammarane-type saponins and nor-cucurbitacins are responsible for the observed antinociceptive activity of the extract and especially the ethyl acetate fraction, on the other hand, the identified phenolic compounds may be responsible for the anti-glycation activity observed specially in the chloroform fraction. Four species of Ziziphus were included in this project to evaluate biological activities, in which, Z. joazeiro and Z. glaziovii presented promising results of bacterial inhibition of Aliivibrio fischeri and Bacillus subtilis, and all extracts showed significant cytotoxic activities against PC- 3 and HT-29. Seventeen compounds were isolated from the chloroform fraction of Z. glaziovii stem extract, one xanthone, one lignan, two lupane-type triterpenes, four ceanothane-type triterpenes and one glycosylated phytosterol, besides seven previously undescribed dammarane-type saponins (ziziglaziovigenin, ziziglaziovigenin 3-O-?-L-arabinopyranoside, ziziglaziovigenin-3-O-?-L-arabinofuranosyl-(1-2)-?-L-arabinopyranoside, ziziglaziovigenin 3-O-?-D-glucopyranosyl-(1-3)-?-L-arabinopyranoside, 16,22:16,30-diepoxy-20-hydroxydammar-24-methylidene 3-O-?-D-apiofuranosyl-(1-3)-O-[6-(3-methoxy-4-hydroxybenzoate)-?-D-glucopyranosyl-(1-2)]-?-D-glucopyranosyl-(1-2)-?-D-glucopyranoside, 16,22-epoxy-15,16,20-trihydroxydammar-24-methylidene 3-O-?-D-apiofuranosyl-(1-3)-O-[6-(3-methoxy-4-hidroxybenzoate)-?-D-glucopyranosyl-(1-2)]-?-D-glucopyranosyl-(1-2)-?-D-glucopyranoside e 16,22:16,30-diepoxy-20-hydroxydammar-24-methylidene 3-O-?-L-arabinofuranosyl-(1-2)-O-[4-O-sodium-sulphate-?-D-glucopyranosyl-(1-3)]-?-L-arabinopyranoside. The compounds evaluated for antibacterial activity, where epigouanic acid and alphitolic acid showed good inhibition of B. subtilis (IC50 of 20 and 12 ?M, respectively). The isolated compounds presented up to a 10 ?M concentration, none or weak cytotoxic activity. UHPLC-MS-MS analysis of the alkaloidal fraction from the crude stem extract of Z. joazeiro stem allowed the identification of eight Ib-type cyclopeptide alkaloids, the structures were suggested by mass fragmentation proposals. |
| publishDate |
2018 |
| dc.date.issued.fl_str_mv |
2018-10-19 |
| dc.date.accessioned.fl_str_mv |
2022-04-03T19:56:19Z |
| 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.citation.fl_str_mv |
SANTOS, Carlos Henrique Corr?a dos. Metab?litos secund?rios e avalia??o de atividades biol?gicas de Siolmatra brasiliensis (Cogn.) Baill. (Cucurbitaceae) e esp?cie do g?nero Ziziphus Mill. (Rhamnaceae) - Vol.1. 2018. 211 f. Tese (Doutorado em Qu?mica) - Instituto de Qu?mica, Universidade Federal Rural do Rio de Janeiro, Serop?dica, 2018. |
| dc.identifier.uri.fl_str_mv |
https://tede.ufrrj.br/jspui/handle/jspui/5514 |
| identifier_str_mv |
SANTOS, Carlos Henrique Corr?a dos. Metab?litos secund?rios e avalia??o de atividades biol?gicas de Siolmatra brasiliensis (Cogn.) Baill. (Cucurbitaceae) e esp?cie do g?nero Ziziphus Mill. (Rhamnaceae) - Vol.1. 2018. 211 f. Tese (Doutorado em Qu?mica) - Instituto de Qu?mica, Universidade Federal Rural do Rio de Janeiro, Serop?dica, 2018. |
| url |
https://tede.ufrrj.br/jspui/handle/jspui/5514 |
| dc.language.iso.fl_str_mv |
por |
| language |
por |
| dc.relation.references.por.fl_str_mv |
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