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  • 1. Ashitani, T.
    et al.
    Kusumoto, N.
    Borg-Karlson, Anna Karin
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Fujita, K.
    Takahashi, K.
    Antitermite activity of β-caryophyllene epoxide and episulfide2013In: Zeitschrift für Naturforschung C - A Journal of Biosciences, ISSN 0939-5075, E-ISSN 1865-7125, Vol. 68 C, no 7-8, p. 302-306Article in journal (Refereed)
    Abstract [en]

    Caryophyllene-6,7-epoxide and caryophyllene-6,7-episulfide can be easily synthesized from β-caryophyllene by autoxidation or episulfidation. The bioactivities of β-caryophyllene and its derivatives were investigated against the subterranean termite Reticulitermes speratus Kolbe. The antifeedant, feeding, and termiticidal activities of each compound were tested using no-choice, dual-choice, and non-contact methods. Antitermitic activities were not shown by β-caryophyllene, but were observed for the oxide and sulfide derivatives. Caryophyllene- 6,7-episulfide showed especially high antifeedant and termiticidal activities. Thus, naturally abundant, non-bioactive β-caryophyllene can be easily converted into an antitermite reagent via a non-biological process.

  • 2. Backman, A. C.
    et al.
    Bengtsson, M.
    Borg-Karlson, Anna-Karin
    KTH, Superseded Departments, Chemistry.
    Liblikas, I.
    Witzgall, P.
    Volatiles from apple (Malus domestica) eliciting antennal responses in female codling moth Cydia pomonella (L.) (Lepidoptera: Tortricidae): Effect of plant injury and sampling technique2001In: Zeitschrift für Naturforschung C - A Journal of Biosciences, ISSN 0939-5075, E-ISSN 1865-7125, Vol. 56, no 04-mar, p. 262-268Article in journal (Refereed)
    Abstract [en]

    The antennal responses of codling moth females, Cydia pomonella, to volatiles from apple branches with green fruits were recorded by electroantennography coupled to gas chromatography. The antennae strongly responded to 4,8-dimethyl-1,3(E),7-nonatriene, linalool, beta -caryophyllene, (E)-beta -farnesene, germacrene D, (Z,E)-alpha -farnesene, (E,E)-alpha -farnesene and methyl salicylate. These compounds were all present in volatile collections on Porapak Q from both living and cut branches. Analysis by the solid phase microextraction technique (SPME) showed that the emission of some electrophysiologically active compounds increased after branches had been cut, especially 4,8-dimethyl-1,3(E),7-nonatriene, linalool and (E,E)-alpha -farnesene. The identification of apple volatiles eliciting antennal responses is the first step towards the identification of compounds mediating host-finding and oviposition in codling moth females.

  • 3. Faldt, J.
    et al.
    Eriksson, M.
    Valterova, I.
    Borg-Karlson, Anna-Karin
    KTH, Superseded Departments, Chemistry.
    Comparison of headspace techniques for sampling volatile natural products in a dynamic system2000In: Zeitschrift für Naturforschung C - A Journal of Biosciences, ISSN 0939-5075, E-ISSN 1865-7125, Vol. 55, no 04-mar, p. 180-188Article in journal (Refereed)
    Abstract [en]

    Commonly used dynamic sorption techniques for collecting biologically active volatile compounds have been compared. Solid phase microextraction (SPME) using two types of fibers (polydimethylsiloxane, PDMS, 100 mu m, and carbowax/divinylbenzene, CW/DVB, 65 mu m) was compared to purge and trap methods (Porapak Q, Tenax TA and charcoal) and a technique based on absorption in methanol in a cooling bath. Sampling was done in a stream of purified air (20 ml/min) in a closed and temperature-regulated (27 degrees C) glass tube, passing over a capillary tube containing a hexane solution of tridecane, heptadecane, 1-octen-3-ol, 1-hexadecanol, ethyl tetradecanoate, alpha-pinene, linalool, terpinen-4-ol, cis-verbenol, verbenone, beta-caryophyllene, E,E-farnesol, and geranylgeraniol. With all of the methods, the sampling was performed for a period of 30 min before extraction and analysis was done on a GC-FID system. In general, SPME gave a higher response for all compounds except for alpha-pinene, which was only extracted by the CW/DVB fiber. Purge and trap methods and methanol absorption gave the same response for all substances extracted. None of the methods extracted hexadecanol and geranylgeraniol under the conditions used. However, the SPME equipped with the PDMS coating extracted heptadecane, E,E-farnesol and ethyl tetradecanoate. Our results show that SPME, when selecting the fibers to fit the polarity and volatility of the compounds, is an outstanding extraction method compared to purge and trap and methanol absorption, especially for a qualitative analysis. The best conditions for storing fibers exposed to compounds of high volatility were at low temperatures (6 degrees C) in sealed vials, while the worst way was to leave the exposed fiber unprotected at room temperature (22 degrees C). The dynamic sampling system was effectively tested on a fruiting body of a polypore fungus (Ganoderma applanatum) emitting 1-octen-3-ol, and again SPME showed to be the most sensitive technique.

  • 4. Karalius, V.
    et al.
    Mozuraitis, R.
    Buda, V.
    Libikas, I.
    Borg-Karlson, Anna-Karin
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Sex attractants for six moth species of the families Brachodidae, Choreutidae and Tineidae from Kazakhstan and Lithuania2005In: Zeitschrift für Naturforschung C - A Journal of Biosciences, ISSN 0939-5075, E-ISSN 1865-7125, Vol. 60, no 08-jul, p. 625-631Article in journal (Refereed)
    Abstract [en]

    Sex attractants were established for one Brachodidae, three Choreutidae and two Tineidae moth species during field screening tests with (2E,13Z)-octadecadien-1-al, (2E,13Z)-, (3E,13Z)-, (3Z,13Z)-octadecadien-1-ols and their acetates (2E,13Z-18:Ald, 2E,13Z-, 3E,13Z-, 3Z,13Z-18:OH/OAc) as well as of binary mixtures of these compounds in West-Kazakhstan and Lithuania. Males of Brachodes appendiculata were attracted by 3E,13Z-18:OAc, Prochoreutis ultimana and P myllerana by 2E,13Z-18:OH, Monopis palidella by 2E,13Z-18:Ald and Triaxomera fulvimitrella by binary mixtures of 3Z,13Z-18:OAc with either 3E,13Z-18:OH in the ratio of 5:5 or 3Z,13Z-18:OH in the ratio of 9:1 (v/v). The 3-component mixture composed of 2E,13Z-18:OH, 3Z,13Z-18:OH and 2E,13Z-18:Ald in the ratio 1:1:1 was developed to attract Prochoreutis sehestediana males. Attraction antagonists for B. appendiculata, P ultimana and M. palidella were shown.

  • 5. Mozuraitis, R.
    et al.
    Karalius, V.
    Buda, V.
    Borg-Karlson, Anna-Karin
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Inter- and intraspecific activities of compounds derived from sex pheromone glands of currant borer, Synanthedon tipuliformis (Clerck) (Lepidoptera: Sesiidae)2006In: Zeitschrift für Naturforschung C - A Journal of Biosciences, ISSN 0939-5075, E-ISSN 1865-7125, Vol. 61, no 04-mar, p. 278-284Article in journal (Refereed)
    Abstract [en]

    Gas chromatography and mass spectrometry analyses of crude sex pheromone gland extracts revealed that virgin Synanthedon tipuliformis (Clerck), currant borer (Lepidoptera: Sesiidae) females, produced 6 compounds, structurally related to sex pheromone components of clearwing moths. By comparison of retention times and mass spectra of natural products with corresponding properties of synthetic standards, these compounds were identified as: (2E,13Z)-octadeca-2,13-dien-1-yl acetate (E2,Z13-18:OAc), (3E,13Z)-octadeca-3,13-dien-1-yl acetate (E3,Z13-18:OAc), (13Z)-octadec-13-en-1-yl acetate (M-18:OAc), (2E,13Z)-octadeca-2,13-dien-1-ol (E2,Z13-18:OH), (13Z)-octadec-13-en-1-ol (M-18:OH) and octadecan-1-ol (18:OH) in the ratio 100:07:2.7:3.2:traces. The first 3 compounds were previously known to occur in the sex pheromone gland extracts of currant borers, while the last 3 chemicals are now reported for the first time. Trapping tests carried out in the black currant field revealed that E2,Z13-18:OAc, when tested separately, attracted S. tipuliformis males, while addition of E3,Z13-18:OAc to the main component increased the effectiveness of E2,Z13-18:OAc over seven times. The attractiveness of 6 component lures did not differ significantly from the one of the binary mixture, confirming that E2,Z13-18:OAc and E3,Z13-18:OAc in the ratio1.00:0.7 are essential sex pheromone components of S. tipuliformis. Trapping tests carried out at the dwelling place of Synanthedon scoliaeformis (Borkhausen) (Lepidoptera: Sesiidae) revealed that, in addition to intraspecific synergistic effect, E3,Z13-18:OAc increased the specificity of the pheromone signal of S. tipuliformis, acting by intraspecific mode as an attraction antagonist against S. scoliaeformis males. By this way, it ensured the specificity of the sex attraction signal of the currant borer. Consequently, both compounds E2,Z13-18:OAc and E3,Z13-18:OAc have to be present in pheromone formulations used for monitoring and/or control of S. tipuliformis to avoid effecting non-target species. Other compounds identified from the sex pheromone gland of S. tipuliformis did not show any significant interspecific activity for males of S. scoliaeformis, however, they provide a basis to achieve specificity of a pheromone signal of S. tipuliformis and could act as attraction antagonists against other clearwing moth species which, like S. tipuliformis, employ E2,Z13-18:OAc as their sex pheromone component.

  • 6.
    Mozuraitis, Raimondas
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Buda, Vincas
    Borg-Karlson, Anna-Karin
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Optimization of Solid-Phase Microextraction Sampling for Analysis of Volatile Compounds Emitted from Oestrous Urine of Mares2010In: Zeitschrift für Naturforschung C - A Journal of Biosciences, ISSN 0939-5075, E-ISSN 1865-7125, Vol. 65, no 1-2, p. 127-133Article in journal (Refereed)
    Abstract [en]

    The solid-phase microextraction (SPME) technique was applied and optimized for collection of volatile compounds emitted from oestrous urine of mares Equs cabalus L (Perissodactyla, Equidae) for GC-MS analyses. Variables Such as type Of SPMF fibre, Collection time of volatiles, and addition of salt were optimized to improve the sampling efficiency ill two aspects: extent and selectivity of absorption/adsorption Of urine volatiles onto SPME fibres. The data revealed that the number of volatiles and the total amount represented as quantitative peak areas of the compounds trapped oil fibres coated either with polydimethylsiloxane-divinylbenzene or with divinylbenzene-carboxen-polydimethylsiloxane were significantly higher compared to those coated with polydimethylsiloxane. polyacrylate, and carbowax-divinylbenzene. The polydimethylsiloxane-divinylbenzene-type of the fibre coating was chosen for optimization of sampling time and effect of salt addition. Sampling periods lasted for 15, 30, 60, 120, and 240 min. The optimal collection time of volatiles from urine maintained at about 36 degrees C was 60 min, as the number Of compounds detected with amounts Sufficient for quantification did not differ significantly from those trapped during longer collection periods. No significant increase in total amount of volatiles trapped was registered after 120 min of sampling. Addition Of 0.3 g NaCl to the 2-ml of samples shortened the collection period from 60 to 15 min during which almost all compounds were trapped. Addition of salt has a significant effect at all sampling periods taking into consideration the total amounts Of volatiles trapped. The total intensities increased about 8, 5, 3, 3, and 2 times at collection periods of 15, 30 60, 120, and 240 min, respectively, when compare with the ones obtained from the urine samples with no salt addition. In oestrous mare's urine. 139 +/- 4 (average number standard +/- deviation) volatile compounds Suitable for quantitative analyses were detected compared to 45 compounds collected by the gas-tight syndrome method.

  • 7.
    Mozuraitis, Raimondas
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Karalius, Vidmantas
    Identification of minor sex pheromone components of the poplar clearwing moth Paranthrene tabaniformis (Lepidoptera, Sesiidae)2007In: Zeitschrift für Naturforschung C - A Journal of Biosciences, ISSN 0939-5075, E-ISSN 1865-7125, Vol. 62, no 1-2, p. 138-142Article in journal (Refereed)
    Abstract [en]

    A chemical analysis of the crude sex pheromone gland extracts of virgin calling Paranthrene tabaniformis females, obtained from the European, part of Kazakhstan, revealed the presence of five compounds: (3E,13Z)-octadeca-3,13-dien-1-ol (E3,Z13-18:OH), (3Z,13Z)octadeca-3,13-dien-l-ol (Z3,Z13-18:OH), (2E,13Z)-octadeca-2,13-dien-1-ol (E2,Z13-18:OH), (13Z)-octadec-13-en-1-ol (Z13-18:OH), and octadecan-1-ol (18:OH) at the ratios 64.0:32.4: 1.4:0.9:1.3, which are structurally related to sex pheromone components of clearwing moths. Our previous field tests showed synergistic effects of Z3,Z13-18:OH and E2,Z13-18:OH to attract P tabaniformis males, when these compounds were tested in binary mixtures with the known sex pheromone E3,Z13-18:OH. The three dienic alcohols should all be considered as sex pheromone components of the P tabaniformis species, while the role of Z13-18:OH and 18:011 remained unclear.

  • 8.
    Mozuraitis, Raimondas
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Murtazina, Rushana
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Nylin, Sören
    Borg-Karlson, Anna-Karin
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Nonvolatile Chemical Cues Affect Host-Plant Ranking by Gravid Polygonia c-album Females2012In: Zeitschrift für Naturforschung C - A Journal of Biosciences, ISSN 0939-5075, E-ISSN 1865-7125, Vol. 67, no 1-2, p. 93-102Article in journal (Refereed)
    Abstract [en]

    In a multiple-choice test, the preference of egg-laying Polygonia c-album (comma butterfly) females was studied for oviposition on plants bearing surrogate leaves treated with crude methanol extracts obtained from leaves of seven host-plant species: Humulus lupulus, Urtica dioica, Ulmus glabra, Salix caprea, Ribes nigrum, Corylus avellana, and Betula pubescens. The ranking order of surrogate leaves treated with host-plant extracts corresponded well to that reported on natural foliage, except R. nigrum. Thus, host-plant choice in P c-album seems to be highly dependent on chemical cues. Moreover, after two subsequent fractionations using reversed-phase chromatography the nonvolatile chemical cues residing in the most polar water-soluble fractions evidently provided sufficient information for egg-laying females to discriminate and rank between the samples of more and less preferred plants, since the ranking in these assays was similar to that for natural foliage or whole methanol extracts, while the physical traits of the surrogate leaves remained uniform.

  • 9.
    Ohlsson, Anna B.
    et al.
    KTH, School of Biotechnology (BIO).
    Segerfeldt, Patrik
    KTH, School of Biotechnology (BIO). KTH, School of Chemical Science and Engineering (CHE), Chemistry.
    Lindström, Anders
    Dalarna University.
    Borg-Karlsson, Anna-Karin M.
    KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
    Berglund, Torkel
    KTH, School of Biotechnology (BIO).
    UV-B Exposure of Indoor-Grown Picea abies Seedlings Causes an Epigenetic Effect and Selective Emission of Terpenes2013In: Zeitschrift für Naturforschung C - A Journal of Biosciences, ISSN 0939-5075, E-ISSN 1865-7125, Vol. 68, no 3-4, p. 139-147Article in journal (Refereed)
    Abstract [en]

    Terpenoids  are  involved  in  various  defensive  functions  in  plants,  especially  conifers.  Epi-genetic  mechanisms,  for  example  DNA  methylation,  can  infl uence  plant  defence  systems. The purpose of the present study was to investigate the infl uence of UV-B exposure on the release  of  terpenoids  from  spruce  seedlings  and  on  needle  DNA  methylation.  Ten-week-old  seedlings  grown  indoors  were  exposed  to  UV-B  radiation  during  4 h,  and  the  volatile compounds  emitted  from  the  seedlings  were  analysed.  Analysis  of  the  volatiles  1,  3,  and 22 d after this UV-B exposure showed that bornyl acetate, borneol, myrcene, and limonene contents increased during the fi rst 3 days, while at day 22 the level of emission had returned to the control level. UV-B exposure decreased the level of DNA methylation in needles of young  seedlings,  refl ected  in  methylation  changes  in  CCGG  sequences.  Exposure  of  young seedlings  to  UV-B  radiation  might  be  a  way  to  potentiate  the  general  defensive  capacity, improving their ability to survive in outdoor conditions. UV-B-induced defence is discussed in the light of epigenetic mechanisms.

  • 10.
    Zhao, Yadong
    et al.
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Wood Chemistry and Pulp Technology.
    Li, Jiebing
    KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology, Wood Chemistry and Pulp Technology.
    Ascidian bioresources: common and variant chemical compositions and exploitation strategy examples of Halocynthia roretzi, Styela plicata, Ascidia sp and Ciona intestinalis2016In: Zeitschrift für Naturforschung C - A Journal of Biosciences, ISSN 0939-5075, E-ISSN 1865-7125, Vol. 71, no 5-6, p. 165-180Article in journal (Refereed)
    Abstract [en]

    To explore abundant marine ascidian bioresources, four species from two orders have been compared in their chemical compositions. After a universal separation of the animal body into two fractions, all tunics have been found rich in carbohydrate contents, while all inner body tissues are richer in proteins. Cellulose is present almost exclusively in the tunics and more in the order Stolidobranchia, while more sulfated polysaccharides are present in Phlebobranchia species. Almost all proteins are collagens with a high essential amino acid index and high delicious amino acid (DAA) content. All fractions also have high contents of good-quality fatty acids and trace minerals but low toxic element contents, with different sterols and glycosaminoglycans. There are species-specific characteristics observed for vanadium accumulation and sterol structures which are also meaningful for ascidian chemotaxonomy and resource exploitation. It is suggested that in addition to the present utilizations of tunics for cellulose production and of some species' inner body tissues as human food, one should explore all species' inner body tissues as human foods and all tunics as food or animal feed with the contained cellulose as dietary fiber. Collagens, sulfated polysaccharides, glycosaminoglycans, sterols and trace elements could be explored as byproducts for, e.g. pharmaceutical and chemical industries.

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