A New Tetraglycosylated Flavonoid from Leaves of Platycyamus regnellii Benth. Isolated by High-Speed Countercurrent Chromatography

Detalhes bibliográficos
Autor(a) principal: Leal,Carla M.
Data de Publicação: 2019
Outros Autores: Borges,Ricardo M., Simas,Rosineide C., Costa,Fernanda N., Leitão,Gilda G.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Journal of the Brazilian Chemical Society (Online)
Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532019001202561
Resumo: A new tetraglycosylated flavonoid derivative of kaempferol was isolated from the butanol extract of leaves of Platycyamus regnellii (Fabaceae) using high-speed countercurrent chromatography (HSCCC). The butanol extract (960.5 mg) was initially fractionated with the solvent system EtOAC-BuOH-H2O 2:8:10 (v/v/v) (elution in normal phase mode). The fractions containing the major tetraglycosylated flavonoid were further purified with the same solvent system by modifying the ratios to 3:7:10 (v/v/v) and alternating the elution to reversed phase mode. The structure of the isolated flavonoid (48.1 mg, 99.7% purity by ultra-high performance liquid chromatography with diode array detector (UHPLC-DAD)) was characterized by spectrometric and spectroscopic methods and identified as kaempferol 3-O-β-D-glucopiranosyl-(1®2)-α-L-rhamnopiranoside-(1®6)-α-L-rhamnopiranoside-7-O-α-L-rhamnopiranoside. Other minor flavonoids were also detected and tentatively identified using ultra-high performance liquid chromatography with diode array detector coupled to mass spectrometry using the electrospray ionization interface (UHPLC-DAD-ESI-MS/MS). By using the latter technique, a second tetraglycosylated flavonol with an O-methyl substituent (either rhamnetin, 3-O-methyl-quercetin or isorhamnetin) was detected, together with a triglycosylated kaempferol and diglycosylated flavonoids (either rhamnetin, 3-O-methyl-quercetin or isorhamnetin).
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spelling A New Tetraglycosylated Flavonoid from Leaves of Platycyamus regnellii Benth. Isolated by High-Speed Countercurrent ChromatographyPlatycyamus regnelliiFabaceaecountercurrent chromatographytetraglycosylated flavonoidA new tetraglycosylated flavonoid derivative of kaempferol was isolated from the butanol extract of leaves of Platycyamus regnellii (Fabaceae) using high-speed countercurrent chromatography (HSCCC). The butanol extract (960.5 mg) was initially fractionated with the solvent system EtOAC-BuOH-H2O 2:8:10 (v/v/v) (elution in normal phase mode). The fractions containing the major tetraglycosylated flavonoid were further purified with the same solvent system by modifying the ratios to 3:7:10 (v/v/v) and alternating the elution to reversed phase mode. The structure of the isolated flavonoid (48.1 mg, 99.7% purity by ultra-high performance liquid chromatography with diode array detector (UHPLC-DAD)) was characterized by spectrometric and spectroscopic methods and identified as kaempferol 3-O-β-D-glucopiranosyl-(1®2)-α-L-rhamnopiranoside-(1®6)-α-L-rhamnopiranoside-7-O-α-L-rhamnopiranoside. Other minor flavonoids were also detected and tentatively identified using ultra-high performance liquid chromatography with diode array detector coupled to mass spectrometry using the electrospray ionization interface (UHPLC-DAD-ESI-MS/MS). By using the latter technique, a second tetraglycosylated flavonol with an O-methyl substituent (either rhamnetin, 3-O-methyl-quercetin or isorhamnetin) was detected, together with a triglycosylated kaempferol and diglycosylated flavonoids (either rhamnetin, 3-O-methyl-quercetin or isorhamnetin).Sociedade Brasileira de Química2019-12-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532019001202561Journal of the Brazilian Chemical Society v.30 n.12 2019reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.21577/0103-5053.20190143info:eu-repo/semantics/openAccessLeal,Carla M.Borges,Ricardo M.Simas,Rosineide C.Costa,Fernanda N.Leitão,Gilda G.eng2019-10-21T00:00:00Zoai:scielo:S0103-50532019001202561Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2019-10-21T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv A New Tetraglycosylated Flavonoid from Leaves of Platycyamus regnellii Benth. Isolated by High-Speed Countercurrent Chromatography
title A New Tetraglycosylated Flavonoid from Leaves of Platycyamus regnellii Benth. Isolated by High-Speed Countercurrent Chromatography
spellingShingle A New Tetraglycosylated Flavonoid from Leaves of Platycyamus regnellii Benth. Isolated by High-Speed Countercurrent Chromatography
Leal,Carla M.
Platycyamus regnellii
Fabaceae
countercurrent chromatography
tetraglycosylated flavonoid
title_short A New Tetraglycosylated Flavonoid from Leaves of Platycyamus regnellii Benth. Isolated by High-Speed Countercurrent Chromatography
title_full A New Tetraglycosylated Flavonoid from Leaves of Platycyamus regnellii Benth. Isolated by High-Speed Countercurrent Chromatography
title_fullStr A New Tetraglycosylated Flavonoid from Leaves of Platycyamus regnellii Benth. Isolated by High-Speed Countercurrent Chromatography
title_full_unstemmed A New Tetraglycosylated Flavonoid from Leaves of Platycyamus regnellii Benth. Isolated by High-Speed Countercurrent Chromatography
title_sort A New Tetraglycosylated Flavonoid from Leaves of Platycyamus regnellii Benth. Isolated by High-Speed Countercurrent Chromatography
author Leal,Carla M.
author_facet Leal,Carla M.
Borges,Ricardo M.
Simas,Rosineide C.
Costa,Fernanda N.
Leitão,Gilda G.
author_role author
author2 Borges,Ricardo M.
Simas,Rosineide C.
Costa,Fernanda N.
Leitão,Gilda G.
author2_role author
author
author
author
dc.contributor.author.fl_str_mv Leal,Carla M.
Borges,Ricardo M.
Simas,Rosineide C.
Costa,Fernanda N.
Leitão,Gilda G.
dc.subject.por.fl_str_mv Platycyamus regnellii
Fabaceae
countercurrent chromatography
tetraglycosylated flavonoid
topic Platycyamus regnellii
Fabaceae
countercurrent chromatography
tetraglycosylated flavonoid
description A new tetraglycosylated flavonoid derivative of kaempferol was isolated from the butanol extract of leaves of Platycyamus regnellii (Fabaceae) using high-speed countercurrent chromatography (HSCCC). The butanol extract (960.5 mg) was initially fractionated with the solvent system EtOAC-BuOH-H2O 2:8:10 (v/v/v) (elution in normal phase mode). The fractions containing the major tetraglycosylated flavonoid were further purified with the same solvent system by modifying the ratios to 3:7:10 (v/v/v) and alternating the elution to reversed phase mode. The structure of the isolated flavonoid (48.1 mg, 99.7% purity by ultra-high performance liquid chromatography with diode array detector (UHPLC-DAD)) was characterized by spectrometric and spectroscopic methods and identified as kaempferol 3-O-β-D-glucopiranosyl-(1®2)-α-L-rhamnopiranoside-(1®6)-α-L-rhamnopiranoside-7-O-α-L-rhamnopiranoside. Other minor flavonoids were also detected and tentatively identified using ultra-high performance liquid chromatography with diode array detector coupled to mass spectrometry using the electrospray ionization interface (UHPLC-DAD-ESI-MS/MS). By using the latter technique, a second tetraglycosylated flavonol with an O-methyl substituent (either rhamnetin, 3-O-methyl-quercetin or isorhamnetin) was detected, together with a triglycosylated kaempferol and diglycosylated flavonoids (either rhamnetin, 3-O-methyl-quercetin or isorhamnetin).
publishDate 2019
dc.date.none.fl_str_mv 2019-12-01
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532019001202561
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532019001202561
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.21577/0103-5053.20190143
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv text/html
dc.publisher.none.fl_str_mv Sociedade Brasileira de Química
publisher.none.fl_str_mv Sociedade Brasileira de Química
dc.source.none.fl_str_mv Journal of the Brazilian Chemical Society v.30 n.12 2019
reponame:Journal of the Brazilian Chemical Society (Online)
instname:Sociedade Brasileira de Química (SBQ)
instacron:SBQ
instname_str Sociedade Brasileira de Química (SBQ)
instacron_str SBQ
institution SBQ
reponame_str Journal of the Brazilian Chemical Society (Online)
collection Journal of the Brazilian Chemical Society (Online)
repository.name.fl_str_mv Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)
repository.mail.fl_str_mv ||office@jbcs.sbq.org.br
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