Antimicrobial and demelanizing activity of Ganoderma lucidum extract, p-hydroxybenzoic and cinnamic acids and their synthetic acetylated glucuronide methyl esters

Detalhes bibliográficos
Autor(a) principal: Heleno, Sandrina A.
Data de Publicação: 2013
Outros Autores: Ferreira, Isabel C. F. R., Esteves, Ana Paula, Ćirić, Ana, Glamočlija, Jasmina, Martins, Anabela, Soković, Marina, Queiroz, Maria João R. P.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/1822/63900
Resumo: Mushroom extracts or isolated compounds may be useful in the search of new potent antimicrobial agents. Herein, it is described the synthesis of protected (acetylated) glucuronide derivatives of p-hydroxybenzoic and cinnamic acids, two compounds identified in the medicinal mushroom Ganoderma lucidum. Their antimicrobial and demelanizing activities were evaluated and compared to the parent acids and G. lucidum extract. p-Hydroxybenzoic and cinnamic acids, as also their protected glucuronide derivatives revealed high antimicrobial (antibacterial and antifungal) activity, even better than the one showed by commercial standards. Despite the variation in the order of parent acids and the protected glucuronide derivatives, their antimicrobial activity was always higher than the one revealed by the extract. Nevertheless, the extract was the only one with demelanizing activity against Aspergillus niger. The acetylated glucuronide derivatives could be deprotected to obtain glucuronide metabolites, which circulate in the human organism as products of the metabolism of the parent compounds.
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spelling Antimicrobial and demelanizing activity of Ganoderma lucidum extract, p-hydroxybenzoic and cinnamic acids and their synthetic acetylated glucuronide methyl estersAcetylationAnti-Infective AgentsBenzoatesCinnamatesEstersGlucuronidesMagnetic Resonance SpectroscopyMelaninsPlant ExtractsReishiSpectrometry, Mass, Electrospray IonizationGanoderma lucidump-Hydroxybenzoic acidCinnamic acidAcetylated glucuronidesChemical synthesisAntimicrobial activityScience & TechnologyMushroom extracts or isolated compounds may be useful in the search of new potent antimicrobial agents. Herein, it is described the synthesis of protected (acetylated) glucuronide derivatives of p-hydroxybenzoic and cinnamic acids, two compounds identified in the medicinal mushroom Ganoderma lucidum. Their antimicrobial and demelanizing activities were evaluated and compared to the parent acids and G. lucidum extract. p-Hydroxybenzoic and cinnamic acids, as also their protected glucuronide derivatives revealed high antimicrobial (antibacterial and antifungal) activity, even better than the one showed by commercial standards. Despite the variation in the order of parent acids and the protected glucuronide derivatives, their antimicrobial activity was always higher than the one revealed by the extract. Nevertheless, the extract was the only one with demelanizing activity against Aspergillus niger. The acetylated glucuronide derivatives could be deprotected to obtain glucuronide metabolites, which circulate in the human organism as products of the metabolism of the parent compounds.The authors are grateful to Fundacao para a Ciencia e a Tecnologia (FCT, Portugal) for financial support to the Portuguese NMR network and to FCT and FEDER-COMPETE/QREN/EU for the financial support through the research project PTDC/AGR-ALI/110062/2009 and the research centres (PEst-C/QUI/UI0686/2011 and PEst-OE/AGR/UI0690/2011). S.A. Heleno (BD/70304/2010) also thanks FCT, POPH-QREN and FSE. The authors also thank to Serbian Ministry of Education and Science (Grant Number 173032) for financial support.Pergamon-Elsevier Science LtdUniversidade do MinhoHeleno, Sandrina A.Ferreira, Isabel C. F. R.Esteves, Ana PaulaĆirić, AnaGlamočlija, JasminaMartins, AnabelaSoković, MarinaQueiroz, Maria João R. P.2013-082013-08-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/1822/63900eng0278-69151873-635110.1016/j.fct.2013.04.02523607932https://www.sciencedirect.com/science/article/pii/S0278691513002688info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2023-07-21T12:01:41ZPortal AgregadorONG
dc.title.none.fl_str_mv Antimicrobial and demelanizing activity of Ganoderma lucidum extract, p-hydroxybenzoic and cinnamic acids and their synthetic acetylated glucuronide methyl esters
title Antimicrobial and demelanizing activity of Ganoderma lucidum extract, p-hydroxybenzoic and cinnamic acids and their synthetic acetylated glucuronide methyl esters
spellingShingle Antimicrobial and demelanizing activity of Ganoderma lucidum extract, p-hydroxybenzoic and cinnamic acids and their synthetic acetylated glucuronide methyl esters
Heleno, Sandrina A.
Acetylation
Anti-Infective Agents
Benzoates
Cinnamates
Esters
Glucuronides
Magnetic Resonance Spectroscopy
Melanins
Plant Extracts
Reishi
Spectrometry, Mass, Electrospray Ionization
Ganoderma lucidum
p-Hydroxybenzoic acid
Cinnamic acid
Acetylated glucuronides
Chemical synthesis
Antimicrobial activity
Science & Technology
title_short Antimicrobial and demelanizing activity of Ganoderma lucidum extract, p-hydroxybenzoic and cinnamic acids and their synthetic acetylated glucuronide methyl esters
title_full Antimicrobial and demelanizing activity of Ganoderma lucidum extract, p-hydroxybenzoic and cinnamic acids and their synthetic acetylated glucuronide methyl esters
title_fullStr Antimicrobial and demelanizing activity of Ganoderma lucidum extract, p-hydroxybenzoic and cinnamic acids and their synthetic acetylated glucuronide methyl esters
title_full_unstemmed Antimicrobial and demelanizing activity of Ganoderma lucidum extract, p-hydroxybenzoic and cinnamic acids and their synthetic acetylated glucuronide methyl esters
title_sort Antimicrobial and demelanizing activity of Ganoderma lucidum extract, p-hydroxybenzoic and cinnamic acids and their synthetic acetylated glucuronide methyl esters
author Heleno, Sandrina A.
author_facet Heleno, Sandrina A.
Ferreira, Isabel C. F. R.
Esteves, Ana Paula
Ćirić, Ana
Glamočlija, Jasmina
Martins, Anabela
Soković, Marina
Queiroz, Maria João R. P.
author_role author
author2 Ferreira, Isabel C. F. R.
Esteves, Ana Paula
Ćirić, Ana
Glamočlija, Jasmina
Martins, Anabela
Soković, Marina
Queiroz, Maria João R. P.
author2_role author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Universidade do Minho
dc.contributor.author.fl_str_mv Heleno, Sandrina A.
Ferreira, Isabel C. F. R.
Esteves, Ana Paula
Ćirić, Ana
Glamočlija, Jasmina
Martins, Anabela
Soković, Marina
Queiroz, Maria João R. P.
dc.subject.por.fl_str_mv Acetylation
Anti-Infective Agents
Benzoates
Cinnamates
Esters
Glucuronides
Magnetic Resonance Spectroscopy
Melanins
Plant Extracts
Reishi
Spectrometry, Mass, Electrospray Ionization
Ganoderma lucidum
p-Hydroxybenzoic acid
Cinnamic acid
Acetylated glucuronides
Chemical synthesis
Antimicrobial activity
Science & Technology
topic Acetylation
Anti-Infective Agents
Benzoates
Cinnamates
Esters
Glucuronides
Magnetic Resonance Spectroscopy
Melanins
Plant Extracts
Reishi
Spectrometry, Mass, Electrospray Ionization
Ganoderma lucidum
p-Hydroxybenzoic acid
Cinnamic acid
Acetylated glucuronides
Chemical synthesis
Antimicrobial activity
Science & Technology
description Mushroom extracts or isolated compounds may be useful in the search of new potent antimicrobial agents. Herein, it is described the synthesis of protected (acetylated) glucuronide derivatives of p-hydroxybenzoic and cinnamic acids, two compounds identified in the medicinal mushroom Ganoderma lucidum. Their antimicrobial and demelanizing activities were evaluated and compared to the parent acids and G. lucidum extract. p-Hydroxybenzoic and cinnamic acids, as also their protected glucuronide derivatives revealed high antimicrobial (antibacterial and antifungal) activity, even better than the one showed by commercial standards. Despite the variation in the order of parent acids and the protected glucuronide derivatives, their antimicrobial activity was always higher than the one revealed by the extract. Nevertheless, the extract was the only one with demelanizing activity against Aspergillus niger. The acetylated glucuronide derivatives could be deprotected to obtain glucuronide metabolites, which circulate in the human organism as products of the metabolism of the parent compounds.
publishDate 2013
dc.date.none.fl_str_mv 2013-08
2013-08-01T00:00:00Z
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://hdl.handle.net/1822/63900
url http://hdl.handle.net/1822/63900
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 0278-6915
1873-6351
10.1016/j.fct.2013.04.025
23607932
https://www.sciencedirect.com/science/article/pii/S0278691513002688
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.publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
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