Chemical characterization, antioxidant and anti-HIV activities of a Brazilian propolis from Ceará state

Detalhes bibliográficos
Autor(a) principal: Silva,Caroline Cristina Fernandes da
Data de Publicação: 2019
Outros Autores: Salatino,Antonio, Motta,Lucimar Barbosa da, Negri,Giuseppina, Salatino,Maria Luiza Faria
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Revista Brasileira de Farmacognosia (Online)
Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0102-695X2019000300309
Resumo: ABSTRACT Propolis (bee glue) a product of Apis mellifera L. is a resinous mixture containing chiefly beeswax and resin harvested by bees from plant leaves, buds and exudates. Extracts of a propolis sample from Salitre, a municipality of Ceará state (northeast Brazil) were obtained with solvents of increasing polarity (hexane, chloroform, ethyl acetate and methanol). A chemical profile was carried out by GC–EI-MS and HPLC–DAD–ESI-MS/MS. Lupenone, lupeol, octanoic acid tetracosyl ester and octanoic acid hexacosyl ester were identified by GC–EI-MS. Antioxidant activity was evaluated by the DPPH and β-carotene discoloring methods, and anti-HIV activity by the in vitro inhibition of HIV-1 reverse transcriptase. The ethyl acetate extract exhibited the highest antioxidant and anti-HIV activity and was fractioned by column chromatography using silica gel and seven different eluents. The active fractions were submitted to semi preparative HPLC and the following compounds were isolated: caffeic acid, p-coumaric acid, diprenylcinnamic acid, quercetin, naringenin, isorhamnetin, quercetin-3-O-diglucoside,4,2′,4′-trihydroxy-2-methoxychalcone, gossypetin-3,3′,4′,7-tetramethyl ether, myricetin-3,7,3′-trimethyl ether and 5-hydroxy-3,6,7,8,4′-pentamethoxyflavone. The ethyl acetate extract and its fractions F5-F7, as well as quercetin, isorhamnetin, myricetin-3,7,3′-trimethyl ether and p-coumaric acid exhibited high antioxidant activity on both DPPH and β-carotene antioxidant methods. Isorhamnetin exhibited moderate inhibitory effect against HIV-1 reverse transcriptase (56.99 ± 3.91%), followed by naringenin (44.22 ± 1.71%), quercetin (43.41 ± 4.56%) and diprenylcinnamic acid (41.59 ± 2.59%). These results agree with previous authors who reported anti-HIV activity of flavonoids.
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spelling Chemical characterization, antioxidant and anti-HIV activities of a Brazilian propolis from Ceará stateAnti-HIVAntioxidantBrazilian propolisFlavonoidsBotanical sourceHIV-1 reverse transcriptaseABSTRACT Propolis (bee glue) a product of Apis mellifera L. is a resinous mixture containing chiefly beeswax and resin harvested by bees from plant leaves, buds and exudates. Extracts of a propolis sample from Salitre, a municipality of Ceará state (northeast Brazil) were obtained with solvents of increasing polarity (hexane, chloroform, ethyl acetate and methanol). A chemical profile was carried out by GC–EI-MS and HPLC–DAD–ESI-MS/MS. Lupenone, lupeol, octanoic acid tetracosyl ester and octanoic acid hexacosyl ester were identified by GC–EI-MS. Antioxidant activity was evaluated by the DPPH and β-carotene discoloring methods, and anti-HIV activity by the in vitro inhibition of HIV-1 reverse transcriptase. The ethyl acetate extract exhibited the highest antioxidant and anti-HIV activity and was fractioned by column chromatography using silica gel and seven different eluents. The active fractions were submitted to semi preparative HPLC and the following compounds were isolated: caffeic acid, p-coumaric acid, diprenylcinnamic acid, quercetin, naringenin, isorhamnetin, quercetin-3-O-diglucoside,4,2′,4′-trihydroxy-2-methoxychalcone, gossypetin-3,3′,4′,7-tetramethyl ether, myricetin-3,7,3′-trimethyl ether and 5-hydroxy-3,6,7,8,4′-pentamethoxyflavone. The ethyl acetate extract and its fractions F5-F7, as well as quercetin, isorhamnetin, myricetin-3,7,3′-trimethyl ether and p-coumaric acid exhibited high antioxidant activity on both DPPH and β-carotene antioxidant methods. Isorhamnetin exhibited moderate inhibitory effect against HIV-1 reverse transcriptase (56.99 ± 3.91%), followed by naringenin (44.22 ± 1.71%), quercetin (43.41 ± 4.56%) and diprenylcinnamic acid (41.59 ± 2.59%). These results agree with previous authors who reported anti-HIV activity of flavonoids.Sociedade Brasileira de Farmacognosia2019-06-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0102-695X2019000300309Revista Brasileira de Farmacognosia v.29 n.3 2019reponame:Revista Brasileira de Farmacognosia (Online)instname:Sociedade Brasileira de Farmacognosia (SBFgnosia)instacron:SBFGNOSIA10.1016/j.bjp.2019.04.001info:eu-repo/semantics/openAccessSilva,Caroline Cristina Fernandes daSalatino,AntonioMotta,Lucimar Barbosa daNegri,GiuseppinaSalatino,Maria Luiza Fariaeng2019-08-22T00:00:00Zoai:scielo:S0102-695X2019000300309Revistahttp://www.sbfgnosia.org.br/revista/https://old.scielo.br/oai/scielo-oai.phprbgnosia@ltf.ufpb.br1981-528X0102-695Xopendoar:2019-08-22T00:00Revista Brasileira de Farmacognosia (Online) - Sociedade Brasileira de Farmacognosia (SBFgnosia)false
dc.title.none.fl_str_mv Chemical characterization, antioxidant and anti-HIV activities of a Brazilian propolis from Ceará state
title Chemical characterization, antioxidant and anti-HIV activities of a Brazilian propolis from Ceará state
spellingShingle Chemical characterization, antioxidant and anti-HIV activities of a Brazilian propolis from Ceará state
Silva,Caroline Cristina Fernandes da
Anti-HIV
Antioxidant
Brazilian propolis
Flavonoids
Botanical source
HIV-1 reverse transcriptase
title_short Chemical characterization, antioxidant and anti-HIV activities of a Brazilian propolis from Ceará state
title_full Chemical characterization, antioxidant and anti-HIV activities of a Brazilian propolis from Ceará state
title_fullStr Chemical characterization, antioxidant and anti-HIV activities of a Brazilian propolis from Ceará state
title_full_unstemmed Chemical characterization, antioxidant and anti-HIV activities of a Brazilian propolis from Ceará state
title_sort Chemical characterization, antioxidant and anti-HIV activities of a Brazilian propolis from Ceará state
author Silva,Caroline Cristina Fernandes da
author_facet Silva,Caroline Cristina Fernandes da
Salatino,Antonio
Motta,Lucimar Barbosa da
Negri,Giuseppina
Salatino,Maria Luiza Faria
author_role author
author2 Salatino,Antonio
Motta,Lucimar Barbosa da
Negri,Giuseppina
Salatino,Maria Luiza Faria
author2_role author
author
author
author
dc.contributor.author.fl_str_mv Silva,Caroline Cristina Fernandes da
Salatino,Antonio
Motta,Lucimar Barbosa da
Negri,Giuseppina
Salatino,Maria Luiza Faria
dc.subject.por.fl_str_mv Anti-HIV
Antioxidant
Brazilian propolis
Flavonoids
Botanical source
HIV-1 reverse transcriptase
topic Anti-HIV
Antioxidant
Brazilian propolis
Flavonoids
Botanical source
HIV-1 reverse transcriptase
description ABSTRACT Propolis (bee glue) a product of Apis mellifera L. is a resinous mixture containing chiefly beeswax and resin harvested by bees from plant leaves, buds and exudates. Extracts of a propolis sample from Salitre, a municipality of Ceará state (northeast Brazil) were obtained with solvents of increasing polarity (hexane, chloroform, ethyl acetate and methanol). A chemical profile was carried out by GC–EI-MS and HPLC–DAD–ESI-MS/MS. Lupenone, lupeol, octanoic acid tetracosyl ester and octanoic acid hexacosyl ester were identified by GC–EI-MS. Antioxidant activity was evaluated by the DPPH and β-carotene discoloring methods, and anti-HIV activity by the in vitro inhibition of HIV-1 reverse transcriptase. The ethyl acetate extract exhibited the highest antioxidant and anti-HIV activity and was fractioned by column chromatography using silica gel and seven different eluents. The active fractions were submitted to semi preparative HPLC and the following compounds were isolated: caffeic acid, p-coumaric acid, diprenylcinnamic acid, quercetin, naringenin, isorhamnetin, quercetin-3-O-diglucoside,4,2′,4′-trihydroxy-2-methoxychalcone, gossypetin-3,3′,4′,7-tetramethyl ether, myricetin-3,7,3′-trimethyl ether and 5-hydroxy-3,6,7,8,4′-pentamethoxyflavone. The ethyl acetate extract and its fractions F5-F7, as well as quercetin, isorhamnetin, myricetin-3,7,3′-trimethyl ether and p-coumaric acid exhibited high antioxidant activity on both DPPH and β-carotene antioxidant methods. Isorhamnetin exhibited moderate inhibitory effect against HIV-1 reverse transcriptase (56.99 ± 3.91%), followed by naringenin (44.22 ± 1.71%), quercetin (43.41 ± 4.56%) and diprenylcinnamic acid (41.59 ± 2.59%). These results agree with previous authors who reported anti-HIV activity of flavonoids.
publishDate 2019
dc.date.none.fl_str_mv 2019-06-01
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dc.identifier.uri.fl_str_mv http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0102-695X2019000300309
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dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.1016/j.bjp.2019.04.001
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
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dc.publisher.none.fl_str_mv Sociedade Brasileira de Farmacognosia
publisher.none.fl_str_mv Sociedade Brasileira de Farmacognosia
dc.source.none.fl_str_mv Revista Brasileira de Farmacognosia v.29 n.3 2019
reponame:Revista Brasileira de Farmacognosia (Online)
instname:Sociedade Brasileira de Farmacognosia (SBFgnosia)
instacron:SBFGNOSIA
instname_str Sociedade Brasileira de Farmacognosia (SBFgnosia)
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reponame_str Revista Brasileira de Farmacognosia (Online)
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