1. Erylusamides: Novel Atypical Glycolipids from Erylus cf. deficiens.
- Author
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Gaspar H, Cutignano A, Grauso L, Neng N, Cachatra V, Fontana A, Xavier J, Cerejo M, Vieira H, and Santos S
- Subjects
- Animals, Atlantic Ocean, COS Cells drug effects, Chlorocebus aethiops, Glycolipids pharmacology, Porifera, Portugal, Structure-Activity Relationship, Glycolipids chemistry
- 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 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 ., Competing Interests: The authors declare no conflict of interest.
- Published
- 2016
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