New cyclotetrapeptides and a new diketopiperzine derivative from the marine sponge-associated fungus Neosartorya glabra KUFA 0702

Detalhes bibliográficos
Autor(a) principal: Zin W.W.M.
Data de Publicação: 2016
Outros Autores: 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.
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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spelling 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
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