Galloylquinic acid derivatives from Byrsonima fagifolia leaf extract and potential antifungal activity
Autor(a) principal: | |
---|---|
Data de Publicação: | 2022 |
Outros Autores: | , , , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Institucional da UNESP |
Texto Completo: | http://dx.doi.org/10.1016/j.jep.2022.115534 http://hdl.handle.net/11449/241372 |
Resumo: | Ethnopharmacological relevance: Byrsonima fagifolia Niedenzu (Malpighiaceae) and other Byrsonima species are popularly employed in Brazilian traditional medicine in the form of preparations as cicatrizing, anti-inflammatory, and antimicrobial. Aim of the study: To characterize the phytochemical profile of the hydromethanolic extract obtained from B. fagifolia leaves (BF extract) and to evaluate the toxicity and the antifungal activity. Materials and methods: The compounds from BF extract were isolated by HPLC and the structures were elucidated based on extensive analyses of 1D and 2D NMR spectra (HMQC, HMBC and COSY) data. The antifungal effect was determined by the broth microdilution method and the toxicity was evaluated on erythrocytes from sheep's blood and Galleria mellonella larvae. Results: Phytochemical investigation of the BF extract led to the isolation and characterization of pyrogallol, n-butyl gallate, 3,4-di-O-galloylquinic acid, 3,5-di-O-galloylquinic acid, 3,4,5-tri-O-galloylquinic acid, and 1,3,4,5-tetra-O-galloylquinic acid. The BF extract showed high content of galloylquinic acid derivatives reaching more than twenty-times the quercetin derivatives content, according to the quantification by HPLC. These galloylquinic acid derivatives, obtained during this study, and quercetin derivatives, previously isolated, were submitted to the antifungal assays. The BF extract inhibited yeast growth mainly against Cryptococcus spp., at concentrations of 1–16 μg/mL, comparable to isolated compounds galloylquinic acid derivatives. However, the quercetin derivatives as well as quinic acid, gallic acid, and methyl gallate showed lower antifungal effect compared with galloylquinic derivatives. In addition, the BF extract had no hemolytic effect and no toxicity on G. mellonella. Conclusion: The phytochemical analysis revealed that galloylquinic acid derivatives are the major compounds in the leaves of B. fagifolia and they are associated to anti-cryptococcal activity and presented reduced toxicity. |
id |
UNSP_8387d64f5c0ebeccd13936ef454a0b47 |
---|---|
oai_identifier_str |
oai:repositorio.unesp.br:11449/241372 |
network_acronym_str |
UNSP |
network_name_str |
Repositório Institucional da UNESP |
repository_id_str |
2946 |
spelling |
Galloylquinic acid derivatives from Byrsonima fagifolia leaf extract and potential antifungal activityAntifungalCryptococcosisCryptococcusGallotanninsGalloylquinic acidsMalpighiaceaeMuriciQuercetin derivativesEthnopharmacological relevance: Byrsonima fagifolia Niedenzu (Malpighiaceae) and other Byrsonima species are popularly employed in Brazilian traditional medicine in the form of preparations as cicatrizing, anti-inflammatory, and antimicrobial. Aim of the study: To characterize the phytochemical profile of the hydromethanolic extract obtained from B. fagifolia leaves (BF extract) and to evaluate the toxicity and the antifungal activity. Materials and methods: The compounds from BF extract were isolated by HPLC and the structures were elucidated based on extensive analyses of 1D and 2D NMR spectra (HMQC, HMBC and COSY) data. The antifungal effect was determined by the broth microdilution method and the toxicity was evaluated on erythrocytes from sheep's blood and Galleria mellonella larvae. Results: Phytochemical investigation of the BF extract led to the isolation and characterization of pyrogallol, n-butyl gallate, 3,4-di-O-galloylquinic acid, 3,5-di-O-galloylquinic acid, 3,4,5-tri-O-galloylquinic acid, and 1,3,4,5-tetra-O-galloylquinic acid. The BF extract showed high content of galloylquinic acid derivatives reaching more than twenty-times the quercetin derivatives content, according to the quantification by HPLC. These galloylquinic acid derivatives, obtained during this study, and quercetin derivatives, previously isolated, were submitted to the antifungal assays. The BF extract inhibited yeast growth mainly against Cryptococcus spp., at concentrations of 1–16 μg/mL, comparable to isolated compounds galloylquinic acid derivatives. However, the quercetin derivatives as well as quinic acid, gallic acid, and methyl gallate showed lower antifungal effect compared with galloylquinic derivatives. In addition, the BF extract had no hemolytic effect and no toxicity on G. mellonella. Conclusion: The phytochemical analysis revealed that galloylquinic acid derivatives are the major compounds in the leaves of B. fagifolia and they are associated to anti-cryptococcal activity and presented reduced toxicity.Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)School of Arts Sciences and Humanities University of São Paulo, São Paulo/SPLaboratory of Chemistry and Biomass and Biofuels Embrapa Agroenergy Brazilian Agricultural Research Corporation, Brasília/DFDepartment of Botany Institute of Biosciences University of São Paulo, São Paulo/SPDepartment of Microbiology Institute of Biomedical Sciences University of São Paulo, São Paulo/SPInstitute of Biosciences São Paulo State University Coastal Campus of São Vicente/SPInstitute of Biosciences São Paulo State University Coastal Campus of São Vicente/SPFAPESP: 2009/52237-9FAPESP: 2020/16554-9FAPESP: 2021/01279-5CNPq: 405556/2018-7Universidade de São Paulo (USP)Empresa Brasileira de Pesquisa Agropecuária (EMBRAPA)Universidade Estadual Paulista (UNESP)Sannomiya, MiriamRodrigues, Clenilson MartinsOliveira, Giovanna Castro AraújoCarvalho, Juliana Cajado Souzada Costa, Letícia SerafimSpadari, Cristina de CastroFerreira, Marcelo José PenaVilegas, Wagner [UNESP]Ishida, Kelly2023-03-01T20:59:04Z2023-03-01T20:59:04Z2022-10-28info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://dx.doi.org/10.1016/j.jep.2022.115534Journal of Ethnopharmacology, v. 297.1872-75730378-8741http://hdl.handle.net/11449/24137210.1016/j.jep.2022.1155342-s2.0-85134539914Scopusreponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengJournal of Ethnopharmacologyinfo:eu-repo/semantics/openAccess2023-03-01T20:59:04Zoai:repositorio.unesp.br:11449/241372Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462023-03-01T20:59:04Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false |
dc.title.none.fl_str_mv |
Galloylquinic acid derivatives from Byrsonima fagifolia leaf extract and potential antifungal activity |
title |
Galloylquinic acid derivatives from Byrsonima fagifolia leaf extract and potential antifungal activity |
spellingShingle |
Galloylquinic acid derivatives from Byrsonima fagifolia leaf extract and potential antifungal activity Sannomiya, Miriam Antifungal Cryptococcosis Cryptococcus Gallotannins Galloylquinic acids Malpighiaceae Murici Quercetin derivatives |
title_short |
Galloylquinic acid derivatives from Byrsonima fagifolia leaf extract and potential antifungal activity |
title_full |
Galloylquinic acid derivatives from Byrsonima fagifolia leaf extract and potential antifungal activity |
title_fullStr |
Galloylquinic acid derivatives from Byrsonima fagifolia leaf extract and potential antifungal activity |
title_full_unstemmed |
Galloylquinic acid derivatives from Byrsonima fagifolia leaf extract and potential antifungal activity |
title_sort |
Galloylquinic acid derivatives from Byrsonima fagifolia leaf extract and potential antifungal activity |
author |
Sannomiya, Miriam |
author_facet |
Sannomiya, Miriam Rodrigues, Clenilson Martins Oliveira, Giovanna Castro Araújo Carvalho, Juliana Cajado Souza da Costa, Letícia Serafim Spadari, Cristina de Castro Ferreira, Marcelo José Pena Vilegas, Wagner [UNESP] Ishida, Kelly |
author_role |
author |
author2 |
Rodrigues, Clenilson Martins Oliveira, Giovanna Castro Araújo Carvalho, Juliana Cajado Souza da Costa, Letícia Serafim Spadari, Cristina de Castro Ferreira, Marcelo José Pena Vilegas, Wagner [UNESP] Ishida, Kelly |
author2_role |
author author author author author author author author |
dc.contributor.none.fl_str_mv |
Universidade de São Paulo (USP) Empresa Brasileira de Pesquisa Agropecuária (EMBRAPA) Universidade Estadual Paulista (UNESP) |
dc.contributor.author.fl_str_mv |
Sannomiya, Miriam Rodrigues, Clenilson Martins Oliveira, Giovanna Castro Araújo Carvalho, Juliana Cajado Souza da Costa, Letícia Serafim Spadari, Cristina de Castro Ferreira, Marcelo José Pena Vilegas, Wagner [UNESP] Ishida, Kelly |
dc.subject.por.fl_str_mv |
Antifungal Cryptococcosis Cryptococcus Gallotannins Galloylquinic acids Malpighiaceae Murici Quercetin derivatives |
topic |
Antifungal Cryptococcosis Cryptococcus Gallotannins Galloylquinic acids Malpighiaceae Murici Quercetin derivatives |
description |
Ethnopharmacological relevance: Byrsonima fagifolia Niedenzu (Malpighiaceae) and other Byrsonima species are popularly employed in Brazilian traditional medicine in the form of preparations as cicatrizing, anti-inflammatory, and antimicrobial. Aim of the study: To characterize the phytochemical profile of the hydromethanolic extract obtained from B. fagifolia leaves (BF extract) and to evaluate the toxicity and the antifungal activity. Materials and methods: The compounds from BF extract were isolated by HPLC and the structures were elucidated based on extensive analyses of 1D and 2D NMR spectra (HMQC, HMBC and COSY) data. The antifungal effect was determined by the broth microdilution method and the toxicity was evaluated on erythrocytes from sheep's blood and Galleria mellonella larvae. Results: Phytochemical investigation of the BF extract led to the isolation and characterization of pyrogallol, n-butyl gallate, 3,4-di-O-galloylquinic acid, 3,5-di-O-galloylquinic acid, 3,4,5-tri-O-galloylquinic acid, and 1,3,4,5-tetra-O-galloylquinic acid. The BF extract showed high content of galloylquinic acid derivatives reaching more than twenty-times the quercetin derivatives content, according to the quantification by HPLC. These galloylquinic acid derivatives, obtained during this study, and quercetin derivatives, previously isolated, were submitted to the antifungal assays. The BF extract inhibited yeast growth mainly against Cryptococcus spp., at concentrations of 1–16 μg/mL, comparable to isolated compounds galloylquinic acid derivatives. However, the quercetin derivatives as well as quinic acid, gallic acid, and methyl gallate showed lower antifungal effect compared with galloylquinic derivatives. In addition, the BF extract had no hemolytic effect and no toxicity on G. mellonella. Conclusion: The phytochemical analysis revealed that galloylquinic acid derivatives are the major compounds in the leaves of B. fagifolia and they are associated to anti-cryptococcal activity and presented reduced toxicity. |
publishDate |
2022 |
dc.date.none.fl_str_mv |
2022-10-28 2023-03-01T20:59:04Z 2023-03-01T20:59:04Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://dx.doi.org/10.1016/j.jep.2022.115534 Journal of Ethnopharmacology, v. 297. 1872-7573 0378-8741 http://hdl.handle.net/11449/241372 10.1016/j.jep.2022.115534 2-s2.0-85134539914 |
url |
http://dx.doi.org/10.1016/j.jep.2022.115534 http://hdl.handle.net/11449/241372 |
identifier_str_mv |
Journal of Ethnopharmacology, v. 297. 1872-7573 0378-8741 10.1016/j.jep.2022.115534 2-s2.0-85134539914 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Journal of Ethnopharmacology |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.source.none.fl_str_mv |
Scopus reponame:Repositório Institucional da UNESP instname:Universidade Estadual Paulista (UNESP) instacron:UNESP |
instname_str |
Universidade Estadual Paulista (UNESP) |
instacron_str |
UNESP |
institution |
UNESP |
reponame_str |
Repositório Institucional da UNESP |
collection |
Repositório Institucional da UNESP |
repository.name.fl_str_mv |
Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP) |
repository.mail.fl_str_mv |
|
_version_ |
1797789287903657984 |