Glucosylated suspensosides, water-soluble pheromone conjugates from the oral secretions of male Anastrepha suspensa.
A diastereomeric mixture of the glycosylated pheromones (6R)-(1a) and (6S)-beta-D-glucopyranosyl 2-(2,6-dimethyl-6-vinylcyclohex-1-enyl)acetate (1b), which we named respectively suspensoside A and suspensoside B, was isolated from the oral secretions of male Caribbean fruit flies, Anastrepha suspensa. The absolute stereochemical configurations were established using microsample NMR instrumentation, chiral gas chromatography, and chemical synthesis utilizing pure enantiomers of anastrephin, (3aS,4R,7aS)-(4a) or (3aR,4S,7aR)-4,7a-dimethyl-4-vinylhexahydrobenzofuran-2(3H)one (4b), as the aglycon precursor.
Walse
Spencer S
SS
United States Department of Agriculture, Agricultural Research Service, Center for Medical, Agricultural, and Veterinary Entomology 1700 S.W. 23rd Drive, Gainesville, Florida 32604, USA.
Lu
Fang
F
Teal
Peter E A
PE
D000818:Animals; D005960:Glucosides / Q000737:chemistry / Q000302:isolation & purification* / Q000378:metabolism*; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000378:metabolism*; D008297:Male; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010675:Pheromones / Q000737:chemistry / Q000302:isolation & purification* / Q000378:metabolism*; D012995:Solubility; D013237:Stereoisomerism; D033621:Tephritidae / Q000378:metabolism*; D014867:Water
D005960:Glucosides; D006027:Glycosides; D010675:Pheromones; C532937:suspensoside A; D014867:Water