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  • 1
    ISSN: 1573-1561
    Keywords: snakes ; prey preference ; chemical senses ; Natrix ; chemical cues ; predator-prey ; ecology ; adaptation
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Three populations of the water snake,Natrix s. sipedon, were tested for their responses to surface water extracts prepared from various prey species. It was clearly shown that these snakes can distinguish between different prey genera on the basis of chemical cues alone. Adult snakes caught at a fish hatchery where goldfish (Carassius auratus) were abundant responded most to goldfish extract, as did laboratory-born snakes reared on goldfish for one year. However, snakes caught in a relatively undisturbed mountain stream environment and naive young born to a mountain female responded more to the extracts of various sympatric-mountain fish and amphibians. The evidence indicates that newborn snakes have genetic predispositions for sympatric species of the classes of prey normally eaten. These preferences can be enhanced or inhibited during ontogeny.
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  • 2
    ISSN: 1573-1561
    Keywords: biocommunication ; defensive secretions ; Gyrinidae ; norsesquiterpenes ; gyrinidal ; isogyrinidal ; gyrinidone ; gyrinidione ; steroid anesthesia
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract By use of a minnow bioassay, toxins were detected in the pygidial secretions of the gyrinid beetlesDineutus assimilis (Kirby) andDineutus nigrior Roberts. The active agents, which may be largely responsible for the relative immunity of the Gyrinidae from predation, were isolated and identified as the norsesquiterpenesgyrinidione [(E)-1-methyl-2-formyl-3-(1′-methylhex-3′-ene-2′,5′-dione)-cyclopentane],gyrinidone [(E,Z)-2-hydroxy-5,9-dimethyl-4-(but-1′-ene-3′-one)-3-oxo-bicyclo[4.3.0]-non-4-ene],gyrinidal [(E,E,E)-3,7-dimethyl-8,11-dioxo-2,6,9-dodecatrienal], andisogyrinidal[(E,E,Z)-3,7-dimethyl-8,11-dioxo-2,6,9-dodecatrienal]. Since gyrinidione and isogyrinidal are being reported for the first time, their physical and chemical properties are presented and biosynthetic relationships of the four norsesquiterpene structures are discussed. About 50% of the beetle defensive material was norsesquiterpenes, 25% polar lipids, and 20% could not be extracted from water into chloroform. As quantified by gas-liquid chromatography,D. assimilis contained 245±73 μg andD. nigrior 144±64 μg norsesquiterpenes per individual. The average relative composition of norsesquiterpenes in the pygidial secretions of both beetle species was constant: isogyrinidal, 6%; gyrinidone, 7%; gyrinidione, 36%; and gyrinidal, 48%. When administered externally in solution to fish, isolated norsesquiterpenes possessed narcotic and toxic activity similar to that of the anesthetic steroids deoxycorticosterone (DOC) and testosterone. Minnow dose-response curves demonstrated that gyrinidione and gyrinidal (LC100=ca. 2 μg/ml) were as toxic to fish as was DOC (LC100=ca. 3 μg/ml). Gyrinidone was less toxic (LC100=ca. 15 μg/ml) while isogyrinidal was relatively inactive (LC100=ca. 90 μg/ml).
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  • 3
    ISSN: 1573-1561
    Keywords: Tortricidae ; redbanded leafroller ; sex pheromone ; sex attractant ; synergist ; inhibitor ; Argyrotaenia velutinana
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Secondary pheromone components of the redbanded leafroller from female moth extracts have been identified as dodecyl acetate andtrans-11-tetradecenyl acetate (t11–14∶Ac). The ratio of t11–14∶Ac to the primary pheromone componentcis-11-tetradecenyl acetate wasca. 9∶91 in abdominal tip extracts and 12∶88 in female effluent collections, whereas the optimal ratio for attraction in field test was 6∶94 in the spring flight and 6–10∶94-90 in the summer flight. Dodecyl acetate was collected from calling females in ratios to the 14-carbon acetates as high as 5∶:4; in field tests these chemicals were the most attractive in ratios of 3∶2 and 2∶1.
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  • 4
    ISSN: 1573-1561
    Keywords: deer ; mammals ; odor preference ; odor specificity ; olfactory discrimination ; pheromone ; sexual isolation ; social odor ; tarsal scent
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Two subspecies of deer, black-tailed deer (Odocoileus hemionus columbianus) and Rocky Mountain mule deer (O. h. hemionus) were exposed to the tarsal scents of both subspecies in a social setting. The scent was sprayed on one individual in a group. The responses, consisting of sniffing, licking, and following, were stronger to each subspecies' own tarsal scent. This discrimination may be important for sexual isolation in areas where the ranges of the two species overlap.
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  • 5
    ISSN: 1573-1561
    Keywords: honey bee ; queen ; drone ; worker ; pheromones ; sex attraction ; swarm attraction ; bioassay ; (E)-9-oxo-2-decenoic acid ; (E)-9-hydroxy-2-decenoic acid
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Synthetic (E)-9-oxo-2-decenoic acid (9-ODA) was as attractive to drones as ether extracts of queen heads, suggesting that 9-ODA is the component of the sex pheromone that attracts drones from a distance. However, other substances produced in the heads of both virgin and mated queens cause drones to hover near a lure. Positive anemotaxis and short-range visual stimuli are also involved in the mate-finding process. “Keeper” substances ensure the gradual release of the pheromone. (E)-9-Hydroxy-2-decenoic acid (9-HDA) did not attract drones from a distance or affect their behavior near a lure. Synthetic 9-ODA was slightly attractive to worker bees from a queenless swarm and 9-HDA was not attractive. However, ether extracts of whole queens or queen heads contain unidentified substances that are highly attractive. These are produced more abundantly by mated laying queens than by virgin queens.
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  • 6
    Electronic Resource
    Electronic Resource
    Springer
    Journal of chemical ecology 1 (1975), S. 171-182 
    ISSN: 1573-1561
    Keywords: allelopathy ; Celtis laevigata ; forest community ; phenolic ; ferulic acid ; caffeic acid ; gentistic acid ; p-coumaric acid ; scopolin ; scopoletin ; phytotoxins
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Hackberry was previously found to produce toxins that inhibit the growth of associated herbaceous species in a grassland community. Nevertheless, it was hypothesized that bare areas under hackberry trees in a bottomland forest community may not be caused by allelopathy, since inhibitory compounds may be leached or metabolized faster than in a grassland community. Investigations indicated that the relatively bare areas under hackberry were not due to competition for minerals, light, or water, or to differences in texture or pH. The percent of soil moisture was always higher under hackberry trees than under bur oak trees where herbaceous species were prominent. Decaying hackberry leaves, leaf leachate, and soil collected from under hackberry trees significantly reduce seed germination and seedling growth of test species. Ferulic, caffeic, gentisic, andp-coumaric acids, and scopolin, and scopoletin were identified as phenolic phytotoxins produced in hackberry leaves. Thus it appears that the reduced growth of herbaceous vegetation associated with hackberry trees in both grassland and forest communities is due primarily to allelopathy, with the initial inhibition being accentuated by competition.
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  • 7
    ISSN: 1573-1561
    Keywords: face fly ; Musca autumnalis De Geer ; pheromone ; sex pheromone ; behavioral bioassay ; (Z)-14-nonacosene ; (Z)-13-nonacosene ; (Z)-13-heptacosene ; mating strike
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Components of a sex pheromone that cause male face flies to strike at females were found to be the straight-chain monoalkenes (Z)-14-nonacosene, (Z)-13-nonacosene, and (Z)-13-heptacosene. Although these compounds were found in the extracts of both sexes, extracts from sexually mature males contained a much higher proportion of nonacosane and heptacosane, which attenuated the activity of the active monoalkenes. The monoalkenes were readily synthesized by a Wittig reaction modified by the use of hexamethylphosphoric triamide as a cosolvent with tetrahydrofuran to produce a product containing 94–96% (Z) isomer.
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  • 8
    ISSN: 1573-1561
    Keywords: sex pheromone ; sex attractant ; Argyrotaenia citrana ; orange tortrix moth
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Female orange tortrix,Argyrotaenia citrana (Fernald), abdominal tip extracts, and effluvia were analyzed, and two pheromone components were identified ascis-11-tetradecenal (c11–14∶ALD) andcis-11-tetradecenyl acetate (c11–14∶Ac). Female extracts contained such very low quantities of c11–14∶ALD relative to c11–14/∶Ac that the aldehyde was frequently undetectable, whereas female effluvia contained these compounds in a ratio of ca. 15∶1. Field attractancy tests showed that traps baited with c11–14∶ALD were attractive, whereas c11–14∶Ac possessed no intrinsic attractiveness. Additionally, traps containing c11–14∶ALD in a range of ratios to the component c11–14∶ Ac (5∶1 to 1∶10) are more competitive forA. citrana males than are live female traps. The females produce purecis isomers (〈0.5%trans), and addition of 〉5% t11–14∶ALD (the geometric isomer of the primary component) reduces attractancy, whereas addition of t11–14∶Ac (the geometric isomer of the secondary component) apparently does not affect attractancy significantly unless c11–14∶Ac is absent.
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  • 9
    ISSN: 1573-1561
    Keywords: Nassarius obsoletus ; Littorina littorea ; Modiolus demissus ; alarm pheromone
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Chemotactic responses of the salt marsh mud snailNassarius obsoktus were tested in the field, to the introduction of a crushed conspecific and to the sympatric gastropodLittorina littorea and the bivalveModiolus demissus. The snails responded with burial and escape to the conspecific stimulus, with strong attraction and feeding toM. demissus, and with attraction and feeding toL. littorea. In blank tests, the numbers of snails fluctuated only slightly during half-hour observation periods. An alarm substance appears to be liberated from woundedN. obsoletus which causes rapid disappearance of conspecific snails in an area of up to 50 cm radius.
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  • 10
    ISSN: 1573-1561
    Keywords: keto-esters ; mass spectra ; insect waxes ; exocrine secretions ; defensive substances
    Source: Springer Online Journal Archives 1860-2000
    Topics: Biology , Chemistry and Pharmacology
    Notes: Abstract Wax (mp 102–103 °C) taken from the cochineal insectDactylopius confusus was saponified to give 11-oxotriacontanoic acid (1) and 15-oxotetratriacontanol (3) in good yields. The structure of these hydrolysis products follows most directly from examination of the mass spectra of the corresponding methyl ester (2) and acetate (4). These spectra are dominated by McLafferty rearrangements initiated by the ketonic carbonyl groups, and resulting in preferential loss of the unfunctionalized hydrocarbon end of the long-chain esters. The structures are confirmed by synthesis of both hydrolysis products via reaction of di-n-nonadecyl cadmium with the appropriate acid chlorides and of the C64 wax ester (5) itself by acid-catalyzed condensation of these moieties. Mass spectral examination of the cochineal wax previously characterized as 15-oxotetratriacontanyl 13-oxodotriacontanoate on the basis of purely chemical evidence confirms the assignment, and the Wooly Alder AphidProciphilus tessalatus is now found to produce the same C66 keto-ester.
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