Racemic 1-octen-3-ol (CH3[CH2]4CH[OH]CH = CH2) is a mono-unsaturated 8-carbon alcohol with carbon 3 being the single stereogenic center (Fig. 1A), hence its composition of two optically active enantiomers, (R)-(—)-1-octen-3-ol and (S)-(+)-1-octen-3-ol. Octenol is a natural compound of plant [28] and animal origin [29], and has been identified from human sweat extracts [30]. (R)-(—)-1-octen-3-ol is the prevailing enantiomer in volatiles collected from cattle with a (R)/(S) ratio between 80% and 92% [29]. While both octenol enantiomers are equally active aggregation pheromones for several beetle species [31] and potent attractants to the tsetse fly, Glossina morsitans [29], many mosquito species exhibit a preference for the (R)-(—) form [32], [33]. This compound alone is an attractant for various hematophagous insects [29], [34] and its behavioral potency is increased when combined with CO2 [35]. OSNs located within the capitate peg sensilla on the maxillary palps of Aedes aegypti [36], Culex quinquefasciatus[33] and Anopheles gambiae [16] mediate the response to octenol and CO2. In the case of An. gambiae, the molecular basis of the octenol response has previously been attributed to An. gambiae OR8 (AgOR8) [16]. We recently identified the Or gene family of Ae. aegypti including the Ae. aegypti orthologue of AgOr8, AaOr8 [37]. In the current study, we establish that octenol is the preferred ligand of the AaOR8/AaOR7 protein complex, and investigate the structure-activity relationship between ligand and receptor, focusing on the enantiomeric discrimination of (R)- and (S)-octenol.
Article Characterization of an Enantioselective Odorant Receptor in ...
Kairomones, Synomones and pheromones fall broadly under the category of Semiochemicals. Kairomones are volatile compounds involved in the mosquito–plant (kairomones produced by flowers, leaves, fruits attracting insects of both sexes towards nectar source) and mosquito–host interactions ( kairomones produced by humans or animals as breath, sweat, or skin emanations attracting female mosquitoes towards sources of blood-feeding). As far as pheromones are concerned, there are several types of behaviourally active compounds described in insects, but in mosquitoes may include sex pheromones and oviposition pheromones . For example, the fatty acid lactone, erythro-6-acetoxy-5-hexadecanolide, is produced and released by ovipositing Culex quinquefasciatus females and significantly enhances oviposition .