A New Tetraglycosylated Flavonoid from Leaves of Platycyamus regnellii Benth. Isolated by High-Speed Countercurrent Chromatography
Autor(a) principal: | |
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Data de Publicação: | 2019 |
Outros Autores: | , , , |
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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Journal of the Brazilian Chemical Society (Online) |
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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 |
_version_ |
1750318182497779712 |