Chirality and insect pheromones

Mori, Kenji

doi:10.1002/(sici)1520-636x(1998)10:7<578::aid-chir5>3.3.co;2-w

Cited by 8 publications

(3 citation statements)

References 33 publications

(36 reference statements)

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“…Although chiral alcohols 1 and 2 seem to play a minor role compared with the major component (i.e., compounds 1 and 2 are less abundant in the extracts and less attractive than compound 4), the absolute configuration of naturally occurring chiral pheromones is essential to have a complete understanding of the relationship between structure and behavioural effects (Mori, 1998). Our preliminary data showed that S .…”

Section: Discussionmentioning

confidence: 99%

Aggregation pheromone of the agave weevil, Scyphophorus acupunctatus

Ruiz-Montiel¹,

García‐Coapio²,

Rojas³

et al. 2008

Entomologia Exp Applicata

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The agave weevil, Scyphophorus acupunctatus Gyllenhal (Coleoptera: Curculionidae), is the most important insect pest of wild and cultivated agaves in the world. Combined gas chromatography‐electroantennography (GC‐EAD) analysis of male volatile extracts showed that four peaks elicited antennal responses from males and females. The peaks were identified by GC‐mass spectrometry (GC‐MS) as 2‐methyl‐4‐heptanol (1), 2‐methyl‐4‐octanol (2), 2‐methyl‐4‐heptanone (3), and 2‐methyl‐4‐octanone (4). Electroantennogram (EAG) recordings of both sexes to 0.01‐, 0.1‐, 1‐, and 10‐µg stimulus load of synthetic compounds showed that the dose of the tested compounds and weevil sex significantly influenced the antennal response of S. acupunctatus. However, there was no sexual dimorphism in the antennal responses to the four synthetic compounds evaluated because the EAG profiles revealed no interaction between doses by sex. Antennae of S. acupunctatus were most sensitive to compounds 2 and 4, reaching the threshold at a 0.01‐µg stimulus load. Weevil antennae were less sensitive to compounds 1 and 3, and the threshold response to these compounds was 0.1 µg. Behavioural evaluation of the synthetic compounds showed them to be attractive to both males and females in a Y‐tube olfactometer. Field experiments confirmed the laboratory results, showing that all components, singly or in blends, were attractive to the weevils. In general, traps baited with the quaternary blend of compounds 1–4 captured significantly more weevils than traps baited with males. However, compounds 3 and 4 were sufficient to obtain captures equivalent to those by the quaternary blend. The potential use of the aggregation pheromone in the development of a mass‐trapping programme as a viable pest management alternative for S. acupunctatus is discussed.

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Section: Discussionmentioning

confidence: 99%

Aggregation pheromone of the agave weevil, Scyphophorus acupunctatus

Ruiz-Montiel¹,

García‐Coapio²,

Rojas³

et al. 2008

Entomologia Exp Applicata

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“…Since the early 1970s, enantioselectivity of insect [3] olfactory systems has been well documented. Evidence ranges from enantiomer driven behaviors [4], [5], [6], [7], [8] and glomerular activation patterns [9] to highly specific olfactory receptor cells for pheromones and plant odorants [10], [11]. In fact, behavioral studies carried out in humans [2], honeybees [12] and mice [13] have clearly demonstrated the ability of these organisms to distinguish between chiral odorants, prompting several authors to postulate the existence of enantioselective ORs.…”

Section: Introductionmentioning

confidence: 99%

Characterization of an Enantioselective Odorant Receptor in the Yellow Fever Mosquito Aedes aegypti

2009

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Enantiomers differ only in the left or right handedness (chirality) of their orientations and exhibit identical chemical and physical properties. In chemical communication systems, enantiomers can be differentially active at the physiological and behavioral levels. Only recently were enantioselective odorant receptors demonstrated in mammals while their existence in insects has remained hypothetical. Using the two-microelectrode voltage clamp of Xenopus oocytes, we show that the yellow fever mosquito, Aedes aegypti, odorant receptor 8 (AaOR8) acts as a chiral selective receptor for the (R)-(—)-enantiomer of 1-octen-3-ol, which in the presence of other kairomones is an attractant used by blood-sucking insects to locate their hosts. In addition to steric constraints, chain length and degree of unsaturation play important roles in this recognition process. This is the first characterization of an enantioselective odorant receptor in insects and the results demonstrate that an OR alone, without helper proteins, can account for chiral specificity exhibited by olfactory sensory neurons (OSNs).

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“…For example, the male pine engraver beetle ( Ips pini ) use one enantiomer (−)‐ipsdienol, the naturally occurring enantiomer, to attract conspecific females . This beetle is a parasitic species managed partially using pheromones, which must be applied at the correct ratio of enantiomers . The process of identifying pheromones has been accelerated in recent years due to advances in modern spectroscopic and stereoselective synthesis methods .…”

Section: Introductionmentioning

confidence: 99%

High‐performance liquid chromatography quantification of enantiomers of a Dihydroxylated tetrahydrofuran natural product

Fissette

Buchinger

et al. 2018

Chirality

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Both enantiomers of petromyroxol are putative pheromones in sea lamprey (Petromyzon marinus). Here, we describe the separation and quantification of the petromyroxol enantiomers using high-performance liquid chromatography tandem mass spectrometry. The separation was tested on a wide range of chiral columns with normal phases, and effects of the chromatographic parameters such as mobile phase and temperature on the separation were optimized. The AD-H column showed the best separation of enantiomers with n-hexane and ethanol as the mobile phase. The enantiomers were detected by multiple reaction monitoring with a positive atmospheric-pressure chemical ionization on triple quadrupole mass spectrometer. Validation revealed that the method was specific, accurate, and precise. The validated method was applied to measure the amount of petromyroxol enantiomers in water conditioned with sea lamprey larvae, the source of the putative pheromone. This method will be applied in quantifying the natural scalemic petromyroxol mixture, enabling further investigations of a rare non-racemic enantiomeric pheromone mixture in a vertebrate species.

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Chirality and insect pheromones

Cited by 8 publications

References 33 publications

Aggregation pheromone of the agave weevil, Scyphophorus acupunctatus

Aggregation pheromone of the agave weevil, Scyphophorus acupunctatus

Characterization of an Enantioselective Odorant Receptor in the Yellow Fever Mosquito Aedes aegypti

High‐performance liquid chromatography quantification of enantiomers of a Dihydroxylated tetrahydrofuran natural product

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