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Anti-aphrodisiac pheromone, a renewable signal in adult butterflies
Stockholm University, Faculty of Science, Department of Zoology.
Stockholm University, Faculty of Science, Department of Environmental Science and Analytical Chemistry.ORCID iD: 0000-0003-2561-6875
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(English)Manuscript (preprint) (Other academic)
National Category
Analytical Chemistry
Research subject
Analytical Chemistry
Identifiers
URN: urn:nbn:se:su:diva-159095OAI: oai:DiVA.org:su-159095DiVA, id: diva2:1240588
Available from: 2018-08-21 Created: 2018-08-21 Last updated: 2018-08-22Bibliographically approved
In thesis
1. Amino acids with relevance to health, climate and the environment: Development of mass spectrometric methods
Open this publication in new window or tab >>Amino acids with relevance to health, climate and the environment: Development of mass spectrometric methods
2018 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

Amino acids play vital roles in health, either in their native form or chemically modified. Some studies have linked certain non-proteinogenic amino acids to neurodegenerative diseases, such as in the case of β-methylaminoalanine (BMAA). Various environmental pollutants, including carcinogenic polycyclic aromatic compounds, are able to react forming adducts with blood proteins. Amino acids may also be essential in chemical ecology as constituents of flower nectar, potentially used by common feeders as butterflies to synthesize pheromones. Additionally, proteinaceous materials have been detected in aerosols with an apparent potential to influence climate, possibly having a role in cloud formation.

The determination of amino acids presents many challenges, due to the fact that they are most often constituents of complex sample matrices that contain a high level of chemical interferences. In this respect, mass spectrometry (MS) is a selective and sensitive analytical tool that can be used to measure amino acids in biological samples.

In this work, several analytical methods based on MS were developed. (i) First, derivatization with a permanently charged N-hydroxysuccinimide ester of N-butylnicotinic acid (C4-NA-NHS) was used to increase the sensitivity and selectivity for amino acids. This strategy was applied to localize BMAA in both visceral and non-visceral parts of blue mussels. (ii) Moreover, a method was developed to separate and determine L- and D- BMAA in cycad seeds by derivatization with a chiral reagent, (+)-1-(9-fluorenyl) ethyl chloroformate (FLEC). Together with L-BMAA, appreciable amounts of D-BMAA (50.13 ± 0.05 and 4.08 ± 0.04 µg BMAA/g Cycas micronesica, wet weight, respectively) were detected for the first time after enzymatic digestion, suggesting D-BMAA may be bound to proteins or may be a conjugate and released only after hydrolysis. (iii) Derivatization with C4-NA-NHS was applied as well for the determination of amino acids in nectar of Bunias orientalis. The presence of tryptophan and phenylalanine, purportedly used to synthesize anti-aphrodisiac pheromones by nectar feeders (adult male butterflies), could then be observed. (iv) Furthermore, the profiling of amino acids in Arctic aerosols was carried out and was used to measure the contribution of free and polyamino acids in aerosol formation. Levels detected were in the range of 0.02-2914 pmol/m3 sampled air. For the first time the measurement of polyamino acids in the Arctic atmosphere was reported. Additionally, possible anthropogenic and marine sources were suggested. The results support the hypothesis that proteinaceous materials act as cloud condensation nuclei over the Arctic. (v) Finally, a method was developed employing selective chromatography/high-resolution MS to identify histidine and lysine adducts in serum albumin of mice exposed to the carcinogen benzo(a)pyrene, as well as in human samples in vivo. Adduct isomers from diol epoxide metabolites could be detected in serum albumin from human samples at attomole/mg levels. This work shows the possibility of future exposure measurements from these compounds in different groups of the population.

This thesis presents the development of improved analytical methodologies for detecting and identifying trace levels of amino acids, to investigate their relevance in health, climate and the environment.

Place, publisher, year, edition, pages
Stockholm: Department of Environmental Science and Analytical Chemistry, Stockholm University, 2018. p. 53
Keywords
amino acids, LC/MS, fixed-charge derivatization, BMAA, chiral separation, pheromones, arctic aerosols, serum albumin adducts, benzo[a]pyrene diol epoxides, high-resolution MS
National Category
Analytical Chemistry
Research subject
Analytical Chemistry
Identifiers
urn:nbn:se:su:diva-158985 (URN)978-91-7797-390-4 (ISBN)978-91-7797-391-1 (ISBN)
Public defence
2018-12-05, Nordenskiöldsalen, Geovetenskapens hus, Svante Arrhenius väg 12, Stockholm, 13:00 (English)
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Note

At the time of the doctoral defense, the following papers were unpublished and had a status as follows: Paper 2: Manuscript. Paper 3: Manuscript. Paper 5: Manuscript.

Available from: 2018-11-12 Created: 2018-08-20 Last updated: 2018-11-12Bibliographically approved

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