title: Absolute configuration of chiral terpenes in marking pheromones of bumblebees and cuckoo bumblebees.
abstract: The absolute configurations of citronellol, 2,3-dihydrofarnesol, and 2,3-dihydrofarnesal in male marking pheromones of seven species of bumblebees and cuckoo bumblebees were determined by enantioselective gas chromatography on a capillary column coated with 60% heptakis(2,3-di-O-acetyl-6-O-TBDMS)-beta-cyclodextrin in polysiloxane PS 268. Pure (-)-S-enantiomers of all three terpenes were found in the labial glands of all investigated specimens of the following species: Bombus (Bombus) terrestris, B. (Bombus) lucorum, B. (Pyrobombus) pratorum, B. (Pyrobombus) pyrenaeus, B. (Pyrobombus) jonellus, B. (Pyrobombus) impatiens, and the cuckoo bumblebee B. (Ashtonipsithyrus) bohemicus. Within species, specimens were collected at different localities and in different years. Except for 2,3-dihydrofarnesol in B. terrestris, this is the first report on the absolute configuration of terpenes in marking pheromones of bumblebees.
authors.affiliation: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Prague, Czech Republic.
authors.forename: Anna
authors.initials: A
authors.lastname: Luxová
authors.forename: Klára
authors.initials: K
authors.lastname: Urbanová
authors.forename: Irena
authors.initials: I
authors.lastname: Valterová
authors.forename: Michael
authors.initials: M
authors.lastname: Terzo
authors.forename: Anna-Karin
authors.initials: AK
authors.lastname: Borg-Karlson
mesh_terms: D000080462:Acyclic Monoterpenes; D000818:Animals; D001516:Bees / Q000737:chemistry*; D002849:Chromatography, Gas; D005204:Farnesol / Q000031:analogs & derivatives* / Q000737:chemistry; D008297:Male; D039821:Monoterpenes / Q000737:chemistry; D010675:Pheromones / Q000737:chemistry* / Q000302:isolation & purification; D013045:Species Specificity; D013237:Stereoisomerism; D013729:Terpenes / Q000737:chemistry*
chemical_list: C470355:2,3-dihydrofarnesol; D000080462:Acyclic Monoterpenes; D039821:Monoterpenes; D010675:Pheromones; D013729:Terpenes; D005204:Farnesol; C007078:citronellol; C084519:farnesal