title: (+)- and (-)-petromyroxols: antipodal tetrahydrofurandiols from larval sea lamprey (Petromyzon marinus L.) that elicit enantioselective olfactory responses.
abstract: (+)- and (-)-petromyroxol [(+)-1 and (-)-1, respectively], two novel tetrahydrofuran (THF)-diol fatty acid enantiomers, were isolated from water conditioned with larval sea lamprey. We herein describe their isolation and subsequent resolution using chiral chromatography. The absolute configuration of each enantiomer was determined by a combination of Mosher ester analysis and comparison with related natural and synthetic products. Electro-olfactogram (EOG) assays indicated that (+)-petromyroxol (1) possesses potent olfactory activity for sea lamprey.
authors.affiliation: Department of Fisheries and Wildlife, Michigan State University , Room 13 Natural Resources Building, 480 Wilson Road, East Lansing, Michigan 48824, United States.
authors.forename: Ke
authors.initials: K
authors.lastname: Li
authors.forename: Mar
authors.initials: M
authors.lastname: Huertas
authors.forename: Cory
authors.initials: C
authors.lastname: Brant
authors.forename: Yu-Wen
authors.initials: YW
authors.lastname: Chung-Davidson
authors.forename: Ugo
authors.initials: U
authors.lastname: Bussy
authors.forename: Thomas R
authors.initials: TR
authors.lastname: Hoye
authors.forename: Weiming
authors.initials: W
authors.lastname: Li
mesh_terms: D000818:Animals; D004952:Esters; D005227:Fatty Acids / Q000737:chemistry* / Q000302:isolation & purification; D005663:Furans / Q000737:chemistry* / Q000302:isolation & purification; D007814:Larva / Q000737:chemistry*; D015394:Molecular Structure; D048428:Petromyzon; D013237:Stereoisomerism
chemical_list: D004952:Esters; D005227:Fatty Acids; D005663:Furans; C000600270:petromyroxol