Erylusamides: Novel Atypical Glycolipids from Erylus cf. deficiens

Detalhes bibliográficos
Autor(a) principal: Gaspar, Helena
Data de Publicação: 2016
Outros Autores: Cutignano, Adele, Grauso, Laura, Neng, Nuno, Cachatra, Vasco, Fontana, Angelo, Xavier, Joana, Cerejo, Marta, Vieira, Helena, Santos, Susana
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10451/41250
Resumo: Among marine organisms, sponges are the richest sources of pharmacologically-active compounds. Stemming from a previous lead discovery program that gathered a comprehensive library of organic extracts of marine sponges from the off-shore region of Portugal, crude extracts of Erylus cf. deficiens collected in the Gorringe Bank (Atlantic Ocean) were tested in the innovative high throughput screening (HTS) assay for inhibitors of indoleamine 2,3-dioxygenase (IDO) and showed activity. Bioassay guided fractionation of the dichloromethane extract led to the isolation of four new glycolipids, named erylusamide A-D. The structures of the isolated compounds were established by 1D and 2D nuclear magnetic resonance (NMR) spectroscopy, high-resolution electrospray ionization mass spectrometry (HR-ESI-MS) and chemical derivatization. The metabolites shared a pentasaccharide moiety constituted by unusual highly acetylated ᴅ-glucose moieties as well as ᴅ-xylose and ᴅ-galactose. The aglycones were unprecedented long chain dihydroxyketo amides. Erylusamides A, B and D differ in the length of the hydrocarbon chain, while erylusamide C is a structural isomer of erylusamide B.
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spelling Erylusamides: Novel Atypical Glycolipids from Erylus cf. deficiensErylusindoleamine 2,3 dioxygenaseglycolipidsmarine natural productsspongesanti-cancererylusamidesAmong marine organisms, sponges are the richest sources of pharmacologically-active compounds. Stemming from a previous lead discovery program that gathered a comprehensive library of organic extracts of marine sponges from the off-shore region of Portugal, crude extracts of Erylus cf. deficiens collected in the Gorringe Bank (Atlantic Ocean) were tested in the innovative high throughput screening (HTS) assay for inhibitors of indoleamine 2,3-dioxygenase (IDO) and showed activity. Bioassay guided fractionation of the dichloromethane extract led to the isolation of four new glycolipids, named erylusamide A-D. The structures of the isolated compounds were established by 1D and 2D nuclear magnetic resonance (NMR) spectroscopy, high-resolution electrospray ionization mass spectrometry (HR-ESI-MS) and chemical derivatization. The metabolites shared a pentasaccharide moiety constituted by unusual highly acetylated ᴅ-glucose moieties as well as ᴅ-xylose and ᴅ-galactose. The aglycones were unprecedented long chain dihydroxyketo amides. Erylusamides A, B and D differ in the length of the hydrocarbon chain, while erylusamide C is a structural isomer of erylusamide B.MDPIRepositório da Universidade de LisboaGaspar, HelenaCutignano, AdeleGrauso, LauraNeng, NunoCachatra, VascoFontana, AngeloXavier, JoanaCerejo, MartaVieira, HelenaSantos, Susana2020-01-19T21:25:55Z20162016-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10451/41250eng1660-339710.3390/md14100179info: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:RCAAP2023-11-08T16:38:06Zoai:repositorio.ul.pt:10451/41250Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T21:53:16.286986Repositório 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 Erylusamides: Novel Atypical Glycolipids from Erylus cf. deficiens
title Erylusamides: Novel Atypical Glycolipids from Erylus cf. deficiens
spellingShingle Erylusamides: Novel Atypical Glycolipids from Erylus cf. deficiens
Gaspar, Helena
Erylus
indoleamine 2,3 dioxygenase
glycolipids
marine natural products
sponges
anti-cancer
erylusamides
title_short Erylusamides: Novel Atypical Glycolipids from Erylus cf. deficiens
title_full Erylusamides: Novel Atypical Glycolipids from Erylus cf. deficiens
title_fullStr Erylusamides: Novel Atypical Glycolipids from Erylus cf. deficiens
title_full_unstemmed Erylusamides: Novel Atypical Glycolipids from Erylus cf. deficiens
title_sort Erylusamides: Novel Atypical Glycolipids from Erylus cf. deficiens
author Gaspar, Helena
author_facet Gaspar, Helena
Cutignano, Adele
Grauso, Laura
Neng, Nuno
Cachatra, Vasco
Fontana, Angelo
Xavier, Joana
Cerejo, Marta
Vieira, Helena
Santos, Susana
author_role author
author2 Cutignano, Adele
Grauso, Laura
Neng, Nuno
Cachatra, Vasco
Fontana, Angelo
Xavier, Joana
Cerejo, Marta
Vieira, Helena
Santos, Susana
author2_role author
author
author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Repositório da Universidade de Lisboa
dc.contributor.author.fl_str_mv Gaspar, Helena
Cutignano, Adele
Grauso, Laura
Neng, Nuno
Cachatra, Vasco
Fontana, Angelo
Xavier, Joana
Cerejo, Marta
Vieira, Helena
Santos, Susana
dc.subject.por.fl_str_mv Erylus
indoleamine 2,3 dioxygenase
glycolipids
marine natural products
sponges
anti-cancer
erylusamides
topic Erylus
indoleamine 2,3 dioxygenase
glycolipids
marine natural products
sponges
anti-cancer
erylusamides
description Among marine organisms, sponges are the richest sources of pharmacologically-active compounds. Stemming from a previous lead discovery program that gathered a comprehensive library of organic extracts of marine sponges from the off-shore region of Portugal, crude extracts of Erylus cf. deficiens collected in the Gorringe Bank (Atlantic Ocean) were tested in the innovative high throughput screening (HTS) assay for inhibitors of indoleamine 2,3-dioxygenase (IDO) and showed activity. Bioassay guided fractionation of the dichloromethane extract led to the isolation of four new glycolipids, named erylusamide A-D. The structures of the isolated compounds were established by 1D and 2D nuclear magnetic resonance (NMR) spectroscopy, high-resolution electrospray ionization mass spectrometry (HR-ESI-MS) and chemical derivatization. The metabolites shared a pentasaccharide moiety constituted by unusual highly acetylated ᴅ-glucose moieties as well as ᴅ-xylose and ᴅ-galactose. The aglycones were unprecedented long chain dihydroxyketo amides. Erylusamides A, B and D differ in the length of the hydrocarbon chain, while erylusamide C is a structural isomer of erylusamide B.
publishDate 2016
dc.date.none.fl_str_mv 2016
2016-01-01T00:00:00Z
2020-01-19T21:25:55Z
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/10451/41250
url http://hdl.handle.net/10451/41250
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 1660-3397
10.3390/md14100179
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
instname_str 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)
repository.name.fl_str_mv Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
repository.mail.fl_str_mv
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