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

Chem Biodivers. 2024 Feb 25:e202301860. doi: 10.1002/cbdv.202301860. Online ahead of print.ABSTRACTThe 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 (2a-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 2a and 2b is S, while that of 2c 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 2a, 2b, and 2c were identified as (1S,4R,1'S,4'R)-, (1S,4R,1'S,4'S)-, and (1R,4R,1'S,4'S)-murgantiol, respectively.PMID:38403856 | DOI:10.1002/cbdv.202301860

Source: Chemistry and Biodiversity - February 25, 2024 Category: Biochemistry Authors: Jo ão P A Souza Dougas J Melo Antonioni A C Moliterno Leonardo Figueiredo Paulo H G Zarbin Source Type: research