Long-chain (Z)-9-alkenes are ‘Psychedelics’ to houseflies with regard to visually stimulated sex attraction and aggregation

Summary Three different tests on houseflies (Musca domestica L.) revealed that both pheromone-free pseudoflies and male partner flies exhibit in the presence of mixtures of long-chain (Z)-9-alkenes or pure (Z)-9-tricosene enhanced releasing effects for two optical cues, which stimulate male houseflies to mating strikes and houseflies of both sexes to aggregation.     

Recombination in the male housefly,Musca domestica

Summary Autosome II recombinations of up to 30.7% were found in male houseflies bearing a Y-chromosome translocation on autosome II. This is the highest recorded rate of recombination found in male houseflies, therefore indicating another possible source of genetic variation. The male crossover rates were related to map distances and resulted in an inaccurate estimate for one of the loci. Explanations are provided. Male crossing-over is related to cytogenetics of the Y-chromosome.     

Response ofHeliothis virescens to pheromonal components and an inhibitor in olfactometers

Summary Laboratory-reared males ofHeliothis virescens (F.) that were released in olfactometers in the laboratory were attracted to theH. virescens synthetic pheromone, but not to (Z)-9-tetradecen-1-ol formate (Z-9-TDF), or to either pheromonal component, (Z)-11-hexadecenal (Z-11-HDAL) or (Z)-9-tetradecenal (Z-9-TDAL). Also, they did not respond to the pheromone when it was dispersed simultaneously with Z-9-TDF. The proximity of the test chemicals in the olfactometer made little, if any, difference in the response ofH. virescens males to the pheromone source. Preexposure to the synthetic pheromone, Z-9-TDF, Z-11-HDAL, or Z-9-TDAL greatly reduced the number ofH. virescens males responding to the pheromone. This reduction was probably caused by habituation of the moths to these chemicals.The authors wish to thank A. H. Baumhover, E. Hart and other personnel of the Tobacco Research Laboratory, Oxford, N. C., for supplying many of the insects used in these studies.     

Chemical analysis of the pheromone blends produced by males and females of the neotropical moth,Mocis megas (Guénée) (Lepidoptera,Noctuidae, Catocalinae)

Summary Pheromonal secretions produced by females and males of the noctuid moth,Mocis megas (Guénée) have been analyzed by gas chromatography and mass spectrometry (EI (electron impact) and CI (chemical ionization)). The female sex pheromone was a blend of (Z,Z,Z) 3,6,9 heneicosatriene (55%) and (Z,Z) 3,6-cis-9S, 10R-epoxyheneicosadiene (45%). Male secretion produced at the level of a prothoracic organ was a blend of two unsaturated major hydrocarbons: (Z,Z) 6,9 heneicosadiene, (64%) and (Z,Z,Z) 3,6,9 heneicosatriene (24%) and C₁₉, C₂₀ and C₂₂ homologues (total ratio 12%), as minor components. The trienic hydrocarbon was present in both sexes. The behavioral role of this male secretion has not yet been elucidated.     

Marine eicosanoids: Occurrence of 8-(R)-HETE in the starfishPatiria miniata

Summary The first isolation of 8-(R)-hydroxy-5Z, 9E, 11Z, 14Z-eicosatetraenoic acid [8-(R)-HETE] from a marine source, the pacific starfishPatiria miniata, is reported. 8-(R)-HETE occurs together with 8-(R)-hydroxy-5Z, 9E, 11Z, 14Z, 17Z-eicosapentaenoic acid.     

Cytopathological effects of aristolochic acid on male houseflies causing sterility

Summary Feeding male houseflies with 0.075% aristolochic acid obtained from the plants of the genusAristolochia induced sterility. High condensation of chromosomes, and breakages, have been shown to be responsible for sterility. When onion roots were exposed to aristolochic acid similar chromosomal aberrations were noticed in cells at the tip.Authors are thankful to Prof. Dr G. Rücker (Universität Bonn) for a generous gift of aristolochic acid.     

Confirmation of sex pheromone biosynthesis from (16-D3)palmitic acid in the turnip moth using capillary gas chromatography

Summary (16-D₃)palmitic acid was applied topically to pheromone glands of the turnip moth. After incubation omega labeled analogues of fatty acid methyl esters and acetates were identified by gas chromatography with flame ionization detection and selected ion monitoring. The pheromone components (Z)-5-decenyl, (Z)-7-dodecenyl- and (Z)-9-tetradecenyl acetate were all biosynthesized from palmitic acid along a common pathway.     

Sex pheromones of the armyworm moth,Spodoptera exempta (Wlk.

Zusammenfassung Es wurden mit gas-chromatographischer Elektroantennogramm-Methode (Z)-9-tetradecenyl-1-acetat und (Z)-9, (E)-12-tetradecadienyl-1-acetat als die Sexuallockstoffe weiblicherSpodoptera exempta (Wlk.) identifiziert.

---

---

Acknowledgment: We are grateful to Mr.C. Rivers, Unit of Insect Virology, University of Oxford Field Station, for supplying insect pupae.     

(Z)-9-tetradecen-1-ol and (Z)-9-tetradecenyl acetate: A potent attractant system for maleSesamia cretica Led. (Lep., Noctuidae)

Summary Field studies have shown that a combination of (Z)-9-tetradecenol with (Z)-9-tetradecenyl acetate is an effective attractant for maleSesamia cretica Led., a pest of sorghum crops. These studies also indicated that the most effective composition is 7525 (alcohol:acetate).We thank Dr E. Berio for the insect determination.     

Sexual dimorphism in the lipid fraction of the defensive secretion ofGastrophysa viridula (Coleoptera: Chrysomelidae)

The lipid fraction of the defensive secretion of adultGastrophysa viridula was analyzed by gas-liquid chromatography and gas chromatography-mass spectrometry. Three long chain acetates and two methyl-branched hydrocarbons were identified and their amounts in the secretion of single field-collected and laboratory-reared beetles determined. The composition of the secretion was affected by the sex, reproductive status, and age of the beetle. The ratio of (Z)-11-eicosenyl acetate to (Z)-13-docosenyl acetate ranged from 0.30 to 0.78 in male beetles and from 1.05 to 2.06 in female beetles. The biological significance of this sexual dimorphism is discussed.     

Laboratory and field studies of the female sex pheromone of the olive moth,Prays oleae

Summary Analysis by GC-EAG indicates that abdominal tip extracts of femalePrays oleae contain a tetradecenal. Synthetic (Z)-7-tetradecenal elicits a strong EAG respones from maleP. oleae and field tests it to be comparable in attractancy with the virgin female moth. (Z)-9-Tetradecenal also produces a strong EAG response but it is not an attractant and, when added to (Z)-7-tetradecenal, markedly reduces trap catches.Acknowledgments. The authors are indebted to Mr N. Psylakis, Agricultural Research Centre, Chania, Crete, and to Dr D. Vassilopoulos, Benaki Phytopathological Institute, for providing facilities for this work. They thank the Commonwealth Institute of Entomology, London, for moth species confirmation.     

Acyl fluorides as reactive mimics of aldehyde pheromones: hyperactivation and aphrodisiac inHeliothis virescens

Summary Substitution of fluorine for the aldehydic hydrogen provides behaviorally active, chemically reactive pheromone mimics. In male moths of the tobacco budwormHeliothis virescens, Z9–14:Acf and Z11–16:Acf cause hyperactivity and irreversible extension of the genitalia in over 80% of treated moths. In addition, a combination of the two components leads to 10–50% of the pairs involving one treated partner becoming locked in copula.Supported by NSF grant PCM-8112755 and DMB-8316931, by a Fellowship from the Alfred P. Sloan Foundation (1981–85), and by Teacher-Scholar Grant from the Camille and Henry Dreyfus Foundation (1981–86) to G.D.P. Address correspondence to G.D.P.     

Methoxymercuration-demercuration and mass spectrometry in the identification of the sex pheromones ofPanolis flammea,the pine beauty moth

Summary The major components of the sex pheromone system ofPanolis flammea, pine beauty moth have been identified as (Z)-9-tetradecenyl acetate, (Z)-11-hexadecenyl acetate and (Z)-11-tetradecenyl acetate in the ratio 10051; the double bond position of these derivatives was established by microscale application of a methoxymercuration-demercuration technique and GC-MS followed by multiple ion monitoring.We thank the Science Research Council and Forestry Commission for financial support. We are grateful for the collaboration of Messrs Stoakley and Bevan, Dr C. Longhurst and Mrs J. Edwards.     

An Argentine ant aggregation factor

Summary (Z)-9-Hexadecenal, a general aggregation factor of the Argentine ant,Iridomyrmex humilis, has been isolated and chemically characterized. It is implicated as a component of the trail-pheromone complex on evidence that it is a constitutent of the ventral gland secretion, and that it both activates and attractsI. humilis workers.Acknowledgments. We thank the Australian Research Grants Committee, and the Reserve Bank of Australia, Rural Credits Development Fund for financial support.     

Marine eicosanoids: Occurrence of 8,11,12-trihydroxylated eicosanoic acids in starfishes

The occurrence of 8,11,12-trihydroxyeicosa-5,14,17(Z),9(E)-tetraenoic acid and 8,11,12-trihydroxyeicosa-5,14(Z),9E-trienoic acid in starfish species, i.e.Patiria miniata, Dermasterias imbricata, Pycnopodia helianthoides, Culcita novaeguinea andNardoa tubercolata is reported.     

Unique sex chromosome mediated behavioral response specificity of hybrid male European corn borer moths

Unlike the narrow response windows exhibited by the parent races, hybrid male European corn borers resulting from crosses of the E and Z races respond to a wide range of sex pheromone blends. The F₁ response profile consists of some individuals that respond to both the Z pheromone and the 6535 E/Z blend produced by F₁ females. Some F₁ males fail to respond to any blend and some do not respond as broadly as others. The hybrid male populations, however, are not tuned optimally to the pheromone blend produced by F₁ females and there is no coupling of F₁ blend production and response.     

Synthesis and cannabinoid receptor binding activity of conjugated triene anandamide,a novel eicosanoid

A polyenoic fatty-acid isomerase (PFI) from a red marine alga was used to convert anandamide (5Z,8Z,11Z,14Z-eicosatetraenoyl-N-ethanolamide) to the 5Z,7E,9E,14Z-eicosatetraenoyl-N-ethanolamide isomer. This novel eicosanoid, termed conjugated triene anandamide (CTA), was assessed for its ability to bind to the cannabinoid receptor in rat brain membrane preparations. CTA is a high affinity cannabimimetic substance whose novel structure provides new insight into structure-activity relationships of cannabinoid receptor ligands. These experiments illustrate the utility of enzymes isolated from marine organisms in the development of pharmacological probes.     

Regulatory steps in sex pheromone biosynthesis inMamestra brassicae L. (Lepidoptera: Noctuidae)

Summary The de novo biosynthesis of (Z)-11-hexadecenyl acetate, the most abundant pheromone component inM. brassicae, starting from acetate via palmitic acid, requires the presence of a pheromone-biosynthesis-activating neurohormone. Moreover, the conversion of palmitic acid to (Z)-11-hexadecenyl acetate is strongly dependent on the presence of the neurohormone. However, no significant dependence was found for the conversion of (Z)-11-hexadecenoic acid to (Z)-11-hexadecenyl acetate. This indicates that the neurohormonal control of pheromone biosynthesis inM. brassicae occurs at the level of palmitic acid.     

A paradoxical concentration effect in the toxicity of fentin acetate for insects

Summary Triphenyltin (fentin) acetate residues on glass resulting from the evaporation of acetonic solutions, turned out to be less toxic on contact and finally non-toxic to houseflies andSpodoptera littoralis larvae with rising concentration. This paradoxical concentration effect may be due to polymerization of the compound in concentrated solutions.Contribution from the ARO, The Volcani Center, 1976 Series, No. 106-E.