Huimin Zhai

Bed Bug Aggregation Pheromone Finally Identified

Bed bugs have become a global epidemic and current detection tools are poorly suited for routine surveillance. Despite intense research on bed bug aggregation behavior and the aggregation pheromone, which could be used as a chemical lure, the complete composition of this pheromone has thus far proven elusive. Here, we report that the bed bug aggregation pheromone comprises five volatile components (dimethyl disulfide, dimethyl trisulfide, (E)-2-hexenal, (E)-2-octenal, 2-hexanone), which attract bed bugs to safe shelters, and one less-volatile component (histamine), which causes their arrestment upon contact. In infested premises, a blend of all six components is highly effective at luring bed bugs into traps. The trapping of juvenile and adult bed bugs, with or without recent blood meals, provides strong evidence that this unique pheromone bait could become an effective and inexpensive tool for bed bug detection and potentially their control.

The Sex Attractant Pheromone of Male Brown Rats: Identification and Field Experiment

Trapping brown rats is challenging because they avoid newly placed traps in their habitat. Herein, we report the identification of the sex pheromone produced by male brown rats and its effect on trap captures of wild female brown rats. Collecting urine- and feces-soiled bedding material of laboratory-kept rats and comparing the soiled-bedding odorants of juvenile and adult males, as well as of adult males and females, we found nine compounds that were specific to, or most prevalent in, the odor profiles of sexually mature adult males. When we added a synthetic blend of six of these compounds (2-heptanone, 4-heptanone, 3-ethyl-2-heptanone, 2-octanone, 2-nonanone, 4-nonanone) to one of two paired food-baited trap boxes, these boxes attracted significantly more laboratory-strain female rats in laboratory experiments, and captured ten times more wild female rats in a field experiment than the corresponding control boxes. Our data show that the pheromone facilitates captures of wild female brown rats.

Effect of Male House Mouse Pheromone Components on Behavioral Responses of Mice in Laboratory and Field Experiments

Urine of male house mice, Mus musculus, is known to have primer pheromone effects on the reproductive physiology of female mice. Urine-mediated releaser pheromone effects that trigger certain behavioral responses are much less understood, and no field studies have investigated whether urine deposits by male or female mice, or synthetic mouse pheromone, increase trap captures of mice. In field experiments, we baited traps with bedding soiled with urine and feces of caged female or male mice, and recorded captures of mice in these and in control traps containing clean bedding. Traps baited with female bedding preferentially captured adult males, whereas traps baited with male bedding preferentially captured juvenile and adult females, indicating the presence of male- and female-specific sex pheromones in soiled bedding. Analyses of headspace volatiles emanating from soiled bedding by gas chromatography/mass spectrometry revealed that 3,4-dehydro-exo-brevicomin (DEB) was seven times more prevalent in male bedding and that 2-sec-butyl-4,5-dihydrothiazole (DHT) was male-specific. In a follow-up field experiment, traps baited with DEB and DHT captured 4 times more female mice than corresponding control traps, thus indicating that DEB and DHT are sex attractant pheromone components of house mouse males. Our study provides impetus to identify the sex attractant pheromone of female mice, and to develop synthetic mouse pheromone as a lure to enhance the efficacy of trapping programs for mouse control.

(7E,11E)-3,5,9,11-Tetramethyltridecadienal: Sex Pheromone of the Strepsipteran Xenos peckii

Xenos peckii is a strepsipteran parasitoid of the common North American paper wasp, Polistes fuscatus. Mate-seeking X. peckii males respond to a long-range sex pheromone emitted by the female, which remains permanently embedded within the abdomen of a mobile host wasp. During peak pheromone signalling, we excised the female from her host, severed the cephalothorax containing the pheromone gland, extracted it in hexane, and analyzed aliquots of combined extracts by coupled gas chromatographic-electroantennographic detection (GC-EAD). These analyses revealed a candidate pheromone component (CPC) that consistently elicited strong responses from male antennae. We identified the CPC as (7E,11E)-3,5,9,11-tetramethyltridecadienal based on its retention indices (RI) on three GC-columns, RI inter-column differentials, mass and NMR spectra, and synthesis of an authentic standard that matched the GC-retention and spectrometric characteristics of the CPC. For a field experiment, we prepared (7E,11E)-3,5,9R,11-tetramethyltridecadienal and (7E,11E)-3,5,9S,11-tetramethyltridecadienal. Xenos peckii males were caught in traps baited with either compound singly or a 1:1 mixture of the two but not in unbaited control traps. The sex pheromone of X. peckii resembles that reported for the strepsipterans Stylops mellittae and S. muelleri, (R,R,R)-3,5,9-trimethyldodecanal, suggesting a common biosynthetic pathway across taxonomic genera.

Total Synthesis, Stereochemical Assignment, and Field-Testing of the Sex Pheromone of the Strepsipteran Xenos peckii

The sex pheromone of the endoparasitoid insect Xenos peckii (Strepsiptera: Xenidae) was recently identified as (7E,11E)-3,5,9,11-tetramethyl-7,11-tridecadienal. Herein we report the asymmetric synthesis of three candidate stereostructures for this pheromone using a synthetic strategy that relies on an sp(3) -sp(2) Suzuki-Miyaura coupling to construct the correctly configured C7-alkene function. Comparison of (1) H NMR spectra derived from the candidate stereostructures to that of the natural sex pheromone indicated a relative configuration of (3R*,5S*,9R*). Chiral gas chromatographic (GC) analyses of these compounds supported an assignment of (3R,5S,9R) for the natural product. Furthermore, in a 16-replicate field experiment, traps baited with the synthetic (3R,5S,9R)-enantiomer alone or in combination with the (3S,5R,9S)-enantiomer captured 23 and 18 X. peckii males, respectively (mean±SE: 1.4±0.33 and 1.1±0.39), whereas traps baited with the synthetic (3S,5R,9S)-enantiomer or a solvent control yielded no captures of males. These strong field trapping data, in combination with spectroscopic and chiral GC data, unambiguously demonstrate that (3R,5S,9R,7E,11E)-3,5,9,11-tetramethyl-7,11-tridecadienal is the X. peckii sex pheromone.

The fly factor phenomenon is mediated by interkingdom signaling between bacterial symbionts and their blow fly hosts: The fly factor is microbe mediated

We tested the recent hypothesis that the “fly factor” phenomenon (food currently or previously fed on by flies attracts more flies than the same type of food kept inaccessible to flies) is mediated by bacterial symbionts deposited with feces or regurgitated by feeding flies. We allowed laboratory‐reared black blow flies, Phormia regina (Meigen), to feed and defecate on bacterial Luria–Bertani medium solidified with agar, and isolated seven morphologically distinct bacterial colonies. We identified these using matrix‐assisted laser desorption/ionization mass spectrometry and sequencing of the 16S rRNA gene. In two‐choice laboratory experiments, traps baited with cultures of Proteus mirabilis Hauser, Morganella morganii subsp. sibonii Jensen, or Serratia marcescens Bizio, captured significantly more flies than corresponding control jars baited with tryptic soy agar only. A mixture of seven bacterial strains as a trap bait was more attractive to flies than a single bacterial isolate (M. m. sibonii). In a field experiment, traps baited with agar cultures of P. mirabilis and M. m. sibonii in combination captured significantly more flies than traps baited with either bacterial isolate alone or the agar control. As evident by gas chromatography‐mass spectrometry, the odor profiles of bacterial isolates differ, which may explain the additive effect of bacteria to the attractiveness of bacterial trap baits. As “generalist bacteria,” P. mirabilis and M. m. sibonii growing on animal protein (beef liver) or plant protein (tofu) are similarly effective in attracting flies. Bacteria‐derived airborne semiochemicals appear to mediate foraging by flies and to inform their feeding and oviposition decisions.

Identification and field testing of floral odorants that attract the rove beetle Pelecomalium testaceum (Mannerheim) to skunk cabbage, Lysichiton americanus (L.)

Western skunk cabbage, Lysichiton americanus (Araceae), is pollinated mainly by the rove beetle Pelecomalium testaceum (Staphylinidae). Our objective was to determine the floral semiochemical(s) of L. americanus that attract(s) P. testaceum. Porapak Q headspace volatile extracts of L. americanus inflorescences were analyzed by gas chromatographic–electroantennographic detection (GC–EAD) and GC–mass spectrometry. In GC–EAD analyses, three floral odorants [(E)-4 nonene, (E)-5-undecene, indole] elicited consistent responses from the antennae of female P. testaceum. In field experiments, traps baited with a blend of these three components (“3-CB”) captured significantly more P. testaceum than unbaited control traps. Traps baited with the 3-CB, the two hydrocarbons, or indole, each captured significantly more beetles than unbaited control traps, indicating redundancy in the semiochemical blend. Moreover, traps baited with indole captured significantly more beetles than traps baited with either the 3-CB, or the hydrocarbons, indicating that indole is a key floral attractant for P. testaceum. Many necrophilous and coprophilous insects respond to indole in search of carrion or feces, but P. testaceum has never been associated with these types of resources. Both electrophysiological and behavioral responses of P. testaceum to two hydrocarbon semiochemicals, which are not signature odorants of carrion or feces, may indicate that the beetles recognize the odor of L. americanus as an honest signal, seek and pollinate its inflorescences, and get rewarded with pollen and on-plant mating opportunities.