Erylusamides: Novel Atypical Glycolipids from Erylus cf. deficiens
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Centro de Química e Bioquímica (CQB), Departamento de Química e Bioquímica, Faculdade de Ciências, Universidade de Lisboa, Campo Grande, Lisboa 1749-016, Portugal
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MARE-Centro de Ciências do Mar e do Ambiente, Faculdade de Ciências, Universidade de Lisboa, Campo Grande, Lisboa 1749-016, Portugal
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CNR-Istituto di Chimica Biomolecolare, Bio-Organic Chemistry Unit, via Campi Flegrei 34, Pozzuoli (NA) 80078, Italy
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Department of Biology and Centre for Geobiology, University of Bergen, P.O. Box 7803, Bergen N-5020, Norway
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Research & Innovation Accelerator, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, Campus de Caparica, Caparica 2829-516, Portugal
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BioISI, Instituto de Biociências e Ciências Integrativas, Faculdade de Ciências, Universidade de Lisboa, Campo Grande, Lisboa 1749-016, Portugal
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Authors to whom correspondence should be addressed.
Academic Editor: Danielle Skropeta
Mar. Drugs 2016, 14(10), 179; https://doi.org/10.3390/md14100179
Received: 11 July 2016 / Revised: 2 September 2016 / Accepted: 15 September 2016 / Published: 11 October 2016
(This article belongs to the Special Issue Deep-Sea Natural Products)
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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Keywords:
Erylus; indoleamine 2,3 dioxygenase; glycolipids; marine natural products; sponges; anti-cancer; erylusamides
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MDPI and ACS Style
Gaspar, H.; Cutignano, A.; Grauso, L.; Neng, N.; Cachatra, V.; Fontana, A.; Xavier, J.; Cerejo, M.; Vieira, H.; Santos, S. Erylusamides: Novel Atypical Glycolipids from Erylus cf. deficiens. Mar. Drugs 2016, 14, 179.
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