New cyclotetrapeptides and a new diketopiperzine derivative from the marine sponge-associated fungus Neosartorya glabra KUFA 0702
Autor(a) principal: | |
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Data de Publicação: | 2016 |
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/10216/120530 |
Resumo: | Two new cyclotetrapeptides, sartoryglabramides A (5) and B (6), and a new analog of fellutanine A (8) were isolated, together with six known compounds including ergosta-4, 6, 8 (14), 22-tetraen-3-one, ergosterol 5, 8-endoperoxide, helvolic acid, aszonalenin (1), (3R)-3-(1H-indol-3-ylmethyl)-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione (2), takakiamide (3), (11aR)-2,3-dihydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H,11aH)-dione (4), and fellutanine A (7), from the ethyl acetate extract of the culture of the marine sponge-associated fungus Neosartorya glabra KUFA 0702. The structures of the new compounds were established based on extensive 1D and 2D spectral analysis. X-ray analysis was also used to confirm the relative configuration of the amino acid constituents of sartoryglabramide A (5), and the absolute stereochemistry of the amino acid constituents of sartoryglabramide A (5) and sartoryglabramides B (6) was determined by chiral HPLC analysis of their hydrolysates by co-injection with the D- and L- amino acids standards. Compounds 1-8 were tested for their antibacterial activity against Gram-positive (Escherichia coli ATCC 25922) and Gram-negative (Staphyllococus aureus ATCC 25923) bacteria, as well as for their antifungal activity against filamentous (Aspergillus fumigatus ATCC 46645), dermatophyte (Trichophyton rubrum ATCC FF5) and yeast (Candida albicans ATCC 10231). None of the tested compounds exhibited either antibacterial (MIC > 256 μg/mL) or antifungal activities (MIC > 512 μg/mL). © 2016 by the authors; licensee MDPI. |
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New cyclotetrapeptides and a new diketopiperzine derivative from the marine sponge-associated fungus Neosartorya glabra KUFA 0702(11ar)2,3 dihydro 1h pyrrolo[2,1 c][1,4]benzodiazepine 5,11(10h,11ah) dione3 (1h indol 3 ylmethyl) 3, 4 dihydro 1h 1,4 benzodiazepine 2,5 dioneacetic acid ethyl esteramino acidaszonalenincyclotetrapeptidediketopiperzineergosta 4,6,8(14),22 tetraen 3 oneergosterol 5,8 endoperoxidefellutanine Afungal extracthelvolic acidsartoryglabramide Asartoryglabramide Btakakiamideunclassified drugantibacterial activityantifungal activityArticleAspergillus fumigatusCandida albicanscontrolled studyEscherichia colifungal strainfungus culturehigh performance liquid chromatographyisolation proceduremarine speciesminimum inhibitory concentrationNeosartoryaNeosartorya glabranonhumannucleotide sequencespectroscopysponge (Porifera)Staphylococcus aureusstereochemistrystructure analysisTrichophyton rubrumX ray analysisTwo new cyclotetrapeptides, sartoryglabramides A (5) and B (6), and a new analog of fellutanine A (8) were isolated, together with six known compounds including ergosta-4, 6, 8 (14), 22-tetraen-3-one, ergosterol 5, 8-endoperoxide, helvolic acid, aszonalenin (1), (3R)-3-(1H-indol-3-ylmethyl)-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione (2), takakiamide (3), (11aR)-2,3-dihydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H,11aH)-dione (4), and fellutanine A (7), from the ethyl acetate extract of the culture of the marine sponge-associated fungus Neosartorya glabra KUFA 0702. The structures of the new compounds were established based on extensive 1D and 2D spectral analysis. X-ray analysis was also used to confirm the relative configuration of the amino acid constituents of sartoryglabramide A (5), and the absolute stereochemistry of the amino acid constituents of sartoryglabramide A (5) and sartoryglabramides B (6) was determined by chiral HPLC analysis of their hydrolysates by co-injection with the D- and L- amino acids standards. Compounds 1-8 were tested for their antibacterial activity against Gram-positive (Escherichia coli ATCC 25922) and Gram-negative (Staphyllococus aureus ATCC 25923) bacteria, as well as for their antifungal activity against filamentous (Aspergillus fumigatus ATCC 46645), dermatophyte (Trichophyton rubrum ATCC FF5) and yeast (Candida albicans ATCC 10231). None of the tested compounds exhibited either antibacterial (MIC > 256 μg/mL) or antifungal activities (MIC > 512 μg/mL). © 2016 by the authors; licensee MDPI.MDPI20162016-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/10216/120530eng1660339710.3390/md14070136Zin W.W.M.Buttachon S.Dethoup T.Fernandes C.Cravo S.Pinto M.M.M.Gales L.Pereira J.A.Silva A.M.S.Sekeroglu N.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:RCAAP2023-11-29T15:52:46Zoai:repositorio-aberto.up.pt:10216/120530Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T00:34:27.585814Repositório 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 |
New cyclotetrapeptides and a new diketopiperzine derivative from the marine sponge-associated fungus Neosartorya glabra KUFA 0702 |
title |
New cyclotetrapeptides and a new diketopiperzine derivative from the marine sponge-associated fungus Neosartorya glabra KUFA 0702 |
spellingShingle |
New cyclotetrapeptides and a new diketopiperzine derivative from the marine sponge-associated fungus Neosartorya glabra KUFA 0702 Zin W.W.M. (11ar)2,3 dihydro 1h pyrrolo[2,1 c][1,4]benzodiazepine 5,11(10h,11ah) dione 3 (1h indol 3 ylmethyl) 3, 4 dihydro 1h 1,4 benzodiazepine 2,5 dione acetic acid ethyl ester amino acid aszonalenin cyclotetrapeptide diketopiperzine ergosta 4,6,8(14),22 tetraen 3 one ergosterol 5,8 endoperoxide fellutanine A fungal extract helvolic acid sartoryglabramide A sartoryglabramide B takakiamide unclassified drug antibacterial activity antifungal activity Article Aspergillus fumigatus Candida albicans controlled study Escherichia coli fungal strain fungus culture high performance liquid chromatography isolation procedure marine species minimum inhibitory concentration Neosartorya Neosartorya glabra nonhuman nucleotide sequence spectroscopy sponge (Porifera) Staphylococcus aureus stereochemistry structure analysis Trichophyton rubrum X ray analysis |
title_short |
New cyclotetrapeptides and a new diketopiperzine derivative from the marine sponge-associated fungus Neosartorya glabra KUFA 0702 |
title_full |
New cyclotetrapeptides and a new diketopiperzine derivative from the marine sponge-associated fungus Neosartorya glabra KUFA 0702 |
title_fullStr |
New cyclotetrapeptides and a new diketopiperzine derivative from the marine sponge-associated fungus Neosartorya glabra KUFA 0702 |
title_full_unstemmed |
New cyclotetrapeptides and a new diketopiperzine derivative from the marine sponge-associated fungus Neosartorya glabra KUFA 0702 |
title_sort |
New cyclotetrapeptides and a new diketopiperzine derivative from the marine sponge-associated fungus Neosartorya glabra KUFA 0702 |
author |
Zin W.W.M. |
author_facet |
Zin W.W.M. Buttachon S. Dethoup T. Fernandes C. Cravo S. Pinto M.M.M. Gales L. Pereira J.A. Silva A.M.S. Sekeroglu N. Kijjoa A. |
author_role |
author |
author2 |
Buttachon S. Dethoup T. Fernandes C. Cravo S. Pinto M.M.M. Gales L. Pereira J.A. Silva A.M.S. Sekeroglu N. Kijjoa A. |
author2_role |
author author author author author author author author author author |
dc.contributor.author.fl_str_mv |
Zin W.W.M. Buttachon S. Dethoup T. Fernandes C. Cravo S. Pinto M.M.M. Gales L. Pereira J.A. Silva A.M.S. Sekeroglu N. Kijjoa A. |
dc.subject.por.fl_str_mv |
(11ar)2,3 dihydro 1h pyrrolo[2,1 c][1,4]benzodiazepine 5,11(10h,11ah) dione 3 (1h indol 3 ylmethyl) 3, 4 dihydro 1h 1,4 benzodiazepine 2,5 dione acetic acid ethyl ester amino acid aszonalenin cyclotetrapeptide diketopiperzine ergosta 4,6,8(14),22 tetraen 3 one ergosterol 5,8 endoperoxide fellutanine A fungal extract helvolic acid sartoryglabramide A sartoryglabramide B takakiamide unclassified drug antibacterial activity antifungal activity Article Aspergillus fumigatus Candida albicans controlled study Escherichia coli fungal strain fungus culture high performance liquid chromatography isolation procedure marine species minimum inhibitory concentration Neosartorya Neosartorya glabra nonhuman nucleotide sequence spectroscopy sponge (Porifera) Staphylococcus aureus stereochemistry structure analysis Trichophyton rubrum X ray analysis |
topic |
(11ar)2,3 dihydro 1h pyrrolo[2,1 c][1,4]benzodiazepine 5,11(10h,11ah) dione 3 (1h indol 3 ylmethyl) 3, 4 dihydro 1h 1,4 benzodiazepine 2,5 dione acetic acid ethyl ester amino acid aszonalenin cyclotetrapeptide diketopiperzine ergosta 4,6,8(14),22 tetraen 3 one ergosterol 5,8 endoperoxide fellutanine A fungal extract helvolic acid sartoryglabramide A sartoryglabramide B takakiamide unclassified drug antibacterial activity antifungal activity Article Aspergillus fumigatus Candida albicans controlled study Escherichia coli fungal strain fungus culture high performance liquid chromatography isolation procedure marine species minimum inhibitory concentration Neosartorya Neosartorya glabra nonhuman nucleotide sequence spectroscopy sponge (Porifera) Staphylococcus aureus stereochemistry structure analysis Trichophyton rubrum X ray analysis |
description |
Two new cyclotetrapeptides, sartoryglabramides A (5) and B (6), and a new analog of fellutanine A (8) were isolated, together with six known compounds including ergosta-4, 6, 8 (14), 22-tetraen-3-one, ergosterol 5, 8-endoperoxide, helvolic acid, aszonalenin (1), (3R)-3-(1H-indol-3-ylmethyl)-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione (2), takakiamide (3), (11aR)-2,3-dihydro-1H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11(10H,11aH)-dione (4), and fellutanine A (7), from the ethyl acetate extract of the culture of the marine sponge-associated fungus Neosartorya glabra KUFA 0702. The structures of the new compounds were established based on extensive 1D and 2D spectral analysis. X-ray analysis was also used to confirm the relative configuration of the amino acid constituents of sartoryglabramide A (5), and the absolute stereochemistry of the amino acid constituents of sartoryglabramide A (5) and sartoryglabramides B (6) was determined by chiral HPLC analysis of their hydrolysates by co-injection with the D- and L- amino acids standards. Compounds 1-8 were tested for their antibacterial activity against Gram-positive (Escherichia coli ATCC 25922) and Gram-negative (Staphyllococus aureus ATCC 25923) bacteria, as well as for their antifungal activity against filamentous (Aspergillus fumigatus ATCC 46645), dermatophyte (Trichophyton rubrum ATCC FF5) and yeast (Candida albicans ATCC 10231). None of the tested compounds exhibited either antibacterial (MIC > 256 μg/mL) or antifungal activities (MIC > 512 μg/mL). © 2016 by the authors; licensee MDPI. |
publishDate |
2016 |
dc.date.none.fl_str_mv |
2016 2016-01-01T00:00:00Z |
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/10216/120530 |
url |
https://hdl.handle.net/10216/120530 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
16603397 10.3390/md14070136 |
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) |
collection |
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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1799136253232283648 |