nepetalactol and nepetalactone

Common green lacewings (Chrysoperla carnea complex) form a group of generalist predators important for biological control. Several reports show attraction of these insects to plant volatiles, and a highly attractive ternary compound floral bait has been developed. With aphids being a preferred prey of larvae, one might expect these lacewings to be attracted to aphid semiochemicals, for instance, to aphid sex pheromones, as found for several other green lacewing species. However, in a previous study, we found that traps containing aphid sex pheromone compounds (1R,4aS,7S,7aR)-nepetalactol (NEPOH), (4aS,7S,7aR)-nepetalactone (NEPONE), and a ternary floral bait attracted fewer individuals than those containing the ternary floral bait alone. In the present study, possible causes for this effect of NEPOH and NEPONE on trap capture were studied. We established that C. carnea complex catches in traps with a ternary floral lure were not influenced by the presence of Chrysopa formosa individuals in traps (attracted by NEPOH and NEPONE) or by synthetic skatole (a characteristic component of Chrysopa defense secretion). A direct negative effect of NEPOH and NEPONE on attraction of C. carnea complex was found, suggesting active avoidance of these aphid sex pheromone components. This finding is surprising as the larvae of these lacewings prey preferentially on aphids. Possible mechanisms underlying this phenomenon are discussed.

Topics: Animals; Aphids; Bridged Bicyclo Compounds, Heterocyclic; Cyclopentane Monoterpenes; Cyclopentanes; Female; Flowers; Food Chain; Insecta; Larva; Male; Nepeta; Oils, Volatile; Pest Control, Biological; Predatory Behavior; Pyrones; Sex Attractants

The deployment of synthetic attractants for the manipulation of lacewing populations as aphid predators is currently used in integrated pest management. This study investigates a synthetic bait comprising floral compounds previously found to attract the Chrysoperla carnea complex, and, for the first time, the aphid sex pheromone components (1R,4aS,7S,7aR)-nepetalactol and (4aS,7S,7aR)-nepetalactone, in field experiments in Hungary, for their ability to manipulate lacewing populations.. The synthetic floral bait attracted both sexes of the Chrysoperla carnea complex, and Chrysopa formosa Brauer showed minimal attraction. The aphid sex pheromone compounds alone attracted males of C. formosa and C. pallens (Rambur). When the two baits were combined, Chrysopa catches were similar to those with aphid sex pheromone baits alone, but carnea complex catches decreased significantly (by 85-88%).. As the floral bait alone attracted both sexes of the carnea complex, it showed potential to manipulate the location of larval density via altering the site of oviposition. Aphid sex pheromone compounds alone attracted predatory males of Chrysopa spp. and can potentially be used to enhance biological control of aphids. For the carnea complex, however, a combination of both baits is not advantageous because of the decrease in adults attracted. Assumptions of intraguild avoidance underlying this phenomenon are discussed.

Topics: Animals; Bridged Bicyclo Compounds, Heterocyclic; Cyclopentane Monoterpenes; Cyclopentanes; Female; Hungary; Insect Control; Insecta; Male; Nepeta; Plant Extracts; Pyrones; Sex Attractants

The sex pheromones of many aphid species from the subfamily Aphididae comprise a mixture of the iridoids (cyclopentanoids) (1R,4aS,7S,7aR)-nepetalactol and (4aS,7S,7aR)-nepetalactone. In this paper, we investigate whether other chemicals, in addition to nepetalactol and nepetalactone, are released from Dysaphis plantaginea (rosy apple aphid) oviparae as part of their sex pheromone. Four compounds present in an air entrainment sample collected from D. plantaginea oviparae feeding on apple (Malus silvestris c.v. Braburn) elicited electrophysiological responses from male D. plantaginea. Active peaks were tentatively identified by gas chromatography (GC) coupled with mass spectrometry, with identification confirmed by peak enhancement with authentic compounds on GC columns of different polarities. The electroantennography-active chemicals were (1R,4aS,7S,7aR)-nepetalactol, (4aS,7S,7aR)-nepetalactone, (1S,2R,3S)-dolichodial, and phenylacetonitrile. (1S,2R,3S)-Dolichodial elicited a behavioral response from male D. plantaginea and naïve-mated female parasitoids, Aphidius ervi. This is the first report of electrophysiological and behavioral responses from any aphid morph to (1S,2R,3S)-dolichodial. Whether or not (1S,2R,3S)-dolichodial is a third component of the aphid sex pheromone is discussed.

Topics: Animals; Aphids; Bridged Bicyclo Compounds, Heterocyclic; Cyclopentane Monoterpenes; Cyclopentanes; Electrophysiological Phenomena; Female; Hymenoptera; Male; Monoterpenes; Pest Control; Pyrones; Sex Attractants; Sexual Behavior, Animal

Insect communication is primarily via chemicals. In Aphidinae aphids, the structure and ratio of iridoid (monoterpenoid) chemicals are known to be important components of the sex pheromone. However, for enhanced species specificity, it has been suggested that release of sex pheromone might be restricted to a narrow time period within the diel cycle. Here, we determine the structure, ratios and release patterns of iridoid chemicals produced by a serious global pest, the rosy apple aphid, Dysaphis plantaginea. Volatiles were collected from batches of oviparae (sexual females) and chemicals identified by gas chromatography, mass-spectrometry and microscale NMR spectroscopy. (1R,4aS,7S,7aR)-Nepetalactol and (4aS,7S,7aR)-nepetalactone were detected in a 3.7:1 ratio. To investigate timing of release, we constructed a sequential sampling device that allowed volatile chemicals to be captured hourly from 95 same-aged oviparae over 20 consecutive days. Release patterns of the two sex pheromone components show that D. plantaginea oviparae release high levels of the two components during photophase and low levels during scotophase. Release of the two components increased significantly during the first 3 h of photophase and thereafter remained at a high level until the onset of scotophase. The ratio of (1R,4aS,7S,7aR)-nepetalactol to (4aS,7S,7aR)-nepetalactone released did not change significantly between days two to 14 of the adult stadium, but from the 15th day onward there was a significant decrease in the relative amount of (1R,4aS,7S,7aR)-nepetalactol. Pheromone release was greatest on the eighth day of the adult stadium, with up to 8.4 ng of pheromone released per ovipara per hour. This is the first report on the full structural identification and ratios of volatile iridoid components collected from D. plantaginea oviparae and is also the most detailed temporal study on sex pheromone release from any aphid species. The lack of a temporally narrow and distinct period of very high sex pheromone release suggests that alternative mechanisms or factors for species recognition and isolation may be important. Findings are discussed broadly in relation to the biology of the aphid.

Topics: Animals; Aphids; Bridged Bicyclo Compounds, Heterocyclic; Cyclopentane Monoterpenes; Cyclopentanes; Darkness; Female; Magnetic Resonance Spectroscopy; Protons; Pyrones; Sex Attractants; Sexual Behavior, Animal

Three nepetalactones were isolated from Nepeta racemosa (mussinii) by traditional methods. An improved method was developed to isolate nepetalactones from N. faassénii. An epimerization procedure was used to prepare the fourth 7S-nepetalactone diastereomer. The cis-fused nepetalactols were prepared by reduction of the corresponding nepetalactones, while the trans-fused nepetalactols were unstable and found to undergo ring-opening reactions yielding iridodials. The characterizations and structural assignments by means of NMR agree with quantum chemical density functional calculations.

Topics: Animals; Aphids; Bridged Bicyclo Compounds, Heterocyclic; Cyclopentane Monoterpenes; Cyclopentanes; Models, Molecular; Molecular Structure; Nepeta; Nuclear Magnetic Resonance, Biomolecular; Pyrones; Sex Attractants; Stereoisomerism

Females of the potato aphid Macrosiphum euphorbiae exhibit typical calling behavior, with virgin female oviparae raising their back legs off the substrate to release sex pheromone from glands on the tibia. Airborne collections from calling oviparae were analyzed by GC and GC-MS to determine if, like the majority of aphids examined to date, they produced (1R,4aS,7S,7aR)-nepetalactol (1) and (4aS,7S,7aR)-nepetalactone (2). Both components were present and produced in ratios that varied with age from 4:1 to 2:1. The relative stereochemical configurations of these components were determined by GC-coinjection of the aphid-derived sample with synthetic standards on both HP-1 and DB-Wax GC columns. The absolute stereochemical configuration of the nepetalactol (determined from approximately 15 microg of material in an air entrainment sample) was determined as (1R,4aS,7S,7aR)-1 by derivatization of the aphid sample with (S)-(+)-alpha-methoxy-alpha-(trifluoromethyl)phenylacetyl chloride (Mosher's acid chloride) to generate a diastereoisomer that was compared to synthetic samples by NMR spectroscopy and GC. In bioassays in the wind tunnel, M. euphorbiae males responded to potato plants with oviparae but not to unattacked plants or those infested with parthenogenetically reproducing apterae. In no-choice laboratory bioassays, the same level of male response was observed to virgins and to the 3:1-5:1 synthetic blends of nepetalactol (1):nepetalactone (2). However, the time taken to reach the source was significantly less to virgin females than to the synthetic pheromone blends. In all cases, males walked rather than flew to the source. Males showed lower responses to a 1:1 synthetic mixture and did not respond to either of the components when presented alone. Under field conditions, few M. euphorbiae males were captured in traps baited with different ratios of the synthetic pheromone. Possible reasons for the different responses under laboratory and field conditions are discussed.

Topics: Animals; Aphids; Bridged Bicyclo Compounds, Heterocyclic; Cyclopentane Monoterpenes; Cyclopentanes; Female; Gas Chromatography-Mass Spectrometry; Magnetic Resonance Spectroscopy; Male; Molecular Conformation; Molecular Structure; Pyrones; Sex Attractants; Sexual Behavior, Animal; Solanum tuberosum; Species Specificity