nepetalactol

Green lacewings (Neuroptera: Chrysopidae) are voracious predators of aphids and other small, soft-bodied insects and mites. Earlier, we identified (1R,2S,5R,8R)-iridodial from wild males of the goldeneyed lacewing, Chrysopa oculata Say, which is released from thousands of microscopic dermal glands on the abdominal sterna. Iridodial-baited traps attract C. oculata and other Chrysopa spp. males into traps, while females come to the vicinity of, but do not usually enter traps. Despite their healthy appearance and normal fertility, laboratory-reared C...

Structures of the iridoid synthase nepetalactol synthase in the presence of NAD(+) , NADPH or NAD(+) /10-oxogeranial were solved. The 10-oxogeranial substrate binds in a transoid-O1-C3 conformation and can be reduced by hydride addition to form the byproduct S-10-oxo-citronellal. Tyr178 Oζ is positioned 2.5 Å from the substrate O1 and provides the second proton required for reaction. Nepetalactol product formation requires rotation about C1-C2 to form the cisoid isomer, leading to formation of the cis-enolate, together with rotation about C4-C5, which enables cyclization and lactol production...

Detecting danger is one of the foremost tasks for a neural system. Larval parasitoids constitute clear danger to Drosophila, as up to 80% of fly larvae become parasitized in nature. We show that Drosophila melanogaster larvae and adults avoid sites smelling of the main parasitoid enemies, Leptopilina wasps. This avoidance is mediated via a highly specific olfactory sensory neuron (OSN) type. While the larval OSN expresses the olfactory receptor Or49a and is tuned to the Leptopilina odor iridomyrmecin, the adult expresses both Or49a and Or85f and in addition detects the wasp odors actinidine and nepetalactol...

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...

Catharanthus roseus [L.] is a major source of the monoterpene indole alkaloids (MIAs), which are of significant interest due to their therapeutic value. These molecules are formed through an intermediate, cis-trans-nepetalactol, a cyclized product of 10-oxogeranial. One of the key enzymes involved in the biosynthesis of MIAs is an NAD(P)(+) dependent oxidoreductase system, 10-hydroxygeraniol dehydrogenase (Cr10HGO), which catalyses the formation of 10-oxogeranial from 10-hydroxygeraniol via 10-oxogeraniol or 10-hydroxygeranial...

Iridoids are key intermediates required for the biosynthesis of monoterpenoid indole alkaloids (MIAs), as well as quinoline alkaloids. Although most iridoid biosynthetic genes have been identified, one remaining three step oxidation required to form the carboxyl group of 7-deoxyloganetic acid has yet to be characterized. Here, it is reported that virus-induced gene silencing of 7-deoxyloganetic acid synthase (7DLS, CYP76A26) in Catharanthus roseus greatly decreased levels of secologanin and the major MIAs, catharanthine and vindoline in silenced leaves...

Behavioral studies using an olfactometer demonstrated that sexual females (oviparae) of the damson-hop aphid,Phorodon humuli, release a pheromone to which males respond. Volatiles produced by the oviparae were analyzed by coupled gas chromatography-single cell recording from the secondary rhinaria on the male antenna and showed the presence of one peak with major activity. Coupled gas chrornatography-mass spectrometry suggested a nepetalactol, which was shown to have the 4aR, 7S, 7aS stereochemistry by synthesis from the corresponding nepetalactone isolated from the labiate plantNepeta mussinii...

Mealy plum, Hyalopterus pruni, and leaf-curl plum, Brachycaudus helichrysi, aphids are the primary arthropod pests in orchards that produce dried plums (i.e., prunes). The sexual stage of their respective lifecycles occurs on prune trees in the fall, during which time males respond to sex pheromones produced by oviparous females. Air-entrainment collections confirmed that oviparous H. pruni and B. helichrysi emitted combinations of (4aS, 7S, 7aR)-nepetalactone and (1R, 4aS, 7S, 7aR)-nepetalactol. The responses of H...

BACKGROUND: 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 ant-associated iridoids nepetalactol, actinidine, dolichodial, isoiridomyrmecin, and dihydronepetalactone were prepared from citronellal using a divergent approach. Key features include a three-step synthesis of the individual antipodes of actinidine by a novel tandem cycloaddition/pyridine formation and a facile diastereoselective synthesis of both enantiomers of dolichodial.

All aphid species studied so far share the same sex pheromone components, nepetalactol and nepetalactone. Variation by different enantiomers and blends of the two components released by different aphid species are limited and can only partially explain species-specific attraction of males to females. While some host-plant odours are known to enhance specific attraction of aphid species, herbivore-induced plant volatiles that synergise attractiveness to the sex pheromone are unknown. Here, we demonstrate that for the host-alternating rosy apple aphid (Dysaphis plantaginea (Passerini)) specificity of attraction of males to females is triggered by female-induced tree odours in combination with a 1:8 ratio of (4aS,7S,7aR)-nepetalactone and (1R,4aS,7S,7aR)-nepetalactol...

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...

Volatiles released by seedlings of Norway spruce infested with the aphid Cinara pilicornis were analyzed using SPME-GC-MS. Among the stress-induced compounds released by the host plant, citronellol, cis-trans-nepetalactone and cis-trans-nepetalactol was found. These compounds originated from the aphids and they were assumed to be pheromone components for this aphid species. To determine the relative stereochemistry of the nepetalactone, a diagnostic method was developed. The method was based on multivariate analysis of tabulated relative intensities of mass fragments of the four nepetalactone diastereomers...

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...

The bird cherry-oat aphid, Rhopalosiphum padi (L.), and the damson-hop aphid, Phorodon humuli (Schrank), migrate at the same time of year and colonize closely related Prunus spp. as primary hosts, but utilize (1R,4aS,7S,7aR)-nepetalactol and (1RS,4aR,7S,7aS)-nepetalactol, respectively, as sex pheromones. Interactions between these sex pheromones and benzaldehyde and methyl salicylate, plant volatiles common to primary hosts of both species, were investigated to assess whether they confer reproductive isolation between these species...

The lacewing Chrysopa septempunctata Wesmael is an important, common predator of several insects in China, Japan, Russia, and many parts of Europe. Our field trapping experiments in northeast China showed that males of this green lacewing are strongly attracted to the lacewing pheromone of Chrysopa oculata Say, (1R,2S,5R,8R)-iridodial. The induced plant volatile, methyl salicylate, was unattractive to C. septempunctata by itself at the concentration tested, but synergistic when combined with iridodial where the lacewing population was high...

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...

It is well documented that host-related odors enable many species of parasitoids and predatory insects to locate their prey and prey habitats. This study reports the first characterization of prey and prey host odor reception in two species of lacewings, Chrysoperla carnea (Say) and Chrysopa oculata L. 2-Phenylethanol, one of the volatiles emitted from their prey's host plants (alfalfa and corn) evoked a significant EAG response from antennae of C. carnea. Traps baited with this compound attracted high numbers of adult C...

Electroantennogram (EAG) responses were recorded from alate fundatrigeniae (spring migrants), gynoparae (the winged female form that produces sexual females) and males, the three migratory forms of the damson-hop aphid, Phorodon humuli (Schrank). EAG responses of gynoparae and males showed typical dose response characteristics to (E)-2-hexenal, (-)-R-carvone, hexanenitrile and (1RS,4aR,7S,7aS)-nepetalactol, the sex pheromone of this species. The 34 plant volatiles elicited broadly similar EAG response profiles in the three migratory forms...

Gas chromatographic-electroantennographic detection (G3C-EAD) experiments showed that antennae of males and females of the goldeneyed lacewing, Chrysopa oculata Say (Co. = Chrysopa), consistently responded to four compounds extracted from the abdominal cuticle of males:nonanal, nonanol, nonanoic acid, and (1R*,2S*,5R*,8R*)-iridodial. These compounds were not detected from abdominal cuticle of females. Thoracic extracts of both sexes contained antennal-stimulatory 1-tridecene and EAD-inactive skatole. Chrysopa oculata adults were most sensitive to (1R,2S,5R,8R)-iridodial standard at an EAD-response threshold between 0...