Deciphering the Absolute Configuration of Murgantiol Isomers in the Pheromone Blend of the Rice Stink Bug, Mormidea v-luteum (Hemiptera, Pentatomidae).

Autor: Souza JPA; Department of Chemistry, Federal University of Parana, 81531-990, Curitiba-PR, Brazil., Melo DJ; Department of Chemistry, Federal University of Parana, 81531-990, Curitiba-PR, Brazil., Moliterno AAC; Department of Chemistry, Federal University of Parana, 81531-990, Curitiba-PR, Brazil., Figueiredo L; Department of Chemistry, Federal University of Parana, 81531-990, Curitiba-PR, Brazil., Zarbin PHG; Department of Chemistry, Federal University of Parana, 81531-990, Curitiba-PR, Brazil.
Jazyk: angličtina
Zdroj: Chemistry & biodiversity [Chem Biodivers] 2024 Apr; Vol. 21 (4), pp. e202301860. Date of Electronic Publication: 2024 Mar 05.
DOI: 10.1002/cbdv.202301860
Abstrakt: The males-produced pheromone blend of the Mormidea v-luteum (Hemiptera, Pentatomidae) consists in two isomers of zingiberenol (1) and three of murgantiol (2). While the absolute configuration of the zingiberenol isomers has been described, the configurations of the murgantiol isomers remained unexplored. So, our objective was to identify the absolute configuration of the murgantiol isomers (2 a-c) in the pheromone blend. To achieve this, we initially performed dehydration of the natural extract followed by enantiomeric resolution and, as a result, the three isomers was identified as (4R,1'S)-murgantiol. By leveraging the fixed cis and trans relationships among all pheromone components, we established the configuration at C-1 for isomers 2 a and 2 b is S, while that of 2 c is R. Finally, employing microchemical Sharples asymmetric dihydroxylation and epoxide ring closure, we determined the absolute configuration of the epoxide ring. Consequently, the natural isomers 2 a, 2 b, and 2 c were identified as (1S,4R,1'S,4'R)-, (1S,4R,1'S,4'S)-, and (1R,4R,1'S,4'S)-murgantiol, respectively.
(© 2024 Wiley‐VHCA AG, Zurich, Switzerland.)
Databáze: MEDLINE
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