Effect of the Stereoselectivity of para-Menthane-3,8-diol Isomers on Repulsion toward Aedes albopictus
| Autor: | Erwann Jeanneau, Estelle Métay, Marc Lemaire, Niryhasinandrianina Ramarosandratana, Mbolatiana T. Andrianjafy, Voahangy Ramanandraibe, Lorenzo G. Borrego |
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| Rok vydání: | 2021 |
| Předmět: | |
| Zdroj: | Journal of Agricultural and Food Chemistry. 69:11095-11109 |
| ISSN: | 1520-5118 0021-8561 |
| DOI: | 10.1021/acs.jafc.1c03897 |
| Popis: | Vector-borne diseases cause around 700,000 deaths every year. Insect repellents are one of the strategies to limit them. Para-menthane-3,8-diol (PMD), a natural compound, is one of the most promising alternatives to conventional synthetic repellents. This work describes a diastereodivergent method to synthesize each diastereoisomer of PMD from enantiopure citronellal and studies their repellence activity against Aedes albopictus. We found that cis-PMD is the kinetic control product of the cyclization of citronellal, while trans-PMD is the thermodynamic control product. X-ray diffraction analysis of crystals highlighted some differences in hydrogen-bond patterns between cis or trans isomers. The present paper demonstrates that (1R)-(+)-cis-PMD has the highest repellency index using a new evaluation system for 24 h. (1S)-(-)-cis-PMD has somewhat lower and (1S)-(+)-trans-PMD and (1R)-(-)-trans-PMD have a slight effect. Volunteer tests show that (1R)-(+)-cis-PMD is the most efficient. This effect could be ascribed to the interaction of PMD/insect odorant receptors and their physical properties, that is, the evaporation rate. |
| Databáze: | OpenAIRE |
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