A new chromene flavanone from Dalea boliviana Britton (Fabaceae) against Candida tropicalis biofilms

Autores
Lombardo, Andrea Laura; Ortega, María Gabriela; Cabrera, Jose Luis; Peralta, Mariana Andrea; Paraje, María Gabriela
Año de publicación
2020
Idioma
inglés
Tipo de recurso
documento de conferencia
Estado
versión publicada
Descripción
Currently, a wide variety of natural products are used for medicinal purposes, both to prevent and treat health problems, as well as in the research and development of new drugs. Previous studies on the species Dalea elegans Gillies ex Hook. et Arn, led to the isolation and elucidation of a prenylated flavonoid: 2’,4’-dihydroxy-5’-(1’’’,1’’’-dimethylallyl)-8 prenylpinocembrin (8PP). This compound exhibited antimicrobial activity against bacterial and fungal strains and was also reported with activity against Candida albicans mature biofilms. This species is the most frequently isolated from candidiasis, however, the incidence of fungal infections produced by C. non-albicans has increased in recent years in Latin America. Antifungal treatment can be difficult, often associated with the ability to form a biofilm, with high resistance to antifungal agents. This work aimed to perform the chemical study and evaluations of the antibiofilm activity of the species D. boliviana Britton (Fabaceae) as a potential source of new structures for the investigation of antifungal drugs. The chemical study of D. boliviana was performed by obtaining the hexane extract from its roots. This extract was purified by column chromatography and thin-laye chromatography. A solid, amorphous, and orange-colored compound (N3) was isolated and purified. N3 structure was determined by spectroscopic methodologies (NMR H1 and C13 in one and two dimensions) and UV-Vis spectrophotometry. N3 activity was evaluated in vitro on mature biofilms of C. tropicalis (NCPF 1111). The mature biofilm was treated with N3 dissolved in dimethyl sulfoxide (2% DMSO), at a final concentration of 25 µg/mL, with Amphotericin B (AmB) at 100 µg/mL, and with the combination of both. The results were reported as relative percentages of inhibition with respect to the control (mature biofilms without treatment). As a result of the analysis of the spectral data, the new structure named 5,2’-dihydroxy-6’’,6’’-dimethylchromeno-(7,8:2’’,3’’)-flavanone (N3), is postulated. It is a chromeno flavanone reported for the first time in the species D. boliviana. Compound N3 by itself reduced 54 ± 4% of the mature biofilm of C. tropicalis, while Amb reduced 86 ± 2%. For the combination of both compounds, the inhibition resulted in 98 ± 3%. In conclusion, this work presents a new compound obtained from the Argentine native flora showing activity against a highly resistant structure such as the mature biofilm of C. tropicalis. Furthermore, when the compound N3 was combined with AmB, the total eradication of the biofilm was obtained. Since Candida biofilms have marked resistance to antifungals for clinical use, it is important to obtain new active compounds against this form of growth, so it would merit the continuity of this research, especially in the search for synergistic combinations and studies on the mechanism of action.
Fil: Lombardo, Andrea Laura. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina
Fil: Ortega, María Gabriela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina
Fil: Cabrera, Jose Luis. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina
Fil: Peralta, Mariana Andrea. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina
Fil: Paraje, María Gabriela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina
LVI Annual Meeting Argentine Society for Biochemistry and Molecular Biology; XV Annual Meeting Argentinean Society for General Microbiology
Argentina
Sociedad Argentina de Investigación en Bioquímica y Biología Molecular
Sociedad Argentina de Microbiología General
Materia
Chromene Flavonone
Dalea boliviana
Biofilms
Candida tropicalis
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/150531

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network_name_str CONICET Digital (CONICET)
spelling A new chromene flavanone from Dalea boliviana Britton (Fabaceae) against Candida tropicalis biofilmsLombardo, Andrea LauraOrtega, María GabrielaCabrera, Jose LuisPeralta, Mariana AndreaParaje, María GabrielaChromene FlavononeDalea bolivianaBiofilmsCandida tropicalishttps://purl.org/becyt/ford/1.6https://purl.org/becyt/ford/1Currently, a wide variety of natural products are used for medicinal purposes, both to prevent and treat health problems, as well as in the research and development of new drugs. Previous studies on the species Dalea elegans Gillies ex Hook. et Arn, led to the isolation and elucidation of a prenylated flavonoid: 2’,4’-dihydroxy-5’-(1’’’,1’’’-dimethylallyl)-8 prenylpinocembrin (8PP). This compound exhibited antimicrobial activity against bacterial and fungal strains and was also reported with activity against Candida albicans mature biofilms. This species is the most frequently isolated from candidiasis, however, the incidence of fungal infections produced by C. non-albicans has increased in recent years in Latin America. Antifungal treatment can be difficult, often associated with the ability to form a biofilm, with high resistance to antifungal agents. This work aimed to perform the chemical study and evaluations of the antibiofilm activity of the species D. boliviana Britton (Fabaceae) as a potential source of new structures for the investigation of antifungal drugs. The chemical study of D. boliviana was performed by obtaining the hexane extract from its roots. This extract was purified by column chromatography and thin-laye chromatography. A solid, amorphous, and orange-colored compound (N3) was isolated and purified. N3 structure was determined by spectroscopic methodologies (NMR H1 and C13 in one and two dimensions) and UV-Vis spectrophotometry. N3 activity was evaluated in vitro on mature biofilms of C. tropicalis (NCPF 1111). The mature biofilm was treated with N3 dissolved in dimethyl sulfoxide (2% DMSO), at a final concentration of 25 µg/mL, with Amphotericin B (AmB) at 100 µg/mL, and with the combination of both. The results were reported as relative percentages of inhibition with respect to the control (mature biofilms without treatment). As a result of the analysis of the spectral data, the new structure named 5,2’-dihydroxy-6’’,6’’-dimethylchromeno-(7,8:2’’,3’’)-flavanone (N3), is postulated. It is a chromeno flavanone reported for the first time in the species D. boliviana. Compound N3 by itself reduced 54 ± 4% of the mature biofilm of C. tropicalis, while Amb reduced 86 ± 2%. For the combination of both compounds, the inhibition resulted in 98 ± 3%. In conclusion, this work presents a new compound obtained from the Argentine native flora showing activity against a highly resistant structure such as the mature biofilm of C. tropicalis. Furthermore, when the compound N3 was combined with AmB, the total eradication of the biofilm was obtained. Since Candida biofilms have marked resistance to antifungals for clinical use, it is important to obtain new active compounds against this form of growth, so it would merit the continuity of this research, especially in the search for synergistic combinations and studies on the mechanism of action.Fil: Lombardo, Andrea Laura. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; ArgentinaFil: Ortega, María Gabriela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; ArgentinaFil: Cabrera, Jose Luis. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; ArgentinaFil: Peralta, Mariana Andrea. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; ArgentinaFil: Paraje, María Gabriela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; ArgentinaLVI Annual Meeting Argentine Society for Biochemistry and Molecular Biology; XV Annual Meeting Argentinean Society for General MicrobiologyArgentinaSociedad Argentina de Investigación en Bioquímica y Biología MolecularSociedad Argentina de Microbiología GeneralTech Science Press2020info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/conferenceObjectReuniónJournalhttp://purl.org/coar/resource_type/c_5794info:ar-repo/semantics/documentoDeConferenciaapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/150531A new chromene flavanone from Dalea boliviana Britton (Fabaceae) against Candida tropicalis biofilms; LVI Annual Meeting Argentine Society for Biochemistry and Molecular Biology; XV Annual Meeting Argentinean Society for General Microbiology; Argentina; 2020; 1-1730327-9545CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://www.saib.org.ar/index.php?q=node/562Nacionalinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T10:11:53Zoai:ri.conicet.gov.ar:11336/150531instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-03 10:11:53.587CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv A new chromene flavanone from Dalea boliviana Britton (Fabaceae) against Candida tropicalis biofilms
title A new chromene flavanone from Dalea boliviana Britton (Fabaceae) against Candida tropicalis biofilms
spellingShingle A new chromene flavanone from Dalea boliviana Britton (Fabaceae) against Candida tropicalis biofilms
Lombardo, Andrea Laura
Chromene Flavonone
Dalea boliviana
Biofilms
Candida tropicalis
title_short A new chromene flavanone from Dalea boliviana Britton (Fabaceae) against Candida tropicalis biofilms
title_full A new chromene flavanone from Dalea boliviana Britton (Fabaceae) against Candida tropicalis biofilms
title_fullStr A new chromene flavanone from Dalea boliviana Britton (Fabaceae) against Candida tropicalis biofilms
title_full_unstemmed A new chromene flavanone from Dalea boliviana Britton (Fabaceae) against Candida tropicalis biofilms
title_sort A new chromene flavanone from Dalea boliviana Britton (Fabaceae) against Candida tropicalis biofilms
dc.creator.none.fl_str_mv Lombardo, Andrea Laura
Ortega, María Gabriela
Cabrera, Jose Luis
Peralta, Mariana Andrea
Paraje, María Gabriela
author Lombardo, Andrea Laura
author_facet Lombardo, Andrea Laura
Ortega, María Gabriela
Cabrera, Jose Luis
Peralta, Mariana Andrea
Paraje, María Gabriela
author_role author
author2 Ortega, María Gabriela
Cabrera, Jose Luis
Peralta, Mariana Andrea
Paraje, María Gabriela
author2_role author
author
author
author
dc.subject.none.fl_str_mv Chromene Flavonone
Dalea boliviana
Biofilms
Candida tropicalis
topic Chromene Flavonone
Dalea boliviana
Biofilms
Candida tropicalis
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.6
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Currently, a wide variety of natural products are used for medicinal purposes, both to prevent and treat health problems, as well as in the research and development of new drugs. Previous studies on the species Dalea elegans Gillies ex Hook. et Arn, led to the isolation and elucidation of a prenylated flavonoid: 2’,4’-dihydroxy-5’-(1’’’,1’’’-dimethylallyl)-8 prenylpinocembrin (8PP). This compound exhibited antimicrobial activity against bacterial and fungal strains and was also reported with activity against Candida albicans mature biofilms. This species is the most frequently isolated from candidiasis, however, the incidence of fungal infections produced by C. non-albicans has increased in recent years in Latin America. Antifungal treatment can be difficult, often associated with the ability to form a biofilm, with high resistance to antifungal agents. This work aimed to perform the chemical study and evaluations of the antibiofilm activity of the species D. boliviana Britton (Fabaceae) as a potential source of new structures for the investigation of antifungal drugs. The chemical study of D. boliviana was performed by obtaining the hexane extract from its roots. This extract was purified by column chromatography and thin-laye chromatography. A solid, amorphous, and orange-colored compound (N3) was isolated and purified. N3 structure was determined by spectroscopic methodologies (NMR H1 and C13 in one and two dimensions) and UV-Vis spectrophotometry. N3 activity was evaluated in vitro on mature biofilms of C. tropicalis (NCPF 1111). The mature biofilm was treated with N3 dissolved in dimethyl sulfoxide (2% DMSO), at a final concentration of 25 µg/mL, with Amphotericin B (AmB) at 100 µg/mL, and with the combination of both. The results were reported as relative percentages of inhibition with respect to the control (mature biofilms without treatment). As a result of the analysis of the spectral data, the new structure named 5,2’-dihydroxy-6’’,6’’-dimethylchromeno-(7,8:2’’,3’’)-flavanone (N3), is postulated. It is a chromeno flavanone reported for the first time in the species D. boliviana. Compound N3 by itself reduced 54 ± 4% of the mature biofilm of C. tropicalis, while Amb reduced 86 ± 2%. For the combination of both compounds, the inhibition resulted in 98 ± 3%. In conclusion, this work presents a new compound obtained from the Argentine native flora showing activity against a highly resistant structure such as the mature biofilm of C. tropicalis. Furthermore, when the compound N3 was combined with AmB, the total eradication of the biofilm was obtained. Since Candida biofilms have marked resistance to antifungals for clinical use, it is important to obtain new active compounds against this form of growth, so it would merit the continuity of this research, especially in the search for synergistic combinations and studies on the mechanism of action.
Fil: Lombardo, Andrea Laura. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina
Fil: Ortega, María Gabriela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina
Fil: Cabrera, Jose Luis. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina
Fil: Peralta, Mariana Andrea. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina
Fil: Paraje, María Gabriela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina
LVI Annual Meeting Argentine Society for Biochemistry and Molecular Biology; XV Annual Meeting Argentinean Society for General Microbiology
Argentina
Sociedad Argentina de Investigación en Bioquímica y Biología Molecular
Sociedad Argentina de Microbiología General
description Currently, a wide variety of natural products are used for medicinal purposes, both to prevent and treat health problems, as well as in the research and development of new drugs. Previous studies on the species Dalea elegans Gillies ex Hook. et Arn, led to the isolation and elucidation of a prenylated flavonoid: 2’,4’-dihydroxy-5’-(1’’’,1’’’-dimethylallyl)-8 prenylpinocembrin (8PP). This compound exhibited antimicrobial activity against bacterial and fungal strains and was also reported with activity against Candida albicans mature biofilms. This species is the most frequently isolated from candidiasis, however, the incidence of fungal infections produced by C. non-albicans has increased in recent years in Latin America. Antifungal treatment can be difficult, often associated with the ability to form a biofilm, with high resistance to antifungal agents. This work aimed to perform the chemical study and evaluations of the antibiofilm activity of the species D. boliviana Britton (Fabaceae) as a potential source of new structures for the investigation of antifungal drugs. The chemical study of D. boliviana was performed by obtaining the hexane extract from its roots. This extract was purified by column chromatography and thin-laye chromatography. A solid, amorphous, and orange-colored compound (N3) was isolated and purified. N3 structure was determined by spectroscopic methodologies (NMR H1 and C13 in one and two dimensions) and UV-Vis spectrophotometry. N3 activity was evaluated in vitro on mature biofilms of C. tropicalis (NCPF 1111). The mature biofilm was treated with N3 dissolved in dimethyl sulfoxide (2% DMSO), at a final concentration of 25 µg/mL, with Amphotericin B (AmB) at 100 µg/mL, and with the combination of both. The results were reported as relative percentages of inhibition with respect to the control (mature biofilms without treatment). As a result of the analysis of the spectral data, the new structure named 5,2’-dihydroxy-6’’,6’’-dimethylchromeno-(7,8:2’’,3’’)-flavanone (N3), is postulated. It is a chromeno flavanone reported for the first time in the species D. boliviana. Compound N3 by itself reduced 54 ± 4% of the mature biofilm of C. tropicalis, while Amb reduced 86 ± 2%. For the combination of both compounds, the inhibition resulted in 98 ± 3%. In conclusion, this work presents a new compound obtained from the Argentine native flora showing activity against a highly resistant structure such as the mature biofilm of C. tropicalis. Furthermore, when the compound N3 was combined with AmB, the total eradication of the biofilm was obtained. Since Candida biofilms have marked resistance to antifungals for clinical use, it is important to obtain new active compounds against this form of growth, so it would merit the continuity of this research, especially in the search for synergistic combinations and studies on the mechanism of action.
publishDate 2020
dc.date.none.fl_str_mv 2020
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dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/150531
A new chromene flavanone from Dalea boliviana Britton (Fabaceae) against Candida tropicalis biofilms; LVI Annual Meeting Argentine Society for Biochemistry and Molecular Biology; XV Annual Meeting Argentinean Society for General Microbiology; Argentina; 2020; 1-173
0327-9545
CONICET Digital
CONICET
url http://hdl.handle.net/11336/150531
identifier_str_mv A new chromene flavanone from Dalea boliviana Britton (Fabaceae) against Candida tropicalis biofilms; LVI Annual Meeting Argentine Society for Biochemistry and Molecular Biology; XV Annual Meeting Argentinean Society for General Microbiology; Argentina; 2020; 1-173
0327-9545
CONICET Digital
CONICET
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