Evaluation of antimicrobial, cytotoxic and chemopreventive activities of carvone and its derivatives

Bibliographic Details
Main Author: Moro, Isabela Jacob [UNESP]
Publication Date: 2017
Other Authors: Gondo, Gabrielle Demmany Gualberto Alexandre [UNESP], Pierri, Elaíse Gonçalves [UNESP], Pietro, Rosemeire Cristina Linharis Rodrigues [UNESP], Soares, Christiane Pienna [UNESP], de Sousa, Damião Pergentino, dos Santos, André Gonzaga [UNESP]
Format: Article
Language: eng
Source: Repositório Institucional da UNESP
Download full: http://dx.doi.org/10.1590/s2175-97902017000400076
http://hdl.handle.net/11449/179540
Summary: Considering the reported activity of carvone in the literature, this study aimed to evaluate the antimicrobial, cytotoxic and chemopreventive activities of (+)- and (-)-carvone, (+)- and (-)- hydroxydihydrocarvone and α,β-epoxycarvone. (+)-Hydroxydihydrocarvone (HC+), (-)-hydroxydihydrocarvone (HC-) and α,β- epoxycarvone (EP) were obtained by synthesis using (+)-carvone (C+) or (-)-carvone (C-) as precursors. The antifungal activity (MIC and MFC) were evaluated against Candida parapsilosis, C. tropicalis, C. krusei and C. albicans and the antibacterial activity (MIC and MBC) against Escherichia coli and Staphylococcus aureus. The cytotoxicity assays were performed with human cancer cell lines HepG- 2 and SiHa and the normal strain MRC-5 through sulphorrodamine B assay. Chemoprevention was evaluated through quinone reductase assay. Our results showed no cytotoxicity on tumor and normal cell lines and no induction of the quinone reductase enzyme. C- and HC- presented activity against E. coli. All compounds presented weak antifungal activity against C. tropicalis and C. parapsilosis. EP and C+ showed moderate activity against C. krusei. Results suggest the potential use of carvones and its derivatives as antifungal agents against Candida yeasts. The absence of cytotoxicity in cell lines indicates safety in the use of these compounds.
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spelling Evaluation of antimicrobial, cytotoxic and chemopreventive activities of carvone and its derivativesCarvone/antifungal activityCarvone/antimicrobial activityCarvone/chemopreventionCarvone/cytotoxicityConsidering the reported activity of carvone in the literature, this study aimed to evaluate the antimicrobial, cytotoxic and chemopreventive activities of (+)- and (-)-carvone, (+)- and (-)- hydroxydihydrocarvone and α,β-epoxycarvone. (+)-Hydroxydihydrocarvone (HC+), (-)-hydroxydihydrocarvone (HC-) and α,β- epoxycarvone (EP) were obtained by synthesis using (+)-carvone (C+) or (-)-carvone (C-) as precursors. The antifungal activity (MIC and MFC) were evaluated against Candida parapsilosis, C. tropicalis, C. krusei and C. albicans and the antibacterial activity (MIC and MBC) against Escherichia coli and Staphylococcus aureus. The cytotoxicity assays were performed with human cancer cell lines HepG- 2 and SiHa and the normal strain MRC-5 through sulphorrodamine B assay. Chemoprevention was evaluated through quinone reductase assay. Our results showed no cytotoxicity on tumor and normal cell lines and no induction of the quinone reductase enzyme. C- and HC- presented activity against E. coli. All compounds presented weak antifungal activity against C. tropicalis and C. parapsilosis. EP and C+ showed moderate activity against C. krusei. Results suggest the potential use of carvones and its derivatives as antifungal agents against Candida yeasts. The absence of cytotoxicity in cell lines indicates safety in the use of these compounds.Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)Laboratory of Pharmacognosy School of Pharmaceutical Sciences São Paulo State University (Unesp)Laboratory of Biotechnology School of Pharmaceutical Sciences São Paulo State University (Unesp)Laboratory of Cell Biology School of Pharmaceutical Sciences São Paulo State University (Unesp)Departament of Pharmaceutical Sciences Health Sciences Center UFPB – Univ Federal da ParaíbaLaboratory of Pharmacognosy School of Pharmaceutical Sciences São Paulo State University (Unesp)Laboratory of Biotechnology School of Pharmaceutical Sciences São Paulo State University (Unesp)Laboratory of Cell Biology School of Pharmaceutical Sciences São Paulo State University (Unesp)Universidade Estadual Paulista (Unesp)Universidade Federal da Paraíba (UFPB)Moro, Isabela Jacob [UNESP]Gondo, Gabrielle Demmany Gualberto Alexandre [UNESP]Pierri, Elaíse Gonçalves [UNESP]Pietro, Rosemeire Cristina Linharis Rodrigues [UNESP]Soares, Christiane Pienna [UNESP]de Sousa, Damião Pergentinodos Santos, André Gonzaga [UNESP]2018-12-11T17:35:35Z2018-12-11T17:35:35Z2017-01-01info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://dx.doi.org/10.1590/s2175-97902017000400076Brazilian Journal of Pharmaceutical Sciences, v. 53, n. 4, 2017.2175-97901984-8250http://hdl.handle.net/11449/17954010.1590/s2175-97902017000400076S1984-825020170004006022-s2.0-85041288751S1984-82502017000400602.pdf17680252903736690000-0003-1740-7360Scopusreponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengBrazilian Journal of Pharmaceutical Sciences0,2140,214info:eu-repo/semantics/openAccess2025-03-29T05:10:32Zoai:repositorio.unesp.br:11449/179540Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestrepositoriounesp@unesp.bropendoar:29462025-03-29T05:10:32Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false
dc.title.none.fl_str_mv Evaluation of antimicrobial, cytotoxic and chemopreventive activities of carvone and its derivatives
title Evaluation of antimicrobial, cytotoxic and chemopreventive activities of carvone and its derivatives
spellingShingle Evaluation of antimicrobial, cytotoxic and chemopreventive activities of carvone and its derivatives
Moro, Isabela Jacob [UNESP]
Carvone/antifungal activity
Carvone/antimicrobial activity
Carvone/chemoprevention
Carvone/cytotoxicity
title_short Evaluation of antimicrobial, cytotoxic and chemopreventive activities of carvone and its derivatives
title_full Evaluation of antimicrobial, cytotoxic and chemopreventive activities of carvone and its derivatives
title_fullStr Evaluation of antimicrobial, cytotoxic and chemopreventive activities of carvone and its derivatives
title_full_unstemmed Evaluation of antimicrobial, cytotoxic and chemopreventive activities of carvone and its derivatives
title_sort Evaluation of antimicrobial, cytotoxic and chemopreventive activities of carvone and its derivatives
author Moro, Isabela Jacob [UNESP]
author_facet Moro, Isabela Jacob [UNESP]
Gondo, Gabrielle Demmany Gualberto Alexandre [UNESP]
Pierri, Elaíse Gonçalves [UNESP]
Pietro, Rosemeire Cristina Linharis Rodrigues [UNESP]
Soares, Christiane Pienna [UNESP]
de Sousa, Damião Pergentino
dos Santos, André Gonzaga [UNESP]
author_role author
author2 Gondo, Gabrielle Demmany Gualberto Alexandre [UNESP]
Pierri, Elaíse Gonçalves [UNESP]
Pietro, Rosemeire Cristina Linharis Rodrigues [UNESP]
Soares, Christiane Pienna [UNESP]
de Sousa, Damião Pergentino
dos Santos, André Gonzaga [UNESP]
author2_role author
author
author
author
author
author
dc.contributor.none.fl_str_mv Universidade Estadual Paulista (Unesp)
Universidade Federal da Paraíba (UFPB)
dc.contributor.author.fl_str_mv Moro, Isabela Jacob [UNESP]
Gondo, Gabrielle Demmany Gualberto Alexandre [UNESP]
Pierri, Elaíse Gonçalves [UNESP]
Pietro, Rosemeire Cristina Linharis Rodrigues [UNESP]
Soares, Christiane Pienna [UNESP]
de Sousa, Damião Pergentino
dos Santos, André Gonzaga [UNESP]
dc.subject.por.fl_str_mv Carvone/antifungal activity
Carvone/antimicrobial activity
Carvone/chemoprevention
Carvone/cytotoxicity
topic Carvone/antifungal activity
Carvone/antimicrobial activity
Carvone/chemoprevention
Carvone/cytotoxicity
description Considering the reported activity of carvone in the literature, this study aimed to evaluate the antimicrobial, cytotoxic and chemopreventive activities of (+)- and (-)-carvone, (+)- and (-)- hydroxydihydrocarvone and α,β-epoxycarvone. (+)-Hydroxydihydrocarvone (HC+), (-)-hydroxydihydrocarvone (HC-) and α,β- epoxycarvone (EP) were obtained by synthesis using (+)-carvone (C+) or (-)-carvone (C-) as precursors. The antifungal activity (MIC and MFC) were evaluated against Candida parapsilosis, C. tropicalis, C. krusei and C. albicans and the antibacterial activity (MIC and MBC) against Escherichia coli and Staphylococcus aureus. The cytotoxicity assays were performed with human cancer cell lines HepG- 2 and SiHa and the normal strain MRC-5 through sulphorrodamine B assay. Chemoprevention was evaluated through quinone reductase assay. Our results showed no cytotoxicity on tumor and normal cell lines and no induction of the quinone reductase enzyme. C- and HC- presented activity against E. coli. All compounds presented weak antifungal activity against C. tropicalis and C. parapsilosis. EP and C+ showed moderate activity against C. krusei. Results suggest the potential use of carvones and its derivatives as antifungal agents against Candida yeasts. The absence of cytotoxicity in cell lines indicates safety in the use of these compounds.
publishDate 2017
dc.date.none.fl_str_mv 2017-01-01
2018-12-11T17:35:35Z
2018-12-11T17:35:35Z
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/10.1590/s2175-97902017000400076
Brazilian Journal of Pharmaceutical Sciences, v. 53, n. 4, 2017.
2175-9790
1984-8250
http://hdl.handle.net/11449/179540
10.1590/s2175-97902017000400076
S1984-82502017000400602
2-s2.0-85041288751
S1984-82502017000400602.pdf
1768025290373669
0000-0003-1740-7360
url http://dx.doi.org/10.1590/s2175-97902017000400076
http://hdl.handle.net/11449/179540
identifier_str_mv Brazilian Journal of Pharmaceutical Sciences, v. 53, n. 4, 2017.
2175-9790
1984-8250
10.1590/s2175-97902017000400076
S1984-82502017000400602
2-s2.0-85041288751
S1984-82502017000400602.pdf
1768025290373669
0000-0003-1740-7360
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Brazilian Journal of Pharmaceutical Sciences
0,214
0,214
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
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 repositoriounesp@unesp.br
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