Stereochemistry of two pheromonal components of the bumblebee wax moth, Aphomia sociella

0522289 - ÚOCHB 2021 RIV GB eng J - Článek v odborném periodiku
Wallin, E. A. - Kalinová, Blanka - Kindl, Jiří - Hedenström, E. - Valterová, Irena
Stereochemistry of two pheromonal components of the bumblebee wax moth, Aphomia sociella.
Scientific Reports. Roč. 10, Feb 7 (2020), č. článku 2094. ISSN 2045-2322. E-ISSN 2045-2322
Grant CEP: GA MŠMT LD15102
Institucionální podpora: RVO:61388963
Klíčová slova: 6,10,14-trimethylpentadecan-2-one * 6,10,14-trimethylpentadecan-2-ol * stereoisomers * Pyralidae * Galleriinae * male sex pheromone * female aphrodisiac pheromone * electroantennography
Obor OECD: Analytical chemistry
Impakt faktor: 4.380, rok: 2020
Způsob publikování: Open access
https://www.nature.com/articles/s41598-020-59069-1

The bumblebee wax moth, Aphomia sociella, is a parasite of bumblebees. In this species, males produce sexual pheromone to attract females, while females produce an aphrodisiac pheromone that initiates male courtship. Both pheromones contain 6,10,14-trimethylpentadecan-2-one (TMPD-one) and the corresponding alcohol, 6,10,14-trimethylpentadecan-2-ol (TMPD-ol) in sex specific quantities. Male sex pheromone consists of 7 components with TMPD-one as a minor one and traces of TMPD-ol. In female aphrodisiac pheromone, TMPD-ol is the major component, while TMPD-one is present in traces. Here we report on the absolute configuration of TMPD-one in male sex pheromone and TMPD-ol in female aphrodisiac pheromone of A. sociella. The configuration was determined from GC/MS of prepared (S)-acetoxypropionyl esters of TMPD-ol. TMPD-one was first reduced to the alcohol that was then derivatized with (S)-acetoxypropionyl chloride. The GC/MS data of obtained diastereoisomers were compared with synthetic standards. The absolute configuration of TMPD-one in the male pheromone was (6R,10R). The configuration of TMPD-ol in the female pheromone was (2R,6R,10R). Electrophysiological experiments showed that TMPD-one and TMPD-ol are perceived by both sexes. The synthetic standards of naturally produced stereoisomers elicited higher responses than mixtures of all stereoisomers.
Trvalý link: http://hdl.handle.net/11104/0306804