| 1. |
- Rao, M. Suri Appa, et al.
(författare)
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Piscidinols H-L, apotirucallane triterpenes from the leaves of Walsura trifoliata and their insecticidal activity
- 2015
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Ingår i: Tetrahedron. - : Elsevier. - 0040-4020 .- 1464-5416. ; 71:9, s. 1431-1437
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Tidskriftsartikel (refereegranskat)abstract
- Five new apotirucallane-type terpenoids, Piscidinols H-L (1-5), were isolated from the leaves of Walsura trifoliate and their structures were fully established on the basis of detailed spectroscopic (especially 20 NMR and mass) analysis. These new compounds possessed tetracyclic and acetal rings. All the new isolates were evaluated for their antifeedant activities in tobacco caterpillar (Spodoptera aura) and castor semilooper (Achaea janata) using a no-choice laboratory bioassay and the test compounds (1-6) exhibited moderate insecticidal activities. (C) 2015 Elsevier Ltd. All rights reserved.
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| 2. |
- Bellenberg, Sören, et al.
(författare)
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Diffusible signal factor signaling controls bioleaching activity and niche protection in the acidophilic, mineral-oxidizing leptospirilli
- 2021
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Ingår i: Scientific Reports. - : Springer Nature. - 2045-2322. ; 11:1
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Tidskriftsartikel (refereegranskat)abstract
- Bioleaching of metal sulfide ores involves acidophilic microbes that catalyze the chemical dissolution of the metal sulfide bond that is enhanced by attached and planktonic cell mediated oxidation of iron(II)-ions and inorganic sulfur compounds. Leptospirillum spp. often predominate in sulfide mineral-containing environments, including bioheaps for copper recovery from chalcopyrite, as they are effective primary mineral colonizers and oxidize iron(II)-ions efficiently. In this study, we demonstrated a functional diffusible signal factor interspecies quorum sensing signaling mechanism in Leptospirillum ferriphilum and Leptospirillum ferrooxidans that produces (Z)-11-methyl-2-dodecenoic acid when grown with pyrite as energy source. In addition, pure diffusible signal factor and extracts from supernatants of pyrite grown Leptospirillum spp. inhibited biological iron oxidation in various species, and that pyrite grown Leptospirillum cells were less affected than iron grown cells to self inhibition. Finally, transcriptional analyses for the inhibition of iron-grown L. ferriphilum cells due to diffusible signal factor was compared with the response to exposure of cells to N- acyl-homoserine-lactone type quorum sensing signal compounds. The data suggested that Leptospirillum spp. diffusible signal factor production is a strategy for niche protection and defense against other microbes and it is proposed that this may be exploited to inhibit unwanted acidophile species.
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| 3. |
- El-Sayed, Ashraf M., et al.
(författare)
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Climate change risk to pheromone application in pest management
- 2021
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Ingår i: The Science of Nature. - : Springer. - 0028-1042 .- 1432-1904. ; 108:6
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Tidskriftsartikel (refereegranskat)abstract
- Since of the first sex pheromone and the adoption of pheromone in pest management, the global pheromone market size has grown to reach USD 2.4 billion per year in 2019. This has enabled the development of environmentally friendly approaches that significantly reduce the application of pesticides. Recently, there have been reports of the failure of various commercial codlemone: (E,E)-8,10-dodecadien-1-ol formulations used for monitoring the apple pest codling moth, Cydia pomonella (L.). This work was initiated to investigate factors behind the lack of efficacy of codlemone lure in the Northern Hemisphere (Germany) and Southern Hemisphere (New Zealand). We hypothesised that the observed failure could be due to two main factors: (a) a shift in the response of male codling moth to codlemone and (b) degradation of codlemone under field conditions that renders the lure less attractive. Field trial tests of various doses and blends containing minor pheromone compounds suggested no change in response of male codling moth. The addition of an antioxidant and a UV stabiliser to codlemone resulted in a significant increase in the number of males caught in Germany, but not in New Zealand. Mean maximum temperatures during the growing season since 2004 indicate a 3 degrees C increase to 35 degrees C in Germany, but just a 1.5 degrees C rise to 30 degrees C in New Zealand. Chemical analysis of the lures used in the field trials in Germany and New Zealand indicated more degradation products and reduced half-life of the lures in Germany compared with those in New Zealand. Heating codlemone lures to 32 degrees C significantly reduced the number of males caught in traps and increased the isomeric and chemical impurities of codlemone compared with unheated lures. Our data provide the first evidence that climate change affects pheromone molecule stability, thus reducing its biological efficacy. Our finding suggests that climate change could be a general problem for chemical communication and, therefore, could affect the integrity of natural ecosystems.
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| 4. |
- El-Sayed, Ashraf M., et al.
(författare)
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Feeding Volatiles of Larval Sparganothis pilleriana (Lepidoptera:Tortricidae) Attract Heterospecific Adults o the European Grapevine Moth
- 2021
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Ingår i: Environmental Entomology. - : Oxford University Press. - 0046-225X .- 1938-2936. ; 50:6, s. 1286-1293
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Tidskriftsartikel (refereegranskat)abstract
- Plants release volatiles in response to caterpillar feeding.These herbivore-induced plant volatiles (HIPVs) attract natural enemies of the herbivores and repel or attract conspecific adult herbivores in a tri-trophic interaction which has been considered to be an indirect plant defense against herbivores. Recently, we demonstrated the attraction of male and female European grapevine moth, Lobesia botrana (Denis & Schiffermuller) (Lepidoptera: Tortricidae) to a blend of phenylacetonitrile and acetic acid, two compounds identified as HIPVs in heterospecific apple-leafroller interactions. The ecological basis of our findings is not clearly understood.Thus, this work was undertaken to investigate HIPVs in the grapevine-leafroller interaction and study the response of heterospecific adults L. botrana, to these volatiles. We collected headspace volatiles emitted from uninfested grapevines and grapevines infested with larvae of a generalist herbivore, the grapevine leafroller moth, Sparganothis pilleriana (Denis & Schiffermuller), and analyzed them using gas chromatography/mass spectrometry. Infested grape leaves released three compounds (phenylacetonitrile, indole, and 2-phenylethanol) not found from uninfested leaves. Nine different blends, comprising a full factorial set of the three oompou nds with each blend containing acetic acid, were tested in a field-cage trial. Only lures containing phenylacetonitrile caused a significant increase in trap catches compared to the other lures and blank traps. Electroantennographic tests show that L botrana can detect the compounds. The results confirm our hypothesis that phenylacetonitrile is released during grapevines infestation with herbivores, and attracts adult L. botrana.
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| 5. |
- Ganji, Suresh, 1984-, et al.
(författare)
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Asymmetric Synthesis of Oxygenated Monoterpenoids of Importance for Bark Beetle Ecology
- 2020
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Ingår i: Journal of Natural Products. - : American Chemical Society (ACS). - 0163-3864 .- 1520-6025. ; 83:11, s. 3332-3337
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Tidskriftsartikel (refereegranskat)abstract
- Herein we report the asymmetric syntheses of a number of oxygenated terpenoids that are of importance in the chemical ecology of bark beetles. These are pinocamphones, isopinocamphones, pinocarvones, and 4-thujanols (= sabinene hydrates). The camphones were synthesized from isopinocampheol, the pinocarvones from beta-pinene, and the thujanols from sabinene. The NMR spectroscopic data, specific rotations, and elution orders of their stereoisomers on a chiral GC-phase (beta-cyclodextrin) are also reported. This enables facile synthesis of pure compounds for biological activity studies and identification of stereoisomers in mixed natural samples.
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| 6. |
- Lindmark, Matilda, et al.
(författare)
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Semiochemicals produced by fungal bark beetle symbiont Endoconidiophora rufipennis and the discovery of an anti-attractant for Ips typographus
- 2023
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Ingår i: PLOS ONE. - : Public Library of Science. - 1932-6203. ; 18:4
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Tidskriftsartikel (refereegranskat)abstract
- Bark beetles vector symbiotic fungal species into their host trees during mass attacks. The symbiotic relationship with blue stain fungi of the Ascomycetes, including genera of Endoconidiophora (syn. = Ceratocystis), promotes successful establishment whereby the microbes help to overcome the host trees' defence and degrade toxic resins. This is the first study to evaluate both the volatile emissions from an insect-associated blue stain fungus over time and the insect response in a field trapping experiment. Volatile emissions from isolates of Endoconidiophora rufipennis (ER) were collected by solid-phase microextraction (SPME) and analysed by gas chromatography-mass spectroscopy (GC-MS) over a period of 30 days. This virulent North American fungus is closely related to E. polonica, a symbiotic fungus known from Eurasian spruce bark beetle Ips typographus.Nine volatiles were emitted by ER in substantial amounts: isoamyl acetate, sulcatone, 2-phenethyl acetate, geranyl acetone, geranyl acetate, citronellyl acetate, (R)- and (S)-sulcatol, and (R)-sulcatol acetate. A late peaking compound was geranyl acetone. In the field trapping experiment, three of the fungal volatiles (geranyl acetone, 2-phenethyl acetate and sulcatone) were tested in combination with a synthetic aggregation pheromone for I. typographus. Traps with geranyl acetone attracted lower numbers of I. typographus compared to traps with 2-phenethyl acetate, sulcatone or the pheromone alone as a control. The results showed that geranyl acetone acts as an anti-attractant and may act naturally on I. typographus as a cue from an associated fungus to signal an overexploited host.
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| 7. |
- Muthusamy, Sarala Devi, et al.
(författare)
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Transient expression and purification of β-caryophyllene synthase in Nicotiana benthamiana to produce β-caryophyllene in vitro
- 2020
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Ingår i: PeerJ. - : PeerJ Inc. - 2167-8359. ; 8, s. 1-21
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Tidskriftsartikel (refereegranskat)abstract
- The sesquiterpene beta-caryophyllene is an ubiquitous component in many plants that has commercially been used as an aroma in cosmetics and perfumes. Recent studies have shown its potential use as a therapeutic agent and biofuel. Currently, beta-caryophyllene is isolated from large amounts of plant material. Molecular farming based on the Nicotiana benthamiana transient expression system may be used for a more sustainable production of beta-caryophyllene. In this study, a full-length cDNA of a new duplicated beta-caryophyllene synthase from Artemisia annua (AaCPS1) was isolated and functionally characterized. In order to produce beta-caryophyllene in vitro, the AaCPS1 was cloned into a plant viral-based vector pEAQ-HT. Subsequently, the plasmid was transferred into the Agrobacterium and agroinfiltrated into N. benthamiana leaves. The AaCPS1 expression was analyzed by quantitative PCR at different time points after agroinfiltration. The highest level of transcripts was observed at 9 days post infiltration (dpi). The AaCPS1 protein was extracted from the leaves at 9 dpi and purified by cobalt-nitrilotriacetate (Co-NTA) affinity chromatography using histidine tag with a yield of 89 mg kg(-1). fresh weight of leaves. The protein expression of AaCPS1 was also confirmed by sodium dodecyl sulfate-polyacrylamide gel electrophoresis (SDS-PAGE) and western blot analyses. AaCPS1 protein uses farnesyl diphosphate (FPP) as a substrate to produce p-caryophyllene. Product identification and determination of the activity of purified AaCPS1 were done by gas chromatography-mass spectrometry (GC-MS). GC-MS results revealed that the AaCPS1 produced maximum 26.5 +/- 1 mg of P-caryophyllene per kilogram fresh weight of leaves after assaying with FPP for 6 h. Using AaCPS1 as a proof of concept, we demonstrate that N. benthamiana can be considered as an expression system for production of plant proteins that catalyze the formation of valuable chemicals for industrial applications.
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| 8. |
- Nasrin, Shamima, et al.
(författare)
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Chloramphenicol Derivatives with Antibacterial Activity Identified by Functional Metagenomics
- 2018
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Ingår i: Journal of natural products (Print). - : American Chemical Society (ACS). - 0163-3864 .- 1520-6025. ; 81:6, s. 1321-1332
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Tidskriftsartikel (refereegranskat)abstract
- A functional metagenomic approach identified novel and diverse soil-derived DNAs encoding inhibitors to methicillin-resistant Staphylococcus aureus (MRSA). A metagenomic DNA soil library containing 19 200 recombinant Escherichia coli BAC clones with 100 Kb average insert size was screened for antibiotic activity. Twenty-seven clones inhibited MRSA, seven of which were found by LC-MS to possess modified chloramphenicol (Cm) derivatives, including three new compounds whose structures were established as 1-acetyl-3-propanoylchloramphenicol, 1-acety1-3-butanoyl-chloramphenicol, and 3-butanoyl-1-propanoylchloramphenicol. Cm was used as the selectable antibiotic for cloning, suggesting that heterologously expressed enzymes resulted in derivatization of Cm into new chemical entities with biological activity. An esterase was found to be responsible for the enzymatic regeneration of Cm, and the gene trfA responsible for plasmid copy induction was found to be responsible for inducing antibacterial activity in some clones. Six additional acylchloramphenicols were synthesized for structure and antibacterial activity relationship studies, with 1-p-nitrobenzoylchloramphenicol the most active against Mycobacterium intracellulare and Mycobacterium tuberculosis, with MICs of 12.5 and 50.0 mu g/mL, respectively.
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| 9. |
- Ninkovic, Velemir, et al.
(författare)
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Effects of Methyl Salicylate on Host Plant Acceptance and Feeding by the Aphid Rhopalosiphum padi
- 2021
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Ingår i: Frontiers in Plant Science. - : Frontiers Media S.A.. - 1664-462X. ; 12
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Tidskriftsartikel (refereegranskat)abstract
- Methyl salicylate (MeSA) is a volatile shown to act as an inducer of plant defense against pathogens and certain herbivores, particularly aphids. It has been shown to have potential for aphid pest management, but knowledge on its mode of action is lacking, particularly induced plant-mediated effects. This study investigated the effects of exposing plants to MeSA on the host searching, host acceptance and feeding behavior of the bird cherry-oat aphid Rhopalosiphum padi. Barley plants were exposed to volatile MeSA for 24 h, after which biological effects were tested immediately after the exposure (Day 0), and then 1, 3 and 5 days after the end of the exposure. Aphid settling on MeSA-exposed plants was significantly reduced on days 0, 1 and 3, but not on day 5. In olfactometer tests, aphids preferred the odor of unexposed plants on days 1 and 3, but not on day 0 or 5. Analysis of volatiles from exposed and unexposed plants showed higher levels of MeSA from exposed plants, most likely absorbed and re-released from plant surfaces, but also specific changes in other plant volatiles on days 0, 1 and 3. High doses of MeSA did not affect aphid orientation in an olfactometer, but lower doses were repellent. Analysis of aphid feeding by Electronic penetration graph (EPG) showed that MeSA exposure resulted in resistance factors in barley plants, including surface factors and induced systemic factors in other tissues including the phloem. The results support the potential of MeSA as a potential tool for management of aphid pests.
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| 10. |
- Schiebe, Christian, et al.
(författare)
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Styrene, (+)-trans-(1R,4S,5S)-4-Thujanol and Oxygenated Monoterpenes Related to Host Stress Elicit Strong Electrophysiological Responses in the Bark Beetle Ips typographus
- 2019
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Ingår i: Journal of Chemical Ecology. - : Springer. - 0098-0331 .- 1573-1561. ; 45:5-6, s. 474-489
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Tidskriftsartikel (refereegranskat)abstract
- Bark beetles kill apparently vigorous conifers during epidemics by means of pheromone-mediated aggregation. During non-endemic conditions the beetles are limited to use trees with poor defense, like wind-thrown. To find olfactory cues that help beetles to distinguish between trees with strong or weak defense, we collected volatiles from the bark surface of healthy felled or standing Picea abies trees. Furthermore, living trees were treated with methyl jasmonate in order to induce defense responses. Volatiles were analyzed by combined gas chromatography and electroantennographic detection (GC-EAD) on Ips typographus antennae. Compounds eliciting antennal responses were characterized by single sensillum recording for identification of specific olfactory sensory neurons (OSN). Release of monoterpene hydrocarbons decreased, while oxygenated compounds increased, from spring to early summer in felled trees. In both beetle sexes particular strong EAD activity was elicited by trace amounts of terpene alcohols and ketones. 4-Thujanol gave a very strong response and the absolute configuration of the tested natural product was assigned to be (+)-trans-(1R,4S,5S)-thujanol by stereoselective synthesis and enantioselective gas chromatography. One type of OSN responded to all ketones and five other OSN were characterized by the type of compounds that elicited responses. Three new OSN classes were found. Of the eight EAD-active compounds found in methyl jasmonate-treated bark, the known anti-attractant 1,8-cineole was the one most strongly induced. Our data support the hypothesis that highly active oxygenated host volatiles could serve as positive or negative cues for host selection in I. typographus and in other bark beetles.
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