In vitro degradation of 10 mono‐ and sesquiterpenes of plant origin by caprine rumen micro‐organisms

The extent of disappearance of 10 mono‐ and sesquiterpenes in presence of mixed rumen micro‐organisms has been measured in 24‐h batch cultures. The molecules that were tested are frequently found in the plants consumed by ruminants in highland pastures (limonene, β‐myrcene, β‐ocimene, α‐pinene, sabinene, γ‐terpinene and thymol) or are potential markers of the diet (camphene, β‐caryophyllene and α‐copaene). All terpenes were tested at 2 µL mL^?1, except α‐copaene and thymol, which were tested at 0.9 µL mL^?1 and 2 mg mL^?1, respectively. Camphene and thymol were not degraded to a significant extent. The disappearance of part of β‐caryophyllene, (?)‐limonene and γ‐terpinene could not be attributed to the direct action of rumen micro‐organisms but rather than to an effect of the extracellular medium. In contrast, a third group of one sesquiterpene (α‐copaene) and four monoterpenes (myrcene, β‐ocimene, α‐pinene and sabinene) was extensively degraded by rumen micro‐organisms, at rates of 1.6, 4.5, 3.5, 4.8 and 5.4 µmol mL^?1 inoculum day^?1, respectively. The preliminary exposure of rumen micro‐organisms to a specific blend of essential oils compounds, containing mainly thymol, guajacol and limonene, increased the extent of disappearance of γ‐terpinene only. Copyright © 2007 Society of Chemical Industry     

Economics of chemical defense in chrysomelinae

Chemical defense in chrysomelid larvae (subtribe Chrysomelina and Phyllodectina) is reviewed. Most species secrete autogenous monoterpenes. The diversity of their secretion is interpreted as a mechanism to reduce adaptation by predacious arthropods. The consequences of a host plant shift to the Salicacae are explored. Salicin from these host plants is used as a precursor for the salicylaldehyde secreted by the larvae of many species. This offers several advantages. It provides the larvae with an inexpensive and efficient defense. The recovery of the glucose moiety of the salicin contributes significantly to the larval energy budget. Adults sequester salicin in the eggs at concentrations which are toxic to ants. Owing to this maternal provisioning, neonate larvae produce salicylaldehyde from hatching onwards, whereas other species secreting monoterpenes are not protected at hatching. The secretion of salicylaldehyde by different species is considered to be chemical mimicry reinforcing visual aposematic signals.     

Isolation and characterization of allelopathic volatiles from mugwort (<Emphasis Type="Italic">Artemisia vulgaris</Emphasis>)

Several volatile allelochemicals were identified and characterized from fresh leaf tissue of three distinct populations of the invasive perennial weed, mugwort (Artemisia vulgaris). A unique bioassay was used to demonstrate the release of volatile allelochemicals from leaf tissues. Leaf volatiles were trapped and analyzed via gas chromatography coupled with mass spectrometry. Some of the components identified were terpenes, including camphor, eucalyptol, -pinene, and -pinene. Those commercially available were tested individually to determine their phytotoxicity. Concentrations of detectable volatiles differed in both absolute and relative proportions among the mugwort populations. The three mugwort populations consisted of a taller, highly branched population (ITH-1); a shorter, lesser-branched population (ITH-2) (both grown from rhizome fragments from managed landscapes); and a population grown from seed with lobed leaves (VT). Considerable interspecific variation existed in leaf morphology and leaf surface chemistry. Bioassays revealed that none of the individual monoterpenes could account for the observed phytotoxicity imparted by total leaf volatiles, suggesting a synergistic effect or activity of a component not tested. Despite inability to detect a single dominant phytotoxic compound, decreases in total terpene concentration with increase in leaf age correlated with decreases in phytotoxicity. The presence of bioactive terpenoids in leaf surface chemistry of younger mugwort tissue suggests a potential role for terpenoids in mugwort establishment and proliferation in introduced habitats.     

Feeding Behavior of Lambs in Relation to Kinetics of 1,8-cineole Dosed Intravenously or into the Rumen

The monoterpene 1,8-cineole is a major constituent of the essential oils that adversely influence intake of sagebrush by herbivores, but little is known about the mechanisms of its action. We investigated the influence of 1,8-cineole on the feeding behavior of two groups of sheep, one group dosed intravenously and the other intraruminally. In the first study, we infused 40 mg/kg BW of 1,8-cineole intravenously into four lambs on wk 1, 2, and 4. In the second, we administered 125 mg/kg BW of 1,8-cineole into the rumen of four lambs as a single-bolus dose in wk 1 and 2. Lambs dosed intravenously spent less time feeding than controls (28 vs. 60 min; P < 0.05), as did lambs dosed intraruminally (35 vs. 60 min; P < 0.05). Dosed lambs ate less than controls during rumen dosing studies (P < 0.05). For the intravenous infusion studies, rates of elimination did not differ among weeks (P < 0.05). For the rumen infusion studies, however, the absorption rate constant increased from 0.035/min to 0.076/min from wk 1 to 2, while the absorption half-life declined from 24 to 10 min (P < 0.05). Maximum plasma concentrations and time to reach maximum plasma concentrations were no faster in wk 2 than wk 1, but the primary elimination rate constant was 2.3 times higher in wk 2 (0.058/min) than in wk 1 (0.025/min) (P < 0.05). Dosed lambs exhibited clinical effects—licking of lips, drowsiness, staggering, and 1,8-cineole-smelling breath—that were much more pronounced with intravenous than rumen infusions. Dosing did not affect the acid–base balance. Collectively, these data suggest 1) rapid absorption and distribution of 1,8-cineole was responsible for initiating satiety, while more prolonged excretion was responsible for the duration of the satiety effect, and 2) lambs more readily adapted to 1,8-cineole in the rumen-dose study than in the intravenous-dose study.     

Volatiles from Potential Hosts of Rhopalicus tutela a Bark Beetle Parasitoid

Host location cues for parasitic wasps that attack bark beetle larvae concealed under the bark of spruce trees were analyzed by collecting odor samples from entrance holes into the bark beetle galleries, isolated larvae, and pupal chambers with or without bark beetle larvae. Odor samples were collected by dynamic headspace adsorptions on Porapak Q or static adsorptions by using solid-phase microextraction (SPME) with Carbowax–divinylbenzene as the adsorbing phase. Samples were analyzed by coupled gas chromatographic–electroantennographic detection (GC-EAD) and GC-mass spectrometry (GC-MS). The antennae of Rhopalicus tutela females responded primarily to oxygenated monoterpenes that are typical for damaged host trees. These compounds are attractive to bark beetle parasitoids in long-range host location, suggesting that they are used in both long- and short-range host location. No differences could be detected between samples collected from pupal chambers with or without mature larvae. Larvae outside pupal chambers emitted low quantities of the same compounds present in empty pupal chambers. The data support the hypothesis that volatiles used by host foraging parasitoids arise from the interaction between introduced microorganisms and the bark and/or vascular tissue of the host tree rather than from the bark beetle larvae.     

(1S,2R,4S,5S)-angelicoidenol-2-o-β-d-glucopyranoside—A moose deterrent compound in Scots pine (Pinus sylvestris L.)

Hydrophilic extracts of Scots pine (Pinus sylvestris L.) twigs have been investigated for palatability to moose in feeding experiments. The predominant repellent effect was observed from the 2-O--d-glucopyranoside of the monoterpene (1S,2R,4S,5S)-angelicoidenol. Of other isolated and tested substances, only taxifolin-3-O--d-glucopyranoside had a deterring effect. One fraction-containing mainly aliphatic compounds-also had a strong effect, but the effect was lost after further fractionation. Tannin-containing fractions had no effect. Angelicoidenol glucoside has not previously been reported fromP. sylvestris. The results are discussed in view of phenols as defense compounds.     

The defensive secretion of Carabus lefebvrei Dejean 1826 pupa (Coleoptera,Carabidae): Gland ultrastructure and chemical identification

This study documents the defensive function of flavored humor secreted by the abdominal glands of Carabus lefebvrei pupae. The morphology and the ultrastructure of these glands were described and the volatile compounds of glands secretion were identified by gas chromatography/mass spectrometry. The ultrastructure analysis shows an acinose complex formed by about 50 clusters. Each cluster has 20 glandular units and the unit—composed of one secretory and one canal cell lying along a duct—belongs to the class 3 cell type of Quennedey (1998). In the cytoplasm, the secretory cell contains abundant rough endoplasmatic reticula, glycogen granules, numerous mitochondria, and many well-developed Golgi complexes producing electron-dense secretory granules. Mitochondria are large, elongated, and often adjoining electronlucent vesicles. The kind and the origin of secretory granules varying in size and density were discussed. The chemical analysis of the gland secretion revealed the presence of a mixture of low molecular weight terpenes, ketones, aldehydes, alcohols, esters, and carboxylic acids. Monoterpenes, especially linalool, were the major products. We supposed that ketones, aldehydes, alcohols, esters, and carboxylic acids have a deterrent function against the predators and monoterpenes provide a prophylaxis function against pathogens. Microsc. Res. Tech., 2009. © 2008 Wiley-Liss, Inc.     

Inhibition of Methane Consumption in Forest Soils by Monoterpenes

Selected monoterpenes were tested for their ability to inhibit atmospheric methane consumption by three forest soils from different vegetation types and by the cultured methanotrophic strain, Methylosinus trichosporium OB3b. Subsurface soil from coniferous (Pinus banksiana), deciduous (Populus tremuloides), and mixed hardwood (Tsuga canadensis and Prunus pensylvanica) stands was used under field-moist (bulk and intact cores) and slurry conditions. Most of the hydrocarbon monoterpenes tested significantly inhibited (40–100%) methane consumption by soils at environmentally relevant levels, with (–)--pinene being the most effective. With the exception of -myrcene, monoterpenes also strongly inhibited methane oxidation by Methylosinus trichosporium OB3b. Carbon dioxide production was stimulated in all of the soils by the monoterpenes tested. In one case, methane production was stimulated by (–)--pinene in an intact, aerobic core. Oxide and alcohol monoterpenoids stimulated methane production. Thus, monoterpenes appear to be potentially important regulators of methane consumption and carbon metabolism in forest soils.     

Attraction of bark beetles,Tomicus piniperda,Hylurgops palliatus,andTrypodendron domesticum and other insects to short-chain alcohols and monoterpenes

Several Scandinavian forest insects,Hylurgops palliatus, Tomicus piniperda, andTrypodendron domesticum (Coleoptera: Scolytidae),Rhizophagus ferrugineus (Coleoptera: Rhizophagidae) andPollenia spp. (Diptera: Calliphoridae) were attracted to window traps baited with ethanol and placed on Scots pine trees (Pinus sylvestris) in May–June, 1986. Release of ethanol at increasing relative rates of 0, 0.01, 0.1 and 1.0 (800 mg/day) from the window traps on trees in 1987 causedH. palliatus, T. domesticum, andR. ferrugineus to be increasingly attracted, whileT. piniperda was equally attracted at both 0.1 and 1.0 rates. The attraction ofT. piniperda to ethanol was weak compared to attraction to a monoterpene mix, (±)--pinene, (+)-3-carene, terpinolene. The terpene mix plus ethanol was significantly more attractive toH. palliatus than ethanol alone, but terpenes significantly reduced the attraction ofT. domesticum to ethanol. Baiting of pipe traps with a series of short-chain alcohols (methanol to hexanol) each alone showed that ethanol was greatly preferred byH. palliatus, T. domesticum, andR. ferrugineus over alcohols of one more or one less carbon, while longer-chain alcohols were not attractive. However,Glischrochilus hortensis (Col.: Nitidulidae) was attracted only to propanol. A series of 10-fold increasing release rates of ethanol (0.0001-1.0, where 1.0=800 mg/day) with either a low or high release of the terpene mix had various effects on the sexes during their attraction to pipe traps and subsequent entering of holes. Release of (–)-verbenone at 0.25 mg/day had no significant effect onH. palliatus orR. ferrugineus attraction to ethanol, but the response ofT. domesticum to ethanol was reduced. Several theories on olfactory mechanisms of host selection byT. piniperda are integrated and placed in ecological perspective.