Bioassay-Guided Fractionation of <i>Siparuna glycycarpa</i> <i>n</i>-Butanol Extract with Inhibitory Activity against Influenza A(H1N1)pdm09 Virus by Centrifugal Partition Chromatography (CPC)
<i>Siparuna glycycarpa</i> occurs in the Amazon region, and some species of this genus are used in Brazilian folk medicine. A recent study showed the inhibitory effect of this species against influenza A(H1N1)pdm09 virus, and in order to acquire active fractions, a polar solvent system &...
| Main Authors: | , , , , , , , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2022-01-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/27/2/399 |
| _version_ | 1797491565105512448 |
|---|---|
| author | Carla Monteiro Leal Suzana Guimarães Leitão Leonardo Luiz Oliveira de Mello Isabel de Castro Rangel Carlos Vinicius Azevedo da Silva Milene Dias Miranda Amanda Resende Tucci Camilla Blanco de Assis Carolina de Queiroz Sacramento Natalia Fintelman-Rodrigues Hector Henrique Ferreira Koolen Boniek Gontijo Vaz Rosineide Costa Simas Gilda Guimarães Leitão |
| author_facet | Carla Monteiro Leal Suzana Guimarães Leitão Leonardo Luiz Oliveira de Mello Isabel de Castro Rangel Carlos Vinicius Azevedo da Silva Milene Dias Miranda Amanda Resende Tucci Camilla Blanco de Assis Carolina de Queiroz Sacramento Natalia Fintelman-Rodrigues Hector Henrique Ferreira Koolen Boniek Gontijo Vaz Rosineide Costa Simas Gilda Guimarães Leitão |
| author_sort | Carla Monteiro Leal |
| collection | DOAJ |
| description | <i>Siparuna glycycarpa</i> occurs in the Amazon region, and some species of this genus are used in Brazilian folk medicine. A recent study showed the inhibitory effect of this species against influenza A(H1N1)pdm09 virus, and in order to acquire active fractions, a polar solvent system <i>n</i>-butanol-methanol-water (9:1:10, <i>v</i>/<i>v</i>) was selected and used for bioassay-guided fractionation of <i>n</i>-butanol extract by centrifugal partition chromatography (CPC). The upper phase was used as stationary phase and the lower phase as mobile (descending mode). Among the collected fractions, the ones coded SGA, SGC, SGD, and SGO showed the highest antiviral inhibition levels (above 74%) at 100 µg·mL<sup>−1</sup> after 24 h of infection. The bioactive fractions chemical profiles were investigated by LC-HRMS/MS data in positive and negative ionization modes exploring the Global Natural Products Social Molecular Networking (GNPS) platform to build a molecular network. Benzylisoquinoline alkaloids were annotated in the fractions coded SGA, SGC, and SGD collected during elution step. Aporphine alkaloids, <i>O</i>-glycosylated flavonoids, and dihydrochalcones in SGO were acquired with the change of mobile phase from lower aqueous to upper organic. Benzylisoquinolinic and aporphine alkaloids as well as glycosylated flavonoids were annotated in the most bioactive fractions suggesting this group of compounds as responsible for antiviral activity. |
| first_indexed | 2024-03-10T00:51:06Z |
| format | Article |
| id | doaj.art-994e43e061c447f096b8a12b70d1b69c |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T00:51:06Z |
| publishDate | 2022-01-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-994e43e061c447f096b8a12b70d1b69c2023-11-23T14:51:25ZengMDPI AGMolecules1420-30492022-01-0127239910.3390/molecules27020399Bioassay-Guided Fractionation of <i>Siparuna glycycarpa</i> <i>n</i>-Butanol Extract with Inhibitory Activity against Influenza A(H1N1)pdm09 Virus by Centrifugal Partition Chromatography (CPC)Carla Monteiro Leal0Suzana Guimarães Leitão1Leonardo Luiz Oliveira de Mello2Isabel de Castro Rangel3Carlos Vinicius Azevedo da Silva4Milene Dias Miranda5Amanda Resende Tucci6Camilla Blanco de Assis7Carolina de Queiroz Sacramento8Natalia Fintelman-Rodrigues9Hector Henrique Ferreira Koolen10Boniek Gontijo Vaz11Rosineide Costa Simas12Gilda Guimarães Leitão13Programa de Pós-Graduação em Biotecnologia Vegetal e Bioprocessos (PBV), Centro de Ciências da Saúde, Universidade Federal do Rio de Janeiro, Rio de Janeiro 21941-902, BrazilFaculdade de Farmácia, Centro de Ciências da Saúde, Universidade Federal do Rio de Janeiro, Rio de Janeiro 21941-902, BrazilInstituto de Pesquisas de Produtos Naturais, Centro de Ciências da Saúde, Universidade Federal do Rio de Janeiro, Rio de Janeiro 21941-902, BrazilInstituto de Pesquisas de Produtos Naturais, Centro de Ciências da Saúde, Universidade Federal do Rio de Janeiro, Rio de Janeiro 21941-902, BrazilGrupo de Pesquisas em Metabolômica e Espectrometria de Massas, Escola Superior de Ciências da Saúde, Universidade do Estado do Amazonas, Manaus 69065-000, BrazilLaboratório de Vírus Respiratórios e do Sarampo, Instituto Oswaldo Cruz, Fundação Oswaldo Cruz, Rio de Janeiro 21041-210, BrazilLaboratório de Vírus Respiratórios e do Sarampo, Instituto Oswaldo Cruz, Fundação Oswaldo Cruz, Rio de Janeiro 21041-210, BrazilLaboratório de Imunofarmacologia, Instituto Oswaldo Cruz, Fundação Oswaldo Cruz, Rio de Janeiro 21041-210, BrazilLaboratório de Imunofarmacologia, Instituto Oswaldo Cruz, Fundação Oswaldo Cruz, Rio de Janeiro 21041-210, BrazilLaboratório de Imunofarmacologia, Instituto Oswaldo Cruz, Fundação Oswaldo Cruz, Rio de Janeiro 21041-210, BrazilGrupo de Pesquisas em Metabolômica e Espectrometria de Massas, Escola Superior de Ciências da Saúde, Universidade do Estado do Amazonas, Manaus 69065-000, BrazilLaboratório de Cromatografia e Espectrometria de Massas (LaCEM), Instituto de Química, Universidade Federal de Goiás, Goiânia 74690-900, BrazilLaboratório de Cromatografia e Espectrometria de Massas (LaCEM), Instituto de Química, Universidade Federal de Goiás, Goiânia 74690-900, BrazilInstituto de Pesquisas de Produtos Naturais, Centro de Ciências da Saúde, Universidade Federal do Rio de Janeiro, Rio de Janeiro 21941-902, Brazil<i>Siparuna glycycarpa</i> occurs in the Amazon region, and some species of this genus are used in Brazilian folk medicine. A recent study showed the inhibitory effect of this species against influenza A(H1N1)pdm09 virus, and in order to acquire active fractions, a polar solvent system <i>n</i>-butanol-methanol-water (9:1:10, <i>v</i>/<i>v</i>) was selected and used for bioassay-guided fractionation of <i>n</i>-butanol extract by centrifugal partition chromatography (CPC). The upper phase was used as stationary phase and the lower phase as mobile (descending mode). Among the collected fractions, the ones coded SGA, SGC, SGD, and SGO showed the highest antiviral inhibition levels (above 74%) at 100 µg·mL<sup>−1</sup> after 24 h of infection. The bioactive fractions chemical profiles were investigated by LC-HRMS/MS data in positive and negative ionization modes exploring the Global Natural Products Social Molecular Networking (GNPS) platform to build a molecular network. Benzylisoquinoline alkaloids were annotated in the fractions coded SGA, SGC, and SGD collected during elution step. Aporphine alkaloids, <i>O</i>-glycosylated flavonoids, and dihydrochalcones in SGO were acquired with the change of mobile phase from lower aqueous to upper organic. Benzylisoquinolinic and aporphine alkaloids as well as glycosylated flavonoids were annotated in the most bioactive fractions suggesting this group of compounds as responsible for antiviral activity.https://www.mdpi.com/1420-3049/27/2/399centrifugal partition chromatographyinfluenza virusmass spectrometryoff-line LC-MS/MSSiparunaceaesolvent system |
| spellingShingle | Carla Monteiro Leal Suzana Guimarães Leitão Leonardo Luiz Oliveira de Mello Isabel de Castro Rangel Carlos Vinicius Azevedo da Silva Milene Dias Miranda Amanda Resende Tucci Camilla Blanco de Assis Carolina de Queiroz Sacramento Natalia Fintelman-Rodrigues Hector Henrique Ferreira Koolen Boniek Gontijo Vaz Rosineide Costa Simas Gilda Guimarães Leitão Bioassay-Guided Fractionation of <i>Siparuna glycycarpa</i> <i>n</i>-Butanol Extract with Inhibitory Activity against Influenza A(H1N1)pdm09 Virus by Centrifugal Partition Chromatography (CPC) Molecules centrifugal partition chromatography influenza virus mass spectrometry off-line LC-MS/MS Siparunaceae solvent system |
| title | Bioassay-Guided Fractionation of <i>Siparuna glycycarpa</i> <i>n</i>-Butanol Extract with Inhibitory Activity against Influenza A(H1N1)pdm09 Virus by Centrifugal Partition Chromatography (CPC) |
| title_full | Bioassay-Guided Fractionation of <i>Siparuna glycycarpa</i> <i>n</i>-Butanol Extract with Inhibitory Activity against Influenza A(H1N1)pdm09 Virus by Centrifugal Partition Chromatography (CPC) |
| title_fullStr | Bioassay-Guided Fractionation of <i>Siparuna glycycarpa</i> <i>n</i>-Butanol Extract with Inhibitory Activity against Influenza A(H1N1)pdm09 Virus by Centrifugal Partition Chromatography (CPC) |
| title_full_unstemmed | Bioassay-Guided Fractionation of <i>Siparuna glycycarpa</i> <i>n</i>-Butanol Extract with Inhibitory Activity against Influenza A(H1N1)pdm09 Virus by Centrifugal Partition Chromatography (CPC) |
| title_short | Bioassay-Guided Fractionation of <i>Siparuna glycycarpa</i> <i>n</i>-Butanol Extract with Inhibitory Activity against Influenza A(H1N1)pdm09 Virus by Centrifugal Partition Chromatography (CPC) |
| title_sort | bioassay guided fractionation of i siparuna glycycarpa i i n i butanol extract with inhibitory activity against influenza a h1n1 pdm09 virus by centrifugal partition chromatography cpc |
| topic | centrifugal partition chromatography influenza virus mass spectrometry off-line LC-MS/MS Siparunaceae solvent system |
| url | https://www.mdpi.com/1420-3049/27/2/399 |
| work_keys_str_mv | AT carlamonteiroleal bioassayguidedfractionationofisiparunaglycycarpaiinibutanolextractwithinhibitoryactivityagainstinfluenzaah1n1pdm09virusbycentrifugalpartitionchromatographycpc AT suzanaguimaraesleitao bioassayguidedfractionationofisiparunaglycycarpaiinibutanolextractwithinhibitoryactivityagainstinfluenzaah1n1pdm09virusbycentrifugalpartitionchromatographycpc AT leonardoluizoliveirademello bioassayguidedfractionationofisiparunaglycycarpaiinibutanolextractwithinhibitoryactivityagainstinfluenzaah1n1pdm09virusbycentrifugalpartitionchromatographycpc AT isabeldecastrorangel bioassayguidedfractionationofisiparunaglycycarpaiinibutanolextractwithinhibitoryactivityagainstinfluenzaah1n1pdm09virusbycentrifugalpartitionchromatographycpc AT carlosviniciusazevedodasilva bioassayguidedfractionationofisiparunaglycycarpaiinibutanolextractwithinhibitoryactivityagainstinfluenzaah1n1pdm09virusbycentrifugalpartitionchromatographycpc AT milenediasmiranda bioassayguidedfractionationofisiparunaglycycarpaiinibutanolextractwithinhibitoryactivityagainstinfluenzaah1n1pdm09virusbycentrifugalpartitionchromatographycpc AT amandaresendetucci bioassayguidedfractionationofisiparunaglycycarpaiinibutanolextractwithinhibitoryactivityagainstinfluenzaah1n1pdm09virusbycentrifugalpartitionchromatographycpc AT camillablancodeassis bioassayguidedfractionationofisiparunaglycycarpaiinibutanolextractwithinhibitoryactivityagainstinfluenzaah1n1pdm09virusbycentrifugalpartitionchromatographycpc AT carolinadequeirozsacramento bioassayguidedfractionationofisiparunaglycycarpaiinibutanolextractwithinhibitoryactivityagainstinfluenzaah1n1pdm09virusbycentrifugalpartitionchromatographycpc AT nataliafintelmanrodrigues bioassayguidedfractionationofisiparunaglycycarpaiinibutanolextractwithinhibitoryactivityagainstinfluenzaah1n1pdm09virusbycentrifugalpartitionchromatographycpc AT hectorhenriqueferreirakoolen bioassayguidedfractionationofisiparunaglycycarpaiinibutanolextractwithinhibitoryactivityagainstinfluenzaah1n1pdm09virusbycentrifugalpartitionchromatographycpc AT boniekgontijovaz bioassayguidedfractionationofisiparunaglycycarpaiinibutanolextractwithinhibitoryactivityagainstinfluenzaah1n1pdm09virusbycentrifugalpartitionchromatographycpc AT rosineidecostasimas bioassayguidedfractionationofisiparunaglycycarpaiinibutanolextractwithinhibitoryactivityagainstinfluenzaah1n1pdm09virusbycentrifugalpartitionchromatographycpc AT gildaguimaraesleitao bioassayguidedfractionationofisiparunaglycycarpaiinibutanolextractwithinhibitoryactivityagainstinfluenzaah1n1pdm09virusbycentrifugalpartitionchromatographycpc |