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Stereochemistry of two pheromonal components of the bumblebee wax moth, Aphomia sociella
Mittuniversitetet, Fakulteten för naturvetenskap, teknik och medier, Institutionen för kemiteknik.
Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Research Group of Infochemicals, Prague, Czech Republic; Czech University of Life Sciences, Prague, Czech Republic.
Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Research Group of Infochemicals, Prague, Czech Republic; Czech University of Life Sciences, Prague, Czech Republic.
Mittuniversitetet, Fakulteten för naturvetenskap, teknik och medier, Institutionen för kemiteknik.ORCID-id: 0000-0002-5543-2041
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2020 (engelsk)Inngår i: Scientific Reports, ISSN 2045-2322, E-ISSN 2045-2322, Vol. 10, nr 1, artikkel-id 2094Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

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. 

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2020. Vol. 10, nr 1, artikkel-id 2094
HSV kategori
Identifikatorer
URN: urn:nbn:se:miun:diva-38422DOI: 10.1038/s41598-020-59069-1Scopus ID: 2-s2.0-85079080717OAI: oai:DiVA.org:miun-38422DiVA, id: diva2:1393476
Merknad

We are grateful to J. Titzenthalerová for her skillful assistance in electrophysiological experiments and to R. Hanus for his help with statistical evaluations of the EAG recordings. This work was financially supported by the Ministry of Education of the Czech Republic (grant No. LD15102). The research was done within the frames of the COST Action Super-B (FA1307). EW and EH are thankful for the funding from ERUF (European regional developmental fund), the region of Jämtland/Härjedalen and the region of Västernorrland.

Tilgjengelig fra: 2020-02-17 Laget: 2020-02-17 Sist oppdatert: 2020-02-17bibliografisk kontrollert

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