title: Erylusamides: Novel Atypical Glycolipids from Erylus cf. deficiens.
abstract: 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 ofErylus cf.deficienscollected 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 erylusamideA-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. ErylusamidesA,BandDdiffer in the length of the hydrocarbon chain, while erylusamideCis a structural isomer of erylusamideB.
authors.affiliation: Centro de Química e Bioquímica (CQB), Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade de Lisboa, Campo Grande, Lisboa 1749-016, Portugal. hmgaspar@ciencias.ulisboa.pt.|MARE-Centro de Ciências do Mar e do Ambiente, Faculdade de Ciências, Universidade de Lisboa, Campo Grande, Lisboa 1749-016, Portugal. hmgaspar@ciencias.ulisboa.pt.
authors.forename: Helena
authors.initials: H
authors.lastname: Gaspar
authors.affiliation: CNR-Istituto di Chimica Biomolecolare, Bio-Organic Chemistry Unit, via Campi Flegrei 34, Pozzuoli (NA) 80078, Italy. acutignano@icb.cnr.it.
authors.forename: Adele
authors.initials: A
authors.lastname: Cutignano
authors.affiliation: CNR-Istituto di Chimica Biomolecolare, Bio-Organic Chemistry Unit, via Campi Flegrei 34, Pozzuoli (NA) 80078, Italy. laura.grauso@icb.cnr.it.
authors.forename: Laura
authors.initials: L
authors.lastname: Grauso
authors.affiliation: Centro de Química e Bioquímica (CQB), Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade de Lisboa, Campo Grande, Lisboa 1749-016, Portugal. ndneng@ciencias.ulisboa.pt.
authors.forename: Nuno
authors.initials: N
authors.lastname: Neng
authors.affiliation: Centro de Química e Bioquímica (CQB), Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade de Lisboa, Campo Grande, Lisboa 1749-016, Portugal. vasco_cachatra@hotmail.com.
authors.forename: Vasco
authors.initials: V
authors.lastname: Cachatra
authors.affiliation: CNR-Istituto di Chimica Biomolecolare, Bio-Organic Chemistry Unit, via Campi Flegrei 34, Pozzuoli (NA) 80078, Italy. afontana@icb.cnr.it.
authors.forename: Angelo
authors.initials: A
authors.lastname: Fontana
authors.affiliation: Department of Biology and Centre for Geobiology, University of Bergen, P.O. Box 7803, Bergen N-5020, Norway. joana.xavier@bio.uib.no.
authors.forename: Joana
authors.initials: J
authors.lastname: Xavier
authors.affiliation: Research & Innovation Accelerator, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, Campus de Caparica, Caparica 2829-516, Portugal. m.cerejo@fct.unl.pt.
authors.forename: Marta
authors.initials: M
authors.lastname: Cerejo
authors.affiliation: BioISI, Instituto de Biociências e Ciências Integrativas, Faculdade de Ciências, Universidade de Lisboa, Campo Grande, Lisboa 1749-016, Portugal. hmvieira@ciencias.ulisboa.pt.
authors.forename: Helena
authors.initials: H
authors.lastname: Vieira
authors.affiliation: Centro de Química e Bioquímica (CQB), Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade de Lisboa, Campo Grande, Lisboa 1749-016, Portugal. smsantos@ciencias.ulisboa.pt.
authors.forename: Susana
authors.initials: S
authors.lastname: Santos
mesh_terms: D000818:Animals; D001267:Atlantic Ocean; D019556:COS Cells / Q000187:drug effects; D002522:Chlorocebus aethiops; D006017:Glycolipids / Q000737:chemistry* / Q000494:pharmacology; D011161:Porifera; D011174:Portugal; D013329:Structure-Activity Relationship
chemical_list: D006017:Glycolipids
keywords: Erylus; anti-cancer; erylusamides; glycolipids; indoleamine 2,3 dioxygenase; marine natural products; sponges