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Absolute Configuration of the Spherical Mealybug Nipaecoccus viridis Sex Pheromone, γ-Necrodyl Isobutyrate: Chemoenzymatic Synthesis and Bioassays
Year:
2021
Authors :
Ben-Aziz, Orna
;
.
Fefer, Daniela
;
.
Kaspi, Roy
;
.
Protasov, Alex
;
.
Zada, Anat Levi
;
.
Volume :
10
Co-Authors:

Levi-Zada, A.,
Steiner, S.,
Ben-Aziz, O.,
Protasov, A.,
Fefer, D.,
Kaspi, R.

Facilitators :
From page:
0
To page:
0
(
Total pages:
1
)
Abstract:

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.

Note:
Related Files :
chemoenzymatic separation
Enantiomers
pheromone
trans-α-necrodol
γ-necrodyl
γ-necrodyl isobutyrate
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More details
DOI :
10.1021/acs.jafc.0c07543
Article number:
0
Affiliations:
Database:
Scopus
Publication Type:
article
;
.
Language:
English
Editors' remarks:
ID:
54415
Last updated date:
02/03/2022 17:27
Creation date:
05/04/2021 17:29
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Scientific Publication
Absolute Configuration of the Spherical Mealybug Nipaecoccus viridis Sex Pheromone, γ-Necrodyl Isobutyrate: Chemoenzymatic Synthesis and Bioassays
10

Levi-Zada, A.,
Steiner, S.,
Ben-Aziz, O.,
Protasov, A.,
Fefer, D.,
Kaspi, R.

Absolute Configuration of the Spherical Mealybug Nipaecoccus viridis Sex Pheromone, γ-Necrodyl Isobutyrate: Chemoenzymatic Synthesis and Bioassays

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.

Scientific Publication
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