J. W. Wheeler

Alkylpyrazine Alarm Pheromones in Ponerine Ants

The mandibular gland secretions of the ponerine ants Odontomachus hastatus, O. clarus, and O. brunneus contain alkylpyrazines. These compounds, 2,5-dimethyl-3-isopentylpyrazine in O. hastatus and O. clarus, and 2,6-dimethyl-3-pentyl-, -butyl-, -propyl-, and -ethyl-pyrazines in O. brunneus, have previously not been found as animal natural products. These compounds function as powerful releasers of alarm behavior for Odontomachus workers and are probably also utilized as defensive compounds.

Macrocyclic lactones and isopentenyl esters in the Dufour's gland secretion of halictine bees (Hymenoptera: Halictidae).

The volatile components of the Dufours gland secretion of female halictid bees have been examined in 18 Nearctic species belonging toAgapostemon, Augochlora, Augochlorella, Augochloropsis, Dialictus, Evylaeus, Halictus, andLasioglossum. Nine saturated and unsaturated macrocyclic lactones ranging from C18 to C26 have been identified. Four of these compounds, the saturated C26 and the unsaturated C20, C22, and C24 lactones, are new natural products reported for halictine bees. A series of eight esters containing branched C5-alkenols and fatty acids has been identified in several species. The cell linings and pollen ball inAugochlora pura pura contain the same major lactones as the Dufours gland. A discussion of the significance of the Dufours gland secretion for apoid systematics and its function in the Halictidae is presented.

Sociochemicals of Bees

The aculeate Hymenoptera include approximately 14 000 species of ants, 16 000 species of wasps and 20000 species of bees world-wide (Wilson, 1971; Michener, 1974). Such insects exhibit diversity both in the chemistry of their exocrine secretions and their behaviors. These compounds range from simple alkanes to terpenoids and triglycerides; social behaviors range from strictly solitary to the complex caste systems of honey bees and stingless bees.

Alkylphenols in the defensive secretion of the nearctic opilionid,Stygnomma spinifera (Arachnida: Opiliones)

The opilionid,Stygnomma spinifera, secretes from a pair of exocrine glands on the cephalothorax between the first and second pair of legs a major volatile component, 2-methyl-5-ethylphenol, and two minor components, 2,3-dimethylphenol and 2,3-dimethyl-5-ethylphenol. These alkylphenols are constituents of a defensive secretion and repel ants, a natural predator of opilionids. The probable significance of this secretion in the biology ofS. spinifera and in the defensive strategies of opilionids in general is discussed.

Mandibular glands of maleCentris adani, (Hymenoptera: Anthophoridae) : Their morphology, chemical constituents, and function in scent marking and territorial behavior.

Males of the solitary Central American beeCentris adani Cockerell possess enlarged mandibular glands filled with a fragrant fluid that was shown by gas chromatographic and mass spectral analysis to consist of nerol, geraniol, neral, ethyl laurate, and geranyl acetate. Male bees set up territories by marking a semicircular array of grass stems with these compounds. Grass stems marked by the bees showed the presence of the same chemicals.

Chemistry of the dufour's gland secretion of halictine bees

Abstract 1. 1. The chemistry of the Dufours gland secretions of nine species of halictine bees in the genera Agapostemon, Augochlorella, Dialictus, Lasioglossum and Evylaeus has been investigated. 2. 2. The macrocyclic lactones octadecanolide, eicosanolide and docosanolide were identified in nearly all species, and octadecenolide was detected in the secretion of at least one species. 3. 3. Docosanolide has not been previously identified as an insect natural product. 4. 4. The hydrocabones n-heptacosane and n-tricosane frequently accompanied the lactones. 5. 5. The biosynthesis of the lactones and their role in halictine biology are discussed.

Exocrine secretions of bees. IV. Macrocyclic lactones and isopentenyl esters in Dufour's gland secretions of Nomia bees (Hymenoptera: Halictidae)

The volatile components of Dufours gland extracts were analyzed in four species of NearcticNomia bees;Nomia (Dieunomia)heteropoda, N. (Tetrazonata)tetrazonata, N. (Epinomia)nevadensis, andN. (Epinomia)triangulifera. A homologous series of five saturated macrocyclic lactones ranging from C18 to C26 was identified. A series of esters (branched C5-alkenols and fatty acids) was also identified in all species investigated. Two of these esters are new natural products reported for bees. A discussion of the significance of the Dufours gland secretion for halictid systematics and its function in the Halictidae is also presented.

Alkylpyrazine alarm pheromones in primitive ants with small colonial units

Abstract 1. 1. 2,5-Dimethyl-3-isopentylpyrazine is the main constituent in the mandibular gland secretions of workers of Hypoponera opacior and Ponera pennsylvanica. 2. 2. 2,5-Dimethyl-3-isopentypyrazine releases escape alarm behavior in workers of H. opacior and P. pennsylvanica. 3. 3. The adaptiveness of a chemical alarm system in ant species which form relatively small colonies is discussed.

1-Pentadecene Production in Tribolium confusum

Odoriferous glands of Tribolium confusum produce volatile compounds which are stored in special reservoirs. Besides the previously reported 2-methyl- and 2-ethyl-1,4-benzoquinones, a new compound, 1-pentadecene, was isolated. The acyclic C14H26O ketone previously reported was not present. 1-Pentadecene is thought to facilitate absorption of the admixed quinones by Tribolium enemies.

N,N-dimethyl-β-phenylethylamine and bornyl esters from the harvestman sclerobunus robustus (arachnida: Opiliones)

Abstract The defensive secretion of Sclerobunus robustus contains camphene, limonene, bornyl acetate, bornyl propionate, nicotine and N,N-dimethyl-β-phenylethylamine, a new natural product, as the major component.