Stereochemistry of two pheromonal components of the bumblebee wax moth, Aphomia sociella
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F20%3A00522289" target="_blank" >RIV/61388963:_____/20:00522289 - isvavai.cz</a>
Alternative codes found
RIV/60460709:41320/20:84431 RIV/60460709:41340/20:84431
Result on the web
<a href="https://www.nature.com/articles/s41598-020-59069-1" target="_blank" >https://www.nature.com/articles/s41598-020-59069-1</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1038/s41598-020-59069-1" target="_blank" >10.1038/s41598-020-59069-1</a>
Alternative languages
Result language
angličtina
Original language name
Stereochemistry of two pheromonal components of the bumblebee wax moth, Aphomia sociella
Original language description
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.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10406 - Analytical chemistry
Result continuities
Project
<a href="/en/project/LD15102" target="_blank" >LD15102: Bumblebee pollinators: Pheromones can help to manage and protect bumblebee colonies.</a><br>
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2020
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Scientific Reports
ISSN
2045-2322
e-ISSN
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Volume of the periodical
10
Issue of the periodical within the volume
Feb 7
Country of publishing house
GB - UNITED KINGDOM
Number of pages
7
Pages from-to
2094
UT code for WoS article
000562828300011
EID of the result in the Scopus database
2-s2.0-85079080717