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Development of Methods for Analysis of Valuable Compounds in By-products from Agricultural and Forestry Industrial Sectors
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - BMC.
2015 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

A growing interest in sustainable development has made efficient utilisation of starting materials and, if they occur, by-products become increasingly important. Vast amounts of by-products are generated by the forestry and food industry. Incineration for energy production is one way to make use of these by-products but some of them contain compounds that would have an increased value if they were extracted, so called “high value species”. The by-products are often very complex, so reliable methods for analysis of the high value species are required in the development of processes to utilise them. A wide range of compounds can be analysed using chromatographic separation coupled to mass spectrometry, making it a powerful tool in the evaluation of methods for extracting high value species from industry by-products.

This thesis is based on four studies of potential high value species. In the first study, methods were developed to differentiate isobaric flavonoids and then use this knowledge to determine the identity of the flavonoids in three different plant extracts. In the second study, three different methods to extract betulin from birch bark were evaluated regarding extracted amount and purity of betulin. One of the methods was then investigated in industrial scale using a model approach. In the third study, the flavonoid contents of lovage were determined and other major extracted compounds were investigated by high performance liquid chromatography coupled to electrospray ionisation mass spectrometry. Gas chromatography and supercritical fluid chromatography were used to obtain complementary information about major components. In the fourth study, high resolution mass spectrometry utilising two different types of fragmentation was used with the purpose of overcoming the shortcomings of the methods developed in the first study. The results indicated that it would be possible to develop methods compatible with chromatographic separation for differentiating different types of isobaric substituents. The ability of performing sequential fragmentation was used to investigate some isobaric aglycones by creating spectral trees, and unique pathways were found for each of them.

Place, publisher, year, edition, pages
Uppsala: Acta Universitatis Upsaliensis, 2015. , 45 p.
Series
Digital Comprehensive Summaries of Uppsala Dissertations from the Faculty of Science and Technology, ISSN 1651-6214 ; 1256
Keyword [en]
industry by-products, flavonoids, triterpenes, mass spectrometry
National Category
Analytical Chemistry
Research subject
Chemistry with specialization in Analytical Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-251352ISBN: 978-91-554-9249-6 (print)OAI: oai:DiVA.org:uu-251352DiVA: diva2:805693
Public defence
2015-06-03, B21, Husargatan 3, Uppsala, 10:15 (English)
Opponent
Supervisors
Available from: 2015-05-12 Created: 2015-04-16 Last updated: 2015-07-07
List of papers
1. Strategies for differentiation of isobaric flavonoids using liquid chromatography coupled to electrospray ionization mass spectrometry
Open this publication in new window or tab >>Strategies for differentiation of isobaric flavonoids using liquid chromatography coupled to electrospray ionization mass spectrometry
2014 (English)In: Journal of Mass Spectrometry, ISSN 1076-5174, E-ISSN 1096-9888, Vol. 49, no 7, 646-663 p.Article in journal (Refereed) Published
Abstract [en]

Flavonoids are a class of secondary plant metabolites existing in great variety in nature. Due to this variety, identification can be difficult, especially as overlapping compounds in both chromatographic separations and mass spectrometric detection are common. Methods for distinguishing isobaric flavonoids using MS2 and MS3 have been developed. Chromatographic separation of various plant extracts was done with RP-HPLC and detected with positive ESI-MS operated in information-dependent acquisition (IDA) mode. Two methods for the determination of flavonoid identity and substitution pattern, both featuring IDA criteria, were used together with the HPLC equipment. A third method where the collision energy was ramped utilized direct infusion. With the developed strategies, it is possible to differentiate between many isobaric flavonoids. Various classes of flavonoids were found in all of the plant extracts, in the red onion extract 45 components were detected and for 29 of them the aglycone was characterized, while the substituents were tentatively identified for 31 of them. For the strawberry extract, those numbers were 66, 30 and 60, and for the cherry extract 99, 56 and 71. The great variety of flavonoids, several of them isobaric, found in each of the extracts highlights the need for reliable methods for flavonoid characterization. Methods capable of differentiating between most of the isobars analyzed have been developed. 

Keyword
flavonoids, multiple reaction monitoring mass spectrometry, fragmentation patterns, plant extracts, energy resolved mass spectrometry
National Category
Chemical Sciences
Identifiers
urn:nbn:se:uu:diva-227458 (URN)10.1002/jms.3386 (DOI)000339614300013 ()
Available from: 2014-06-26 Created: 2014-06-26 Last updated: 2017-12-05Bibliographically approved
2. Evaluation and Analysis of Environmentally Sustainable Methodologies for Extraction of Betulin from Birch Bark with Focus on Industrial Feasibility
Open this publication in new window or tab >>Evaluation and Analysis of Environmentally Sustainable Methodologies for Extraction of Betulin from Birch Bark with Focus on Industrial Feasibility
Show others...
2016 (English)In: Green Chemistry, ISSN 1463-9262, E-ISSN 1463-9270, Vol. 18, no 2, 516-523 p.Article in journal (Refereed) Published
Abstract [en]

Betulin from birch bark was extracted using two principally different extraction methodologies - classical Reflux Boiling (RB) and Pressurized Liquid Extraction (PLE). The extraction methods were analyzed based on both recovery and purity as well as for RB industrial feasibility. The purity and recovery for the different extraction methods were analyzed using High Performance Liquid Chromatography (HPLC) coupled with three different detection principles: Diode Array Detection (DAD), Mass Spectrometry (MS) and Charged Aerosol Detection (CAD). The chromatographic purity was determined by all detections whereas the DAD was used also for complementary gravimetric calculations of the purity of the extracts. The MS detection (in MS and MS/MS modes) was mainly used to characterize the impurities. Two steps to increase the purity of RB extracts were evaluated - pre-boiling the bark in water and precipitation by adding water to the extract. Finally, the methods were compared in terms of amounts of betulin produced and solvent consumed. The RB method including a precipitation step produced the highest purity of betulin. However, results indicate that PLE using three cycles with the precipitation step gives similar purities as for RB. The PLE method produced up to 1.6 times higher amount of extract compared to the RB method. However, the solvent consumption (liter solvent per gram product) for PLE was around 4.5 times higher as compared to the classical RB. PLE performed with only one extraction cycle gave results more similar to RB with 1.2 times higher yield and 1.4 times higher solvent consumption. The RB process was investigated on an industrial scale using a model approach and several important key-factors could be identified. The most energy demanding step was the recycling of extraction solvent which motivates that solvent consumption should be kept low and calculations show a great putative energy reduction by decreasing the ethanol concentration used in the RB process to lower than 90%.

Keyword
betulin; energy calculations; extraction; mass spectrometry; pressurized liquid extraction; purification; reflux boiling; supercritical fluid extraction
National Category
Analytical Chemistry
Identifiers
urn:nbn:se:uu:diva-249296 (URN)10.1039/c5gc00519a (DOI)000369534500024 ()
Funder
Swedish Research Council Formas, 229-2009-1527
Available from: 2015-04-13 Created: 2015-04-13 Last updated: 2017-12-04Bibliographically approved
3. Analysis of Lovage (Levisticum officinale W.D.J. Koch) using Chromatographic Techniques Hyphenated to Mass Spectrometry
Open this publication in new window or tab >>Analysis of Lovage (Levisticum officinale W.D.J. Koch) using Chromatographic Techniques Hyphenated to Mass Spectrometry
(English)In: Natural Product Research, ISSN 1478-6419, E-ISSN 1478-6427, ISSN 1478-6419Article in journal (Refereed) Submitted
Keyword
lovage; piperine; flavonoids; chromatography; mass spectrometry
National Category
Analytical Chemistry
Identifiers
urn:nbn:se:uu:diva-249297 (URN)
Funder
Swedish Research Council Formas, 229-2009-1527
Available from: 2015-04-13 Created: 2015-04-13 Last updated: 2017-12-04
4. Differentiation of isobaric flavonoids utilizing high resolution, high accuracy mass spectrometry
Open this publication in new window or tab >>Differentiation of isobaric flavonoids utilizing high resolution, high accuracy mass spectrometry
(English)Manuscript (preprint) (Other academic)
National Category
Analytical Chemistry
Identifiers
urn:nbn:se:uu:diva-249299 (URN)
Funder
Swedish Research Council Formas, 229-2009-1527
Available from: 2015-04-13 Created: 2015-04-13 Last updated: 2015-05-12

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Fridén, Mikael E

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