title: Isolation of steroidal glycosides from the Caribbean sponge Pandaros acanthifolium.
abstract: Four new steroidal glycosides, acanthifoliosides G-J (1-4), were isolated as minor constituents from the Caribbean marine sponge Pandaros acanthifolium. These metabolites are characterized by a highly oxygenated D ring and the presence of a disaccharide rhamnose-glucose residue and a rhamnose at positions C-3 and C-15, respectively. Their structures were established on the basis of extensive interpretation of 1D and 2D NMR data and HRESIMS analyses. The absolute configurations of the glucose and rhamnose sugars were determined by preparing aldose o-tolylthiocarbamate derivatives and comparison to authentic standards by LC/HRESIMS. Acanthifolioside G (1) exhibited antioxidant and cytoprotective activities.
authors.affiliation: Department of Chemistry, Atlantic Veterinary College, University of Prince Edward Island, Charlottetown, PEI C1A 4P3, Canada.
authors.forename: Fabrice
authors.initials: F
authors.lastname: Berrué
authors.forename: Malcolm W B
authors.initials: MW
authors.lastname: McCulloch
authors.forename: Patricia
authors.initials: P
authors.lastname: Boland
authors.forename: Saskia
authors.initials: S
authors.lastname: Hart
authors.forename: Mary Kay
authors.initials: MK
authors.lastname: Harper
authors.forename: James
authors.initials: J
authors.lastname: Johnston
authors.forename: Russell
authors.initials: R
authors.lastname: Kerr
mesh_terms: D000818:Animals; D000975:Antioxidants / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001254:Astrocytoma / Q000188:drug therapy; D017691:Caribbean Region; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006801:Humans; D008297:Male; D008386:Marine Biology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011161:Porifera / Q000737:chemistry*; D013256:Steroids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
chemical_list: D000975:Antioxidants; D006027:Glycosides; D013256:Steroids; C578401:acanthifolioside G