Nachweis einer durch symbiontische Mikroorganismen bewirkten Sterinsynthese in künstlich ernährten Aphiden (Homoptera,Rhynchota, Insecta)

Summary Up to now the aphid,Neomyzus circumflexus Bckt., has been reared on a synthetic, sterile diet for 11 successive generations. The culture is still going. The defined diet contains no sterol or any other lipid. Nevertheless the sterol content of the artificially fed aphids remains constant over 8 generations. Ingestion of sodium acetate-1-C¹⁴ with the diet by the aphids leads to the appearance of a labelled sterol in the tissues of the insects. Incorporation of radioactivity into sterols was not found in aphids free of symbionts.     

A reinvestigation of the chemistry of the Dufours gland of the formicine ant,Anoplolepis custodiens

The components of individual Dufours glands excised fromAnoplolepis custodiens workers were analysed by GC-MS. In addition to then-alkanes andn-alkenes previously reported² in these glands, primary alcohols (C₁₉-C₂₂), secondary alcohols (C₂₀-C₂₃), 2-ketones (C₂₀-C₂₃) and possibly carboxylate ethyl esters (C₁₉ and C₂₁) were identified as components of these glands. It seems possible that these high-boiling compounds are used by the workers in laying trails on the hot sandy surfaces of their characteristic habitat and in lining of the inner walls of nests, but no standard compounds have been available to us for any behavioral studies.     

Sterols of the lobster (Homarus americanus) and the shrimp (Pandalus borealis)

Summary In this study we have analyzed the sterol compositions of two continental shelf species of crustacea, the lobster (Homarus americanus) and the shrimp (Pandalus borealis). Cholesterol was found to be the most abundant sterol in these two species with smaller amounts of desmosterol, 24-methylcholesterol, 24-ethylcholesterol, 24-methylenecholesterol and 22-dehydrocholesterol. Woods Hole Oceanographic Institution Contribution Number 3494. This work was supported by the Office of Sea Grant of the National Oceanic and Atmospheric Administration, U.S. Department of Commerce. Special thanks are extended to Ms.R. Beebe-Center, who was responsible for a large part of the isolation work described here.     

Transfer of secondary metabolites from the spongesDysidea fragilis andPleraplysilla spinifera to the mantle dermal formations (MDFs) of the mudibranchHypserlodoris webbi

The opisthobranch molluscHypselodoris webbi is able to select, among its potential preys, sponges chemically rich in furanosesquiterpenoids. The sequestered secondary metabolites act as defensive allomones against predators and are accumulated in some dorsal glands (MDFs). This transfer from sponges to MDFs has been proven by maintainingH. webbi together with some selected sponges in an aquarium for a prolonged period.     

The male pheromone of the old house borerHylotrupes bajulus (L.) (Coleoptera: Cerambycidae): Identification and female response

We report here the identification of the long-range, male-produced sex pheromone of the Old house borerHylotrupes bajulus. Chemical analysis of hexane extracts obtained by surface extraction from dissected prothoracic glands and from headspace samples of the two sexes, revealed male-specific compounds: (3R)-3-hydroxy-2-hexanone, 2-hydroxy-3-hexanone, the diastereomeric diols (2R, 3R)-2,3-hexanediol and (2S, 3R)-2,3-hexanediol, 2,3-hexanedione, as well as 1-butanol.In wind tunnel bioassays we tested the influence of these male-specific compounds from the prothoracal glands on the behaviour of unmated and mated females. Specific behavioural sequences of the tested females (activity, running behaviour, searching, cleaning, flying, extension of ovipositor) were recorded. Unmated females were attracted by male beetles, headspace extracts of males, synthetic blends of the major pheromone compounds as well as by the components (3R)-3-hydroxy-2-hexanone, and the diastereomeric diols. Hexane, female beetles and 2,3-hexanedione did not attract unmated females. The reactions of mated females to male beetles and headspace samples did not differ significantly from those of the controls.The results of the bioassays show that the two-stage premating behaviour is initiated by emission of a long-range sex pheromone from the male prothoracal glands, which functions as an activator, attractant, and possibly aphrodisiac for unmated females.     

Pectinoacetals A-C: novel sterol hemiacetals from the gorgonianCtenocella pectinata

Three polyhydroxylated sterol hemiacetals, pectinoacetals A-C (1–3) have been isolated as their acetyl derivatives (4–6) from the acetic anhydride treated organic extract of the Indo-Pacific gorgonianCtenocella pectinata. These natural products were found to undergo very rapid epimerization at the C-18 chiral center and thus exist only as an equilibrium mixture of two diastereomers. The structure assignments are based on spectral studies and chemical modifications of the natural products.     

In vitro biosynthesis of juvenile hormone III by the corpora allata ofCalliphora vomitoria and its role in ovarian maturation and sexual receptivity

Summary JH III is the only JH detected by GLC-MS in medium from in vitro incubations of corpora allata of adult females ofCalliphora vomitoria. When corpora allata were removed from females at various times during the reproductive cycle and the JH III produced by the glands in vitro measured by a JH III radioimmunoassay, an increase in the level of synthesis was found to occur before previtellogenesis (0–24 h). A second increase appeared at the onset of vitellogenesis (72–83 h) and continued until the end of vitellogenesis (96 h) and the occurrence of chorionation (120 h). Since sexual receptivity develops with vitellogenesis, the significantly higher levels of JH III biosynthesis in vitro at this time supports a possible role for JH in the acquisitive of receptivity.     

Conversion of clionasterol into both fucosterol and isofucosterol by the insectTenebrio molitor

Summary [7,7-³H₂]Clionasterol was synthesized and fed, together with [4-¹⁴C]sitosterol, toTenebrio molitor larvae; fucosterol and isofucosterol, recovered from the sterol fraction were found to be doubly labeled, indicating that clionasterol is converted into both the ethylidenic compounds.     

Photoperiodic induction of diapause in an insect is vitamin A dependent

Summary A photoperiodic response was found to be absent in larvae of the parasitoid waspApanteles glomeratus when its host (caterpillars ofPieris brassicae) was reared on a low-carotenoid artificial diet. Addition of vitamin A to the host's diet restored the response to short-day photoperiods in the wasp larvae, thus showing that vitamin A is essential for photoperiodic induction of diapause. Possibly vitamin A or a derivative of vitamin A functions as the photoreceptor pigment for the photoperiodic reaction in this species of insect.     

Ecdysteroids in vitro promote differentiation in the accessory glands of male mealworm beetles

Summary Physiological peak doses of 20-hydroxyecdysone were added to organ cultures of young pupal accessory glands of maleTenebrio molitor. During subsequent culture in vitro or in vivo, the glands accumulated adult-specific antigens. Control organ cultures showed no such antigen accumulation. In this system, ecdysteroid controls not only cell cycles but also differentiation.21 October 1986This research was supported in part by a National Institutes of Health Research Service Award F32 AM7515 (KAG) and NIH grants GM26140 and AI15662 (GMH). We thank Toshinobu Yaginuma for help in developing the transplantation technique.     

Biotransformation of a dietary sesterterpenoid in the Mediterranean nudibranchHypselodoris orsini

The metabolic relationship between the marine molluscHypselodoris orsini and the spongeCacospongia mollior has been reinvestigated. The predator-prey association has been confirmed even though the metabolic patterns of the two invertebrates are substantially different. Most probably the nudibranch converts the main sponge metabolite, the sesterterpenoid scalaradial (1), into a less oxygenated related metabolite, deoxoscalarin (4), followed by a second chemical transformation leading to a new sesterterpenoid, 6-keto-deoxoscalarin (5) which is selectively compartmentalized into some dorsal glands, mantle dermal formations (MDFs), strategically distributed near the gills. 6-keto-deoxoscalarin (5) has been characterized by 1D and 2D NMR methods. Finally, the unusual association of some Chromodorididae molluscs with sponges containing sesterterpenoids suggests a further analysis of their taxonomical collocation is required.     

Effect of dietary antagonists and corresponding nutrients on growth and reproduction of the flour mite (Acarus siro L.)

The flour miteAcarus siro L. (Acaridae, Astigmata) was reared on an axenic diet with the addition of various nutrient antagonists, with and without supplementation by the corresponding nutrients. The deficiency symptoms induced by dietary antagonists, and the reversibility of the former by nutrient administration, indicated that folic acid, riboflavin, thiamine, niacin, pyridoxine, biotin and a sterol are essential for the growth and reproduction of the flour mite. It was also demonstrated that the population density and generation sequence of this species can be suppressed to the level of acaristasis by nutrient antagonists, owing to inhibited nutrient utilization.Durch die Zugabe von Antiwuchsstoffen können wir nachweisen, daß das Wachstum der betreffenden Organismen gehemmt wird, und daß diese Hemmung durch die Zugabe des entsprechenden Wuchsstoffes wieder aufgehoben wird.Nielsen, N., Wuchsstoffe und Antiwuchsstoffe der Mikroorganismen. Verlag Gustav Fischer, Jena 1945.     

Makisterone A and 24-methylenecholesterol from the ovaries of the honey bee,Apis mellifera L

Summary Makisterone A, a 28-carbon ecdysteroid (molting hormone) has been isolated from the ovaries of queen bees. Analysis by reversed-phase and silica high performance liquid chromatography (HPLC) in conjunction with a radioimmune assay (RIA) revealed about 11 ng of makisterone A present per gram of ovaries on a fresh weight basis. No C₂₇ ecdysteroids were detected. The predominant neutral sterol present was 24-methylenecholesterol.     

7-Dehydrosterols in prothoracic glands of the silkworm,Bombyx mori

Summary Sterol analysis of prothoracic glands of the silkworm,Bombyx mori revealed the presence of 7-dehydrocampesterol and 7-dehydrositosterol together with 7-dehydrocholesterol. It was also found that the amounts of these 7-dehydrosterols were increased in proportion to the ecdysone titer.     

Sex pheromone blend of the codling moth,Cydia pomonella: Evidence for a behavioral role of dodecan-1-ol

Summary Pheromone glands and effluvia of the codling moth female containE-8, E-10-dodecadien-1-ol as main component, accompanied by its geometric isomers, the corresponding acetate and aldehyde (both in gland extracts only),E-9-dodecen-1-ol and saturated alcohols of 10 to 18 carbons. Dodecan-1-ol as the most abundant secondary component (about 30% of the female blend) acts in the wind tunnel by widening the dose range over which codling moth males are optimally attracted toE-8, E-10-dodecadien-1-ol.This research was supported by the Swiss National Science Foundation. We thank W. Riggenbach for supplying moths and T. Wildbolz, P. Charmillot and M. Tóth for conducting field trials.     

A simple method for in vivo testing of glandular enzymatic activity on potential precursors of larval defensive compounds inPhratora species (Coleoptera: Chrysomelinae)

The presence of glandular -glucosidase and oxidase-specific activities, and the possible role of phenolglucosides and related compounds as precursors for larval defensive compounds, were directly demonstrated by introducing salicin, saligenin and helicin into the defensive glands ofPhratora species.Ph. tibialis andPh. laticollis that normally secrete endogenously-produced iridoid monoterpenes and do not use phenolglucosides from their food sources as precursors, were able to produce salicyladehyde from helicin when the latter was introduced into the defensive glands.     

Brain factor fromGalleria mellonella (Lepidoptera) stimulating silk gland activity

Brain extracts from day 1–4 last instar larvae ofGalleria mellonella (Lepidoptera) stimulate RNA synthesis in cultured silk glands from day 3 last instar larvae. When the fibroin-synthesizing posterior parts of silk glands were incubated for 3 h in vitro in the presence of brain extract (0.1 brain equivalent), [³H]-uridine incorporation into RNA was stimulated more than twofold. The stimulating effect of brain extract showed a dose response relationship. It is suggested that the heat-resistant and protease-sensitive brain factor is a peptide.     

3-Ethyl-2,5-dimethylpyrazine,a component of the trail pheromone of the antMessor bouvieri

Summary 3-Ethyl-2,5-dimethylpyrazine, found in the poison gland of workers, induces trail following in the Mediterranean harvester antMessor bouvieri. The poison gland contains on average 9 ng of this trail pheromone component. The alkaloids anabasine and anabaseine are also present in this gland, but induce no reaction in workers. Trail following is also induced by substances present in the Dufour gland, but the combined effect of both glands shows no synergism.     

Origin and identification of bacteria which produce kairomones in the frass ofAcrolepiopsis assectella (Lep., Hyponomeutoidea)

The volatiles used by the parasitoidDiadromus pulchellus to find its host, the leek moth, are produced by the bacteria developing in the frass of the host larvae. The origin and the nature of these bacteria were investigated. Samples were taken from healthy leeks and from infested leeks in the field, as well as from the frass of larvae reared in the laboratory either on the host plant or on an artificial diet. The various species of bacteria identified were cultured in the presence of precursors of leek sulphur volatiles and their volatile emissions were analysed.Klebsiella oxytoca and variousBacillus, common decomposers of plant matter, were the principal species producing active volatiles which were alkyl disulphides.     

Accumulation of phenylpropanoids in the rectal glands of males of the Oriental fruit fly,Dacus dorsalis

Summary Two phenylpropanoid compounds, 2-allyl-4,5-dimethoxyphenol(II) and coniferyl alcohol(III), were characterized from body tissue of wild males of the Oriental fruit fly,Dacus dorsalis. These compounds accumulated in the rectal glands only when laboratory-reared males were fed with methyl eugenol. Compound II was released into the air during dusk, which coincides with the fly courtship period. Pheromonal and allomonal effects of the phenylpropanoids were examined.