| Title: | "Synthesis of Enantiopure Alicyclic Ethers and Their Activity on the Chemosensory Organ of the Ectoparasite of Honey Bees, Varroa destructor" |
| Author(s): | Pinnelli GR; Singh NK; Soroker V; Plettner E; |
| Address: | "Department of Chemistry, Simon Fraser University , Burnaby, British Columbia V5A 1S6, Canada. Agricultural Research Organization, Volcani Center , Bet Dagan 75359, Israel" |
| ISSN/ISBN: | 1520-5118 (Electronic) 0021-8561 (Linking) |
| 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)-beta-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, cy4,1, and (cis-1-ethoxy-5-(2'ethoxyethyl)cyclopent-2-ene, cy2,2-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 cy4,1 and cy2,2, but that responses to (E)-beta-ocimene were decreased significantly only by (+)-cy4,1 (1R,5S) and (-)-cy2,2 (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" |
| Keywords: | Acaricides/chemical synthesis/chemistry/*pharmacology Animal Structures/drug effects/physiology Animals Bees/*parasitology Ethers/chemistry/pharmacology Smell Stereoisomerism Structure-Activity Relationship Varroidae/*drug effects/physiology Varroa forele; |
| Notes: | "MedlinePinnelli, Govardhana R Singh, Nitin K Soroker, Victoria Plettner, Erika eng 2016/10/30 J Agric Food Chem. 2016 Nov 16; 64(45):8653-8658. doi: 10.1021/acs.jafc.6b03492. Epub 2016 Nov 7" |
