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Högberg, Hans-Erik
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Anderbrant, O., Löfqvist, J., Hedenström, E., Bång, J., Tai, A. & Högberg, H.-E. (2010). Field Response of Male Pine Sawflies, Neodiprion sertifer (Diprionidae), to Sex Pheromone Analogs in Japan and Sweden. Journal of Chemical Ecology, 36(9), 969-977
Öppna denna publikation i ny flik eller fönster >>Field Response of Male Pine Sawflies, Neodiprion sertifer (Diprionidae), to Sex Pheromone Analogs in Japan and Sweden
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2010 (Engelska)Ingår i: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 36, nr 9, s. 969-977Artikel i tidskrift (Refereegranskat) Published
Abstract [en]

The pine sawfly Neodiprion sertifer (Geoffroy) uses the acetate or propionate of (2S,3S,7S)-3,7-dimethyl-2-pentadecanol (diprionol) as pheromone components, with the (2S,3R,7R)-isomer being antagonistic, synergistic, or inactive according to the population tested. In this study, we tested the attraction of males to the acetates of three analogs of diprionol, each missing one methyl group, viz. (2S,7S)-7-methyl-2-pentadecanol, (2S,6S)-2,6-dimethyl-1-tetradecanol, and (2S,3S)-3-methyl-2-pentadecanol. None of the analogs alone, or in combination with diprionol acetate, was attractive in Sweden, even at 100 times the amount of diprionol acetate attractive to N. sertifer. In Japan, the acetate of (2S,3S)-3-methyl-2-pentadecanol attracted males when tested in amounts 10–20 times higher than the acetate pheromone component. The acetate esters of the (2S,3R)-analog and the (2S,3R,7R)-isomer of diprionol also were tested in combination with the pheromone compound (acetate ester). Both compounds caused an almost total trap-catch reduction in Sweden, whereas in Japan they appear to have relatively little effect on trap capture when added to diprionol acetate. Butyrate and iso-butyrate esters of diprionol were unattractive to N. sertifer in Sweden. In summary, there exists geographic variation in N. sertifer in responses to both diprionyl acetate and some of its analogs.

Nationell ämneskategori
Kemi
Identifikatorer
urn:nbn:se:miun:diva-11946 (URN)10.1007/s10886-010-9834-y (DOI)000281971400006 ()2-s2.0-77956886375 (Scopus ID)
Tillgänglig från: 2010-09-01 Skapad: 2010-09-01 Senast uppdaterad: 2017-12-12Bibliografiskt granskad
Hedenström, E., Högberg, H.-E., Anderbrant, O., Wang, H., Zhang, Z. & Chen, G. (2010). Sex pheromone for monitoring flight periods and population densities of the pine sawfly, Diprion jingyuanensis Xiao et Zhang (Hym.: Diprionidae). In: John A Parrotta and Mary A Carr (Ed.), Forests for the Future - Sustaining Society and the Environment: Abstracts. Paper presented at XXIII IUFRO Word Congress, 23-28 August 2010, Seoul, Republic of Korea (pp. 369-369). , 12(5)
Öppna denna publikation i ny flik eller fönster >>Sex pheromone for monitoring flight periods and population densities of the pine sawfly, Diprion jingyuanensis Xiao et Zhang (Hym.: Diprionidae)
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2010 (Engelska)Ingår i: Forests for the Future - Sustaining Society and the Environment: Abstracts / [ed] John A Parrotta and Mary A Carr, 2010, Vol. 12, nr 5, s. 369-369Konferensbidrag, Publicerat paper (Refereegranskat)
Serie
International forestry review, ISSN 1465-5489 ; 12(5)
Nationell ämneskategori
Kemi
Identifikatorer
urn:nbn:se:miun:diva-12614 (URN)
Konferens
XXIII IUFRO Word Congress, 23-28 August 2010, Seoul, Republic of Korea
Projekt
Skogen som resurs
Tillgänglig från: 2010-12-13 Skapad: 2010-12-13 Senast uppdaterad: 2016-09-29Bibliografiskt granskad
Högberg, H.-E. (2008). Exploiting enantioselectivity of hydrolases in organic solvents. In: Organic Synthesis with Enzymes in Non-Aqueous Media: (pp. 73-112). Weinheim: Wiley-VCH Verlagsgesellschaft
Öppna denna publikation i ny flik eller fönster >>Exploiting enantioselectivity of hydrolases in organic solvents
2008 (Engelska)Ingår i: Organic Synthesis with Enzymes in Non-Aqueous Media, Weinheim: Wiley-VCH Verlagsgesellschaft, 2008, s. 73-112Kapitel i bok, del av antologi (Övrigt vetenskapligt)
Abstract [en]

In modern organic chemistry the synthesis of chiral enantiopure compounds is an extremely important objective. To achieve this, biocatalysts have emerged as key tools. The broad reactivity of hydrolytic enzymes combined with their ability to discriminate between enantiomers make them ideal catalysts for resolving racemic organic compounds to provide enantiomerically enriched products. This chapter gives an overview of how the enantioselectivity of hydrolases can be exploited to furnish virtually enantiopure compounds via kinetic resolution of racemic compounds and desymmetrisation of symmetric compounds. Enantioselectivity and E-values are discussed. Reversibility of hydrolase-catalysed reactions and how it can be avoided by using various irreversible acyl donors as well as the determination and optimization of enantioselectivity are briefly discussed. The bulk of the chapter consists of selected examples of hydrolase catalysed reactions of some important classes of compounds. Thus the usefulness of hydrolase-catalyzed reactions is demonstrated by several examples of reactions in organic solvents of primary, secondary, tertiary alcohols, various amines, and acid derivatives.

Ort, förlag, år, upplaga, sidor
Weinheim: Wiley-VCH Verlagsgesellschaft, 2008
Nyckelord
enantioselectivity, hydrolases, lipases, organic solvents, desymmetrization, kinetic
Nationell ämneskategori
Kemi
Identifikatorer
urn:nbn:se:miun:diva-4384 (URN)10.1002/9783527621729.ch4 (DOI)2-s2.0-84889472284 (Scopus ID)5291 (Lokalt ID)9783527318469 (ISBN)978-352731846-9 (ISBN)5291 (Arkivnummer)5291 (OAI)
Tillgänglig från: 2008-09-30 Skapad: 2009-03-19 Senast uppdaterad: 2016-09-20Bibliografiskt granskad
Högberg, H.-E. (2007). Biosignal and Organic Chemistry: IOBC wprs Working Group Meeting - The Scanian Journey. Pheromones and Other Semiochemicals in Integrated Production. Lund, September 9-14, 2007. Lecture.
Öppna denna publikation i ny flik eller fönster >>Biosignal and Organic Chemistry: IOBC wprs Working Group Meeting - The Scanian Journey. Pheromones and Other Semiochemicals in Integrated Production. Lund, September 9-14, 2007. Lecture
2007 (Engelska)Konferensbidrag, Publicerat paper (Övrigt vetenskapligt)
Abstract [en]

The role of organic Synthesis in the Mistra-program Biosignal.

Nyckelord
Semiochemicals, synthesis
Nationell ämneskategori
Kemi
Identifikatorer
urn:nbn:se:miun:diva-5092 (URN)5500 (Lokalt ID)5500 (Arkivnummer)5500 (OAI)
Tillgänglig från: 2008-09-30 Skapad: 2008-09-30Bibliografiskt granskad
Verheggen, F., Ryne, C., Olsson, P. O., Arnaud, L., Lognay, G., Högberg, H.-E., . . . Löfstedt, C. (2007). Electrophysiological and Behavioral Activity of Secondary Metabolites in the Confused Flour Beetle, Tribolium confusum. Journal of Chemical Ecology, 33(3), 525-539
Öppna denna publikation i ny flik eller fönster >>Electrophysiological and Behavioral Activity of Secondary Metabolites in the Confused Flour Beetle, Tribolium confusum
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2007 (Engelska)Ingår i: Journal of Chemical Ecology, ISSN 0098-0331, E-ISSN 1573-1561, Vol. 33, nr 3, s. 525-539Artikel i tidskrift (Refereegranskat) Published
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.

Nyckelord
Tribolium confusum, pheromone, synthesis
Nationell ämneskategori
Kemi
Identifikatorer
urn:nbn:se:miun:diva-3907 (URN)10.1007/s10886-006-9236-3 (DOI)000244296400007 ()2-s2.0-33847306041 (Scopus ID)4269 (Lokalt ID)4269 (Arkivnummer)4269 (OAI)
Tillgänglig från: 2008-09-30 Skapad: 2008-09-30 Senast uppdaterad: 2017-12-12Bibliografiskt granskad
Högberg, H.-E. (2006). Ekologisk kemi: Enantioselektiv syntes av några seskvi och diterpener: 20:e Organikerdagarna, 12-15 juni 2006, Plenary lecture.
Öppna denna publikation i ny flik eller fönster >>Ekologisk kemi: Enantioselektiv syntes av några seskvi och diterpener: 20:e Organikerdagarna, 12-15 juni 2006, Plenary lecture
2006 (Svenska)Konferensbidrag, Publicerat paper (Övrigt vetenskapligt)
Nyckelord
germacradienol, torreyol, prenylbisabolane, syntheses
Nationell ämneskategori
Kemi
Identifikatorer
urn:nbn:se:miun:diva-1341 (URN)4270 (Lokalt ID)4270 (Arkivnummer)4270 (OAI)
Tillgänglig från: 2008-09-30 Skapad: 2008-09-30Bibliografiskt granskad
Isaksson, D., Sjödin, K. & Högberg, H.-E. (2006). Enantiomerically enriched cryptone by lipase catalysed kinetic resolution. Tetrahedron: asymmetry, 17(2), 275-280
Öppna denna publikation i ny flik eller fönster >>Enantiomerically enriched cryptone by lipase catalysed kinetic resolution
2006 (Engelska)Ingår i: Tetrahedron: asymmetry, ISSN 0957-4166, E-ISSN 1362-511X, Vol. 17, nr 2, s. 275-280Artikel i tidskrift (Refereegranskat) Published
Abstract [en]

Thiophenol was added to racemic cryptone (4-isopropyl-2-cyclohexene-1-one) and the resulting 1,4-addition products, cis- and trans-4-isopropyl-3-(phenylsulfanyl)cyclohexanone) were separated and the latter reduced to rac-1,3-cis-1,4-trans-4-isopropyl-3-(phenylsulfanyl)cyclo¬he¬xanol which was subjected to lipase catalysed resolution by acylation catalysed by CAL-B (Candida antarctica lipase B). The remaining alcohol was separated from the produced acetate, which was hydrolysed to the alcohol. The enantiomeric alcohols so obtained were oxidised. The initial products, probably sulfoxidoketones spontaneously decomposed to furnish enantiomerically enriched (R)- and (S)-cryptone with up to 76% and 98% ee, respectively.

Nyckelord
cryptone, resolution, lipase, CAL-B
Nationell ämneskategori
Kemi
Identifikatorer
urn:nbn:se:miun:diva-3720 (URN)10.1016/j.tetasy.2005.12.012 (DOI)000235579500018 ()2-s2.0-32444442897 (Scopus ID)3886 (Lokalt ID)3886 (Arkivnummer)3886 (OAI)
Anmärkning

Corrigendum to "Enantiomerically enriched cryptone by lipase catalysed kinetic resolution". [Tetrahedron: Asymmetry 17 (2006) 275] (DOI:10.1016/j.tetasy.2005.12.012)

Tetrahedron Asymmetry Volume 17, Issue 8, 18 April 2006, Page 1318

DOI: 10.1016/j.tetasy.2006.04.028

ScopusID: 2-s2.0-33646837669

Tillgänglig från: 2008-09-30 Skapad: 2008-09-30 Senast uppdaterad: 2017-12-12Bibliografiskt granskad
Isaksson, D., Högberg, H.-E. & Sjödin, K. (2006). Enantioselektiv syntes av seskviterpenen torreyol och andra kadinenderivat: 20:e Organikerdagarna, 12-15 juni 2006, Kalmar, Poster.
Öppna denna publikation i ny flik eller fönster >>Enantioselektiv syntes av seskviterpenen torreyol och andra kadinenderivat: 20:e Organikerdagarna, 12-15 juni 2006, Kalmar, Poster
2006 (Svenska)Konferensbidrag, Publicerat paper (Övrigt vetenskapligt)
Nyckelord
torreyol
Nationell ämneskategori
Kemi
Identifikatorer
urn:nbn:se:miun:diva-1342 (URN)4271 (Lokalt ID)4271 (Arkivnummer)4271 (OAI)
Tillgänglig från: 2008-09-30 Skapad: 2008-09-30Bibliografiskt granskad
Lyytikäinen-Saarenmaa, P., Varama, M., Anderbrant, O., Kukkola, M., Kokkonen, A.-M., Hedenström, E. & Högberg, H.-E. (2006). Monitoring the European pine sawfly with pheromone traps in maturing Scots pine stands. Agricultural and Forest Entomology, 8(1), 7-15
Öppna denna publikation i ny flik eller fönster >>Monitoring the European pine sawfly with pheromone traps in maturing Scots pine stands
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2006 (Engelska)Ingår i: Agricultural and Forest Entomology, ISSN 1461-9555, Vol. 8, nr 1, s. 7-15Artikel i tidskrift (Refereegranskat) Published
Abstract [en]

1. During 1989-93, field studies were conducted in Finland to develop a method based on pheromone traps to monitor and forecast population levels of the European pine sawfly (Neodiprion sertifer Geoffr.) and tree defoliation. 2. Three traps per site were baited with 100 μg of the N. sertifer sex pheromone, the acetate ester of (2S,3S,7S)-3,7-dimethyl-2-pentadecanol (diprionol), in maturing pine stands in southern and central Finland. In addition, three different dosages (1, 10 and 100 μg) of the pheromone were tested in 1991-92. 3. The highest number of males was observed in traps baited with the highest dose. On average, there was a 10-fold increase in trap catch between lure doses. 4. Density of overwintering eggs was used to evaluate the effectiveness of pheromone traps in predicting sawfly populations. The proportion of healthy overwintering eggs was determined each year. A model based on the number of current shoots on sample trees, diameter at breast height and tree height was formulated to estimate eggs per hectare. 5. Linear regression analysis produced high coefficients of determination between number of males in traps and density of total eggs in the subsequent generation, when populations were at peak densities. The relationships were not significant for low population densities. The results indicate a risk of moderate defoliation when the seasonal trap catch is 800-1000 males per trap or higher.

Nyckelord
Monitoring, Pine sawfly, pheromone, Neodirion sertifer
Nationell ämneskategori
Kemi Biologiska vetenskaper
Identifikatorer
urn:nbn:se:miun:diva-3644 (URN)10.1111/j.1461-9555.2006.00275.x (DOI)000236018000002 ()2-s2.0-33645093445 (Scopus ID)3702 (Lokalt ID)3702 (Arkivnummer)3702 (OAI)
Anmärkning

VR-Biology

Tillgänglig från: 2008-09-30 Skapad: 2008-09-30 Senast uppdaterad: 2016-09-29Bibliografiskt granskad
Eriksson, C., Schlyter, F., Sjödin, K. & Högberg, H.-E. (2006). Syntes av 2,6-disubstituerade piperidinalkaloider, potentiella gnaghämmare mot snytbaggen Hylobius abietis: 20:e Organikerdagarna, 12-15 juni 2006, Kalmar, föredrag.
Öppna denna publikation i ny flik eller fönster >>Syntes av 2,6-disubstituerade piperidinalkaloider, potentiella gnaghämmare mot snytbaggen Hylobius abietis: 20:e Organikerdagarna, 12-15 juni 2006, Kalmar, föredrag
2006 (Svenska)Konferensbidrag, Publicerat paper (Övrigt vetenskapligt)
Nyckelord
Pine weevil antifeedants
Nationell ämneskategori
Kemi
Identifikatorer
urn:nbn:se:miun:diva-1343 (URN)4272 (Lokalt ID)4272 (Arkivnummer)4272 (OAI)
Tillgänglig från: 2008-09-30 Skapad: 2008-09-30 Senast uppdaterad: 2011-04-06Bibliografiskt granskad
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