Queen Recognition Pheromone Research Articles

Total Synthesis of (-)-Invictolide

A convergent approach to the total synthesis of (–)-invictolide, a component of the queen recognition pheromone of <i>Solenopsis­ invicta</i>, is described. Key steps involve the desymmetrization of a bicyclic olefin with Brown’s chiral hydroboration, C–C bond formation, 1,3-<i>syn</i> reduction, and oxidative lactonization of a 1,3,5-triol with TEMPO/PhI(OAc)₂.

ChemInform Abstract: 3,6,7‐Tri‐epi‐invictolide, a Diastereomer of Queen Recognition Pheromone, and Its Analogue from a Marine‐Derived Actinomycete.

AbstractStereochemistry and biosynthetic origin of tri‐epi‐invictolide (Ia) and its analog (Ib) are investigated.

3,6,7-tri-epi-invictolide, a diastereomer of queen recognition pheromone, and its analog from a marine-derived actinomycete

3,6,7-tri -epi -invictolide, a diastereomer of queen recognition pheromone, and its analog from a marine-derived actinomycete

The function of abdominal stroking in the paper wasp, Polistes fuscatus (Hymenoptera Vespidae)

The functional significance of abdominal stroking was investigated in a field study of the paper wasp, Polistes fuscatus. The experimental design consisted of approximating intraspecific usurpation by switching nestboxes containing combs between unrelated queens and comparing the behavior of these alien queens with matched, control queens in blind observations (n = 26 matched colonies). In postworker colonies, the tolerance of alien queens by workers was compared to the time an alien queen had been on the comb prior to first worker emergence. In preworker colonies, alien queens spent significantly more time stroking the comb than control queens. Both alien queens and control queens spent significantly more time stroking before workers emerged than after. Finally, workers' tolerance of alien queens was significantly positively correlated with the length of time alien queens were on the nest prior to first worker emergence. These three results are consistent with the hypothesis that abdominal stroking functions to apply the queen's recognition pheromone to the comb.

Multiple glandular origins of queen pheromones in the fire ant Solenopsis invicta

The poison sac of the fire ant Solenopsis invicta is the only identified glandular source of pheromones produced by a functional ant queen. This structure, which contains the poison gland, has previously been shown to be the source of a releaser pheromone that mediates queen recognition and tending by workers. The poison sac has also been demonstrated to be the source of a primer pheromone that inhibits winged, virgin queens from shedding their wings (dealating) and developing their ovaries. To determine if the poison sac was the only source of these pheromones, we excised the poison sac from queens and observed whether operated queens retained their pheromonal effects. In a first experiment, the poison sac was removed from functional (egg-laying) queens which were then paired with unoperated nestmate queens in small colonies. Counts of the workers surrounding each queen two weeks after the operation showed that queens without poison sac were as effective as their unoperated nestmates in attracting worker retinues. In a second experiment, we removed the poison sacs of virgin queens which had not yet begun laying eggs and thus had not begun producing queen pheromone. After allowing them to develop their ovaries, these individuals produced amounts of queen recognition pheromone comparable to those secreted by unoperated or sham operated virgin queens as determined by bioassay. Testing the head, thorax and abdomens of functional queens separately revealed that the head was the most attractive region in relation to its relative surface area. Bioassays of extracts of two cephalic glands—the mandibular gland and postpharyngeal gland—showed that the postpharyngeal gland is a second source of the queen recognition pheromone. Finally, we found that virgin queens whose poison sacs were removed before they began producing queen pheromone initiated production of a primer pheromone that inhibits winged virgin queens from dealating, indicating that this pheromonal effect also has an additional but as yet undetermined source. These results parallel those on the honey bee in which several of the pheromonal effects of functional queens appear to have multiple glandular sources.

A concise enantiospecific synthesis of (−)-invictolide

(−)-Invictolide, a component of the queen recognition pheromone of Solenopsis invicta, was stereoselectively synthesized starting from (−)-carvone, where the regioselective carbon-carbon bond cleavage reaction of γ-halo ester with samarium diiodide was successfully involved as an important reaction.

Stereoselective total synthesis of (.+-.)-invictolide. An efficient preparation of a trisubstituted .delta.-lactone from aldol precursors

The stereoselective total synthesis of (±)-invictolide (1), a component of the queen recognition pheromone of Solenopsis invicta, is described. The TiCl 4 -mediated addition of silyl ketene thioacetal 8 to (±)-3-(benzyloxy)-2-methylpropionaldehyde afforded exclusively thioester 10, in 65% yield, which was straightforwardly converted to diol 5 (ca. 31% yield). Diol 5 was also prepared after LiAlH 4 reduction of the major aldol formed in the condensation between the lithium enolate of 2,6-di-tert-butyl-4-methylphenyl propanoate and (±)-2-methylvaleraldehyde (ca. 50% overall yield). Intramolecular alkylation (t-BuOK, THF) of 6 or 7 gave a 40:60 mixture of rac-1 and its C(3) epimer. catalytic hydrogenation of unsaturated lactone 17 afforded rac-1 in 80% yield

Queen Pheromone Production and Its Physiological Correlates in Fire Ant Queens (Hymenoptera: Formicidae) Treated with Fenoxycarb1

Biological assays were used to evaluate the effect of the insect growth regulator fenoxycarb (ethyl (2- p -phenoxyphenoxy) ethyl carbamate) on production of queen-derived dealation inhibitory pheromone and the queen recognition pheromone of Solenopsis invicta Buren. Treated virgin and mated queens weighed less and were less capable of inhibiting dealation by female alates than were nontreated controls. Virgin queens that gained weight during the experimental trials produced more dealation inhibitory pheromone and more queen recognition pheromone than virgin queens that lost weight. Treated virgin queens with fenoxycarb-induced ovary dysfunction inhibited dealation in proportionally fewer alates than treated virgin queens of similar weight that possessed functional ovaries. However, complete ovarian dysfunction in fenoxycarb-treated virgin queens was not associated with reduced quantities of queen recognition pheromone in queen poison sacs. These data support the views that nutritional as well as endocrine factors regulate queen pheromone release and that dissemination of both queen pheromone components is a function of oviposition rate.

Identification and source of a queen-specific chemical in the pharaoh's ant,Monomorium pharaonis (L.)

Fertile queens of the antMonomorium pharaonis produce a chemical substance which is not present in worker ants or in young, alate (virgin) queens. The material has been identified as (E,E,E)-1-isopropenyl-4,8,12-trimethylcyclotetradeca-3,7,11-triene (neocembrene). This chemical is produced in the Dufour's gland of fertile queens and may serve as a queen-recognition pheromone.

ChemInform Abstract: The Queen Recognition Pheromone of Solenopsis invicta, Preparation of (E)‐6‐(1‐Pentenyl)‐2H‐pyran‐2‐one. Synthesis and Stereochemistry of Tetrahydro‐3,5‐dimethyl‐6‐(1‐methylbutyl‐2H‐pyran‐2‐one, a Component of the Queen Recognition Pheromone of Solenopsis invicta.

AbstractDie aus Ameisen‐Königinnen erhältlichen Inhaltsstoffe (IV) und (XI) werden in der angegebenen Weise synthetisiert.

Behavior of Workers of Solenopsis invicta (Hymenoptera: Formicidae) to the Queen Recognition Pheromone: Laboratory Studies with an Olfactometer and Surrogate Queens1

Red imported fire ant (RIFA), Solenopsis invicta Buren, queens produce a queen recognition pheromone that attracts daughter or conspecific worker ants singly or in groups. Their attractiveness ceases if they are separated from their colony for more than 30 min, but returns immediately when they are reunited with their workers. Whole-body queen extracts of the pheromone are attractive when carried by an air stream into an olfactometer or when applied to surrogate queens (pieces of rubber septa). Extracts of the pheromone induce some attraction at a concentration of 0.01 queen equivalent, with maximum response at concentrations of 0.5 to 5.0 queen equivalents. The response of workers to extracts of other RIFA castes was significantly less than that to queen extracts in all bioassays.

Synthesis and stereochemistry of tetrahydro-3, 5-dimethyl-6-(1)methylbutyl)-2H-pyran-2-one, a component of the queen recognition pheromone of [formula omitted

One of the diastereomers of the title compound, I , isolated from imported fire ant queens, has been prepared and named invictolide . It is responsible, in part, for “queen recognition” by workers of the species.