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Synthesis of Enantiopure Alicyclic Ethers and Their Activity on the Chemosensory Organ of the Ectoparasite of Honey Bees, Varroa destructor
Year:
2016
Authors :
Singh, Nitin Kumar
;
.
Soroker, Victoria
;
.
Volume :
64
Co-Authors:
Pinnelli, G.R., Department of Chemistry, Simon Fraser University, Burnaby, BC, Canada
Singh, N.K., Agricultural Research Organization, Volcani Center, Bet Dagan, Israel
Soroker, V., Agricultural Research Organization, Volcani Center, Bet Dagan, Israel
Plettner, E., Department of Chemistry, Simon Fraser University, Burnaby, BC, Canada
Facilitators :
From page:
8653
To page:
8658
(
Total pages:
6
)
Abstract:
The preparation of enantiopure conformationally restricted alicyclic ethers and their inhibitory activities on the chemosensory organ of the Varroa destructor, a parasite of honey bees, are reported in this article. We tested the effect of enantiopure ethers of cis-5-(2′-hydroxyethyl)cyclopent-2-en-1-ol on the Varroa chemosensory organ by electrophysiology, for their ability to inhibit the responses to two honey bee-produced odors that are important for the mite to locate its host: nurse bee head space odor and (E)-β-ocimene, a honey bee brood pheromone. Previous work with the racemic compounds showed that they suppress the mite's olfactory response to its bee host, which led to incorrect host choice. Based on a structure-activity relationship, we predicted that the two most active compounds - cis-1-butoxy-5-(2′-methoxyethyl)cyclopent-2-ene, cy{4,1}, and (cis-1-ethoxy-5-(2′ethoxyethyl)cyclopent-2-ene, cy{2,2} - could have opposite active enantiomers. Here we studied the enantiomers of both ethers, whose preparation involved enzymatic resolution of racemic diol cis-5-(2′-hydroxyethyl)cyclopent-2-en-1-ol using Lipase AK with vinyl acetate. The racemic diol was prepared from commercially available 2,5-norbornadiene. We observed that the responses of the chemosensory organ to honey bee head space volatiles were significantly decreased by both enantiomers of cy{4,1} and cy{2,2}, but that responses to (E)-β-ocimene were decreased significantly only by (+)-cy{4,1} (1R,5S) and (a)-cy{2,2} (1S,5R) and not by their respective enantiomers. The importance of this result is that the racemates could be used to inhibit olfactory detection of bee odors by mites, without a loss in activity relative to the more expensive enantiopure compounds. © 2016 American Chemical Society.
Note:
Related Files :
Enantiomers
Enantiopure
enantiopure synthetic odors
Ethers
Food Products
odors
Structure activity relationships
Show More
Related Content
More details
DOI :
10.1021/acs.jafc.6b03492
Article number:
0
Affiliations:
Database:
Scopus
Publication Type:
article
;
.
Language:
English
Editors' remarks:
ID:
30100
Last updated date:
02/03/2022 17:27
Creation date:
17/04/2018 00:52
Scientific Publication
Synthesis of Enantiopure Alicyclic Ethers and Their Activity on the Chemosensory Organ of the Ectoparasite of Honey Bees, Varroa destructor
64
Pinnelli, G.R., Department of Chemistry, Simon Fraser University, Burnaby, BC, Canada
Singh, N.K., Agricultural Research Organization, Volcani Center, Bet Dagan, Israel
Soroker, V., Agricultural Research Organization, Volcani Center, Bet Dagan, Israel
Plettner, E., Department of Chemistry, Simon Fraser University, Burnaby, BC, Canada
Synthesis of Enantiopure Alicyclic Ethers and Their Activity on the Chemosensory Organ of the Ectoparasite of Honey Bees, Varroa destructor
The preparation of enantiopure conformationally restricted alicyclic ethers and their inhibitory activities on the chemosensory organ of the Varroa destructor, a parasite of honey bees, are reported in this article. We tested the effect of enantiopure ethers of cis-5-(2′-hydroxyethyl)cyclopent-2-en-1-ol on the Varroa chemosensory organ by electrophysiology, for their ability to inhibit the responses to two honey bee-produced odors that are important for the mite to locate its host: nurse bee head space odor and (E)-β-ocimene, a honey bee brood pheromone. Previous work with the racemic compounds showed that they suppress the mite's olfactory response to its bee host, which led to incorrect host choice. Based on a structure-activity relationship, we predicted that the two most active compounds - cis-1-butoxy-5-(2′-methoxyethyl)cyclopent-2-ene, cy{4,1}, and (cis-1-ethoxy-5-(2′ethoxyethyl)cyclopent-2-ene, cy{2,2} - could have opposite active enantiomers. Here we studied the enantiomers of both ethers, whose preparation involved enzymatic resolution of racemic diol cis-5-(2′-hydroxyethyl)cyclopent-2-en-1-ol using Lipase AK with vinyl acetate. The racemic diol was prepared from commercially available 2,5-norbornadiene. We observed that the responses of the chemosensory organ to honey bee head space volatiles were significantly decreased by both enantiomers of cy{4,1} and cy{2,2}, but that responses to (E)-β-ocimene were decreased significantly only by (+)-cy{4,1} (1R,5S) and (a)-cy{2,2} (1S,5R) and not by their respective enantiomers. The importance of this result is that the racemates could be used to inhibit olfactory detection of bee odors by mites, without a loss in activity relative to the more expensive enantiopure compounds. © 2016 American Chemical Society.
Scientific Publication
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