Bis-indolyl benzenoids, hydroxypyrrolidine derivatives and other constituents from cultures of the marine sponge-associated fungus aspergillus candidus KUFA0062
Autor(a) principal: | |
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Data de Publicação: | 2018 |
Outros Autores: | , , , , , , , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | https://hdl.handle.net/10216/120275 |
Resumo: | A previously unreported bis-indolyl benzenoid, candidusin D (2e) and a new hydroxypyrrolidine alkaloid, preussin C (5b) were isolated together with fourteen previously described compounds: palmitic acid, clionasterol, ergosterol 5,8-endoperoxides, chrysophanic acid (1a), emodin (1b), six bis-indolyl benzenoids including asterriquinol D dimethyl ether (2a), petromurin C (2b), kumbicin B (2c), kumbicin A (2d), 2”-oxoasterriquinol D methyl ether (3), kumbicin D (4), the hydroxypyrrolidine alkaloid preussin (5a), (3S, 6S)-3,6-dibenzylpiperazine-2,5-dione (6) and 4-(acetylamino) benzoic acid (7), from the cultures of the marine sponge-associated fungus Aspergillus candidus KUFA 0062. Compounds 1a, 2a–e, 3, 4, 5a–b, and 6 were tested for their antibacterial activity against Gram-positive and Gram-negative reference and multidrug-resistant strains isolated from the environment. Only 5a exhibited an inhibitory effect against S. aureus ATCC 29213 and E. faecalis ATCC29212 as well as both methicillin-resistant S. aureus (MRSA) and vancomycin-resistant enterococci (VRE) strains. Both 1a and 5a also reduced significant biofilm formation in E. coli ATCC 25922. Moreover, 2b and 5a revealed a synergistic effect with oxacillin against MRSA S. aureus 66/1 while 5a exhibited a strong synergistic effect with the antibiotic colistin against E. coli 1410/1. Compound 1a, 2a–e, 3, 4, 5a–b, and 6 were also tested, together with the crude extract, for cytotoxic effect against eight cancer cell lines: HepG2, HT29, HCT116, A549, A 375, MCF-7, U-251, and T98G. Except for 1a, 2a, 2d, 4, and 6, all the compounds showed cytotoxicity against all the cancer cell lines tested. © 2018 by the authors |
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Bis-indolyl benzenoids, hydroxypyrrolidine derivatives and other constituents from cultures of the marine sponge-associated fungus aspergillus candidus KUFA00622'' oxoasterriquinol D methyl ether3,6 dibenzylpiperazine 2,5 dione4 (acetylamino)benzoic acidantibiotic agentasterriquinol D dimethyl etherbenzene derivativebenzoic acidbis indolyl benzenoidcandidusin Dchrysophanic acidcolistindoxorubicinfungal extractkumbicin Akumbicin Bkumbicin Doxacillinpetromurin Cpreussinpreussin Cpyrrolidine derivativeunclassified drugvancomycinanisomycinantiinfective agentantineoplastic agentpreussinpyrrolidine derivativeterphenyl derivativeA-375 cell lineA-549 cell lineantibacterial activityantineoplastic activityArticleAspergillus candidusAspergillus candidus KUFA 0062biofilmcell viabilitycontrolled studydrug cytotoxicitydrug identificationdrug isolationdrug potentiationEnterococcus faecalisEscherichia colifungal strainfungus cultureHCT 116 cell lineHep-G2 cell lineHT-29 cell linehumanhuman cellIC50in vitro studyMCF-7 cell linemethicillin resistant Staphylococcus aureusminimum bactericidal concentrationminimum inhibitory concentrationnonhumanPseudomonas aeruginosaStaphylococcus aureusT98G cell lineU-251MG cell linevancomycin resistant Enterococcusanalogs and derivativesanimalantibiotic resistanceAspergillusbacteriumchemistrydrug effectisolation and purificationmicrobial sensitivity testmicrobiologysponge (Porifera)tumor cell lineAnimalsAnisomycinAnti-Bacterial AgentsAntineoplastic AgentsAspergillusBacteriaCell Line, TumorDrug Resistance, BacterialDrug SynergismHumansInhibitory Concentration 50Microbial Sensitivity TestsPoriferaPyrrolidinesTerphenyl CompoundsA previously unreported bis-indolyl benzenoid, candidusin D (2e) and a new hydroxypyrrolidine alkaloid, preussin C (5b) were isolated together with fourteen previously described compounds: palmitic acid, clionasterol, ergosterol 5,8-endoperoxides, chrysophanic acid (1a), emodin (1b), six bis-indolyl benzenoids including asterriquinol D dimethyl ether (2a), petromurin C (2b), kumbicin B (2c), kumbicin A (2d), 2”-oxoasterriquinol D methyl ether (3), kumbicin D (4), the hydroxypyrrolidine alkaloid preussin (5a), (3S, 6S)-3,6-dibenzylpiperazine-2,5-dione (6) and 4-(acetylamino) benzoic acid (7), from the cultures of the marine sponge-associated fungus Aspergillus candidus KUFA 0062. Compounds 1a, 2a–e, 3, 4, 5a–b, and 6 were tested for their antibacterial activity against Gram-positive and Gram-negative reference and multidrug-resistant strains isolated from the environment. Only 5a exhibited an inhibitory effect against S. aureus ATCC 29213 and E. faecalis ATCC29212 as well as both methicillin-resistant S. aureus (MRSA) and vancomycin-resistant enterococci (VRE) strains. Both 1a and 5a also reduced significant biofilm formation in E. coli ATCC 25922. Moreover, 2b and 5a revealed a synergistic effect with oxacillin against MRSA S. aureus 66/1 while 5a exhibited a strong synergistic effect with the antibiotic colistin against E. coli 1410/1. Compound 1a, 2a–e, 3, 4, 5a–b, and 6 were also tested, together with the crude extract, for cytotoxic effect against eight cancer cell lines: HepG2, HT29, HCT116, A549, A 375, MCF-7, U-251, and T98G. Except for 1a, 2a, 2d, 4, and 6, all the compounds showed cytotoxicity against all the cancer cell lines tested. © 2018 by the authorsMDPI20182018-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/10216/120275eng1660339710.3390/md16040119Buttachon S.Ramos A.A.Inácio Â.Dethoup T.Gales L.Lee M.Costa P.M.Silva A.M.S.Sekeroglu N.Rocha E.Pinto M.M.M.Pereira J.A.Kijjoa A.info: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:RCAAP2023-11-29T13:26:30Zoai:repositorio-aberto.up.pt:10216/120275Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T23:40:32.370711Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse |
dc.title.none.fl_str_mv |
Bis-indolyl benzenoids, hydroxypyrrolidine derivatives and other constituents from cultures of the marine sponge-associated fungus aspergillus candidus KUFA0062 |
title |
Bis-indolyl benzenoids, hydroxypyrrolidine derivatives and other constituents from cultures of the marine sponge-associated fungus aspergillus candidus KUFA0062 |
spellingShingle |
Bis-indolyl benzenoids, hydroxypyrrolidine derivatives and other constituents from cultures of the marine sponge-associated fungus aspergillus candidus KUFA0062 Buttachon S. 2'' oxoasterriquinol D methyl ether 3,6 dibenzylpiperazine 2,5 dione 4 (acetylamino)benzoic acid antibiotic agent asterriquinol D dimethyl ether benzene derivative benzoic acid bis indolyl benzenoid candidusin D chrysophanic acid colistin doxorubicin fungal extract kumbicin A kumbicin B kumbicin D oxacillin petromurin C preussin preussin C pyrrolidine derivative unclassified drug vancomycin anisomycin antiinfective agent antineoplastic agent preussin pyrrolidine derivative terphenyl derivative A-375 cell line A-549 cell line antibacterial activity antineoplastic activity Article Aspergillus candidus Aspergillus candidus KUFA 0062 biofilm cell viability controlled study drug cytotoxicity drug identification drug isolation drug potentiation Enterococcus faecalis Escherichia coli fungal strain fungus culture HCT 116 cell line Hep-G2 cell line HT-29 cell line human human cell IC50 in vitro study MCF-7 cell line methicillin resistant Staphylococcus aureus minimum bactericidal concentration minimum inhibitory concentration nonhuman Pseudomonas aeruginosa Staphylococcus aureus T98G cell line U-251MG cell line vancomycin resistant Enterococcus analogs and derivatives animal antibiotic resistance Aspergillus bacterium chemistry drug effect isolation and purification microbial sensitivity test microbiology sponge (Porifera) tumor cell line Animals Anisomycin Anti-Bacterial Agents Antineoplastic Agents Aspergillus Bacteria Cell Line, Tumor Drug Resistance, Bacterial Drug Synergism Humans Inhibitory Concentration 50 Microbial Sensitivity Tests Porifera Pyrrolidines Terphenyl Compounds |
title_short |
Bis-indolyl benzenoids, hydroxypyrrolidine derivatives and other constituents from cultures of the marine sponge-associated fungus aspergillus candidus KUFA0062 |
title_full |
Bis-indolyl benzenoids, hydroxypyrrolidine derivatives and other constituents from cultures of the marine sponge-associated fungus aspergillus candidus KUFA0062 |
title_fullStr |
Bis-indolyl benzenoids, hydroxypyrrolidine derivatives and other constituents from cultures of the marine sponge-associated fungus aspergillus candidus KUFA0062 |
title_full_unstemmed |
Bis-indolyl benzenoids, hydroxypyrrolidine derivatives and other constituents from cultures of the marine sponge-associated fungus aspergillus candidus KUFA0062 |
title_sort |
Bis-indolyl benzenoids, hydroxypyrrolidine derivatives and other constituents from cultures of the marine sponge-associated fungus aspergillus candidus KUFA0062 |
author |
Buttachon S. |
author_facet |
Buttachon S. Ramos A.A. Inácio Â. Dethoup T. Gales L. Lee M. Costa P.M. Silva A.M.S. Sekeroglu N. Rocha E. Pinto M.M.M. Pereira J.A. Kijjoa A. |
author_role |
author |
author2 |
Ramos A.A. Inácio Â. Dethoup T. Gales L. Lee M. Costa P.M. Silva A.M.S. Sekeroglu N. Rocha E. Pinto M.M.M. Pereira J.A. Kijjoa A. |
author2_role |
author author author author author author author author author author author author |
dc.contributor.author.fl_str_mv |
Buttachon S. Ramos A.A. Inácio Â. Dethoup T. Gales L. Lee M. Costa P.M. Silva A.M.S. Sekeroglu N. Rocha E. Pinto M.M.M. Pereira J.A. Kijjoa A. |
dc.subject.por.fl_str_mv |
2'' oxoasterriquinol D methyl ether 3,6 dibenzylpiperazine 2,5 dione 4 (acetylamino)benzoic acid antibiotic agent asterriquinol D dimethyl ether benzene derivative benzoic acid bis indolyl benzenoid candidusin D chrysophanic acid colistin doxorubicin fungal extract kumbicin A kumbicin B kumbicin D oxacillin petromurin C preussin preussin C pyrrolidine derivative unclassified drug vancomycin anisomycin antiinfective agent antineoplastic agent preussin pyrrolidine derivative terphenyl derivative A-375 cell line A-549 cell line antibacterial activity antineoplastic activity Article Aspergillus candidus Aspergillus candidus KUFA 0062 biofilm cell viability controlled study drug cytotoxicity drug identification drug isolation drug potentiation Enterococcus faecalis Escherichia coli fungal strain fungus culture HCT 116 cell line Hep-G2 cell line HT-29 cell line human human cell IC50 in vitro study MCF-7 cell line methicillin resistant Staphylococcus aureus minimum bactericidal concentration minimum inhibitory concentration nonhuman Pseudomonas aeruginosa Staphylococcus aureus T98G cell line U-251MG cell line vancomycin resistant Enterococcus analogs and derivatives animal antibiotic resistance Aspergillus bacterium chemistry drug effect isolation and purification microbial sensitivity test microbiology sponge (Porifera) tumor cell line Animals Anisomycin Anti-Bacterial Agents Antineoplastic Agents Aspergillus Bacteria Cell Line, Tumor Drug Resistance, Bacterial Drug Synergism Humans Inhibitory Concentration 50 Microbial Sensitivity Tests Porifera Pyrrolidines Terphenyl Compounds |
topic |
2'' oxoasterriquinol D methyl ether 3,6 dibenzylpiperazine 2,5 dione 4 (acetylamino)benzoic acid antibiotic agent asterriquinol D dimethyl ether benzene derivative benzoic acid bis indolyl benzenoid candidusin D chrysophanic acid colistin doxorubicin fungal extract kumbicin A kumbicin B kumbicin D oxacillin petromurin C preussin preussin C pyrrolidine derivative unclassified drug vancomycin anisomycin antiinfective agent antineoplastic agent preussin pyrrolidine derivative terphenyl derivative A-375 cell line A-549 cell line antibacterial activity antineoplastic activity Article Aspergillus candidus Aspergillus candidus KUFA 0062 biofilm cell viability controlled study drug cytotoxicity drug identification drug isolation drug potentiation Enterococcus faecalis Escherichia coli fungal strain fungus culture HCT 116 cell line Hep-G2 cell line HT-29 cell line human human cell IC50 in vitro study MCF-7 cell line methicillin resistant Staphylococcus aureus minimum bactericidal concentration minimum inhibitory concentration nonhuman Pseudomonas aeruginosa Staphylococcus aureus T98G cell line U-251MG cell line vancomycin resistant Enterococcus analogs and derivatives animal antibiotic resistance Aspergillus bacterium chemistry drug effect isolation and purification microbial sensitivity test microbiology sponge (Porifera) tumor cell line Animals Anisomycin Anti-Bacterial Agents Antineoplastic Agents Aspergillus Bacteria Cell Line, Tumor Drug Resistance, Bacterial Drug Synergism Humans Inhibitory Concentration 50 Microbial Sensitivity Tests Porifera Pyrrolidines Terphenyl Compounds |
description |
A previously unreported bis-indolyl benzenoid, candidusin D (2e) and a new hydroxypyrrolidine alkaloid, preussin C (5b) were isolated together with fourteen previously described compounds: palmitic acid, clionasterol, ergosterol 5,8-endoperoxides, chrysophanic acid (1a), emodin (1b), six bis-indolyl benzenoids including asterriquinol D dimethyl ether (2a), petromurin C (2b), kumbicin B (2c), kumbicin A (2d), 2”-oxoasterriquinol D methyl ether (3), kumbicin D (4), the hydroxypyrrolidine alkaloid preussin (5a), (3S, 6S)-3,6-dibenzylpiperazine-2,5-dione (6) and 4-(acetylamino) benzoic acid (7), from the cultures of the marine sponge-associated fungus Aspergillus candidus KUFA 0062. Compounds 1a, 2a–e, 3, 4, 5a–b, and 6 were tested for their antibacterial activity against Gram-positive and Gram-negative reference and multidrug-resistant strains isolated from the environment. Only 5a exhibited an inhibitory effect against S. aureus ATCC 29213 and E. faecalis ATCC29212 as well as both methicillin-resistant S. aureus (MRSA) and vancomycin-resistant enterococci (VRE) strains. Both 1a and 5a also reduced significant biofilm formation in E. coli ATCC 25922. Moreover, 2b and 5a revealed a synergistic effect with oxacillin against MRSA S. aureus 66/1 while 5a exhibited a strong synergistic effect with the antibiotic colistin against E. coli 1410/1. Compound 1a, 2a–e, 3, 4, 5a–b, and 6 were also tested, together with the crude extract, for cytotoxic effect against eight cancer cell lines: HepG2, HT29, HCT116, A549, A 375, MCF-7, U-251, and T98G. Except for 1a, 2a, 2d, 4, and 6, all the compounds showed cytotoxicity against all the cancer cell lines tested. © 2018 by the authors |
publishDate |
2018 |
dc.date.none.fl_str_mv |
2018 2018-01-01T00:00:00Z |
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 |
https://hdl.handle.net/10216/120275 |
url |
https://hdl.handle.net/10216/120275 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
16603397 10.3390/md16040119 |
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 |
MDPI |
publisher.none.fl_str_mv |
MDPI |
dc.source.none.fl_str_mv |
reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação instacron:RCAAP |
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Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
instacron_str |
RCAAP |
institution |
RCAAP |
reponame_str |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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