Mandibular gland chemistry of four Caribbean species of Camponotus (Hymenoptera: Formicidae).

The volatile components of whole-body extracts of males, females and workers were analyzed in four species of Neotropical ants in the formicine genus, Camponotus. The species, C. kaura, C. sexguttatus, C. ramulorum and C. planatus, represent three different subgenera. Volatile mandibular gland components were found only in male extracts in three of the species. In C. ramulorum, volatile components were found in male and female reproductives and workers. 3,4-Dihydro-3,5-dihydroxy-6-methylpyran-4-one and octanic acid were found in different sets of three of the species. Methyl 6-methyl salicylate was found in two species and the isocoumarin, mellein, was found in a third species. The significance of the mandibular gland secretion for formicid systematics is discussed.

Exocrine secretions of bees X. 3,7-Dimethyldeca-2,6-dien-1,10-diol: A sex-specific compound fromNomada annulata (Hymenoptera: Anthophoridae).

3,7-Dimethyldeca-2,6-dien-1,10-diol was isolated from male cephalic extracts of the cleptoparasitic or "cuckoo" bee,Nomada annulata. The compound is absent in female head extracts. This diol, previously known only from a male danaid butterfly, is a new bee natural product and is not found in the volatile exocrine secretions of the host bee,Andrena macra. The role of this compound in this parasite-host system, including the chemical basis ofNomada-Andrena associations, is discussed.

Mandelonitrile in larval secretion of mountain ash sawfly,Pristiphora geniculata (Hymenoptera: Tenthredinidae).

The larval defensive secretion of the mountain ash sawfly,Pristiphora geniculata, contains seven volatile components. They include benz-aldehyde, borneol, bornyl acetate, mandelonitrile, and C14, C16, and C18 acetates.

Metasternal gland secretion of the locust tree borer, Megacyllene robiniae (Coleoptera: Cerambycidae).

1. The volatile components of metasternal gland extracts of male and female Megacyllene robiniae have been analyzed by gas chromatography-mass spectroscopy. 2. The major component was identified as 2-(1,3-hexadien-1-yl)-5-methyltetrahydrofuran, a new natural product. 3. 1-Phenylethanol is present only in male extracts. 4. Acetates of hexadecanol and octadecanol are also present.

Exocrine secretions of bees : VI. Unsaturated ketones and aliphatic esters in the Dufour's gland secretion ofDufourea novaeangliae (Hymenoptera: Halictidae).

The volatile components of the Dufour's gland extracts ofDufourea novaeangliae were analyzed by gas chromatography-mass spectroscopy. The following were identified: a series of five bis-homologous unsaturated ketones ranging from C10 to C18, a series of nine bis-homologous hexanoates ranging from C8 to C24, a series of three bis-homologous octanoates ranging from C8 to C12, and hexanoic, hexadecanoic, and octadecanoic acids. The ketones are all new natural products reported for bees. Several of these unsaturated ketones were also identified in extracts of the provision masses from their nest cells. Male mandibular gland extracts contained citral.

Exocrine secretions of bees--VII. Aliphatic esters in the Dufour's gland secretion of Svastra obliqua obliqua (Hymenoptera: Anthophoridae).

The chemistry of the Dufour's gland secretion of Svastra obliqua obliqua is reported. A series of 32 aliphatic esters were identified. The Dufour's secretion of Svastra obliqua obliqua contains the most complex mixture of volatile compounds in bee extracts examined to date.

Exocrine secretions of bees V. Terpenoid esters in the Dufour's secretions ofPanurginus bees (Hymenoptera: Andrenidae).

The volatile components of Dufour's gland extracts were analyzed in two species of HolarcticPanurginus bees:Panurginus pontentillae andP. atramontensis. Two terpenoid esters, citronellyl citronellate and citronellyl geranate, were identified inP. pontentillae, whereas only the latter was inP. atramontensis. Citronellyl citronellate was identified in pollen ball extracts ofP. pontentillae. Mandibular gland extracts from male and femaleP. pontentillae contained neral and geranial. The significance of the Dufour's gland secretion in andrenid systematics and its function in the Andrenidae are discussed.

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

The volatile components of Dufour's 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 Dufour's gland secretion for halictid systematics and its function in the Halictidae is also presented.

Anabaseine: venom alkaloid of aphaenogaster ants.

Anabaseine, a tobacco alkaloid, is identified as a poison gland product in Aphaenogaster ants, in which it functions as an attractant.

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

The volatile components of the Dufour's 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 Dufour's gland. A discussion of the significance of the Dufour's gland secretion for apoid systematics and its function in the Halictidae is presented.

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.

Chemistry of the Dufour's gland secretions of North American andrenid bees (Hymenoptera: Andrenidae).

The volatile components of the Dufour's gland secretions were examined in 22 Nearctic species of andrenid bees representing 10 subgenera. Farnesyl hexanoate was the dominant component in the secretion of 17 species. In others, various terpenoid esters such as geranyl octanoate, farnesyl octanoate and geranylgeranyl octanoate were the major components. Approximately 30 compounds have been identified in the secretions; many are newly identified in andrenid bees. Three different groups of secretions are discerned with "exceptions." A discussion of the possible function of the Dufour's gland secretion in the biology of, and its use in, the systematics of these bees is presented.

Caste-specific compounds in male carpenter ants.

Three caste-specific substances new to arthropod glandular secretions occur in the mandibular glands of male ants of five species in the genus Camponotus. These volatile compounds, which are not found in alate females or workers, have been identified as methyl 6-methyl salicylate, 2,4-dimethyl-2-hexenoic acid, and methyl anthranilate. The free acid has not been described previously.