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  • 101. Verheggen, F
    et al.
    Ryne, C
    Olsson, P. O. C.
    Arnaud, L
    Lognay, G
    Högberg, Hans-Erik
    Mittuniversitetet, Fakulteten för naturvetenskap, teknik och medier, Institutionen för naturvetenskap.
    Persson, D
    Haubruge, E
    Löfstedt, C
    Electrophysiological and Behavioral Activity of Secondary Metabolites in the Confused Flour Beetle, Tribolium confusum2007Ingår i: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 33, nr 3, s. 525-539Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    Several previous studies have addressed pheromone communication in various flour beetles (Coleoptera: Tenebrionidae), including the confused flour beetle, Tribolium confusum (du Val). Different stereoisomers of 4,8-dimethyldecanal (DMD) were reported as the only components of an aggregation pheromone, but the behavioral activity of DMD is low. In the present study, additional previously reported secondary metabolites (benzoquinones and hydrocarbons) were tested for electrophysiological activity (EAG) with both sexes of T. confusum. Two benzoquinones and three monoenic hydrocarbons elicited significant EAG activity from both male and female antennae. There was an elevated male EAG response (vs. the females) to two out of the three hydrocarbons and for both quinones. The EAG-active compounds were subsequently investigated for behavioral activity in a walking bioassay. Benzoquinones are considered toxic and have been assigned a function as alarm substances in flour beetles, but we found that methyl-1, 4-benzoquinone in intermediate concentrations was attractive to both male and female beetles and could therefore act as an aggregation pheromone component. Males were also attracted to ethyl-1,4-benzoquinone. The corresponding hydroquinones, presumed precursors of the benzoquinones, did not elicit any electrophysiological response and were not tested for behavioral activity. The unsaturated hydrocarbons (1-tetradecene, 1-pentadecene, and 1-hexadecene) elicited significant EAG responses from both male and female antennae and were also attractive in the behavioral assay. Our results show that several beetle-produced compounds, in addition to 4,8-dimethyldecanal, may be part of a complex pheromone system in flour beetles and play a role in mediating aggregation in T. confusum.

  • 102.
    Vörde, Carin
    et al.
    Mittuniversitetet, Fakulteten för naturvetenskap, teknik och medier, Institutionen för naturvetenskap.
    Högberg, Hans-Erik
    Mittuniversitetet, Fakulteten för naturvetenskap, teknik och medier, Institutionen för naturvetenskap.
    Hedenström, Erik
    Mittuniversitetet, Fakulteten för naturvetenskap, teknik och medier, Institutionen för naturvetenskap.
    Resolution of 2-Methylalkanoic esters: Enantioselective Aminolysis by (R)-1-Phenylethyl-amine of Ethyl 2-Methyloctanoate Catalysed by Lipase B from Candida antarctica1996Ingår i: Tetrahedron: Asymmetry, ISSN 0957-4166, Vol. 7, nr 5, s. 1507-1513Artikel i tidskrift (Refereegranskat)
  • 103. Wassgren, A.-B.
    et al.
    Anderbrant, O.
    Löfqvist, J.
    Hansson, B. S.
    Bergström, G.
    Hedenström, Erik
    Mittuniversitetet, Fakulteten för naturvetenskap, teknik och medier, Institutionen för naturvetenskap.
    Högberg, Hans-Erik
    Mittuniversitetet, Fakulteten för naturvetenskap, teknik och medier, Institutionen för naturvetenskap.
    Pheromone Related Compounds in Pupal and Adult Female Pine Sawflies, Neodiprion sertifer, of different Age and in different Parts of the Body1992Ingår i: Journal of Insect Physiology, ISSN 0022-1910, Vol. 38, nr 11, s. 885-893Artikel i tidskrift (Refereegranskat)
  • 104. Wassgren, A.-B.
    et al.
    Bergström, G.
    Sierpinski, A.
    Anderbrant, O.
    Högberg, Hans-Erik
    Mittuniversitetet, Fakulteten för naturvetenskap, teknik och medier, Institutionen för naturvetenskap.
    Hedenström, Erik
    Mittuniversitetet, Fakulteten för naturvetenskap, teknik och medier, Institutionen för naturvetenskap.
    Sex Pheromone of the Pine Sawfly Macrodiprion nemoralis (Hymenoptera : Diprionidae): Identification of (2S,3R,7R,9S)-3,7,9-Trimethyl-2-tridecanol as the Precursor for the Active Pheromone Acetate2000Ingår i: Die Naturwissenschaften, ISSN 0028-1042, E-ISSN 1432-1904, Vol. 87, nr 1, s. 24-29Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    The main component of the sex pheromone precursor in females of Macrodiprion nemoralis was identified as a threo-3,7,9-trimethyl-2-tridecanol isomer, approximately 800 pg per female, by gas chromatography-mass spectrometry. Comparison of mass spectrometric ion chromatograms showed that the natural compound in the female extract has the same retention time and mass spectrum as one of the two synthetic threo peaks. The acetate of the synthetic 16-isomer mixture caught a large number of males in the field, confirming the structure of the active pheromone. Comparison of gas chromatograms of the natural female extract with the eight synthetic threo stereoisomers showed that the pheromone is the (2S,3R,7R,9S)-stereoisomer of 3,7,9-trimethyl-2-tridecyl acetate.

  • 105. Zhang, Zhen
    et al.
    Wang, Hongbin
    Chen, Guofa
    Anderbrant, Olle
    Zhang, Yun
    Zhou, Shuzhi
    Hedenström, Erik
    Mittuniversitetet, Fakulteten för naturvetenskap, teknik och medier, Institutionen för naturvetenskap.
    Högberg, Hans-Erik
    Mittuniversitetet, Fakulteten för naturvetenskap, teknik och medier, Institutionen för naturvetenskap.
    Sex pheromone for monitoring flight periods and population densities of the pine sawfly, Diprion jingyuanensis2005Ingår i: Journal of Applied Entomology, ISSN 0931-2048, Vol. 129, nr 7, s. 368-374Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    Sex pheromone for monitoring flight periods and population densities of the pine sawfly, Diprion jingyuanensis

  • 106. Östrand, Fredrik
    et al.
    Anderbrant, Olle
    Wassgren, Ann-Britt
    Bergström, Gunnar
    Hedenström, Erik
    Mittuniversitetet, Fakulteten för naturvetenskap, teknik och medier, Institutionen för naturvetenskap.
    Högberg, Hans-Erik
    Mittuniversitetet, Fakulteten för naturvetenskap, teknik och medier, Institutionen för naturvetenskap.
    Nguyen, Ba-Vu
    Mittuniversitetet, Fakulteten för naturvetenskap, teknik och medier, Institutionen för naturvetenskap.
    Larsson, Michael
    Stereoisomeric composition of the sex pheromone of the pine sawfly Microdiprion pallipes (Hym., Diprionidae)2003Ingår i: Chemoecology, ISSN 0937-7409, E-ISSN 1423-0445, Vol. 13, nr 3, s. 155-162Artikel i tidskrift (Refereegranskat)
    Abstract [en]

    The basic chemical structure of the sex pheromone of the pine sawfly Microdiprion pallipes (Fallen) has earlier been identified as the propionate ester of (2S,3S,7 R/S,11 R/S)/(2R,3R,7 R/S,11 R/S)-3,7,11-trimethyl-2-tridecanol. We now report the results from further investigations on the male response to individual stereoisomers and to blends of stereoisomers, both in electroantennographic (EAG) recordings and in field trapping experiments. We also present our attempts to determine the stereochemistry of the compounds present in females of M. pallipes. By comparing gas chromatograms and mass spectra obtained from natural extracts with those from synthetic compounds it was found that the females contain one or more of the four (2S,3S,7 R/S,11 R/S)-3,7,11-trimethyl-2-tridecanol isomers (SS++-1). The active pheromone component is the corresponding propionate ester 2. In EAG experiments, males responded most strongly to five propionate ester samples, namely two four-isomer blends: SS++-2 and SR++-2, and three individual stereoisomers: SSSR-, SRRR- and SRSR-2. In a series of field trapping experiments it was found that males were attracted to the SR++-2 four-isomer blend and to the individual isomer SSSR-2. Based on the EAG-recordings and field responses of males and the stereoisomers found in the females, we suggest that the propionate ester of (2S,3S,7S,11R)-3,7,11-trimethyl-2-tridecanol (SSSR-2) is used as a main component of the sex pheromone in M. pallipes. Apparently the males react to other stereoisomers in addition to that or those produced by the females.

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