Absolute Configuration of the Spherical Mealybug Nipaecoccus viridis Sex Pheromone, γ-Necrodyl Isobutyrate: Chemoenzymatic Synthesis and Bioassays
| Autor: | Alex Protasov, Anat Levi-Zada, Daniela Fefer, Orna Ben-Aziz, Roy Kaspi, Sara Steiner |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
0106 biological sciences
Lavender Lavandula 010401 analytical chemistry General Chemistry Biology biology.organism_classification 01 natural sciences 0104 chemical sciences law.invention Horticulture law Sex pheromone Bioassay PEST analysis Mealybug General Agricultural and Biological Sciences Chirality (chemistry) Essential oil 010606 plant biology & botany |
| Zdroj: | Journal of Agricultural and Food Chemistry. 69:3026-3031 |
| ISSN: | 1520-5118 0021-8561 |
| DOI: | 10.1021/acs.jafc.0c07543 |
| Popis: | The spherical mealybug, Nipaecoccus viridis (Hemiptera: Pseudococcidae), is a major global pest causing feeding damage to leaves and fruits of citrus varieties, soybean, mango, pomegranate, and grapevines. Females of the mealybug release a sex pheromone that was identified recently as a mixture of γ-necrodyl isobutyrate and γ-necrodol. The identification required synthesis based on a natural source of trans-α-necrodol, of unknown chirality, obtained from essential oil of Spanish lavender, Lavandula luisieri. To determine the chirality of the sex pheromone, here, we synthesize the γ-necrodyl acetate enriched in (+)-(S)-enantiomer and separate the enantiomers using a lipase enzyme. We confirm that the natural components, both in the mealybug and in the lavender essential oil, consist of (-)-(R)-enantiomers. Bioassays conducted in the lab and field show that males are attracted to (-)-(R)-γ-necrodyl isobutyrate alone. |
| Databáze: | OpenAIRE |
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