New antifeedant triterpene glycosides from the Caribbean sponge Erylus formosus.
Two groups of antifeedant triterpene glycosides were identified from the Caribbean sponge Erylus formosus. The structure of formoside B, a novel N-acetyl amino derivative of the known penasterol tetrasaccharide formoside, was elucidated using NMR and mass spectral data. Four triterpene hexasaccharides and two triterpene trisaccharides, characterized by a 31-carbon aglycone, proved difficult to isolate and therefore only the structure of their aglycone was determined. Gas chromatographic analysis of derivatized saccharides from these mixtures established the carbohydrate content of these compounds. All of the triterpene glycosides isolated contributed to the chemical defenses of this sponge, although with differing activities.
Kubanek
J
J
Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California-San Diego, La Jolla 92093-0204, USA.
Fenical
W
W
Pawlik
J R
JR
D000606:Amino Sugars / Q000032:analysis; D000818:Animals; D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000998:Antiviral Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001089:Arabinose / Q000032:analysis; D002176:Candida albicans / Q000187:drug effects; D017691:Caribbean Region; D002849:Chromatography, Gas; D002851:Chromatography, High Pressure Liquid; D003352:Corynebacterium / Q000187:drug effects; D025141:Drug Resistance, Fungal; D005247:Feeding Behavior / Q000187:drug effects; D005690:Galactose / Q000032:analysis; D005947:Glucose / Q000032:analysis; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D018259:Herpesvirus 1, Human / Q000187:drug effects; D055666:Lipopeptides; D013058:Mass Spectrometry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D009842:Oligopeptides / Q000494:pharmacology; D011161:Porifera / Q000737:chemistry*; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D014994:Xylose / Q000032:analysis
D000606:Amino Sugars; D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D000935:Antifungal Agents; D000998:Antiviral Agents; D006027:Glycosides; D055666:Lipopeptides; D009842:Oligopeptides; D014315:Triterpenes; C447242:formoside; C447243:formoside B; C004423:amphomycin; D014994:Xylose; D001089:Arabinose; D005947:Glucose; D005690:Galactose