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Article: A Facile and Efficient Method for the Synthesis of Labeled and Unlabeled Very Long Chain Polyunsaturated Fatty Acids

Hamberg, Mats

The journal of the American Oil Chemists' Society. 2021 May, v. 98, no. 5

2021

Abstract: Several methods are available for elongation of fatty acid acyl chains. The present paper describes adaptation to the fatty acid field of a previously published protocol for manganese‐based Wurtz type coupling of alkyl bromides. 22‐Bromo‐3(Z),6(Z),9(Z), ... ...

Abstract	Several methods are available for elongation of fatty acid acyl chains. The present paper describes adaptation to the fatty acid field of a previously published protocol for manganese‐based Wurtz type coupling of alkyl bromides. 22‐Bromo‐3(Z),6(Z),9(Z),12(Z),15(Z),18(Z)‐docosahexaene, easily prepared from 4(Z),7(Z),10(Z),13(Z),16(Z),19(Z)‐docosahexaenoic acid, was coupled to homologous ω‐bromoesters by stirring for 4 hours at 40°C in the presence of manganese powder, a nickel catalyst and terpyridine. This afforded in yields of 70–75% a series of ω3‐hexaenoates of chain lengths of 32–40 carbons. The corresponding fatty acids of >98% purity were obtained following saponification and final purification. By using methyl [2,2,3,3,4,4‐²H₆]10‐bromodecanoate as coupling partner it was possible to prepare a very long chain fatty acid in isotopically labeled form, i.e., [2,2,3,3,4,4‐²H₆]14(Z),17(Z),20(Z),23(Z),26(Z),29(Z)‐dotriacontahexaenoic acid. Also prepared were the monounsaturated long chain fatty acids 15(Z)‐octadecenoic acid and 15(Z)‐tetracosenoic acid. Very long chain fatty acids have been isolated from retina and other tissues and are of biological relevance. The methodology described will assist in further analytical and biological studies in this field.
Keywords	catalysts ; isotope labeling ; manganese ; nickel ; oils ; retina ; saponification
Language	English
Dates of publication	2021-05
Size	p. 489-494.
Publishing place	John Wiley & Sons, Inc.
Document type	Article
Note	JOURNAL ARTICLE
ZDB-ID	240684-6
ISSN	1558-9331 ; 0003-021X
ISSN (online)	1558-9331
ISSN	0003-021X
DOI	10.1002/aocs.12484
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Article ; Online: Efficacy of Biological and Chemical Control Agents against

Piri, Tuula / Saarinen, Markku / Hamberg, Leena / Hantula, Jarkko / Gaitnieks, Talis

Journal of fungi (Basel, Switzerland)

2023 Volume 9, Issue 3

Abstract: Treatment of conifer stumps with a control agent effectively ... ...

Abstract	Treatment of conifer stumps with a control agent effectively prevents
Language	English
Publishing date	2023-03-11
Publishing country	Switzerland
Document type	Journal Article
ZDB-ID	2784229-0
ISSN	2309-608X ; 2309-608X
ISSN (online)	2309-608X
ISSN	2309-608X
DOI	10.3390/jof9030346
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Article ; Online: Charge migration fragmentation in the negative ion mode of cyclopentenone and cyclopentanone intermediates in the biosynthesis of jasmonates.

Oliw, Ernst H / Hamberg, Mats

Rapid communications in mass spectrometry : RCM

2020 Volume 34, Issue 8, Page(s) e8665

Abstract: ... also from 12-oxo-10-phytoenoic acid (12-OPEA) in fungi. Collision-induced dissociation (CID) of [M-H ... Methods: We investigated the CID of the [M-H]: Results: CID of [6,6,7,7-: Conclusions: CID of 12 ... OPDA and 12-OPEA generates cyclopentanone enolate anions at m/z 165 by charge-driven hydride transfer ...

Abstract	Rationale: Jasmonates are formed from 12-oxo-10,15(Z)-phytodienoic acid (12-OPDA) in plants and also from 12-oxo-10-phytoenoic acid (12-OPEA) in fungi. Collision-induced dissociation (CID) of [M-H] Methods: We investigated the CID of the [M-H] Results: CID of [6,6,7,7- Conclusions: CID of 12-OPDA and 12-OPEA generates cyclopentanone enolate anions at m/z 165 by charge-driven hydride transfer as a common mechanism and by bond cleavage between C-7 and C-8 of the carboxyl side chains with either gain or loss of a hydrogen atom.
MeSH term(s)	Anions/chemistry ; Anions/metabolism ; Biosynthetic Pathways ; Cyclopentanes/chemistry ; Cyclopentanes/metabolism ; Fatty Acids, Unsaturated/chemistry ; Fatty Acids, Unsaturated/metabolism ; Fungi/chemistry ; Fungi/enzymology ; Fungi/metabolism ; Oxylipins/chemistry ; Oxylipins/metabolism ; Plants/chemistry ; Plants/enzymology ; Plants/metabolism ; Spectrometry, Mass, Electrospray Ionization ; Tandem Mass Spectrometry
Chemical Substances	12-oxo-phytoenoic acid ; Anions ; Cyclopentanes ; Fatty Acids, Unsaturated ; Oxylipins ; cyclopentanone (220W81TN3S) ; 12-oxophytodienoic acid (67204-66-4) ; jasmonic acid (6RI5N05OWW) ; cyclopentenone (Q0U2IGF9CK)
Language	English
Publishing date	2020-01-16
Publishing country	England
Document type	Journal Article
ZDB-ID	58731-x
ISSN	1097-0231 ; 0951-4198
ISSN (online)	1097-0231
ISSN	0951-4198
DOI	10.1002/rcm.8665
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Article ; Online: Treatment with mycophenolate mofetil is associated with improved nailfold vasculature in systemic sclerosis.

Wildt, Marie / Andréasson, Kristofer / Hamberg, Viggo / Hesselstrand, Roger / Wuttge, Dirk M

Rheumatology (Oxford, England)

2023 Volume 63, Issue 2, Page(s) 385–391

Abstract: Objective: To investigate the evolution of nailfold capillary density in patients with SSc in relation to immunosuppressive treatment and autoantibodies.: Methods: This was a prospective study cohort. Consecutive newly diagnosed SSc patients were ... ...

Abstract	Objective: To investigate the evolution of nailfold capillary density in patients with SSc in relation to immunosuppressive treatment and autoantibodies. Methods: This was a prospective study cohort. Consecutive newly diagnosed SSc patients were included into this study who, in a retrospective review, had at least two nailfold capillary microscopy measurements performed during the first 48 months of follow-up. Capillary density per 3 mm was measured with widefield nailfold capillary microscopy. Improvement of capillary density per finger and mean capillary density were analysed. Longitudinal measurements of mean capillary density were analysed by generalized estimating equation. Results: Eighty patients (68 women, 12 men) met the inclusion criteria. The median follow-up time was 27 months. Twenty-eight patients had an improved capillary density in per-finger analysis. MMF was associated with fewer numbers of fingers that had worsened in capillary density. Anti-topoisomerase antibodies were associated with low mean capillary density. Anti-RNA polymerase III antibodies were associated with improvement and anti-centromere antibodies with worsening of capillary density in per-finger analysis. MMF treatment was associated with less steep capillary density decline in a moderated generalized estimating equation model including presence of anti-topoisomerase antibodies and the interaction of MMF with follow-up time. Conclusion: Nailfold capillary density improved over time in a substantial proportion of SSc patients. MMF treatment had a positive impact on the evolution of capillary density in these patients. SSc autoantibody phenotype may affect the capillary density development. The data support previous hypotheses that early immunosuppression may favourably affect vascular regeneration in SSc.
MeSH term(s)	Male ; Humans ; Female ; Mycophenolic Acid/therapeutic use ; Prospective Studies ; Scleroderma, Systemic/complications ; Capillaries ; Autoantibodies ; Microscopic Angioscopy ; Nails/blood supply
Chemical Substances	Mycophenolic Acid (HU9DX48N0T) ; Autoantibodies
Language	English
Publishing date	2023-05-08
Publishing country	England
Document type	Journal Article
ZDB-ID	1464822-2
ISSN	1462-0332 ; 1462-0324
ISSN (online)	1462-0332
ISSN	1462-0324
DOI	10.1093/rheumatology/kead207
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Article ; Online: Monitoring the temporal changes in herbicide-resistant Amaranthus tuberculatus: a landscape-scale probability-based estimation in Iowa.

Hamberg, Ryan C / Yadav, Ramawatar / Dixon, Philip M / Licht, Mark A / Owen, Micheal Dk

Pest management science

2023 Volume 79, Issue 12, Page(s) 4819–4827

Abstract: Background: A landscape-scale probability-based sampling of Iowa soybean [Glycine max (L.) Merr.] fields was conducted in 2013 and 2019; Amaranthus tuberculatus [Moq.] J.D. Sauer seed was collected from 97 random geospatial selected fields. The ... ...

Abstract	Background: A landscape-scale probability-based sampling of Iowa soybean [Glycine max (L.) Merr.] fields was conducted in 2013 and 2019; Amaranthus tuberculatus [Moq.] J.D. Sauer seed was collected from 97 random geospatial selected fields. The objectives were to evaluate the prevalence and distribution of herbicide-resistant A. tuberculatus (waterhemp) in soybean fields and evaluate temporal changes over 6 years. Amaranthus tuberculatus seedlings were evaluated for resistance to imazethapyr, atrazine, glyphosate, lactofen and mesotrione at 1× and 4× label rates. Results: Resistance to imazethapyr, glyphosate, lactofen and mesotrione at the 1× rate increased significantly from 2013 to 2019 and was found in 99%, 97%, 16% and 15% of Iowa A. tuberculatus populations in 2019, respectively. Resistance to atrazine at the 4× rate increased over time; atrazine resistance was found in 68% of populations in 2019. Three-way multiple herbicide-resistant A. tuberculatus was the most frequent and increased significantly to 4× rates from 16% in 2013 to 43% of populations in 2019. All A. tuberculatus populations resistant to HPPD-inhibitor herbicides also were resistant to atrazine. Conclusion: To the best of our knowledge, this is the first probability-based study that presented evolution of A. tuberculatus herbicide resistance over time. The results demonstrated that imazethapyr, atrazine and glyphosate resistance in Iowa A. tuberculatus populations was frequent whereas resistance to lactofen and mesotrione was less frequent. Most Iowa A. tuberculatus populations evolved resistance to multiple sites of action over time. The results of our study are widely applicable given the similarities in weed management practices throughout the Midwest United States. © 2023 The Authors. Pest Management Science published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.
MeSH term(s)	Amaranthus ; Atrazine ; Herbicide Resistance ; Herbicides/pharmacology ; Iowa ; Glycine max
Chemical Substances	Atrazine (QJA9M5H4IM) ; Herbicides ; lactofen (L44N8UV47O) ; mesotrione (48TR68G21T)
Language	English
Publishing date	2023-08-11
Publishing country	England
Document type	Evaluation Study ; Journal Article
ZDB-ID	2001705-4
ISSN	1526-4998 ; 1526-498X
ISSN (online)	1526-4998
ISSN	1526-498X
DOI	10.1002/ps.7682
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Article ; Online: In vitro and in vivo evaluation of the antimicrobial effectiveness of non-medicated hydrophobic wound dressings.

Malone, Matthew / Nygren, Erik / Hamberg, Tina / Radzieta, Michael / Jensen, Slade O

International wound journal

2023 Volume 21, Issue 2, Page(s) e14416

Abstract: There is an increasing use of non-medicated wound dressing with claims of irreversible bacterial binding. Most of the data are from in vitro models which lack clinical relevance. This study employed a range of in vitro experiments to address this gap and ...

Abstract	There is an increasing use of non-medicated wound dressing with claims of irreversible bacterial binding. Most of the data are from in vitro models which lack clinical relevance. This study employed a range of in vitro experiments to address this gap and we complemented our experimental designs with in vivo observations using dressings obtained from patients with diabetes-related foot ulcers. A hydrophobic wound dressing was compared with a control silicone dressing in vitro. Test dressings were placed on top of a Pseudomonas aeruginosa challenge suspension with increasing concentrations of suspension inoculum in addition to supplementation with phosphate buffered saline (PBS) or increased protein content (IPC). Next, we used the challenge suspensions obtained at the end of the first experiment, where bacterial loads from the suspensions were enumerated following test dressing exposure. Further, the time-dependent bacterial attachment was investigated over 1 and 24 h. Lastly, test dressings were exposed to a challenge suspension with IPC, with or without the addition of the bacteriostatic agent Deferiprone to assess the impacts of limiting bacterial growth in the experimental design. Lastly, two different wound dressings with claims of bacterial binding were obtained from patients with chronic diabetes-related foot ulcers after 72 h of application and observed using scanning electron microscope (SEM). Bacteria were enumerated from each dressing after a 1-h exposure time. There was no statistical difference in bacterial attachment between both test dressings when using different suspension inoculum concentrations or test mediums. Bacterial attachment to the two test dressings was significantly lower (p < 0.0001) when IPC was used instead of PBS. In the challenge suspension with PBS, only the hydrophobic dressing achieved a statistically significant reduction in bacterial loads (0.5 ± 0.05 log colony forming units; p = 0.001). In the presence of IPC, there was no significant reduction in bacterial loads for either test dressing. When bacterial growth was arrested, attachment to the test dressings did not increase over time, suggesting that the number of bacteria on the test dressings increases over time due to bacterial growth. SEM identified widespread adsorption of host fouling across the test dressings which occurred prior to microbial binding. Therein, microbial attachment occurred predominantly to host fouling and not directly to the dressings. Bacterial binding is not unique to dialkylcarbamoyl chloride (DACC) dressings and under clinically relevant in vitro conditions and in vivo observations, we demonstrate (in addition to previously published work) that the bacterial binding capabilities are not effective at reducing the number of bacteria in laboratory models or human wounds.
MeSH term(s)	Humans ; Diabetic Foot/drug therapy ; Anti-Infective Agents/therapeutic use ; Bandages ; Foot Ulcer ; Bacteria
Chemical Substances	Anti-Infective Agents
Language	English
Publishing date	2023-09-28
Publishing country	England
Document type	Journal Article
ZDB-ID	2170920-8
ISSN	1742-481X ; 1742-4801
ISSN (online)	1742-481X
ISSN	1742-4801
DOI	10.1111/iwj.14416
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Article ; Online: How persons with systemic mastocytosis describe the time between symptom onset and receiving diagnosis.

Hamberg Levedahl, Kerstin / Nilsson, Annika / Johansson, Birgitta / Hedström, Mariann

Primary health care research & development

2022 Volume 23, Page(s) e54

Abstract: Aim: The aim of the study was to explore how persons with systemic mastocytosis (SM) described the time between the onset of symptoms and signs and getting the diagnosis.: Background: SM is a rare disease caused by the accumulation of clonal mast ... ...

Abstract	Aim: The aim of the study was to explore how persons with systemic mastocytosis (SM) described the time between the onset of symptoms and signs and getting the diagnosis. Background: SM is a rare disease caused by the accumulation of clonal mast cells with abnormal function. The symptoms and signs of the disease are varied, often diffuse and affect individuals differently. Due to this complexity, a multi-disciplinary diagnostic approach is required, in which general practitioners play an important part in identifying and referring patients relevant for such investigations. Methods: Sixteen persons with SM were interviewed about their experiences of the time before the diagnosis was received. Systematic text condensation was used in the analysis process. Findings: The time between symptom and signs onset and diagnosis was perceived as difficult. SM often had a complex and unpredictable effect on a person's daily life, long before diagnosis. In the analysis, three themes were found.
MeSH term(s)	Humans ; Mast Cells ; Mastocytosis, Systemic/diagnosis ; Surveys and Questionnaires
Language	English
Publishing date	2022-09-07
Publishing country	England
Document type	Journal Article
ZDB-ID	2027892-5
ISSN	1477-1128 ; 1477-1128
ISSN (online)	1477-1128
ISSN	1477-1128
DOI	10.1017/S146342362200024X
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Article ; Online: Biosynthesis of Jasmonates from Linoleic Acid by the Fungus Fusarium oxysporum. Evidence for a Novel Allene Oxide Cyclase.

Oliw, Ernst H / Hamberg, Mats

Lipids

2019 Volume 54, Issue 9, Page(s) 543–556

Abstract: Fusarium oxysporum f. sp. tulipae (FOT) secretes (+)-7-iso-jasmonoyl-(S)-isoleucine ((+)-JA-Ile) to the growth medium together with about 10 times less 9,10-dihydro-(+)-7-iso-JA-Ile. Plants and fungi form (+)-JA-Ile from 18:3n-3 via 12-oxophytodienoic ... ...

Abstract	Fusarium oxysporum f. sp. tulipae (FOT) secretes (+)-7-iso-jasmonoyl-(S)-isoleucine ((+)-JA-Ile) to the growth medium together with about 10 times less 9,10-dihydro-(+)-7-iso-JA-Ile. Plants and fungi form (+)-JA-Ile from 18:3n-3 via 12-oxophytodienoic acid (12-OPDA), which is formed sequentially by 13S-lipoxygenase, allene oxide synthase (AOS), and allene oxide cyclase (AOC). Plant AOC does not accept linoleic acid (18:2n-6)-derived allene oxides and dihydrojasmonates are not commonly found in plants. This raises the question whether 18:2n-6 serves as the precursor of 9,10-dihydro-JA-Ile in Fusarium, or whether the latter arises by a putative reductase activity operating on the n-3 double bond of (+)-JA-Ile or one of its precursors. Incubation of pentadeuterated (d
MeSH term(s)	Cyclopentanes/chemistry ; Cyclopentanes/metabolism ; Fusarium/chemistry ; Fusarium/metabolism ; Intramolecular Oxidoreductases/metabolism ; Linoleic Acid/chemistry ; Linoleic Acid/metabolism ; Molecular Conformation ; Oxylipins/chemistry ; Oxylipins/metabolism
Chemical Substances	Cyclopentanes ; Oxylipins ; jasmonic acid (6RI5N05OWW) ; Linoleic Acid (9KJL21T0QJ) ; Intramolecular Oxidoreductases (EC 5.3.-) ; hydroperoxide isomerase (EC 5.3.99.6)
Language	English
Publishing date	2019-07-28
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	241539-2
ISSN	1558-9307 ; 0024-4201
ISSN (online)	1558-9307
ISSN	0024-4201
DOI	10.1002/lipd.12180
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Article: Long-term effects of biological sprout control of unwanted hardwoods on conifer sites

Hamberg, Leena / Laine, Tiina / Hantula, Jarkko / Saksa, Timo

Forest ecology and management. 2021 Aug. 01, v. 493

2021

Abstract: ... the number of cases when competing deciduous trees occurred within a 1 m sample plot around the investigated ...

Abstract	Long-term investigations revealing the effects of a decay fungus, Chondrostereum purpureum (Pers. Ex Fr.) Pouzar on competition between deciduous and conifer tree species in young forests are missing. Therefore, the effects of three different sprout control treatments were tested in young Norway spruce (Picea abies (L.) H. Karst.) and Scots pine (Pinus sylvestris L.) stands by evaluating sprouting ability of deciduous tree stumps, and competition level around cultivated conifers five years after the treatments. Sprouting control was performed (i) by cutting only (control), and ii) by applying low-concentration (dilution 1:400) or iii) high-concentration (dilution 1:100) C. purpureum preparates (mycelial solutions) on stumps immediately after cutting. Deciduous saplings were cut, and fungal inoculum was applied by spreading it onto freshly cut stump surfaces. Following high-concentration fungal treatment, the number of young deciduous trees cut in the treatment was by 25% lower compared to control; moreover, the number of sprouts per stump was also significantly negatively affected by the fungal treatment. As a result, the number of cases when competing deciduous trees occurred within a 1 m sample plot around the investigated conifers was 40% lower following high-concentration fungal treatment than in the control, resulting in better height and diameter development of conifers. Thus, additional sprout control is not necessarily needed after the high-concentration fungal treatment.
Keywords	Chondrostereum purpureum ; Picea abies ; Pinus sylvestris ; administrative management ; conifers ; decay fungi ; forest ecology ; inoculum ; mycelium
Language	English
Dates of publication	2021-0801
Publishing place	Elsevier B.V.
Document type	Article
Note	NAL-AP-2-clean
ZDB-ID	751138-3
ISSN	0378-1127
ISSN	0378-1127
DOI	10.1016/j.foreco.2021.119288
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Article ; Online: Diamond-based dielectric laser acceleration.

Chlouba, Tomas / Shiloh, Roy / Forsberg, Pontus / Hamberg, Mathias / Karlsson, Mikael / Kozák, Martin / Hommelhoff, Peter

Optics express

2022 Volume 30, Issue 1, Page(s) 505–510

Abstract: ... higher acceleration gradient (60 MeV/m) compared to silicon gratings designed for a similar electron ... energy. Using more complex geometries, GeV/m acceleration gradients are within reach for subrelativistic ...

Abstract	The field of dielectric laser accelerators (DLA) garnered a considerable interest in the past six years as it offers novel opportunities in accelerator science and potentially transformative applications. Currently, the most widespread approach considers silicon-based structures due to their low absorption and high refractive index in the infrared spectral region and the well-developed silicon processing technology. In this paper we investigate a diamond as an alternative to silicon, mainly due to its considerably higher damage threshold. In particular, we find that our diamond grating allows a three times higher acceleration gradient (60 MeV/m) compared to silicon gratings designed for a similar electron energy. Using more complex geometries, GeV/m acceleration gradients are within reach for subrelativistic electrons.
Language	English
Publishing date	2022-02-21
Publishing country	United States
Document type	Journal Article
ZDB-ID	1491859-6
ISSN	1094-4087 ; 1094-4087
ISSN (online)	1094-4087
ISSN	1094-4087
DOI	10.1364/OE.442752
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